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Family Travel Guide - Tips for families on the move

It feels like winter has been sticking around forever, but I know that spring is just around the corner, and with it comes Spring Break. In my family, we look forward to taking this week off all year. We most often go to South Florida to warm up, but two years ago we used HomeAway to rent two condos in Puerto Rico for the week since we were traveling with my in-laws. It worked out perfectly.



If Spring Break is a vacation week that you look forward to all year, don’t let plans get tripped up by decisions like where to go and where to stay. Take the five tips below to heart as you begin to plan out the best vacation week of the year (at least according to every school-aged child).



1. Have a Pre-Vacation Planning Meeting: If your kids are older or you’re planning to travel with extended family (parents, in-laws, aunts, uncles), have a sit-down meeting or a video chat to talk through where you want to go for vacation. You want to make sure that everyone is on board and happy before you begin to book accommodations and firm up travel plans. Consider all factors including costs, travel time, airfares, on-site activities, etc.



2. Give People Space: When you travel, you don’t want to skimp on accommodations. Long gone are the college days when you would book eight people in a room that only sleeps four. Find a place to stay that gives family the room they need to have their own personal space and doors to close at the end of the evening for privacy. I like my own space, which is why we booked two condos in Puerto Rico and have already booked a six-bedroom house through HomeAway for an Orlando vacation in November.



3. Plan Out Your Meals: Decide ahead of time whether you want to cook family meals or eat out at restaurants every day. The first option is certainly cheaper and can give you more flexibility. It’s nice for kids to be able to grab a granola bar or make a bowl of cereal when they first wake up. When we travel, we like to eat breakfast at home, then eat lunch while we’re out during the day. For dinner, sometimes we eat out, sometimes we prepare meals at home in the kitchen available to us in our vacation rental.



4. Make Sure Everyone Feels Happy: What I mean by this is, make sure that everyone feels like they have their say in vacation decisions, even little ones, and that everyone is going to be able to see or visit something they really like during the vacation. You don’t want your disappointed kids and other family members moping around during your vacation, potentially ruining the trip for everyone.



5. Take Time to Relax: I’ve been on many vacations that were spent running around from attraction to attraction all day with little time spent back in the room. Maybe that was because once back in the room there was little space for each person and we were all stuck watching the one TV. Today, all that running around is a prescription for a meltdown. So, don’t rush, make time to relax. When we travel, we like to visit attractions in the morning, then come back mid-afternoon to our vacation rental to relax, read, take a dip in the pool or take a nap. Everyone is definitely happier that way.



Do you have any favorite tips for planning a perfect Spring Break family getaway? Let us know in the comments section below.


Thanks for reading!



Planning a family ski trip can be tricky. Especially when it involves young children. From the pounds of equipment you have to lug around, to managing ski school, lift tickets and navigating unknown terrain, families can be intimidated by the mountain experience. Crossing as many items off of our “prep list” as possible, my family and I recently took a trip to Keystone, Colorado and found that the stresses of ski traveling aren’t quite so burdensome when you find the right resort.


When researching our options, we settled on Keystone for the many kid-friendly amenities they offered. We were quickly sold on the "Kids Ski Free" program for families staying two or more nights in one of the resort's accommodations, which was a great selling point for our family of three since ski trips can get expensive. It was the first ski experience for our three-year-old, and we were most concerned about giving him the best introduction to a potential life-long activity.


The resort also happened to be offering "Kidtopia" family programming while we were in town, featuring activities and events including the fourth installment of the World's Largest Snowfort for kids to climb through; snow tubing for little ones of all sizes, weekly parades; fresh-baked aprés ski afternoon cookies; mountaintop fireworks; stargazing parties and scavenger hunts. This year, following a particularly blustery mountain day, we were able to take advantage of the Kidtopia indoor activities as well, including a little pottery painting at the Ready, Paint, Fire shop in River Run Village.



Accommodations are plentiful on the resort, but for ski getaways, vacation rentals are great because you can recreate a sense of familiarity even though you’re away from home. We like enjoying a few meals out at resort restaurants, but it’s nice to be able to wake up each morning and have a home-cooked breakfast around the kitchen table in our  pajamas before hitting the slopes. Vacation rentals also offer the benefit of more space at an affordable value. We were able to stay in a two-bedroom unit with a full kitchen, living room and dining space that allowed our little one his own bedroom in addition to a large master suite that allowed a little privacy for us adults—a challenging thing to find with most hotels. We stayed in a ski-in/ski-out condominium in the River Run Village area, which was walking distance to an array of shops, restaurants and ski lifts. is a great resource for finding these kinds of properties.


As a family, we were also able to enjoy the new "Schoolmarm" family ski trail, which was designed specifically to engage skiers of all ages and ability levels to enjoy together with different terrain features that helped us take our skills to the next level. IMG_9474.jpg


For our little one, we took advantage of Keystone's ski school, which engages kids as young as three years old from the second they step in the door with everything from custom equipment fitting to interactive games that help build on ski abilities. Within minutes, our little tyke was up on skis and on the magic carpet conveyor belt along with his instructor for his first run. It was thrilling to see his first run down the hill - and there were many more that followed throughout the weekend.


His three-day enrollment in school guaranteed him the same instructor each day, which allowed him to transition into new learning throughout each class. As parents, we were also able to meet him at the end of each day with his instructor to pick up tips on how we could help him progress when skiing together as a family.


While it was often great to enjoy dining together in the comfort our condo, we also took advantage of some of Keystone's unique dining options, including the Bavarian-inspired Der Fondue Chessel, which hosts a family-style fondue experience at the top of an 11,400-foot mountain. To get there, you have to take the gondola up the peak, which can be pretty chilly, even with the gondola blankets the resort provides at the base of the mountain. But the festive experience is well worth the effort, and there’s really nothing quite as fun as dipping all sorts of treats into a bowl of warm, gooey cheese to warm the soul. Western-themed dinner sleigh rides are also available led by a team of Belgian Draft horses through a snow-covered valley to historic Soda Creak Homesteads. Be sure to wear warm layers for the brisk ride that leads you to a rustic cabin for a pioneer-style dinner served by friendly horse wranglers. Pre-fixe dinner options vary, but the warm cup of soup with fresh biscuits that greet you at your arrival are a mainstay of the experience.


