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5 Bucket List Summer Vacations for Multi-Generational Families

Reunite with loved ones at these unforgettable destinations

multi-gen family vacation
Getty Images
By
Gina DeCaprio Vercesi
 
Published June 14, 2021

| During the pandemic, many of us have missed two things especially: traveling and seeing loved ones. Now that CDC guidelines allow fully vaccinated people to do both, the dream of taking a big family trip is again becoming a reality.

The best destinations for multigenerational getaways offer spacious accommodations, a beautiful setting and a host of activities that include something for everyone. Here are five fantastic ones.

cabin in the Adirondacks
White Pine Camp

1. Old-fashioned summer escape in the Adirondacks 

With more than 6 million acres of unspoiled wilderness, New York’s Adirondack Mountains have been luring nature seekers since the late 19th century. Back then, prominent Gilded Era families — the Astors, Vanderbilts and Rockefellers, to name a few — built spectacular “great camps” along the shores of the region’s lakes. Although many of those estates fell into disrepair over the decades, a few have been transformed into unique vacation destinations that offer a glimpse into the rustic elegance of a bygone era.

Consider White Pine Camp (518-327-3030), an assemblage of 13 charming cabins and cottages complete with comfortable period furnishings and full kitchens tucked into the forest on Osgood Pond. Built in 1907 for New York banker Archibald S. White and his wife, the camp served as the summer White House of President Calvin Coolidge for three months in 1926. Today it’s a great home base for families looking for an old-fashioned summertime escape.

Spend your days paddling, fishing and swimming in the clear waters of Osgood Pond, hiking the mile-long shoreline trail, bowling in the Camp’s 1911 game room, or watching the sunset with a glass of wine by the historic Japanese Tea House. Veteran naturalist Ed Kanze leads weekly onsite nature walks as well as offering private guide services for folks looking to explore further afield. Just 20 minutes from Camp, you’ll find the picturesque town of Saranac Lake, known as the heart of the Adirondacks. Shop for local produce and other goodies at the Saturday farmers market, browse the art galleries, or stop into the Adirondack Center for Loon Conservation to learn about one of the region’s most important natural icons. Little ones will love the town’s whimsical carousel, with its hand-carved woodland creatures. 

Kayaking at Kiawah Island Golf Resort
Kiawah Island Golf Resort

2. Lowcountry fun on South Carolina’s Kiawah Island

Tucked between the Kiawah River and the Atlantic Ocean, just 25 miles from Charleston, this lush barrier island with 10 miles of beautiful coastline may just be the ultimate family retreat.

Kiawah Island Resort has a vast inventory of condos and private homes, some of which can accommodate up to 20 guests, plus activities that will appeal to people of different ages, including golf on five award-winning courses, tennis, beach yoga, surfing lessons, and arts and crafts. Families can also join the resort’s engaging naturalist guides to explore the island’s habitats, from lush maritime forest to salt marsh, coastal grasslands and intertidal creeks. Adventures on the water set out from Mingo Point and include shelling expeditions, dolphin- and birdwatching cruises, creek fishing and kayaking Kiawah’s pristine estuaries. Mingo Point is also the place to be on Monday evenings throughout the summer, when it plays host to Kiawah’s legendary oyster roast, a bona fide Lowcountry tradition.

Throughout the island, 30 miles of paved bike trails wind beneath towering palmettos and massive live oaks dripping with Spanish moss. Rent bikes at the resort’s West Beach Bike Shop or at Seacoast Sports and Outfitters in Freshfields Village, Kiawah’s open-air marketplace. Be sure to pop into Vincent’s Drugstore & Soda Fountain for hot dogs and old-timey ice cream treats — and the opportunity to introduce the grandkids to an egg cream.

The Cliffs at Princeville
The Cliffs at Princeville

3. Tropical splendor on Kauai’s North Shore (Hawaii)  

Note: Be sure to check Kauai’s current COVID-19 policies before you go.

While most Kauai visitors make a beeline to the bustling south shore resort hub of Poipu, the island’s northern coast, with its dramatic emerald sea cliffs and golden beaches, is one of the most spectacular spots in the Hawaiian archipelago — and quite possibly the world.

