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Family Travel Guide - Tips for families on the move

In this day and age, when vacations are few and far between, planning a vacation with the entire family can be both be economical and a lot of fun.  Once the hard part is over (the vacation is planned), you can sit back and soak it in because the memories made will deepen the bond between generations. Why is this important? In the busy world we live in, it’s easy to forget, “our lives, both start and end with family.” And this is certainly something to celebrate – but that doesn’t mean that planning a trip for a dozen people with different agendas and ages’ ranging from 6 to 76 is an easy task (something I recently did).



Multi-generation travel is growing in popularity as families are now spread across countries. Getting everyone together can be made easy when you meet in a neutral zone – a vacation destination. By booking a vacation rental you can easily find a home that comfortably sleeps everyone and boasts communal spaces – decks, patios, living rooms, spacious kitchens and private bathrooms and sleeping rooms that everyone craves.  Below are three strategies to keeping the entire family happy on your next multi-generation trip from toddler to elders.


Pictured on the left: this is the youngest on our trip trying out synthetic skating. It was ideal after a long walk to the park because there were food trucks and picnic benches for my grandmother to watch the kids while resting their feet!


Plan ahead – but don’t plan too much


While the planning stage can be overwhelming, it’s important that you take the time to ask questions – who wants to go, what’s the destination that would work for everyone (while limiting layovers) and what are people looking for…the beach, mountains, city, or even history? A fun way to get everyone involved in the planning practice is to create a Pinterest account where everyone can pin his or her favorite images and ideas of the ultimate vacation.



For those less tech savvy or too little to participate in Pinterest, they could cut out of magazines to create a vision board of their dream vacation. From there you can start to craft something that will meet in the middle and please everyone. I always find the pre- vacation work helps to amplify the excitement of the actual vacation!


Don’t plan too much. Once you have the destination and the long list of what everyone hopes to accomplish, be realistic with what you can get done in a day and be mindful of what people can physically do. For example – a 12-hour day at Disney might be ideal for some but is too much for little ones and great grandparents.


It’s also important to leave a piece of the day un-planned so that everyone in the group can choose to relax or keep going. This is a sure-fire way to keep everyone refreshed, happy and satisfied with the vacation. For example, the boys in our group wanted to try a wild boar hunt. So while they went hunting, the ladies in the family visited a spa.


Mindful of Money


Planning a multi-generation trip can be economical as there are opportunities to share costs and even get group discounts. Before booking your destination and accommodations set a budget that is within everyone’s means.


Have conversations ahead of time about how many meals you will go out for versus eating in and share the tasks of grocery shopping and cooking so that everyone has the opportunity to both participate and save.


Many vacation rental owners offer services that will have the groceries stocked at the home before you arrive to take away the stress of shopping for a large group. If you want to make dinner interesting, my family is a fan of playing “Chopped” where another person chooses ingredients and the Chef is surprised but has to make a meal in about an hour with what they are presented.



Celebrate Togetherness

Planning a vacation with multiple generations in tow can feel more stressful then a bad day for an air traffic controller. Remember – it’s about bringing everyone together and enjoying the uninterrupted time.


So don’t stress the small hiccups of travel, be sure to power down electronics when everyone’s together and celebrate the down time. With my family our best times on vacation is when we have nothing planned and aren’t spending money. We are simply hanging around the kitchen or living room sharing stories, laughing and eating…which is what makes renting a vacation rental perfect for gatherings.


Let’s be honest, how often do you get everyone under one roof? Get planning and get ready to enjoy every minute of it!


I’ll admit it, checking into a hotel and having daily maid service is a luxury I look forward to when travelling with my family. As a Mom, there is nothing better than having someone else make your bed, bring you fresh towels and turndown your bed each night. After all, isn’t vacation is supposed to be a break from your normal routine at home? The prospect of my family of four bunking together in one room for a week never bothered me. I actually looked forward to it. The kids were little, and were just going to be sleeping in our hotel room, right? Wrong.


Somewhere around the ages of 8 and 11 it stopped being fun to share one room with our kids.  No longer did the two of them want to sleep in the same bed. Once we added a rollaway into the mix our already small room, with two double beds, suddenly just got a whole lot smaller. Pile in everyone’s clothes, shoes, electronics and toiletries and suddenly we were cramped and cranky. We needed more space. When we considered the price of a one-bedroom suite, or even two connecting rooms, it just made sense to look at renting a home instead.


We turned to HomeAway to find our prefect rental. With over 625,000 listings worldwide, we were sure we’d find the right home to suit our needs. When we started looking at the advantages vs. the disadvantages, the reasons to rent a home just started to stack up.




