America’s Best Island Vacations (No Passport Required)
Island getaways are typically reserved for all-inclusive Caribbean idylls, but we've got plenty of sensational stays right in our backyard. From the New England summer colonies favored by socialites and celebs, to miles of tropical sugar-sand beaches off of Florida's west coast, here are the best island vacations in the US of A.
A Brooklyn-based writer and editor, Chelsea's work has appeared in Matador Network, The Huffington Post, the TripAdvisor blog, and more. When not planning her next trip, you'll usually find her drinking way too much iced coffee (always iced—she’s from New England) or bingeing a Netflix original series.
Martha's Vineyard, Massachusetts
Martha’s Vineyard has made quite the name for itself as a New England summer staple for affluent locals, socialites, celebs, and democratic bigwigs-alike (we see you, Obamas and Clintons). That said, what’s all the hype about? Well, barring a lengthy laundry list of accolades, MV wows with high-end gastronomic options, a rich history and pure scenic beauty throughout it’s six towns. Food options here are endless, but ask around and you’ll find Among the Flowers Cafe, in Edgartown, is the place for breakfast and you can guess what Larsen’s Fish Market, in Menemsha, is good for. This summer, for a midnight snack, traipse to the actual back door of Martha’s Vineyard Gourmet Café & Bakery for Back Door Donuts. The treats are served from 7:00 pm to 1:00 am on the dot. Ride that sugar high through till morning when you storm the island by moped. Wednesdays and Saturdays are reserved for sifting through vintage finds at the Chilmark Flea Market, while the shops and gingerbread cottages on Circuit Avenue in Oak Bluffs are always there when you have time. Keep things cozy at the Harbor View Hotel, a collection of seaside-chic cottages just a stone’s throw from the historic mansions of downtown Edgartown.
Marco Island, Florida
Not far from the Everglades and Naples, connected to the mainland by a series of bridges, Marco Island is the largest developed chunk of Florida’s “Ten Thousand Islands.” Poised in the Gulf of Mexico, it has all of the Floridian mainstays holiday-seekers are accustomed to finding: luxury resorts, sun-washed beaches and a tropical climate that hovers in the 80s, rarely dipping into the 50s, even in the dead of winter. For an Everglades experience without actually stepping foot in the Everglades, hit the mile-long boardwalk at Collier-Seminole State Park. The system of mangrove swamps and salt marshes is home to rare flora and fauna like the royal palm, American alligators and crocodiles, and Florida black bears. For a gourmet bite, La Tavola serves up a mean grilled Spanish octopus with andouille sausage, red peppers, fig balsamic, fresh herbs and greens. When it comes to choosing a stay, your pick is between a slew of well-known mega-resorts, and tiny inns, but you’ll be comfortable whether you retire at the massive Marco Island Marriott Beach Resort Golf Club & Spa, or mini Marco Island Lakeside Inn.
Nantucket joins Martha’s Vineyard in Massachusetts’ roster of highly-flocked to summer colonies. Thirty miles off the coast of Cape Cod, the seaport stunner doesn’t have to clamor for attention, but just sits back and reels it all in with its perfectly-worn wharves, shingled family homes, cobblestoned streets and sandy dunes. Drop your bags in your own apartment-style loft at the harbor-front White Elephant and take to the island by bike, or board with a little aid from the Nantucket Island Surf School. Energy spent, direct your remaining attention to Oran Mar where exquisitely plated, incredibly colorful dishes are the name of the game. Not ordering the entire menu is an exercise in self constraint, but we wouldn’t fault you for going for a couple plates, say the garlic-laced roasted Pocmo Meadow oysters, black truffle bucatini and Berkshire pork belly.
Hilton Head Island, South Carolina
Just 45 minutes from Savannah and Beaufort, this low-country island is all about southern hospitality. Between hitting the links – the resort town is lauded for its world-class golf courses (it does host the PGA tour Heritage Golf Classic) – you can hit the sands at Coligny Beach, or stop in Harbour Town, marked by its eponymous and iconic red and white-striped lighthouse, to take a gander at the yacht basin and peruse the shops, ice cream cone in hand. When it comes time to really chow down, a low-country inspired meal at Live Oak is always the answer. If you catch them during Saturday or Sunday brunch, you can recline with $8 unlimited Mimosas and $10 bottomless Bloody Marys (living in NYC, it pains me to write this). Otherwise, start with skillet bacon cornbread with pimento cheese, honey butter and jalapeno marmalade, then go for something classic like shrimp and grits or southern fried chicken. In the Palmetto Dunes neighborhood of Hilton Head, fresh off of a $17 million redesign, the Omni Hilton Head Oceanfront Resort waits with spacious, brightly-appointed suites and 11-miles of lagoon ready for kayaking.
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Ask nearly anyone and they’ll tell you that Maui doesn’t just land the list of America’s most beautiful islands, but the world’s, too. Luxury resorts and plush guest homes meet every watersport imaginable (the diving is a must) sprawling gardens right on the ocean’s edge, volcanic landscapes pocketed by dormant craters, and the food isn’t too shabby, either. At the Lumeria Maui, a restored, elegant 1909 estate, six manicured acres of lush garden cocoon yoga, meditation, and gardening classes along with an expansive indoor/outdoor wellbeing center and saltwater pool. For a meal that hasn't failed to impress locals and visitors for the last 26 years, head west to the Lahaina Grill. A menu spilling over with contemporary bistro cuisine means you'll be eating your weight in ahi poke, crisp Shanghai spring rolls, and Kona coffee roasted rack of lamb.