For family accommodations, consider The Cliffs at Princeville, an affordable collection of breezy suites with full kitchens, private lanais and lovely furnishings perched on a bluff overlooking the Pacific. A lushly landscaped pool area, tennis courts with complimentary rackets, and bike rentals are all available onsite. Golfers will want to tee off at the award-winning Princeville Makai Golf Club, which is just down the road. But the best part is the resort’s wholehearted commitment to sustainability. The Cliffs, which has been awarded the state of Hawaii Green Business certification two years running, generates more than half of its electricity with solar panels. The property also recently joined Surfrider Kaua’i’s Ocean Friendly Visitors Program with the goal of minimizing plastic pollution and working to protect the island’s beaches, reefs and marine life. Borrowing a cleanup bucket and heading to the beach to collect marine debris is a great way to lend a hand and teach kids about the ocean’s fragile ecosystems.

A short drive along the winding, two-lane Kuhio Highway takes you to Hanalei, a quaint rural outpost that oozes vintage Hawaiian charm and aloha spirit. Mom-and-pop shops line the main drag, taking up residence in colorful wooden buildings with patinaed metal roofs. Sample Hawaii’s quintessential frozen treat at Wishing Well Shave Ice, where you’ll find island flavors like lychee, hibiscus-lime, coconut and guava. Later, while away the hours at Hanalei Bay beach, a picture-perfect turquoise crescent with the verdant peak of Bali Hai, the forbidden mountain made famous by the movie South Pacific, looming in the distance.

Hayride at White Stallion Ranch
SAIJA LEHTONEN

4. Western ranch vacation in Tucson, Arizona

Owned and operated by the True family for three generations, the all-inclusive White Stallion Ranch (520-297-0252) makes it easy to enjoy some Western-themed fun. With their sleeves rolled up, the Trues have their hands in every aspect of ranch operations — from flipping pancakes and grilling steaks to wrangling horses and overseeing ranch staff. Their love for the land and warm hospitality seeps into everything they do.

Set on 3,000 acres in the rugged Tucson Mountains, the ranch owns one of the largest private herds of horses in Arizona, and the staff is skilled at pairing guests of all ages with the perfect steed. Gentle morning rides through the desert, accompanied by the sweet, earthy smell of creosote, give newbies a feel for the saddle. When you’re ready to graduate to the next level, fast rides — available to anyone over the age of 8 who can pass a loping test — take you galloping past soaring saguaro cacti and offer an exhilarating way to experience the Sonoran Desert. Not into horses? Guided activities like hiking, fat-tire biking and rock climbing are another way to enjoy the desert landscape and can be tailored to meet the needs of everyone in the family.

The ranch’s 43 rooms and suites feature tile floors and rustic Southwestern décor. Many rooms connect to accommodate large families, and all are spread throughout a collection of low-slung, adobe-style buildings surrounded by cactus gardens.

Hearty meals are served family-style in the dining room or out on the patio, and a full, self-service honor bar, complete with saddle seats, adds to the ambience. In the evenings, wrangle the whole clan for live animal presentations, country line dancing, or a cowboy sing-along by the campfire under the stars.

family at St. Thomas
Gary Felton

5. Island-hopping in the U.S. Virgin Islands

Note: Check the U.S. Virgin Islands website for current information on COVID-19 protocols for travelers.

With powder white beaches, palm-studded cays and translucent turquoise seas, the U.S. Virgin Islands — St. Thomas, St. John, St. Croix and more than 50 smaller islands and islets — represent some of the Caribbean’s most idyllic sailing grounds. Warm sunshine and gentle trade winds equate to mellow days spent dropping anchor in hidden bays or motoring the dingy to castaway watering holes where putting on a pair of flip-flops counts as dressing up.

Reserve a boat through The Moorings in St. Thomas, the region’s first and most-established charter company, which has an extensive fleet of catamarans and monohulls that can accommodate up to 13 guests. Chartering in the off-season (summer through fall) is surprisingly affordable, and The Moorings makes it a breeze for everyone from landlubbers to old salts to get out on the water. Folks without sailing experience can hire a regular skipper or an instructional one to show them the ropes. As an added bonus, these local captains can give you insider tips on everything from where to find the best reefs for snorkeling to the bars offering the most delicious “painkillers” — nutmeg-dusted concoctions of rum, pineapple and coconut.

You’ll cast off from the port city of Charlotte Amalie’s bustling harbor on St. Thomas to explore the islands. Favorite stops on the charter circuit include St. John’s stunning Maho Bay — the calm, crystal-clear waters here are ideal for beginner snorkelers, and green sea turtles love to munch on the tall grasses that grow up from the ocean floor — and magical, secluded pockets like Lovango Cay and Turtle Cove. Kayaks and stand-up paddleboards can be added to your charter, and the kids will love paddling around dreamy anchorages beneath the setting sun.

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