Size/Cost Ratio – The last 2-bedroom house we rented in the Caribbean averaged $392/night for 1900 sq. ft. A 1-bedroom suite at hotel* on the same island averages $1399/night and has only 950 sq. ft.


Multiple bedrooms and bathrooms – Hooray for space! Renting a house also allows for traveling with another family. This brings the cost down even further and actually lets you vacation together. Visiting with friends while staying in individual hotel rooms really just isn’t the same.




Full Kitchen – No more emptying out the hotel mini-fridge to make room for a quart of milk or getting dinged every time your kid wants something to eat from the over priced ‘munchie box’. Plus having your own kitchen allows you to make your own inexpensive meals. I don’t know about you, but paying $20 for a bagel, cereal and juice at a hotel drives me nuts --especially when the kids don't even finish it.


Dishwasher – When our children were little, I used to spend hours washing bottles, sippy cups and snack containers in the hotel sink. Having a dishwasher eliminates that task.


Laundry – We pack less and for Mom there is nothing better than going home with a suitcase full of clean clothes.


Games  –  Most homes come stocked with board games, books and some even have video game players.




Privacy – No more loud voices or slamming doors coming from the hotel hallways. Plus, depending on the type of property you rent, you don’t have to share a hot tub or pool with other guests.


Wi-fi – Don’t even get me started on how many hotels still charge for Internet access.


DVD players – When is the last time you relented and let your kids charge an $18 movie to the room?


Parking – Ok, so there is no valet, but there is no fee with a home rental either.


Kid friendly amenities – Lots of homes come with cribs, highchairs, pack-n-plays, beach toys, bikes and more.  Less you need to lug from home!




Room For RoverHomeAway has a “pets considered” option right in the search filters. Sure, you can find a few hotel chains now that will allow you to bring you dog, but HomeAway has 168,467 properties where your hound is welcome.






No daily maid service – However with many you can rentals you can pay for extra for this option.


No room service – Some rentals offer private chef services and grocery delivery at an extra cost.


No Concierge – In all of our rentals thus far we have had a concierge binder filled with dinning options, attractions, maps and more. Also many times the homeowner is available to answer these types of questions.


Minimum Stay - Some rentals require minimum number of nights.



Bottom Line: If you are a whatever, whenever kind of traveler then staying in a hotel is going to be a better option for you. Or if you are in town for only 1-2 nights, staying in a hotel might be more desirable. But if you want to spend less, have more room for your family and likely a better property, then look into home rental for your next vacation. Don’t let the fluffy bathrobe and mini toiletries sway you.


*The Cove – Eleuthera, Bahamas


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!



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.

Fall Leaves_Boys.jpg


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.


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.

homeaway_breakfast 2.jpg


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.


The family vacation experts at HomeAway recently surveyed more than 5,000 dads to find out what they really want for Father's Day. To spice things up a bit, HomeAway also checked in with the ladies to see what they think tops their husbands’ wish lists.


So just how in tune are men and women when it comes to picking out the perfect gift for Father's Day? The results just might surprise you, make you giggle, or even blush just a little.


Family vacations top dads’ wish list for Father’s Day

FAther's Day - 72%.jpg

According to the survey, dads would prefer a family vacation over any other gift for Father’s Day (35%), including new technology (11%), a new set of golf clubs (6%), a luxury watch (3%), home theater equipment (3%), or a riding lawn mower (2%), etc.


Overall, 72 percent of dads said they'd like to receive some sort of vacation or trip for Father's Day. When we asked dads what kind of vacation trip they’d like to take, the majority of dads chose a family vacation (49%) – even over a romantic getaway with their significant other (38%). Only a small group of dads said they'd prefer a guys' trip with their friends (just 13%).


Gift ideas from the kids

We asked dads what they’d like to receive from their children, specifically, for Father’s Day. At the top of the list, 31 percent of dads said the gift they want most from their kids is unplugged time with the family (no texting, social media, iPads, etc.).


Coming in at a close second, dads said they’d also like to get something homemade from their kiddos (25%). Check out the HomeAway Father’s Day Pinterest board for homemade gift ideas and inspiration.


Not surprisingly, only 12 out of 1,097 dads said they’d like to get a neck or bow tie.


And from the significant other…

On the flip side, we asked dads what they want from their significant others for Father’s Day, and then compared it to what women told us they think their husbands want from them for Father’s Day. The result? Women assume husbands want sex as a gift from their wives, when they'd really just prefer a romantic meal, instead.


According to the old saying, the way to a man’s heart is through his stomach, so not surprisingly, 46% (the majority) of men said they’d like a romantic dinner from their wife.


