Vacation Ownership: Your Ticket to Stress-Free Multigenerational Travel

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Hilton Grand Vacations is sponsoring this look at multigenerational travel and family vacation ideas. 

Did you grow up traveling with extended family? Nowadays, we’ve given it a fancy name — multigenerational travel. In the 1950s, I called it “going to the beach with Pop and Mamie.”

I remember sitting in the backseat of my grandparents’ Oldsmobile with Aunt Joan and my two sisters. Pop, Mamie and my mother sat in the front seat. Family stories indicate that my five-year-old self talked or sang all the way from Atlanta to Daytona Beach. Poor them.

My grandparents would rent a small bungalow on the beach. The adults cooked meals in the tiny kitchen while the kids played in the sand. Going out to dinner wasn’t realistic or part of the budget. And, if it rained, all of us crammed into the bungalow’s small living area.

Those trips forged bonds and created lasting memories. But I’m glad that in 2020, we have better options like vacation ownership. In today’s travel world, those bonds and lasting memories are made in spacious surroundings at destinations filled with plenty to do.

The benefits of multigenerational travel

Grandparents hiking across a creek with grandkids

Traveling with the extended family provides precious time together away from busy lives. And, in many cases, families are spread all over the country. Choosing one time a year for a week or two of bonding is imperative for keeping those close ties.

Traveling with family offers the chance to create shared passions. Show your love of hiking to the grandkids. Learn to scuba together. Laugh with the family as everyone struggles over their first cross-country ski lesson. Doing something together, no matter the activity, is like relationship glue. It keeps you sticking together.

Multigenerational travel ideas with Hilton Grand Vacations

Interior of a hotel atrium

While being together and participating in joint activities is the main focus of a multigenerational trip, where you stay matters — a lot.

A spacious 2- or 3-bedroom suite gives everyone plenty of space for being together and for those all-important alone times. Quiet moments and naps are a necessary part of rejuvenating after an active morning of fun.

pancakes being served to a child

Of course, a fully equipped kitchen makes meal preparation easier, especially if your family includes young children. Eating every meal out isn’t realistic or budget-friendly. Be sure to divide duties between the adults so that no one person is doing all the cooking or cleanup.

Timeshare with Hilton Grand Vacations is a smart money move. Have you read my vacation ownership tips?

Perhaps you’re a grandparent who wants to treat your offspring to a “free” vacation. Hilton Grand Vacations makes that possible. But where should you go?

Take them to the beach

A multigenerational beach getaway is fun for the entire family, but it’s especially appealing to those with small children. The beach provides most of the entertainment, while a comfortable suite allows for rest time and dining in.

Grandparents playing on the beach with grandkids on a family vacation.

Ocean Oak Resort by Hilton Grand Vacations is located in one of my favorite beach destinations — Hilton Head, South Carolina. While there’s plenty of shorelines to explore, there are also pools and a kid-friendly Activity Center to provide even more fun. Maybe it’s time to introduce the teens in the family to a new hobby at one of the island’s famous golf courses.

interior of a hotel room

Two-bedroom suites include two bathrooms and sleeps six. A private balcony, a fully equipped kitchen, and separate living and dining areas complete the picture. Who wouldn’t want to stay on an island and enjoy the sounds of lapping ocean waves and the sight of moss dripping from huge live oak trees?

whale tale going into the water

When families want to celebrate a special event, Hawaii often comes to mind, especially Maui. 

Why not take the grandkids to Maui Bay Villas by Hilton Grand Vacations?

Opening in Q1 2021, enjoy the relaxed ambiance of 1-, 2- and 3-bedroom suites along Maalaea Bay in Kihei. You’ll be staying in the perfect headquarters for activities like whale watching, snorkeling or an ATV adventure in the West Maui Mountains. This is an especially good choice if you have a wide range of ages to entertain.

Explore American history together

Family visiting a museum

Are you interested in showing the grandkids American history? There’s no better place to start their education than Washington D.C. From the Space Museum to the U.S. Capitol building, show them what you cherish about our country.

interior of a hotel room

Of course, all that touring requires a comfortable place to stay, something hard to come by in big-city hotels. The District by Hilton Club, located on the top floors of Embassy Suites by Hilton, offers roomy suites for relaxing between visiting museums and monuments. 2-bedroom, 2-bath suites that sleep six include two living areas and two kitchenettes. Plus, there’s a pool for soaking away the day’s excursions.

Don’t forget Orlando

expansive hotel lobby

If you want to see broad smiles and happy faces, take them to Orlando, Florida. This paradise of family fun is filled to the brim with multigenerational travel experiences — Walt Disney World®, SeaWorld®, Universal Studios® — it makes this granny tired just thinking about it.

But if my family and I stay at Hilton Grand Vacations at Tuscany Village, there will be plenty of rest and relaxation sandwiched between all the magical fun. A 3-bedroom suite means that there’s room for everyone! And I can slip off to the spa while the young’uns traipse off to ride Magic Mountain for the third time.

Travel Tips For a Multigenerational Trip

Parents grandparents, grandkids walking the beach

Set boundaries: Make it clear that everyone gets to rest and relax, including grandpa and grandma.

Include everyone in the planning: When all family members get a say in the itinerary, consensus happens. Assigning trip research to older children makes them feel a part of the process, too.

Insist on me time: If your family isn’t used to spending many hours of in-person time together, taking a break from each other will diffuse any budding arguments. Encourage naps for the little ones and oldsters, outdoor breaks like walking or enjoying an afternoon at the pool or a day of going your separate ways.

Be flexible: When traveling in a group, family members must be willing to change plans or adjust expectations. Bad weather happens. Little kids get sick. Grandpa and grandma tire more easily. Remember that flexibility is the key to a good time.

Remember, you’re traveling to have fun together. Enjoy the memory-making!

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