Terri Marshall a RoamRight Blog Author

Perfect Destinations For Your Next Multigenerational Trip

When it comes to planning a multi-generational getaway, choosing the right location is key to a stress-free memory-making trip. My family spans four generations and ranges in age from 7 to 79 with interests all over the map. When I’m planning a getaway for our group, I focus on a place that provides just the right amount of time together balanced with enough space to keep everyone sane. Our goal is to make priceless memories and still like each other when the trip is over. Some locales work better for this type of trip than others. Here are a few of my favorites.

Basin Harbor Club: Lake Champlain, Vermont

Situated at the edge of shimmering Lake Champlain, Basin Harbor Club has been a destination for families to play, relax and reconnect for more than a century. I’m not sure if it’s the lakeside setting, the large verandahs, or the summer sounds of the wooden screen doors slamming as children run in and out, but this place reminds me of the classic movie, Dirty Dancing. There are plenty of scheduled activities including fitness boot camps, golf lessons, and tennis. For the younger family members, Kids Clubs offer arts and crafts, sports, fishing, and games like Capture the Flag, scavenger hunts and water carnivals. 

Adirondack chairs scattered throughout the resort invite you to sit, sip a glass of wine and soak in the sunshine as it glistens off the lake. Or enjoy a little family competition with classic lawn games like croquet, badminton, giant chess and volleyball. Paddleboats, kid’s boats and a giant water trampoline make full use of the lake. There are also movie nights at the pool to entertain the entire family.

Lodging options include 45 charming guestrooms located in four guesthouses: The Main Lodge, The Homestead, Champlain House and Summit. If you prefer more togetherness, there are 74 private lakeside cottages ranging from studio to 3-bedrooms, each with its own unique personality…just like your family members.

Start the day with an extensive breakfast buffet at Ardelia’s, the property’s lakeside restaurant.  The restaurant also offers an upscale dining experience each evening. For more casual fare, the Red Mill Restaurant located in a renovated 1940s sawmill is a resort favorite. Menu offerings feature locally sourced ingredients along with signature Vermont beers. Outside a playground will entertain the kids if the adults prefer to linger. And, there’s a landing strip for private planes that captures everyone’s attention. 

Old Kinderhook Resort: Lake of the Ozarks, Missouri

A master-planned community situated on more than 700 acres, Old Kinderhook Resort makes an ideal base for exploring the Lake of the Ozarks region. The resort’s centerpiece is a Tom Weiskopf signature golf course carved from the Ozark Hills. The challenging course includes valleys, waterfalls, hills, trees, water hazards and elevation changes, along with breathtaking views. If you need a little help with your game, book a lesson with one of the resort’s pros. I recommend Robert Wilson, perhaps one of the most patient instructors on earth—I know this because he survived my lesson. 

Old Kinderhook offers a wide variety of options for lodging. The Lodge at Old Kinderhook overlooks the golf course and offers 84 impeccably decorated rooms. Amenities include indoor and outdoor pools and the Old Kinderhook Spa for family members in need of pampering. Other lodging options include golf cottages, patio homes, villas and estate homes with three to four bedrooms scattered throughout the golf course. 

Should you decide to venture out to explore the Lake of the Ozarks region, you’ll find a wealth of outdoor activities including boating, fishing, hiking and caving. 

And after a full day, there’s nothing better than sitting down to a fantastic meal in the resort’s restaurant, The Trophy Room, which overlooks the course. While everything that Executive Chef Thomas Robinett makes is wonderful, make sure you try the Old Kinderhook salad with Parmesan tuile and their own house-made dressing. There’s a reason it’s one of their signature menu items.

Palm Island Resort: Cape Haze, Florida

Located on Florida’s Southwest Gulf Coast approximately fifty miles north of Fort Myers, Palm Island is a place where you can while away the days searching for shark’s teeth on the beach, fishing in the surf or exploring by golf carts or on bicycles. 

With oodles of old-style Florida charm, the resort is comprised of one, two and three- bedroom villas, each with a fully equipped kitchen and full laundry room. Each villa is privately owned so décor varies, but every unit has a screened terrace overlooking either the pool or the Gulf of Mexico. The two-story buildings of four to eight villas each are arranged in clusters around a heated pool, Hydra Spa and gas barbecue. 

Fully equipped kitchens and plenty of barbecue grills make it easy to prepare your own meals. But if you choose to take a break, Rum Bay restaurant is located on the island and offers reasonably priced dining options for lunch and dinner including specialties like native grouper and baby back ribs. Johnny Leverock’s Seafood House overlooks the Palm Island Marina on the mainland serving a variety of fresh seafood. A water taxi runs between the island and mainland.

For active pursuits, there are 11 tennis courts. Lessons and clinics are available with the resort’s tennis director. Family adventure packages can be arranged through several independent companies for fishing, sightseeing, sandbar eco-adventures and wildlife viewing. Rental items like kayaks, canoes, boogie boards, rafts and snorkeling gear help to maximize the water fun.

The island’s resident pirate, Red Beard and his trusty parrot add more entertainment for the kids. Red Beard is always happy to teach the little ones how to make sand art and pirate beads while he regales them with stories of his fights with the evil Pirate Black Beard.

Of course, one of the best experiences at Palm Island is watching the sunset over the Gulf of Mexico as dolphins, silhouetted against the fading sunlight, play in the warm waters. 

What’s your family’s favorite multi-generational destination?

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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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