Skip navigation

Join the Vacation Rentals Conversation!

Get answers to all of your questions from fellow owners and travelers.

Join the CommunityX

CommunitySeek, Ask, and Share in the Vacation Rentals Community

Family Travel Guide

Tips for families on the move
3 Posts tagged with the rentals tag
0

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.

family.jpg
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 Totsy.com. You can follow Diana on Twitter @ParentingsATrip or read more at her blog: ParentingsATrip.com.

1

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.

 

Driving.png

 

Day 1

 

Ahhh, home sweet home!

 

We arrived at our amazing, contemporary Montauk vacation rental (that we found on HomeAway.com) 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!

 

Day2Beach.png

 

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.

Day2puttputt.pngSoleEast.png

 

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.

End of Day2.png

 

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.

 

Day3.png

 

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

Dinner.png

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 http://www.parentingsatrip.com. She is also the Chief Mom, both at home to her two girls and at Totsy.com. You can follow Diana on Twitter @ParentingsATrip.

1

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.