When it comes to gifts in the bedroom, women actually overestimated their husbands’ desire for something more intimate for Father’s Day. The number-one answer women thought their husbands would choose when it comes to a personal gift from their significant other was to “make love” – when actually only 22% of men listed it as their first preference.


The very bottom of the list? Only 19 out of 1,061 dads said they’d like to receive cologne from their wives for Father’s Day.


Where to take dear old dad?

So now that you know what dad wants, what kind of trip should you plan for him this summer? According to the survey, dads want to head for a beach or lake (48%).  Surprisingly, golf (5%), gambling (2%), camping (3%), vineyard (5%), sporting event (3%), theme park (4%), and fishing / hunting (4%) trips came in at the very bottom of dads’ wish list for Father’s Day.


Here are the top 10 destinations dads said they'd like to go for Father's Day:

  1. Florida
  2. Hawaii
  3. France
  4. Italy
  5. California
  6. Colorado
  7. Nevada (Las Vegas)
  8. Mexico
  9. Canada
  10. London


For additional ideas of where to take dad, homemade gifts and crafts, recipes and more to make this year extra special, check out HomeAway's Father's Day board on Pinterest.


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!


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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!


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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


Family vacations are usually busy with activities, sightseeing and more. But, another big component of vacationing in the summer in my family is spending time at the pool.



One of the reasons we love vacation rentals so much is because we can have our own private pool. With two small children, privacy is a big advantage. A hotel pool or public pool, for instance, doesn’t offer us the same unique opportunities to play with our kids freely without the worry of getting in the way of other guests. Mostly though, having a private pool is the safest way for us to keep an eye on the Littles while giving us some time for R&R.



Girls in Grandaddy's Pool summer 2011.jpgAny parent can attest lazy pool days aren’t quite as lazy once you have kids. If you’ve ever chased your toddler around a pool trying to rub her down with sunscreen, then you know what I’m talking about. However, Hubs and I both agree we have a lot more fun by the pool now that we have the Littles and there’s nothing we would trade that for.



We have also learned that a little structure can go a long way, so we fill our day with a good mix of games and break times to make sure the Littles don’t get too tired or lose interest. 



One of our favorite pool time activities is encouraging playful physical challenges like, “who can jump into the water the farthest” or “kick your legs like a froggy.” We’ve found this helps them develop new swimming skills and keeps them entertained. 



We also try to bring along a few pool accessories if there’s room in our suitcases. Inflatable items that pack flat are the best and luckily for us, Hubs has big lungs! If we’re road-tripping and have more room, we are huge fans of the PuddleJumper® floatation device. 



Also, even though they may fight the notion of getting out of the pool, we always make it a point to take a few small breaks throughout the day. Grabbing some shade under an umbrella or even going inside for a light snack keeps the Littles energized and ready for more summer fun! Plus, even though the kidlets may be full of pool water, we always make sure to keep them hydrated with actual water or a drink with electrolytes. Pool water, sun and hours of activity can easily dehydrate all of us.



Another thing that’s very important to me is sun protection. I grew up on the Gulf Coast of Mississippi and both of my young parents have already had skin cancer spots removed; so I’m a little OCD on the sunscreen front.



Whether we’re playing at a pool or hiking in the mountains, we always pack plenty of sunscreen on our summer vacations since UV exposure is greatest from May-August in the United States.



The Environmental Working Group (EWG) offers an in-depth Sunscreen Guide that keeps parents up-to-date on all the latest guidelines and includes an extensive list of every sunscreen on the market with the EWG’s ranking of each one.


Here are some other good Sunscreen 101 tips:


  • Only use products labeled “Broad Spectrum,” meaning they protect against both harmful UVA rays and sunburn-causing UVB rays
  • You should apply sunscreen every 2 hours and more often if you’re exposed to extreme water or sports activity. Do not let higher SPF numbers give you a false sense as to how long the sun protection will last
  • Be generous in your applications. The recommended amount for an adult body is about the size of a shot-glass and a teaspoon for your face. Obviously this should be less for children, but make sure they’re adequately covered
  • Nothing provides better sunscreen than covering up with a long-sleeved shirt and hat. You can even add SPF to clothes or buy them with SPF already built in. To make your own, wash tightly woven cotton clothes in a UPF rinse, which can raise the SPF value up to a level of SPF 30.




When you travel with your family, how much time do you spend by the pool?


Have fun splashing into summer on your vacation this year! 


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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.