And let's be honest, no ski trip with the kiddos is complete without a little "me time" for mom. I scheduled some time at the Keystone Lodge & Spa where they offer any number of luxury massage, facial or hand and foot treatments are available to restore a little order back to the one person who's likely organized the majority of the trip. It was one of the better spa experiences I've had! There's nothing like feeling warm and cozy during an invigorating massage or facial while watching the snowsoftly fall on the mountain terrain outside.


When it comes to family vacations, the most important thing is the memories you take away. For us, everything about our Keystone experience, from our adventures on the slopes to the quiet moments relaxing in our vacation rental, was unforgettable and will provide us with a lifetime of memories to enjoy for years to come.




Jessica Dupuy is a freelance writer with writing credits for National Geographic Traveler, Imbibe, The Hollywood Reporter, Texas Monthly, Texas Highways, Fodor’s Travel Publications, and numerous regional publications. She has also written Uchi: The Cookbook, in conjunction with James Beard Award-winning Executive Chef, Tyson Cole and The Salt Lick Cookbook: A Story of Land, Family and Love on the iconic Texas barbecue restaurant.


My father-in-law’s favorite holiday is Thanksgiving. He loves everything about making the turkey, baking the pumpkin pie and setting out the seasonal decorations. Fortunately, all of the above are easy to do whether spending the holiday at home or away on vacation.



When we travel, we most often stay in vacation rentals with full kitchens, which makes it a snap to prepare dinner as a family. Two years ago, we spent Thanksgiving week in a fantastic rental in the Orlando area with my in-laws. We took the kids to the Magic Kingdom in the morning, and had a traditional Thanksgiving feast in the late-afternoon. We enjoyed the best of both worlds being on vacation while celebrating Thanksgiving in a very similar way to how we would at home. It was perfect.


If you’re thinking about taking a family vacation over the Turkey Day holidays, but want to incorporate traditional holiday elements, take a look at the ten suggestions below. If you’re not sure where to go, you may also want to look at vacation rentals in some of the most popular travel destinations, like Gatlinburg, Tennessee, Palm Springs, California and Breckenridge, Colorado, as identified by HomeAway as holiday hotspots for November getaways.


1) Enjoy a Traditional Thanksgiving Meal: Hit the grocery store as a family, shopping list in hand, to pick up a turkey, potatoes and green beans to prepare your feast in a full kitchen in your vacation rental. Or, order the entire spread from the local supermarket or catering company. Many restaurants also offer traditional Turkey Day fare for families. Wherever you are, it’s fun and easy to enjoy a turkey and all the trimmings together as a family.


2) Create Seasonal Decorations: Have fun with your kids creating handprint turkeys, toilet paper roll pilgrims and teepee centerpieces and display them wherever you may be, whether a vacation rental on the beach or at Aunt Sally’s house. There are many fun crafts that are easy to make and don’t require a trip to the craft store. A quick search on Pinterest will help you find lots of ideas to keep your kids busy and in the spirit of Thanksgiving.


3) Go to a Parade: Just because you’re away from home in a vacation rental doesn’t mean you can’t enjoy a good parade complete with floats, marching bands and baton twirling. Many towns put on Thanksgiving festivities, including parades and festivals, so pick up a local paper when you get in town to see what’s going on. It’s also fun to see how other towns celebrate Thanksgiving in their own way.


4) Run or Walk in a Turkey Trot: It’s our annual family tradition to run or walk in our neighborhood Turkey Trot 5K on Thanksgiving Day. We’ve been doing this for more than 10 years, and it’s such a great way to start the day off right as a family. Just type “turkey trot” and the name of the town where you’ll be renting a vacation home for Thanksgiving into a search engine to find nearby races.


5) Gather Around the Television: I’m not advocating a day in front of the television, but if you stay in a vacation rental over the holidays, gather up and watch football or the Macy’s Thanksgiving Day Parade as you might do at home. Many vacation rentals have generous living areas and big screen TVs, so this is a fun way to spend time as a family.

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6) Throw Around a Football: While some people spend the day watching football on TV, other families like to throw around the football on Thanksgiving Day. Fortunately, many vacation rentals have sporting equipment stored away, so be on the hunt or ask the owners if they have a football to throw around in a family game.


7) Take a Walk: Once the meal is over and we’re all nice and full, we like to take a walk around the neighborhood, which is something you can easily do while staying in a vacation rental. It’s fun to explore a new community or neighborhood, while engaging each other as a family in fun conversation.


8) Play Board Games: When we stayed in a vacation home over Thanksgiving two years ago, the owners had a closet full of board games for renters. The kids had so much fun checking out all the games for different age groups before we sat down to play UNO and Monopoly. Board games are a great way to come together as a family and many rentals have board games, even video games, for everyone to play.


9) Enjoy a Nap: Who doesn’t love taking a nap after a big Turkey Day meal? Fortunately, in a vacation home you aren’t all on top of each other like you might be in a hotel room. I love that I can close the door to my room, and to my kids’ rooms, so we can all drift off into dreamland after a delicious meal. This is one of my favorite benefits of a vacation rental!


10) Get Creative with Leftovers: Have fun with the kids creating unique combinations of Thanksgiving leftovers. Since you have a kitchen in a vacation home, it’s easy to save leftovers for meals later in the week so you don’t need to eat out in restaurants. Plus, it’s fun to see what the kids come up with using the extra turkey, green beans and cranberry sauce to eat later in the week.



Do you have any favorite Thanksgiving Day activities that can easily be done whether at home or away on vacation? Let us know in the comments section below.


Hidden Wine Country

Posted by jennifer.boden Sep 24, 2013

Napa and Sonoma are kind of like Disneyland for adults – there’s almost too much to enjoy. Wineries, restaurants, museums and castles…you can’t go ten feet without tripping over some new fun thing to do. It’s a good problem to have, but you still need to make choices, and a good way to start is to find out what the locals do. There are hidden treasures all over wine country; you just have to know where to look.



There is no wine country without wineries, so let’s start there. I’m always looking for that perfect combination of great wine and beautiful surroundings. While there are many wineries in Napa and Sonoma that easily meet these requirements, here are a few I’m particularly fond of.Chateau St. Jean.jpg.jpeg


If you want the chateau experience but don’t want to go all the way to France, let me recommend Chateau St. Jean. This winery offers a couple of different ways to sample their excellent wines. The main tasting room, in the visitor center, offers the widest variety. However, for a little bit more, you can taste some of their reserve and limited release wines in the chateau. 


