Summer-season islands are typically overrun with tourists for three or four months a year — as anyone who’s strolled around Nantucket in July can attest — but they can be delightfully laid back in fall, winter and spring. Here are five islands that welcome visitors in the off-season, so there’s no need to wait until Memorial Day to enjoy them.
Vancouver Island – Canada
There’s so much natural beauty — soaring pine forests, rocky coastlines, picturesque bays — on this rugged island located to the west of Vancouver, British Columbia, that it’s season-less. While summer draws active travelers looking to hike, surf, fly fish and whale watch, winter also lures romantics seeking to snuggle, sip wine by a roaring fireplace and gaze out at dramatic waves rolling in from the Pacific (some 15-20 feet in height). Yes, storm watching is a thing, and it peaks from December to February. And it’s hard to beat the view from the Wickaninnish Inn in Tofino. Vancouver Island is also home to the charming capital city of Victoria, and a world-class dining scene (fresh oysters, local salmon and BC wine) that makes it perfect for a Canadian version of hygge, the popular Danish notion of cozy camaraderie.
Looking to step back in time on a pre-Christmas getaway that’s fun, festive and full of charm? This Massachusetts island may be more famous for its sand dunes and July 4th clambakes, but come December the streets of its historic downtown are lined with hundreds of decorated fir trees, setting the scene for the Nantucket Christmas Stroll, a four-decade-long tradition that resembles a jolly block party of holiday cheer. Shop, sip hot chocolate and mulled cider, join local carolers and welcome Santa and Mrs. Claus who arrive via Coast Guard cutter. Even after the Stroll weekend is over, you can peruse local shops and galleries (most stay open through Christmas), take a beach walk and visit Cisco Brewers to sip a Winter Shredder. Two top properties remain open for most of the winter: The Nantucket Hotel and The Jared Coffin House.
This 21-square-mile island is located 570 miles off the coast of North Carolina in the Atlantic, so it’s high season is generally during the summer months. But if golf’s your game, six world-famous courses and mild winter temperatures (60 to 70 degrees) make Bermuda perfect for an off-season getaway. Even non-golfers can enjoy the island’s scenic beauty — pink-sand beaches, picturesque coves and charming cottage-style architecture — and relax during a spa treatment, traditional afternoon tea or a tasting of Gosling’s famous dark rum. History buffs can explore the island’s maritime legends, shoppers can buy Bermuda-style decor or beachwear and foodies can enjoy the island’s seafood specialties (it’s spiny lobster season from September to March). Plus, there’s a resort to suit any style — including the Hamilton Princess for traditionalists, Rosewood Tucker’s Point for luxury-seekers and The Reefs for cliffside romance — all are open year-round.
Aquidneck Island, Rhode Island
Never heard of it? This 44-square-mile island in Rhode Island’s Narragansett Bay is home to the state’s most famous city: Newport. And the off-season here has plenty to offer, beginning with the annual Christmas at the Newport Mansions extravaganza. From Nov. 18, 2017, to Jan. 1, 2018, three of the destination’s most famous historic mansions — The Breakers, The Elms and Marble House — will be decorated to the hilt with Christmas gilt. Newport also has a Holiday Stroll (the first two weekends of December) featuring shopping, live entertainment, hot cider and warm-you-up New England clam chowder. Newport puts on the glitz into the New Year with the annual Winter Festival (Feb. 16-25, 2018) featuring daily events that include ice sculpting, warm drink contests and the Illuminated Garden in Ballard Park. The perfect spot to warm up: a lavish suite at The Chanler at Cliff Walk, where the cozy bar beckons you to sip a hot toddy beside the antique fireplace.
Long Island, New York
Planning a winter escape to New York City? Add to your enjoyment by pairing one of the world’s most famous islands, Manhattan, with the charming, farmhouse-lined landscapes of the North Fork on this fish-shaped island to the east. While Long Island’s South Fork is synonymous with summer (it’s home to the Hamptons), its North Fork has a wine trail featuring more than 35 vineyards, many with tasting rooms that are open year-round. Check out Raphael in Peconic, Lieb Cellars in Cutchogue and Sherwood House Vineyards in Jamesport. Check in at the Jedediah Hawkins Inn in Jamesport, offering easy access to several tasting rooms.