Terri Marshall a RoamRight Blog Author

Tips For Choosing A Multi-Generational Holiday Destination

With a family spanning four generations and four states, the holidays often mean travel. And while I would love to host the entire family in my one-bedroom New York City apartment—it’s just not going to happen. The solution? Find a great holiday destination that works for everyone. Here are some things to consider.

What’s Your Family’s Holiday Style?

The first thing to consider is your family’s holiday style. Do they prefer the traditional Norman Rockwell holiday where landscapes are blanketed with snow and horse-drawn sleighs remind you why Jingle Bells is a favorite holiday tune? Or, does your family prefer a tropical climate where Santa arrives in swim trunks and sunglasses? If the family is divided in preference, consider alternating destinations from year to year.

How Much Togetherness Do You Really Want?

Yes, we all want to spend time with our families. But, how much togetherness do you really want? If you love spending your early mornings, afternoons, evenings and late nights with every family member, a vacation rental is ideal. Look for a home with several bedrooms, a living room, kitchen and dining room with plenty of time for togetherness. A vacation rental is also good for families who prefer to cook their holiday dinner rather than eating at restaurants

However, if your family has varying sleep patterns and prefers more privacy for each group, a hotel or a resort with separate condos may be the way to go. 

For Togetherness Without Any Work, Consider a Cruise

A cruise is one of the simplest ways to have a stress-free holiday. If your family doesn’t mind forgoing the sleigh bells, snow and winter wonderland of a traditional Christmas, book a cruise through the Caribbean. With kids’ clubs to entertain the youngest family members, pool decks for sunning and a myriad of optional excursions, a cruise is often the easiest way to enjoy a holiday together. And no one needs to go food shopping or cook! If your family includes young children, it’s hard to beat a Disney cruise. And you can add on a few days at one of your family’s favorite Disney parks.

What’s Your Family History?

When a family spans several generations there’s a good chance Grandpa or Great Grandpa is going to have a story about his experiences. Does your family have a war veteran? Or, have you tracked your family’s DNA to discover your ancestry? Consider planning a trip where the family explores its history. 

One family I know visited Normandy over the holidays because the grandfather had served in the military there. The trip gave Grandpa the opportunity to share his experiences. And the youngest family members were rewarded with a new appreciation for their beloved grandfather. Overall, the experience brought the family closer together through its shared history—a priceless holiday gift for all.

For the Family That Prefers a Wintry Holiday, Consider Hershey

While some families are happy with sunshine and warm temperatures year-round, others enjoy the seasonally cool temperatures of winter and the possibility of a white Christmas. If your family embraces the season, the Hotel Hershey is an ideal venue for your multi-generational holiday experience.

With configurations of two to four bedrooms plus a common space, the resort’s Woodside Cottages are an excellent lodging option. Each cottage room has a private entrance and at the center of the cottage there’s a multi-functional common space for families to socialize and dine together.

Other advantages include the hotel’s restaurants which serve a delicious seasonal menu. No one needs to spend hours laboring in the kitchen to roast the perfect turkey!

The annual Hersheypark Christmas Candylane—the town wide celebration of Christmas with more than 4 million twinkling lights, rides for all ages and festive decorations—will please every generation of your family. Don’t miss Hershey Sweet Lights, a holiday drive through spectacular boasting nearly 600 illuminated, animated displays from the comfort of your car as you drive through two miles of wooded trails. And for those wanting to be pampered, the Chocolate Spa awaits your call. What’s not to love about that?

What is your family’s holiday style?

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Note: Available plans and coverages may have changed since this blog was published.


About the Author

Terri Marshall

Terri Marshall, a RoamRight Blog Author

Terri Marshall is a New York City based freelance writer whose work includes travel, spirits, and all things chocolate. Terri's work appears in several publications. She has been a featured guest on Peter Greenberg's Worldwide Travel radio program and Denver's KZKO Radio Morning Express show. Terri will not hesitate to go to the source for great chocolate - even if that means hiking through the jungle and picking cacao pods herself.


Happiest when she's globetrotting, Terri has covered destinations all over the United States, Europe, and into Central and South America. Favorite adventures include reindeer driving in Norway and fishing for piranhas in the Amazon jungle of Peru. You can keep up with Terri's adventures on her website www.TrippingwithTerri.com. You can also find her on Facebook, Twitter and Instagram.

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