Another must-see wine country vineyard is Ledson winery. Their gorgeous castle features several tasting rooms, multiple reds and whites to choose from and even a hotel. Ledson Winery.jpg.jpeg


You can book a room, set up a private tasting or attend one of their many events. This Fall will be the 6th annual Corvettes at the Castle event where you can drink wine, mingle with other Corvette lovers and enjoy a picnic under the Oak trees. Another memorable event that’s coming up is Ledson’s Holiday Open House. Cozy up to their fireplaces with your favorite glass of wine and take in the joy of season in the most royal manner.


If it’s a medieval castle you’re after, then be sure to visit Castello di Amorosa. Owner Dario Sattui spent many years researching medieval architecture, which resulted in the authentically-styled 13th century Tuscan castle and winery. Castello di Amorosa offers tours, barrel tastings and events. Have a glass while getting lost in history. Castello di Amorosa.jpg.jpeg


For something more rustic, but equally tasty, I recommend the Long Meadow Ranch Winery and Farmstead in St. Helena. This organic farm produces beef, eggs, honey, fruits, vegetables and, of course, wine. Dine at their restaurant, visit their farmer’s market or take advantage of one of their wine or olive oil tastings.

Long Meadow Ranch.jpg.jpeg

And remember, food and wine belong together. St Francis Vineyards offers amazing pairings, gourmet small plates with hand-picked wines. Be sure to make a reservation.


For a different experience, I recommend Sterling Vineyards in Calistoga. Their aerial tram is the only one of its kind in Napa Valley, offering stunning panoramic views as visitors are carried up 300 feet to the winery. At the top, guests are greeted with a glass of wine to enjoy while strolling through art galleries, overlooks, and elevated walkways that provide a glimpse into the winemaking process, from grape to glass.



Nothing pairs better with fine wine than fine music. Nestled at the base of the Sonoma Mountains in the heart of wine country, you’ll find The Green Music Center. This world-class complex includes famous performances by Chris Botti, Josh Groban and the San Francisco Symphony.


If visual arts and artisanal wines are more your style, be sure to visit Ma(i)sonry Napa Valley. This historic building features a rotating collection of limited-production wines from 20+ esteemed vintner partners, along with internationally renowned art and furnishings to appreciate and acquire.


History, Shopping and Food

One of the coolest things about wine country is that it’s no one-trick pony. Yes, there are amazing wineries, but there’s also excellent shopping and wonderful restaurants. One of the best places to go is Sonoma Plaza, in the town of Sonoma. At the center of the Plaza is a beautiful park, a great place to relax for a few minutes between destinations. Enjoy a romantic stroll or a family outing. The park is complete with a playground for kids, plenty of picnic benches, fountains, and a duck pond. Concerts, and festivals are also held there along with a Farmer’s Market on Tuesdays. Be sure to stop by the market for local gourmet ice cream, fresh cut flowers, hand-made Sonoma jewelry, and of course the delicious food. The Farmer’s Market runs May through the end of October.


Surrounding the park are historic buildings, and lovely boutiques - check out SummerVine and Sonoma Home. If wine is still calling your name, pop by a few of the many wine tasting rooms, I recommend Sigh champagne room, Roche winery, and Highway 12 winery. If you have a sweet tooth, you’re invited to a charming shop on the Plaza called Wine Country Chocolates, for a delightful chocolate tasting.


When you work up an appetite, stop by one of my favorite restaurants, the Sonoma-Meritage Martini Oyster Bar & Grille, owned by Executive Chef, Carlo Cavallo, for delicious pasta, fish, beef and an incredible raw bar. The restaurant is reasonably priced and open every evening for dinner. Yountville is another must-see town that offers some amazing activities for visitors. Book a hot air balloon ride, visit on of the fine art galleries, enjoy the Lincoln Theater, or simply savor a nice leisurely lunch or dinner. Yountville is a true culinary destination, with literally dozens of restaurants - from fine dining at Thoma's Keller's The French Laundry to more casual options. I recommend the food at Étoile restaurant, located at the Chandon winery, is spectacular. The heirloom tomatoes are to die for.


Relax in Your Vacation Home

The beauty of Napa and Sonoma is that you can do a little bit of everything or a lot of nothing. There are more places to see than you can possibly do in a week, a month, or even a year, so pace yourself. Sometimes it’s best to just grab a nice bottle of wine, some hors d'oeuvres and enjoy the sunset from your patio. There are a lot of beautiful condos and villas for rent that make the perfect home base, especially if traveling with friends or family. It’s nice to have a private pool or spa for soaking at the end of a long day and a kitchen to store the treasures you picked up along the way. If traveling in a group, you can even rent a villa on its own vineyard and prices are often cheaper than a hotel when you split the costs. Let wine country be your relaxing home away from home.


Jennifer Boden is a wine and travel expert. Become a fan of her facebook page by visiting California Wine and Travel. 


While summer is winding down, many still have vacation on their minds. While it’s tough to vacation on a budget with sky-high airfares and fast-rising gas prices, there are a lot of easy ways to save money on your next vacation. You just need to have a few tips and tricks up your sleeve. Take a look at five of my favorite ways to save money without sacrificing any of the fun of a much-deserved vacation.


Set Up Airfare Alerts

Go online to set up airfare alerts so you’re among the first to know about price drops to your destination. Two of my favorite sites for airfare alerts are Kayak and Airfarewatchdog, which can alert you once a day about current airfare prices. I also like Airfarewatchdog’s Anywhere That’s Cheap Alert for a list of the best round-trip fares departing from your home airport. This is fantastic when you’re still considering where to go for your vacation. Also, try FareCompare’s Where-to-Go Getaway Map for the best fares to global destinations that have been found in the last four hours. Since airfare can be such a big chunk of any vacation budget, it’s smart to stay on top of prices.