Let's Talk About Family Travel

Posted by dianah May 1, 2012

My name is Diana Heather (yes, Heather is my last name) and I’m the proud mommy of almost 3-year-old, Khloe, and 1½-year-old, Lola. I refer to our girls as “Little” and “Littler” or collectively as “the Littles.” They truly are the joys of my life and I couldn’t be happier to be a mom, despite how chaotic life can be with two toddlers that are only 15 months apart!231086_10150579323195063_852305062_18120896_7793193_n.jpg

My goal in writing this blog is to advocate family travel. With all its crazy ups and downs there’s nothing better than watching your toddler dreaming away while in a rented stroller at the end of her first day at Walt Disney World, or during a beach vacation pondering the questions, “How much sand can an infant actually eat? Why is my infant eating sand in the first place? Doesn’t it taste bad?”

The course my life has taken thus far has given me a great appreciation and love of travel, but since having children of my own, travel has taken on a whole new meaning and I’m excited to now be able to experience destinations through their eyes, as well as my own!


5206_243201755062_852305062_7988344_7303853_n.jpgI’m a Mississippi girl that had the privilege of growing up on the Gulf Coast - think white sand beaches, family-owned businesses, casino fun, water skiing on the bayou, crawfish boils and Mardi Gras! However, after a childhood vacation to New York City, I fell in love with palpable energy and inspirational atmosphere of life in the Big Apple, and knew I had to live there! After getting my bachelor’s degree in Journalism and Public Relations, then graduating from law school, I had brief stint working with my father at a legal practice, before “retiring” from my law career to follow my dreams and move to New York.  I’ve now had the good fortune of doing PR and social media for incredible brands like Mikasa, Henri Bendel and Harry Winston, and couldn’t be happier in my new home!   

Two days after moving to the Big City, I met my amazing, fabulous, magnificent husband, Ashley, (aka Hubs), who hails from England. As fate would have it, he also left home and moved to New York to pursue his career as an entrepreneur (lucky for me!), but my in-laws still live across the pond, about a four-hour drive north of London - five hours if it’s Christmas Eve with a 6-month old baby – happy to tell you that story if you’d like!



I've been traveling with family in one form or another for most of my 35-year life. We were lucky to get to travel frequently as kids, leaving me with many great memories, from my first plane ride at the age of 3 to Austin, TX, to my brother and I learning to water ski in the Caribbean. Growing up in Mississippi, we also took many road trips to Disney World – every kid’s dream! It took us two days to get there and I distinctly remember my dad using an Atlas for that trip. He and I share a love of maps and I can recall many maps in my travel history. 141_13375525062_852305062_1483116_7644_n.jpg

In college, I traveled with classmates to Europe and hopped trains from country to country.  By the end of the summer we’d been to Belgium, Germany, Italy, France, Switzerland, Prague, and even Budapest and we did it all with our maps, our guide books and our big American backpacks in tow. 

After moving to New York and meeting Hubs, who as I mentioned is from England, travel became even more important, since we were quite a ways away from both sets of parents. Since we’ve been together, we’ve received countless new stamps in our passports and even decided to have a destination wedding in Barbados!

Since having our oldest daughter, Khloe, we’ve visited the in-laws in England, grandparents on the Gulf Coast and Savannah, and recently had our first trip to Disney World (more to come on that in another post!). No invitation for a birthday party or baptism is ever turned down. Even if it requires great-granddad Bill in Vancouver to hop a plane to the Coast or if 80-year old GG needs to update her passport for family Christmas in England! You’d be shocked by how many times in the last five years our entire extended families have actually all been together for one event or another.

However, it’s true that kids change the game - and it’s especially true when it comes to family travel [I used to have a carry on and a checked bag both for me, now I’m lucky to have one corner of one bag for the entire trip. Nothing in my carry-on is actually for me anymore. Nothing! ]  But seeing our family and experiencing all the world has to offer are the most important things to my husband and I, and its part of why we’re together. Geography doesn’t get in our way. We agree, based on both our own childhoods, that travel and family are both invaluable parts of what made us who we are.





Here, I hope you’ll learn from my travel smarts and experiences and as well as from my travel mistakes. I’m going tell you every thing I know and everything I’ve ever tried when it comes to the sometimes mind boggling topic of family travel.

You can expect to read how to make traveling with your family easier, lighter, safer, cheaper and ultimately way more fun!

Hopefully you’ll be inspired to travel with MORE of your family, MORE often, because nothing compares to the memories you’ll create for your kids and yourself, and the stories you’ll one day be able to tell your grandchildren!

Together, lets have fun, travel with our families and create many family vacation photo albums together (online of course- I can’t scrap book)!

Stay tuned here for tips on family travel and updates about the places I’ll go both in life and in parenthood.


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.