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Mackinac Island, Michigan
Stepping onto the resort Mackinac Island is like stepping back in time. The 3.8 miles of land floating in Michigan’s Lake Huron is home to less than 500 year-round residents, but that's just the start of its small town feel. Visitors are instantly captivated by the unmistakable Americana and early 1900s atmosphere the island evinces, due in large part to horse buggies (the island’s car-free), monumental historic hotels (that happen to have the longest porch in America) and a Main Street brimming with the bright, columned facades of general stores, inns, and artist markets. Despite a count-them-all-on-one-hand populace, the island has a wealth of tasty restaurants. The waterfront patio at the Pink Pony slings a pretty good bistro burger and rum runner (that’s the talk of the island). If you’re looking to keep the night going, the Cuppola Bar at the top of the Grand Hotel is what follows. Grab a drink and sit back to enjoy the live music, but beware, the one-of-a-kind Carleton Varney decor might just steal the show (get a load of the chandelier). Head home at the end of the day to The Inn At Stonecliffe, a Tudor Revival mansion kitted out with new and old-world touches like original stained glass windows, clawfoot tubs and a former-library-turned bar.
San Juan Islands, Washington
The San Juan Islands off the northwest corner of Washington state comprise some 172 land masses and reef bodies, but it’s Orcas, Lopez, Shaw and San Juan (singular) that hold all the goods. Hopping a quick ferry or flight from Seattle, Bellingham, or Vancouver, you’ll be mesmerized by the archipelago’s rugged Pacific Northwest landscape – subalpine forests, rocky beaches and reef-studded bays. Your trip calls for a stay at the Friday Harbor House in San Juan where after days of exploring the island’s thriving art scene, covering the streets of the seaport inch by inch (it’s only a mile) and visiting the Pelindaba Lavender Farm during the “peak of purpleness” (July and August), you’ll lounge fireside in your own oversized tub, taking in the island’s bluffs through your room’s picture window. Dedicate a day to the San Juan Islands Scenic Byway which connects the beaches, alpaca farms, mountains, harbors and vineyards of the archipelago’s many hamlets and fit in a whale watching excursion as the island's are famous for their three pods of killer whales. When hunger strikes, find a table at Coho Restaurant where seasonal Pacific-style meals are spun with a Mediterranean twist.
Block Island, Rhode Island
Just about 14-miles equidistance off the coasts of Montauk and mainland Rhode Island, Block Island is an enchanting summer destination chock full of New England-style inns, B&Bs and guesthouses. Ringing in at around 9 miles – but with 17 beachy miles of coastline – the island tempts guests with bicycling, yachting, specialty boutiques and art galleries. Since the tiny slice of land is home to only 900 year-round residents, it maintains a level of rustic simplicity with steep ocean bluffs, winding roads and stoic 18th-century lighthouses (which were once architectural marvels). Scarf down the freshest lobster rolls at Southeast Light Delights on the Mohegan Bluffs near Southeast Lighthouse, or if you’re anti-seafood, try out a ricotta grilled cheese on sourdough, stuffed with local blueberries, blackberries and strawberries, and then drizzled with honey. For a sweet stay that’s removed from the 24/7 comings and goings of downtown – but don’t worry, you’re only a mile off the beaten path – tuck your things away at waterfront Payne’s Harbor View Inn. The three-story retreat has just 10 rooms and 3 grand balconies with sweeping views of the ocean and New Harbor.
Catalina Island, California
Santa Catalina, or just Catalina, as it’s known to those who frequent it, has everything the jetsetting elite are keen on (Marilyn Monroe herself once called the island home) – namely swaying palms, white sandy beaches, exquisite dive sites, and a soothing island vibe. Getting there is a cinch, with ferries regularly leaving from Long Beach, Dana Point, Newport Beach and San Pedro, and once you’re on the island, in main town Avalon, which is only a mile, you’ll see everyone gets around on foot (no joke, there’s a 14-year wait list for residents to get a car on the island). Take lunch at the Inn on Mt. Ada where your meal will be met with panoramic views of Avalon Bay, the island’s blissful backcountry and a clear view of chewing gum-tycoon William Wrigley Jr.'s mansion. If you’re planning an overnight, Snug Harbor Inn should serve as your temporary home base. The Cape Cod-style charmer is a favorite among celebs trying to avoid having their vacay splashed across the homepages of TMZ and Perez Hilton.
What to wear on an American island:
Women’s Outfit to Wear in the Hamptons
Men’s Beach Trip Date Outfit
Women’s Swimsuit for Laying Out in Los Cabos
Men’s Beach Look for your Passport-less Tropical Vacation
Women’s Beach Outfit for your All-Inclusive Resort Trip to the Caribbean
Men’s Day Style for the Most Beautiful Places in Europe
Women’s Casual Outfit for a Food Town
Men’s Relaxed Fit for an Adults-Only All-Inclusive Resort in the Caribbean
Women’s Swimsuit Cover Outfit (Amazon-based)
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