Book a Vacation Rental

I’m still new to using vacation rentals, but have now used HomeAway three times to book houses and apartments for my family. What I love is that homeaway_france.jpegvacation rentals can often provide twice the space for half the price of a hotel. Most recently, my daughters and I stayed in a beautiful apartment in Prague within easy walking distance of both Prague Castle and Old Town Square. The apartment was quiet, safe and even more affordable and spacious than a hotel room.


There was a kitchen, a washing machine and web access – everything we needed. Plus, it was great to have a door to close between my bedroom and where the girls were sleeping. I love my girls, but after a long day, it’s nice to have a little space of your own, and that’s not always possible in a hotel. HomeAway has more than 775,000 property listings for every budget in 170+ countries, so it’s worth a look as you plan your next family getaway.



Bring Your Own Food

One of the easiest places to trim your vacation budget is through the food and groceries line item. Don’t spend $6 on a cup of coffee and a bagel every morning. Instead, pack a suitcase full of food, like cereals, granola bars, juice boxes and snacks (especially snacks if you have little ones). Also, pack paper plates and plastic utensils if you’ll be staying in a hotel. Even if you end up paying a baggage fee, you’ll still end up better off, especially if you seek out grocery deals and use coupons.

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If you’re staying in a vacation rental, it’s still a good idea to bring food with you, especially if you’ll be arriving late and may not have time to get to a grocery store your first night in town. Before you shop, take stock of what you have and make a list so you can avoid making multiple trips to the supermarket.


Get Hip to Discount Programs

It’s not hard to find discounts on just about every attraction you may plan to visit. The annual Entertainment Book is a great resource for city-specific discounts on local dining, attractions, and even movie passes, which are nice for rainy days. Another worth checking out is the Go City Card program for nine top cities, including San Diego and Chicago. Pay one fee and save on dozens of local attractions. Since you receive so many discounts, these are generally best for multiple-day vacations.activities_hiking_binoculars_kid.jpg


It’s easy to find free coupons as well if you head online to a site like Coupons for Fun, which compiles printable coupons for attractions across the country. Or, check in with your local tourism bureau for offerings like the free Monster Coupon Book, which has discounts for Myrtle Beach attractions. And, of course, don’t forget about AAA if you are a member since they offer loads of deals on theme parks, museums, water parks and more.


Seek Out Free Local Activities

Many zoos, museums, art galleries and aquariums offer free days either once a week or once a month, offering a significant cost savings for a


family of four, for example. It’s also wise do a web search for “free things to do” in the city you plan to visit. You’ll be amazed by how many fun free events and attractions are pulled up for your city. When you arrive at your destination, be sure to also scour the local newspapers for free events you may not have known about otherwise.

Do you have any favorite tips or tricks for saving money on your vacation? Let us know in the comments section below.


beach-1.jpgIt’s no secret vacations are important to families – or that they can be stressful. What is shocking, however, is 40 percent of U.S. travelers admitted to not being able to fully enjoy their vacation because of stress, according to a new survey from HomeAway.


On the other hand, according to the same survey, 78 percent of travelers wouldn’t give up their family vacation for anything – not even permanent weight loss of 20 pounds, housekeeping services for a year or dinner with their favorite celebrity.


So what’s a family to do?


Here are five ways vacation rentals can help travelers RECLAIM their family vacation, ensuring they return from their next trip more relaxed and reconnected than ever before!


- Reclaim your destination. According to research from HomeAway, choosing where to go on vacation is the number one cause of family squabbles.

In order to avoid the arguments, consider including your kids in the destination discussion early on and use sites like for vacation inspiration. By browsing through the inventory, families can get new ideas for places off the beaten path, which they may not have previously considered.


Here’s a list of the most popular family vacation destinations we’re seeing on for summer 2013:

  1. Ocean City, Md.
  2. Gulf Shores, Ala.
  3. Destin, Fla.
  4. Virginia Beach, Va.
  5. Bethany Beach, Del.


- Reclaim where to stay. Where you stay is just as important as where you go.

Most families automatically default to a hotel when planning their vacation. However, 80 percent of travelers agree that staying in a vacation rental helps reduce their vacation stress. That’s not surprising when you consider the amenities and features of a vacation home, which can make life easier and save you money (e.g., kitchen, washer/dryer, private pool, pet-friendly). Eating out three times per day is expensive, especially for larger families, and having the option to do laundry along the way will spare you the headache of facing a zillion loads when you get home. And, because no two rentals are alike, there’s sure to be a perfect match for every family’s styles, preferences and needs.


- Reclaim your budget. It’s always about getting more bang for your buck.

According to the HomeAway survey, the average summer family vacation costs $3,382, with $1,603 (almost 50%) spent solely on accommodations. For that much, you better be getting more than just a bed, a bathroom and a mini bar! Vacation rentals are inherently a great value, typically costing half as much as a hotel, but including twice the space. Thanks to the extra bedrooms and living areas, there’s also more flexibility to invite friends and/or other family members along and split costs. Plus, amenities like kitchens and washer/dryers, as well as free parking and Internet, spare your wallet by saving on the additional fees that tend to add up quickly at a hotel.


- Reclaim your space. While we love our families, everyone knows that too much togetherness is not always a great thing.

The best vacations strike the right balance between time and space – time together as well as time apart. Vacation rentals are ideal for this because they offer both communal areas for spending time together – playing board games in the living room or recounting the day’s adventures around the kitchen table – as well as the benefit of having your own room, and in return, the freedom to stay up and enjoy some adult time after the kids are in bed. The experience just can’t be beat, especially when you consider the alternative – cramming your family of four into one room for a week. Eeek!


- Reclaim your schedule. When staying in a hotel, you’re often forced to vacation on someone else’s schedule.

From having to wait an hour for room service when you’re starving, to just missing the pool or gym hours, to wasting time waiting for the entire family to get ready (with only one bathroom!), it’s not fun having to operate on someone else’s timeline, especially on vacation. In fact, HomeAway’s new family travel survey found that “wasting time” was one of the top causes of stress while on vacation. With vacation rentals, families have the freedom to determine their own schedules (a major plus for families with young children). Go ahead, choose for yourself when and what you’d like to eat, and hit the pool when you’re ready to swim…just maybe not one right after the other!


If you’re one of the 73 percent of travelers planning to get away with your family this summer, consider vacationing outside of the (hotel) box. With only a few vacation days per year, family trips are too precious to waste a single minute stressing over factors that can easily be eliminated by staying (in a) home!


