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Changuu Island, also known as Prison Island, is about a 30-minute boat ride from Stone Town. The water around the island is crystal-clear and cerulean blue, which makes snorkeling here hard to resist, but a visit also lets you gain an understanding of a grim period of Zanzibar history. In 1860, the small island was used as a prison for disobedient slaves. By 1893, construction of an actual prison complex was completed, but instead of housing prisoners, it was used to quarantine yellow fever cases. Nowadays, the island is home to some endangered Aldabra giant tortoises, given to the island in 1919 by the British governor of the Seychelles. Some of those original tortoises are supposedly still alive here to this day!

In the Caribbean’s Windward Islands, a string of some 600 islands and islets dot the sea between St. Lucia and Grenada. It’s a paradise for yachters, where you can drop anchor off an uninhabited island and live out your Robinson Crusoe fantasies. A handful of these islands are home to resorts, including the private Palm Island, first leased to an American couple in 1966 for $1 per year. They established the ten-room Palm Island Beach Club, which over the years has grown—though there are still only a total of 43 guest rooms on this single-resort island.

Wine is an integral part of life on the Dalmatian Coast, a region with many indigenous varietals; a visit to Dubrovnik shouldn’t go by without a glass of local wine. Tucked away on Palmotićeva Street off the main Stradun, D’Vino offers cozy interiors as well as atmospheric seating at tables set on the narrow thoroughfare outside. Try a glass of something new from the impressive selection of local producers—the knowledgeable staff can help guide you in choosing one. D’Vino features several tasting experiences that highlight the region’s star wines: the Konavle Valley’s refreshing Malvazija, potent Plavac Mali reds from the Pelješac Peninsula, and Korčula Island’s fruity Pošip whites. Pair the wines with a platter of prosciutto and Croatian cheeses for a wonderful welcome to Dubrovnik and its wine region.

Located along the eastern border of the four-million-acre Tasmanian Wilderness World Heritage Area, the island’s first national park mixes swamp gums, stringybarks, and massive tree ferns with snow gums and deciduous beech trees at higher elevations. Depending on the season, you might walk the suspension bridge to the three-tier stunner Russell Falls or take the Pandani Grove walk around Lake Dobson—keep your eyes peeled for platypus. In winter, skiers, snowboarders, and backcountry trekkers can explore the lakes and glacial terrain of the Tarn Shelf. In autumn, the same area blazes red and orange on hikes to the Twilight Tarn Hut, an unofficial ski museum. Five other huts offer basic accommodation year-round at 3,280 feet.

An hour’s cross-island drive takes you to Kalinago Territory, officially established in 1903 as the Caribbean’s only autonomous enclave for indigenous people. The settlement covers six square miles, and many of its 3,000 inhabitants live in traditional wooden huts. Guests are welcome at a model village, where they can watch dance performances and shop for reed baskets and other crafts.

After driving just over six hours from Denver into the northern reaches of Wyoming, I needed to crash for the night. Taking the Buffalo (population 4,585) exit off the interstate, I cruised towards downtown passing a Holiday Inn Express, a Super 8, and a Day’s Inn. Did I really have to spend the night in a modern matchbox of a room? No, in fact, I didn’t. I used one of my lifelines and called a friend, asking her to do a quick Google search. Bingo! She said, “Go to the Occidental!” almost in the same tone Horace Greeley had uttered, Go West, young man.” In the front window, a sign read: “Wireless in 1880 and still wireless. Internet in all rooms!” I opened the front door and walked directly into the 19th century – a Tiffany chandelier, an embalmed moose head, and a roaring fireplace in the lobby of this 130-year-plus historic hotel. According to the owner, the Occidental’s been witness to a parade of Western icons: Butch Cassidy, Calamity Jane, Buffalo Bill, Owen Wistler, and Teddy Roosevelt. I kind of liked the idea I’d be sleeping under the same roof, as had this gang of five. Fully restored in 2007, the names of the rooms themselves conjure up another era: The Bordello, Cowboy Bunkhouse, and Madam’s Retreat, to name a few. I happily wound up in the Cottonwood Suite, boasting a four-poster king bed, an ensuite bathroom, and dressing room. Twenty-first century comfort amidst 19th century antiques. If you’re in the area, this is the place to spend the night.

