When we think of a beach vacation, we often picture ourselves on an idyllic island—palm trees swaying, a slower pace of life, crystal-clear waters gently lapping at the soft sand, a cool drink in hand. There’s just something about an island vacation that gives us that you’ve arrived feeling. So, we’ve compiled six of the best islands to visit as inspiration for your next beach vacation.
From the all-American islands of New England to the emerald-green isles of Hawaii, down to the serene island nations of the Caribbean—and beyond—Inspirato offers plenty of luxury accommodations on some of the world’s most sought-after islands, as well as a few hidden gems.
See some of our top picks below, including three U.S. islands and three international escapes. Not to brag, but all six destinations have been featured on Condé Nast Traveler’s Readers’ Choice Awards for best islands.
Best Islands to Visit in the U.S.
Kiawah Island, South Carolina
A barrier island outside of Charleston, Kiawah Island is marked by miles of wide, sandy beaches with plenty of room to spread out and explore. The Lowcountry isle offers miles of biking paths, making it easy to pedal from your home to the beach—and firmly packed sand makes beach cruising a cinch. Stay just a few minutes from the shores at one of ten stunning Inspirato homes like Tupelo, Driftwood Dunes, Jessamine, and Azalea.
Florida Keys, Florida
A little slice of the Caribbean awaits in the storied Florida Keys, where white-sand beaches provide a welcome respite that feels a world away. Sample sumptuous key lime pie, or try your hand at world-class fishing and diving—you’d be hard pressed to find a better place to in the U.S. Stay at one of four breezy, spacious Inspirato homes within the Islands of Islamorada resort like three-story Palomar and Halyard. Plus, it’s fun to island hop on the Overseas Highway stretching from Key Largo down to Key West.
Wailea, Maui, Hawaii
Maui is one of the world’s favorite vacation destinations, having earned the title of Best U.S. Island from Condé Nast Traveler’s Reader’s Choice Awards for many years. Inspirato’s accommodations in Wailea — located on Maui’s southwestern coast — are tucked inside three award-winning resorts. At the Fairmont Kea Lani, the club’s residences have private plunge pools just steps from secluded Polo Beach. Our striking contemporary villas at the Andaz Maui at Wailea Resort have serene ocean views, while a stay at Ho’olei at Grand Wailea grants access to the many amenities of its namesake resort next door.
Best Island to Visit in Europe
Sicily, Italy
The largest isle in the Mediterranean, Sicily promises tourists a glimpse into a glamorous bygone Italian era, with miles of sandy beaches, open-air street markets, incredibly preserved architectural ruins, and one of Europe’s most volatile volcanoes towering above it all.
Inspirato’s sophisticated Villa Agata is nestled along Sicily’s southwestern coast at Rocco Forte’s Verdura Resort, just a quick drive from some of the island’s best beaches. The villa boasts its own private pool and sweeping views of the Mediterranean.
Best Caribbean Islands to Visit
St. Kitts and Nevis, West Indies
The dual-island nation of St. Kitts and Nevis is the ideal destination for travelers with rest and relaxation in mind. Situated between the Atlantic Ocean and Caribbean Sea, these West Indies paradises offer stretches of pristine, quiet beaches and a slower pace of life. Fun fact: Alexander Hamilton, one of the founding fathers of the United States, was born and raised here.
The perfect place to experience the island life is Maison Tortue, Inspirato’s five-bedroom home overlooking Turtle Beach features an infinity-edge pool and panoramic views of the Caribbean from every bedroom. Not to mention, a game room, home theater, and private sauna.
Scrub Island, British Virgin Islands
It’s a tiny speck of land in the British Virgin Islands nestled between Tortola and Virgin Gorda—just 1.5 miles long—but what Scrub Island lacks in size, it more than makes up for in exclusivity. If you’ve ever dreamed of staying on a private island paradise, Scrub Island Resort is for you.
The entire island is an exclusive, AAA Four Diamond award-winning resort, meaning the only way you can stay is as an overnight guest in one of its 52 hotel rooms, or two-, three-, four-, and six-bedroom villas, including Reef House, Hibiscus Villa, and Drake House. The island is nearly car-free, as well; the only transportation you’ll see are resort shuttles.