Go on…RECLAIM your family vacation!


Traveling with children is stressful enough without the added pressure of having extra people around judging my parenting capabilities during some of the most difficult parenting situations - long flights, potty training days in an airport, meltdowns from the overwhelming nature of everything being new. It used to feel like the thought of my parents and/or in-laws traveling with us on family vacations to witness that show on the road only added to the pressure.

Needless to say, I’ve come a LONG way.


I have found that traveling with your extended family is one of the greatest gifts you can give to yourself, your spouse, your children and especially your parents and in-laws.


I always wonder what my mom, even my in-laws think about traveling with all of us. I knew if I asked them, I wouldn’t get the whole scoop. Recently, a friend put me in touch with a Mother and Son traveling duo, and by the time I had discussed the topic of multigenerational travel with both of them, I had a treasure chest full of perspective on the challenges and how to solve them.


Justin, a dad to two kids under five years old, regularly plans trips all over the world with his family of four and their extended family including his mom, Barbara, and her husband; his dad and his dad’s wife; as well as his in-laws.

Diana's extended family on vacation in Orlando

Incuding Justin's kids, Barbara has seven grandchildren. She’s a huge travel nut, but aside from her personal travel schedule, she regularly- up to four or more times per year- ventures out with her husband on multigenerational trips with her kids, step kids and their families.  Both Justin and Barbara shared the secrets to their multigenerational travel success. Here’s what they said:


Why take the show on the road? Isn’t it easier to just have relatives come to your house or vice versa?

Justin’s Take: When you travel someplace new with your family, you get to enjoy the sights, sounds, smells and flavors around you, and it brings you all closer together because the normal daily routines and distractions of everyday life at home fall away.

Barbara’s Take: I think doing this is very healthy- it's good for children because there is something very wholesome about all being together even if it means a little chaos. It’s a growth experience for everyone. Kids experience being a part of a larger family unit and I think that grounds them. 


Is it hard for the one making the plans to keep everyone happy?

Barbara: You really just have to ask everybody what they are looking to get out of that particular trip. What are everyone’s goals? Once you know the answers to that question, then choose a place that has something for everyone.


Speaking of choosing the right destination, how do you do that? What destinations work best for multigenerational trips?

Justin: I recommend to anyone who hasn’t done it yet to try a cruise. With a cruise, no one is ever far from a buffet or a nap, no matter who needs it. That gives everyone built in flexibility right there. Also, transportation is already taken care of. Most cruises have a variety of activities built in that appeal to all ages. 


Barbara: Pick a place that has something for everybody. You don’t want teenagers pouting in the corner while grandma is yucking it up with her sisters. Likewise, don’t drag grandma through Disney if that’s not what she wants.


What type of accommodations does your family typically look for when planning multigenerational trips?

Barbara: We’ve done it all. Rented houses, done timeshares, cruises, you name it. So, for us the answer is to switch it up and keep things unique.


Recently, we rented a HomeAway vacation rental in Cape Cod and we were able to accommodate friends at the beginning of week and then family at the end of the week. Having a house made it so comfortable and we were able to create lasting memories. Right now I can picture myself sitting on the front porch with my three-year-old grandson talking about cars. I’ll always remember that seemingly small moment as something much bigger.


Justin: We find vacation rentals to be a better value for the money, and it makes it easy to have everyone in one place. I like to make sure I’m in walking- or short driving distance from grocery, shops and other main venues.


What about the kids? Do they enjoy traveling with extended family?
My Own Take: My kids wouldn’t know their three cousins (who live in London) very well at all if it weren’t for our multigenerational trips. Sure, they see them every other year for the holidays, but that’s only for a few short days. Last spring, my family, Hubs’ parents, and his brother’s family all descended upon Walt Disney World. Because of the new adventures they shared in a new place, my girls and their older boy cousins are now connected for life. They email, Skype, send birthday cards to each other and talk about each other in a way that you’d think they were just down the street, rather than across an ocean.

Justin: Many times, a vacation can mean no meals to cook or errands to run, so kids get concentrated time with the family members they’re traveling with. For us, the travel my kids have done with their grandparents has intensified those relationships.


What are the best things about traveling with extended family?
Barbara: Entertainment and brainpower! You get to use other people’s strengths for the good of the group and you have built-in entertainment because with many people of many ages, there is always somebody doing something. You can join in if you want to.  


Justin: The opportunity to divide costs, of course and, especially if your parents are longing for that quality bonding time with the kids, some help with childcare and babysitting.


How do you handle the babysitting offers on multigenerational trips? I’ve personally had a hard time finding the balance between letting grandparents have quality time and not leaving anyone feeling exhausted or taken advantage of.
Barbara: Everyone has to talk about these things in advance and be honest with their responses. It’s up to the parents to make sure they know what their parents or relatives are looking to get out of the vacation and how much time they are willing or wanting to babysit. Also, the ‘babysitter’ has to be honest about how long at one time they are capable of handling the kids. Maybe they want the kids for a few hours each day, but they can’t handle hours and hours on end without a break. If it’s hammered out in advance, it takes the pressure off of everyone and no one will have unmet expectations about sharing the caretaking responsibilities.

My Own Take: The mistake we make is not talking about it upfront. Barbara’s spin on it is an “ah ha moment”. We have traveled with everyone under the sun in our family and sometimes Hubs and I are the selfish ones. We feel like if the family hasn’t seen the Littles that they should ‘want’ to spend all of their time with them. It’s eye-opening to understand it from all perspectives.


Barbara and Justin both agree, relationships will change over time and every new trip will have its own unique feel. As long as everyone is willing to keep open lines of communication then multigenerational trips can become the new norm for your family vacations.


Diana Heather is the Chief Mom, both at home to her two girls and at You can follow Diana on Twitter @ParentingsATrip or read more at her blog:


When my Husband suggested Montauk, as in, the beachy tip at the very end of Long Island, for our summer vacation my first reaction was, “That’s too close to home! We can’t go there for vacation.” (We live in Manhattan.)


Then, the beauty of vacationing near home hit me like a ton of bricks: no airport security; no long flight with toddlers; no requirement to stay gone longer than we’d really like - just a perfect family vacation to a place we’ve never been before that is known for being low key!


