The World’s 7 Best Small Islands

Island life. Those two words conjure up a thousand images—coconuts and palm trees, shimmering white sand and blazing sapphire water, cool mojitos and salty margaritas. It’s one of those things you dream about during endless afternoons at work. Here are seven beautiful small islands to consider for your next vacation.

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The world's best small islands
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Small Islands Worth Adding to Your Bucket List

The best islands? They’re the small ones. These little rocks out on the water are places where the amenities are limited, the locals are friendly, and you can truly get away from it all. Although these seven picture-perfect small islands aren’t all tropical, each one offers its own unique local culture and plenty of opportunities to kick up your feet, relax, and enjoy. 

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Small islands: Barbuda
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1. Barbuda, Antigua and Barbuda

Home to a large colony of soaring frigates, there’s a good chance birds actually outnumber humans on the small island of Barbuda—Antigua’s lesser known Caribbean sibling. Though its sister island is well known for its beaches, even Antiguans will tell you that Barbuda’s are better. Mostly undeveloped and completely unspoiled, the beaches boast silky white and pink sand, stretching as far as the eye can see. There’s only a handful of resorts and restaurants, mostly unpretentious beach bars and grills, but make sure to stop by Uncle Roddy’s, which serves up cold drinks and some of the freshest seafood you’ll ever find. Fancy a sun destination that’s a bit more bustling? Check out the best the Cayman Islands have to offer.

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Small islands: Four Seasons Lanai
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2. Lana’i, Hawaii, USA

Formerly famous for its pineapples, this small island just off the coast of Maui is now known for its luxury. For years owned by Dole, Lana’i supplied 75 per cent of the world’s pineapples during its peak years of production. After Dole packed up and left town for cheaper places to plant, Four Seasons swooped in. The luxe hotelier now owns and operates two very distinct properties here: one (the Lodge at Koele) a mountain hideaway (complete with a roaring stone fireplace in the lobby) nestled under towering Cook pines on the ridge that runs down the small island’s spine; the other (Lanai at Manele Bay, above) a seaside spot so breathtaking that Bill and Melinda Gates chose it as the site of their nuptials. Here’s what you need to consider when planning your own destination wedding.

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Best small islands: Grand Manan Island
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3. Grand Manan Island, New Brunswick, Canada

While you won’t find any palm trees here, Grand Manan still offers a relaxed pace. Connected to mainland New Brunswick by ferry, the small island is home to charming villages, the vertiginous Southwest Head sea cliffs, and the idyllic Swallow Tail Lighthouse—the second-most photographed lighthouse in all of Atlantic Canada. Take a whale-watching cruise (minkes, finbacks and humpbacks all swim nearby in the summer months), do a little sea kayaking on the Bay of Fundy (home to the highest tides in the world), hike to picturesque Hole-in-the-Rock or along the beach at Dark Harbour, or just sit back and enjoy the peace and quiet. Here are 25 more essential experiences to add to your Canadian travel bucket list.

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Best small islands: Cayo Guillermo, Cuba
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4. Cayo Guillermo, Cuba

Until the Cuban government decided to develop it as a tourist destination in the early ’90s, this small island was known only to the hardy fishermen who plied its two-tone blue waters. Part of the Jardines del Rey (Gardens of the King), a long string of keys that runs along Cuba’s northern coast, it now hosts a handful of five-star resorts. Cayo Guillermo in many ways still feels unsettled, with large areas of open space, virgin beaches, and a colony of pink flamingos. It was also one of Ernest Hemingway’s favourite fishing spots, so much so that he actually wrote about it in his posthumously released novel, Islands in the Stream. Playa Pilar, which is often regarded as the top beach in Cuba and one of the best in all of the Caribbean, has been named in his honour—it now bears the name of Papa’s beloved boat, Pilar. While you’re there, don’t miss these top 10 attractions in Cuba.

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Small islands: Schoolhouse Beach, Washington Island, WI
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5. Washington Island, Wisconsin, USA

Located at the intersection of Lake Michigan and Green Bay, Washington Island is a fun, quirky place. Although it boasts fewer than 700 residents, the island is home to a replica Norwegian stave church, and Schoolhouse Beach (above), known for its crystal clear water and smooth, rounded limestone rocks—one of only a handful of such beaches in North America. Tour the island on the Cherry Train, climb the lookout tower, or rent a bike and cycle the miles of empty roads. Retire for the night at the regal Hotel Washington, a century-old landmark inn with a fabulous restaurant featuring fresh, local, organic fare and the opportunity to cook your own brick oven pizza.

Do you tend to let your stomach guide your travel plans? These are the 10 best foodie cities in the world!

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Best small islands: Santorini, Greece
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6. Santorini, Greece

With glowing white buildings, blue domes, and ancient Greek windmills clinging to the side of towering sea cliffs, the small island of Santorini has become a staple of glossy travel books and swoon-worthy Pinterest boards. The product of a catastrophic Bronze Age volcanic eruption—one of the largest in recorded history—Santorini, seen from the air, forms the outer edges of an enormous volcanic cone. The result is an amazing landscape, with lava rock still smoking in the middle of the caldera, red sand beaches on the south side of the island, and black sand beaches on the east coast. Grab some warm bread with tzatziki and a glass of ouzo and watch the blazing sun dip below the horizon from Oia, one of the world’s best places to watch the sunset. Here are 17 more Greek islands worth visiting.

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Best small islands: Key West
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7. Key West, Florida, USA

As the southernmost point of the United States, located at the end of the famous Florida Keys, Key West has a fascinating history. Tennessee Williams is said to have written the first draft of A Streetcar Named Desire here. Ernest Hemingway spent many a night rollicking in the bars of Old Town, now a historic district filled by wood-frame buildings with quaint gingerbread trim, pastel tones and louvered shutters. (You won’t believe what happened to Hemingway’s Key West home.) Take in the island’s famous lighthouse (which reportedly helped guide an inebriated Hemingway to his nearby home), photograph some of the free-roaming chickens (the descendants of those set free decades ago when cock fighting was outlawed), then settle in for the daily Sunset Celebration on Mallory Square.

Looking for more vacation inspiration? Check out our countdown of the world’s best beaches!

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