13 Ridiculously Awesome Islands You've Never Heard of Featured in Playboy

Jonesing to go where no man has gone before? Tired of doing the typical spring break location all of your bros have done before? Or maybe you just have a dormant alter-ego pirate within. Whatever your motivation is, these lesser-known islands deliver intrigue (and plenty of Insta-worthy photos) in spades.

So, next time you’re considering a Maui or St. Maarten vacation, change it up for these off-the-beaten-path islands.

A ‘dismal unfortunate island, which I call’d the Island of Despair’ is how Daniel Defoe described the island in his 1719 “Robinson Crusoe” classic. Lucky for you, things have improved since then. Located off the west coast of Chile and the largest of the Juan Fernández Islands, you can join an island tour for a novel-themed vacay to follow in the footsteps of Alexander Selkirk or explore on your own. Although it’s not the fictional palm tree-dotted Caribbean island Defoe describes, the landscape— sheer cliffs, jagged coastlines and soaring mountains—is just as dramatic. Snorkel, hike, diving, horseback ride, and fish by day. By night, kick back at the Crusoe Lodge or Nautical Lodge with a locally brewed Alex Selkirk stout and dig into as much lobster (one of the island’s main exports) as you can handle.

Sexy, dramatic, and a little saucy. What else would you expect from an exotic Spanish island? Situated off the coast of Morocco, Tenerife is the largest of Spain’s Canary Islands. The island becomes one giant, rhythmic party every February/March as it hosts the world’s second largest Carnaval celebration (after Rio). Beyond the party, half of Tenerife is a protected nature reserve, highlighted by Mount Teide. The mountain rises out of a volcanic crater 30 miles in circumference and is the highest peak in Spain (and third largest volcano in the world.) The mountain hasn’t erupted in 100 years, so chances are you’ll be able to explore the mountain without getting burned up. The island has your pick of luxury resorts (Four Seasons and Hard Rock), though for a more chill experience, try a bed and breakfast like Casa Guiliana.

Don’t let its small size (six miles long by four miles wide) fool you. Porto Santo is filled with history…and wine grapes. Before his iconic discovery, Christopher Columbus set up shop on Porto Santo. Fast forward 500 years and his house is now the Christopher Columbus Museum. Don’t miss exploring snorkeling atop a Madeirense shipwreck just off the shore and exploring all the insane Mederia food—from chocolates to Pestana Porto Santo Beach Resort and Spa (part owned by Medeira legend Cristiano Ronaldo) is the place to stay.

Although it’s just a 15-minute ferry ride from Seattle’s downtown waterfront, Bainbridge feels like a state of its own…a state dedicated to the outdoors with a huge dose of craft beer and cannabis. We can’t argue with that. Hike or mountain bike in Fort Ward State Park, or visit one of the island’s many beaches. These aren’t usually bikini-warranted beaches, so afterwards, you’ll want to warm up with some grain-to-glass whiskey at Bainbridge Distillery and then check out Paper & Leaf, the island’s styling pot shop. For hotels, best to opt for a bed and breakfast or if you’re a Lord of The Rings fan, stay at the Hobbit House.

Maybe you’ve never heard of Saba (pronounce say-ba) before but you’ve probably seen it before. This five square mile-island was where King Kong swept his sweet lady Jane off to in the flick. So, after you’ve picked up some famous Saba lace and Saba Spice (rum-based liqueur) for mom and dad as souvenirs, check into your sweet villa you scored on AirBnB and head for the hills for a hike. Sights include epic oceanscapes, wild orchids, old ruins and tide pools. The trails can go missing in spots, so best to hire a guide with The Saba Conservation Foundation. As part of the Netherlands (formerly) and the first to legalize gay marriage, Saba definitely has its own breed of Caribbean vibe—a quintessential chill with a load of diversity.

It’s no surprise Red Bull founder has such a ridiculously sick island. Like a playground for eh, well playboys, Laucula Island is extreme in every good sense of the word. It’s the only island resort in the world with a submarine for guests and highest staff-to-guest ratio of any hotel—the ultimate ‘fantasy island’ escapade.