So, off we went to the perfect vacation rental home, on the perfect family vacation in perfect little Montauk.




Day 1


Ahhh, home sweet home!


We arrived at our amazing, contemporary Montauk vacation rental (that we found on with a sun-drenched deck, huge backyard and children's jungle gym with bikes, ice chest, and other essentials, just before noon. The homeowner met us upon arrival to give us the keys, a tour of the home and tons of advice about the area. It was beautiful. It had tons of room and natural light and was in a great location near everything we had planned.


Meanwhile, my Mom (“Nonna” to my girls) landed at La Guardia and hopped a ride on The Jitney to meet us in Montauk.


Around lunchtime, we drove in to town to pick her up at the bus stop and enjoyed a lovely lunch in the quaint downtown area, sitting outside in the breeze. We finally felt like we were on vacation!


But, it wasn’t long before we realized there’s no time to dally in Montauk! My husband had planned an adventure-packed itinerary so we needed to get started.


Day1.pngMontauk Point Lighthouse, the oldest lighthouse in New York State, was our first destination. The Lighthouse, authorized by the Second Congress, under President George Washington, is still an active aid to navigation today. Our 3-year-old met the minimum height requirement (41” or more) and was allowed to climb to the top with us to check out the view. It was peaceful and amazing all at once.


After all of that hard work climbing up and down the 137 iron steps, we headed over to the gift shop and restaurant for cocktails and milkshakes. 


Later that day, we headed over to Monday night "Concerts on the Green," a free family event sponsored by the chamber of commerce.  A few lawn chairs, some chilled wine and a pizza from the local pizzeria, and we were all set for one of the best nights we've had all year. The band was singing tunes like “Pretty Woman” and kids, young and old, were swinging to the beat. This is how a sunset was mean to be enjoyed. It was like we were in a TV show or a movie, only better - it was real!


After the Littles had their baths, we all snuggled up on the over-sized couches in the living room of our vacation rental and watched Team USA take the gold in Womens’ Gymnastics. Inspired by the win, the Littles attempted their own acrobatics solidifying a "perfect 10" for our first day of vacation!




Day 2


Our second day in Montauk started with everyone slathering on the sunscreen before we headed out to a sun-filled day of activities – mostly on the beach. (Check out my post “A Parent’s Guide to Pool Time on Vacation” for more tips on sun protection). We always make sure all of us are well-coated before we get dressed and leave for the day.


Our first stop was Gin Beach where we took advantage of gorgeous morning and skipped stones. Then we collected sea shells, driftwood and even sea greenery growing on the sand dunes to fill up three glass globes we bought to remember our vacation.  Day2Stables.png


Lunch had us heading over to Navy Beach, a famous restaurant in Montauk where the fresh seafood is really amazing. Its super kid-friendly since they can run around on the beach while you wait for your food, which makes it worth the pricey fare. After lunch, we took a quick nap at our comfy vacation rental, then we were ready for more!


Rita’s Stables was next on the agenda and the perfect place for the Littles to enjoy something right up their alley. It was so fun watching them experience their first saddle rides. It made my mom and I nostalgic for the first time my brother and I rode horseback with my grandparents in Columbus, MS. The petting zoo at Rita’s was a big hit, too. Of course, our littlest wanted to HOLD the animals (not just pet them).


Next up was a quick game of mini-golf at the local Puff & Putt to fill the gap of time between horse riding and our dinner reservation. Note to self: Toddlers don’t play mini golf. It was fun to watch anyway.



One of the best parts about Montauk is that all of the great restaurants you’re dying to visit are family friendly in the early evening hours. We ALL had a great time at Solé East in their beautifully landscaped backyard dining area. All of the money we saved by staying in a vacation rental allowed us to enjoy some restaurants that wouldn’t have otherwise fit in our budget.

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I never get to hit up the Momofuko Milk Bar in NYC so I was determined to visit their Montauk outpost for dessert. We got carry-out to enjoy back at the house around the kitchen table together. 


After spotting two bunnies and four deer (that were on their own family vacation, according to the girls) in the backyard, our elated Littles enjoyed a cool nighttime romp on the jungle gym before bath time put an end to our second day.


Day 3


As early risers, we easily made the 10 am ferry to Block Island, Mass., a place I knew nothing about.


Hubs insisted we bring our bikes so we could all bike around the island together. Once I realized that there was only one ferry a day to and from Block Island, and that both directions take at least an hour, I was a little nervous that this might be an ambitious plan for our multigenerational band of merry travelers.


Hubs and the oldest Little had a great time biking all over the island, shopping, eating and hitting up yet another petting zoo. Nonna, Littler, our friend and myself had a less fun day after a series of near fatal biking accidents. Ok, maybe I’m being a tad dramatic. But there was more than one accident and there was blood. And it was mine. Enough said.




We did manage to get ourselves to the Old Town area of Block Island, where Littlest promptly put herself up for sale for fear we might put her on the


back of  another bicycle.


Leaving Block Island was more enjoyable as it included cocktails on the dock and a chance to watch real fishermen cleaning their catch of the day while we waited to board the ferry.


Not a moment too soon, Hubs had arranged for a little vacation romance on our final night!


My husband definitely knows how to plan a date! We indulged at the hottest dinner spot in town, Byron at Surf Lodge and had the best table there. Afterwards, we pretended we were slightly younger than we are and headed to Rushmeyers Electric Eel Bar for Comedy Night with Seth Herzog where we laughed and recovered from the day’s adventures. Perhaps Hubs read my post, "Rest, Relaxation & Romance" about spending quality couple time during a family vacation.


Day 4


After a lazy morning with the girls, Hubs surprised us all with the perfect souvenir t-shirts on our last day. In no time, we were packed and ready to hit the road. Montauk: The End!


The End.png


Diana Heather writes at She is also the Chief Mom, both at home to her two girls and at You can follow Diana on Twitter @ParentingsATrip.


Packing Light for Kids

Posted by dianah Sep 21, 2012

58034_10150359329860063_852305062_16170580_5170166_n.jpgYou can totally pack two kids in one suitcase for your family vacation!


Ok, well I don’t mean packing the actual kids in the suitcase, but you get the picture! We’re talking about packing light when traveling, and in my experience, I can pack everything both of the Littles need into one suitcase! And the great thing is, you can use these same rules for any family members just by adjusting the size of the suitcase.


Instead of trying to pack your kids’ clothes into your bag – get them their own. They will LOVE having their very own suitcase and it will get them more excited about the vacation.  We love the Trunki by Melissa & Doug® – it’s an adorable, colorful, hard suitcase on wheels. Not only can they personalize it with stickers and their names, but they can also RIDE on it. It’s made to operate as both a suitcase and a toy, so it’s a lot of bang for your buck. My girls LOVE their Trunki suitcase.


As for packing them up in one suitcase, you can do that easily as long as you remember this simple rule:


Don’t over pack. Resist the temptation!


I edit my kids’ travel wardrobes by asking specific questions like, “Are we REALLY going to put her in that frilly dress?” and, “Do we need 28 colors of hair bows?”  The answer is almost always, “No.” Kids are stinking cute no matter what they’re wearing and no one is wondering where their special shoes are.


When packing – start with the basics. Lay out one outfit for each day you’ll be away on vacation, including every single part of the outfit for that day and keeping in mind any activities you’ll do when you get there - socks, underwear, layers, swimsuits, etc. Then, add pajamas. PJs get worn so much that they get dirty fast. If they’re worn during breakfast, they’re dirty; dinner = dirty; late night snack or milk = dirty.  If you’re staying with family, friends or have a vacation rental you can always wash them if need be. Keep these things in mind as you make your choices.


You can usually get away with just one pair of shoes per child - the ones on their feet the day you travel. If they do need more, it should only be one extra pair.


Last in are necessary accessories. Depending on what time of year you’re traveling, this could be sunscreen, sun hats, water shoes, winter hats, gloves, scarves, etc. For my girls, I also have to pack a few of their favorite things to keep them happy. For example, they like their own little special toothbrushes so I need those to keep the good tooth brushing mojo working.  Plus, they each need their favorite sippy cup and nighttime blanket.


After everything’s laid out, I condense their clothes into little vacuum-sealed bags. One large-sized bag for each child, and that’s it! I like the Original Space Bag® and you can get an 8-piece travel pack for about $20 from major stores like Bed Bath & Beyond. When the bag is full, you know that’s all you need to pack. I don’t even use a vacuum cleaner to seal them – I just roll them airtight. My friend swears Ziploc® bags work the same way. Just close the “zipper” about 95 percent of the way, roll the air out and finish sealing. I’ve even packed this way for winter in England and  just had the girls wear their big coats on the plane. I was able to pack all their layers, including bulky sweaters and socks, this way for the holidays last year. So, I know this works wonders. Imagine how much we saved in checked baggage fees!


Separate from their suitcase, I also recommend packing at least one lightweight, “emergency” outfit per child and keeping it in your carry-on for easy access. Something like a t-shirt and leggings should do the trick. You never know when your luggage will get lost, or if your child will have a major spill!


I hope sharing my thought process helps making your packing faster and easier. Just remember the golden packing rule – resist the temptation to over pack – and keep in mind that for most trips, you can buy anything you forget when you arrive!


Diana Heather writes at She is also the Chief Mom, both at home to her two girls and at You can follow Diana on Twitter @ParentingsATrip


I’m excited so many people are taking advantage of vacation rentals. They are an especially great option for families because they offer much more space for the money than is available in a hotel. That means you can invite the grandparents or family friends to join!


You also have all the luxuries of home in a vacation rental, which is so important when you’re traveling with kids. When a kid wakes up in the middle of the night in a hotel, it is such a pain to try and mix a bottle of formula or get milk. In a vacation rental, you’re able to pop into the kitchen, do your thing and hang out with your babies when they need you without waking up the whole house – everyone will appreciate that!


My family just took a trip to the beach for our summer vacation and stayed in this Montauk vacation rental from  While we loved our home away from home, I have three simple tips that can help make your vacation rental even more comfortable for your family. For more details, watch my video, "How We Made the Most of Our Summer Vacation Rental."



1. Familiar Scents


"Smell is a potent wizard that transports you across thousands of miles and all the years you have lived.'' - Helen Keller


It’s amazing what an impact scents can have on your emotions. For my family, just walking in the door and smelling something familiar can make us feel calm and comfortable when we’re staying someplace new. Often it can be very light, common scents such as vanilla, lemon or cinnamon that create connections to contentment.


To start your vacation off right, pack a few of your favorite scents! One of my favorite ways to do this is with the new Glade® Solid Air Fresheners because they are inexpensive and lightweight for travel or can be picked up locally if traveling by plane.


2. Food


What food you pack will depend on how you travel to your destination. When you fly, you’ll only carry the basics to get you through the flight like favorite snacks and formula. If you’re driving, you can pack an ice chest with additional necessities or even leftovers like we did when we traveled from NYC to Montauk. In any case, you’ll want to locate a grocery store convenient to your vacation rental so you can easily pick up anything else you need for the week. Also, come equipped with a shopping list of basics. You won’t want to sit and explain what you need to a well-meaning husband or friend, let alone think about making a list when you get there, so doing this ahead of time is hugely helpful.


For us, breakfast is the meal we all eat together. Kids wake up hungry – at least mine do – and coffee is an immediate must for this Mommy.  So I make sure we have our favorite cereal, milk, coffee, and the kids’ favorite bowls, bibs and placemats – all of which are lightweight, small and easy to pack, and SO worth having. All in all, the kids’ breakfast-time ritual remains the same as every other day – meaning vacation days start off stress free for mom and dad!


3. Bed and Bath Time


When we get home from a long day of vacation adventures, the last thing we want is to fight the bath/bed battle; so, to ensure things go smoothly, we make sure to have everything the kids love on hand. For example, we always bring our girls’ hooded towels for after bath time - the familiarity of being hooded, wrapped and snuggled after a bath is important to them. Plus, each girl has a favorite blanket they love to sleep with, so it’s a no brainer to bring that with us, as well.


It really doesn’t take much, and a little will go a long way toward making your family comfortable when traveling.


What makes you feel at home when you’re on vacation? I’d love to talk with you about it in the comments section below.


Also, I wanted to share a few fun family photos from our summer vacation. Enjoy!