Within a 40-minute flight from Miami, you’ll be sinking your toes into deserted, white sand beaches as serene and untouched as they were 5,000 years ago. The Exumas, an archipelago of over 360 islands, has, literally, hundreds of remote beaches where you can pretend you’re Richard Branson with your very own slice of paradise. And the dream-like adventure continues with an adventure like no other in the world—swim with swine in Big Majors Cay. Like dogs, these ocean-loving pigs are very friendly—especially if you feed them a hot dog— their favorite snack, a hot dog. (Just avoid the cannibal thing and opt for chicken links). Don’t miss seeing what else swims in the sea with an island hopping tour to snorkel with dolphins, sharks, sea turtles and exotic fish.

Truly a hidden gem of the South Pacific – 15 islands in all, 12 that are inhabited – #nofilter photos are easy to nab with its white sands, turquoise waters and swaying palm trees. To boot, you’ll get a non-touristy taste of Polynesian culture—it’s been pretty sheltered from modernity (in a good way). Trek through the jungles with a medicine man named Pa on the island of Rarotonga, join in on an ancient drinking ceremony on Aitu or score a rare and bizarre passport stamp on Aitutaki. Fun fact: Despite popular belief, Captain Cook did not discover the islands. It was actually the Russians who named in 1823 after the famous buccaneer.

Nestled about 45 miles off Nicaragua’s east coast, Little Corn is all about kicking off your shoes—literally, locals rarely wear them—and unplugging. Getting around the island is also low-fi—either by foot, boat or horse. Highlights include white sandy beaches, colorful coral reefs, fresh-caught lobster and live reggae music at one of the rustic bars. Locals are mix of Euro expats, artists and native Nica islanders. Hot tip: Yemaya Island Hideaway is a chic, new boutique opening early 2017. Upgrade to the deluxe rooms—you’ll thank us later for having your own plunge pool. Plus, you can test your drinking skills while atop a balance board or walking a tight rope held by two coconut palms.

Holbox (pronounced hole-bosh) Island, a 26-mile stretch of land, is not easy to get to. Imagine a 2.5 hour drive from the airport in Cancun, a 25-minute ferry and then a golf cart ride(!). But that’s exactly what sets it apart from Cancun’s crowds. On this near no-car island, a cool Italian pirate-meets-Mayan culture awaits. Really, where else on the planet can you score Mexican-Italian food? Other fun things to do include: going on a crocodile safari; checking out tons of street art and public murals (the island is home to an annual art fest): renting a golf cart to explore the surrounding area; and swimming with whale sharks (June - September).

A pirate’s lair. A leper colony. A prison for violent criminals. Sure, Ilha Grande’s had some rough times in her past, but who hasn’t? If you’re looking for a low-fi (no cars or banks) getaway of pristine beaches and untouched rainforests on a budget, this is it. Charter a boat out to the Blue Lagoon, beach hopping through Ilha Grande Bay along the way. In the evening, order up Brazil’s national cocktail, the caipirinha, at bar or cafe at Vila do Abraao— the island’s main town. Lots of affordable, cool pousadas (bed and breakfasts in Portuguese) abound.

Mud bogging? Hell, yes—in fact, it’s going on four months of the year. In addition to the down-and-dirty racing op, POW (as the locals call it) is awesome for wildlife photography, fishing, hunting and spelunking in massive limestone caves. There’s a salty lodge, formerly a salmon cannery, to stay at—accessible only by air or sea— and a good crew of local characters to share a brew with at the lodge’s Lagoon Saloon.

Want to visit the only slice of North America to escape the last two ice ages? And a spot that’s home to 40 unique species of animals and plants? Yes, you do. Haida Gwaii (The Galapagos of the North, as it’s been aptly nicknamed) is an archipelago of 150 islands off the coast of British Columbia, Canada (though only two of the islands have roads). The islands are home not just to bald eagles and some of the world’s tallest spruce trees, but native Haida villagers who have lived there for over 8000(!) years. With the hinterland quality of Haida Gwaiii, a tour is a good bet. For the full experience, consider staying at Copper Beech House, a five room B & B full of color and kitsch. And don’t miss Moon Over Naikoon - a cafe…in the woods…housed in a school bus.