Collage Big Montauk.jpgCollage.jpg



Diana Heather writes at She is also the Chief Mom, both at home to her two girls and at You can follow Diana on Twitter @ParentingsATrip


As a follow up to my previous post, International Family Travel (Part 1): Passports, Jetlag and New Food, Oh My!, I’ve included a few more tips here to help make your family vacation more like something you want to make a photo book out of and less like something out of a horror story.


What to Pack:

Make a list and check it twice. I like to make a checklist as I go through a normal day with my kids - this way I don't forget anything when I’m preparing to globetrot with them. While this tactic is useful for any type of family vacation, it’s particularly helpful when traveling abroad because there is more to keep track of. 


> Baby items. It can be stressful to travel with tons of baby gear (see Tips for Flying with a Newborn or Infant), so it’s always a good idea to keep your child’s gear needs in mind when deciding on a place to stay. Your choice can cut down on how much you end up bringing from home. Many hotels will offer a crib and maybe even a highchair, but if you need more than that, it’s often easy to find vacation rental homes pre-stocked with additional baby-friendly extras like bouncy chairs, swings, toys and more. You can also consider a baby gear rental company for bigger items; however, you’ll have to search locally at your destination for these services.


For every-day items, sites like can ship baby supplies like diapers, wipes, formula and more to your destination ahead of time. They have great packages that can jump-start your own packing list and have an experience-driven international shipping policy. When traveling to Mexico, Mexico Lots for Tots provides both daily-use items and rental gear. As they say on their website, “Enfamil, Enfapro and Similac infant formulas are readily available in Mexico, so why not order before you go?” 


If you're traveling with infants, in my experience, it’s easiest to pack powdered formula because it’s lighter than liquid and won’t spoil. Also, when I have access to a microwave, Medela Quick Clean Micro-Steam bags are my secret weapon for sterilization on the go. (Hello clean bottles, teething rings and pacifiers!)


> Medication. I recommend bringing a few basic over-the-counter (OTC) medicines in addition to any prescription meds your family takes regularly. Especially for your kids, pack at least one medication for common ailments such as pain, cold/cough and stomachaches. I travel with basics like children's ibuprofen, allergy medicine and homeopathic teething drops. 


Also, make sure to pack a travel-sized first aid kit, or at least the basic items from one. You never know when you might need something simple like a Band-Aid or antibiotic ointment – or as my kids call it "hurt cream." Find out how to put a great travel first aid kit together at


If you purchase OTC meds at your destination, remember that the dosage can be different there and it may not measure the way you're used to (metric system, for instance). Another thing to remember in this regard: know the current weight of your kids for before you travel (you may also need to know how to make weight conversions for proper dosage).


Medical Needs:

> Getting your shots. There are all sorts of things you and your kids can be exposed to when traveling to a foreign country. Let your doctor and your kids' doctor know where you’re headed as soon as you book your trip so you can plan any  shots needed ahead of time. Some shots require an incubation period before they become effective making it necessary to get them weeks before you leave.  


It’s a good idea to make a copy of your family’s vaccination records and keep them with you while traveling. Also, scan them and email them to yourself so you have duplicate access on the road in addition to hard copies. My favorite new app is called Genius Scan, which makes a scanner out of your iPhone. It doesn’t get any easier than that.


> Medical treatment abroad. Each country is different in the way they handle patients and if you do end up needing a doctor you'll want to know ahead of time exactly what to do and what you’ll need. It’s always a good idea to call your health insurance company before you leave to find out if you have coverage abroad. Ask questions like: Does your health insurance work at your destination? Do you need your medical records with you if someone in your family suffers a chronic illness? And, make sure to carry your medical insurance card with you, regardless.


I hope you enjoy globetrotting with your kids as much as I have.


Diana Heather writes at She is also the Chief Mom, both at home to her two girls and at You can follow Diana on Twitter @ParentingsATrip


Rest, Relaxation and Romance

Posted by dianah Jul 23, 2012

Finding a babysitter and having a dreamy date night with your partner may seem like the ultimate way to squeeze in some romance while vacationing with your kids in tow; but Hubs and I have discovered you can find romance wherever your travels take you – you just have to be creative!


One of the toughest things about traveling with the Littles is finding time to be alone with your partner. However, we’ve found that staying in a vacation rental home or condo versus a hotel provides significantly more opportunities for “R,R & R” [Rest, Relaxation and Romance]. Once we put the kids to bed in their room, there’s plenty of space for Hubs and I to hang out without disturbing them – no babysitter required.  However, having the extra space also means we can invite grandparents or other families along on vacation, and trade off on nights out on our own. Grandparents in our family are really sweet about picking up on our subtle hints of longing for a grown-up night away.


Another option is using a service to find pre-vetted babysitters, such as Lucky Lil’ Darlings. I chatted with Lindsay Bell, Founder and President of the company recently and they are highly committed to helping families find safe childcare.


You don't have to have a dinner date to be romantic either. Try securing childcare in the middle of the day and do something new or adventurous. One time when Hubs and I were in Barbados, we rented a tiny sail boat that we could man ourselves. Unfortunately, we caught some extra wind and got slightly nervous we would lose our way (and did I mention I was seven months pregnant at the time?), but at the end of the day we learned something new – together – and it was totally romantic and exciting.


Never underestimate the power of something simple. If childcare isn’t an option, try taking a walk with the kids in their stroller while they nap. Even short amounts of time alone can allow the two of you to connect. Also, little gestures mean a lot. Picking a flower for your wife or writing a note to your husband in the sand can be very romantic, and requires little time and effort.  


Sometimes, having your little ones around can serve as a reminder of what the two of you have created together. A family and all it comes with is romantic all on its own. We sometimes can forget how incredible living that dream really is. I had the most heart-warming call with my husband while I was traveling with one daughter and he was at home with the other. The call included all four of us on the phone together and the Littles were talking to each other saying how much they love and miss one another. It was so sweet! Hubs and I were beaming to each other despite being a million miles apart.


The number one thing that adds romance to my relationship when we travel with the kids is staying relaxed. We are much more apt to hold hands, steal a kiss or share a loving glance throughout our adventure when we are both relaxed, on the same page and sharing the responsibilities as a team. It’s during those fun times that we enjoy the little moments our family shares, the funny things our kids do and we can feel the true respect and admiration we share for one another that sometimes gets lost in the daily grind.