The centerpiece of Turks and Caicos is Grace Bay, on the island of Providenciales (known locally as Provo), where the miles-long sugar-sand shore routinely tops “best beach” lists for the Caribbean and the world. The inland area along this stretch of northern shoreline is where you’ll find most of Provo’s hotels, shopping, and restaurants. Grace Bay is part of the Princess Alexandra National Park. It has calm waters and a sandy seafloor with no rocks or corals to step on, making Grace Bay the perfect place for swimming, splashing along the shoreline, parasailing, and stand-up paddleboarding.

Expect no less than over-the-top extravagance at Laucala, a resort island in Fiji with its own rental submarine. Bring friends: The island has 25 villas spread out over 4.6 square miles, with a rain forest, beaches, cliffs, a lagoon, and one of the island’s highest hilltops literally in their backyards.

A private-island resort six minutes by boat off the coast of Antigua, Jumby Bay is one of the Caribbean’s top luxury, all-inclusive stays, and one of its most environmentally aware. A $28 million renovation in 2010, which included the addition of 28 suites and a first-ever spa, gave it all the digital-age essentials: 42-inch flat-screen TVs, iPod docking stations, Bose sound systems, free Wi-Fi. Yet its underlying spirit of environmental responsibility, highlighted by its hawksbill sea turtle preservation program and its banishment of wheeled vehicles except for golf carts and bicycles (every room comes with two bikes), continues to reign. Rosewood manages the resort, but it belongs to an association of island homeowners, some offering their properties for rent. So if, say, a 1,346-square-foot beach-view pool suite isn’t big enough, it is possible to do as celebs such as Hillary Swank, Jim Carey, and Paul McCartney have done and plop down up to $20,000 per night for a private villa or estate home. Couples can be perfectly content here, but it is especially attractive to families, who appreciate programs like the Rose Buds kids’ club.

Serenity is easy to come by on the private-island resort of Petit St. Vincent, a 115-acre property from the 1960s. It recently underwent a multimillion-dollar renovation but retains its original charms—there are no cars or in-room televisions (and don’t even think about WiFi) in the 22 cottages and suites, and anything you might need arrives at your doorstep with the simple raise of a yellow flag. A Balinese-inspired spa soothes the body, while two open-air yoga pavilions quiet the mind. If you’re looking for more action, you can explore the island’s pristine reef formations with expert divers through Jean-Michel Cousteau’s only Caribbean scuba center, or rent one of four yachts to catch local mahi mahi—then have the chefs prepare it for you beachside back at the resort.

Why we love it: A sleek property with the perfect combination of comfort and upscale amenities

Highlights:
- Gorgeous views of Dominica’s northern coast
- An emphasis on adventure travel
- Smart design that incorporates local art and products

The Review:
At Wanderlust Caribbean Boutique Hotel, five tropical-themed condos overlook Hodges Bay on Dominica’s rugged northern coast, near the village of Calibishie. Each room features a private oceanfront balcony for taking in the views, complete with a sunbed, hammock, and small table crafted from wood from the surrounding forest. Also included are a kitchen and sitting area, plus a spacious bathroom with a powerful shower. Expect tropical hardwood accents, plus bright pops of local art reflecting the ocean and island life. Two of the condos have air conditioning, and all boast fans and louvered windows with mosquito screens. Amenities like free Wi-Fi, high-quality linens, and in-room dining plush up the experience, while details like refrigerators, board games, DVDs, and Dominican coffee make guests feel at home.

After a rebranding, Wanderlust now focuses on pampering adventure travelers. Owners Tom and Sharie Decherd—longtime Dominican residents—offer guided tours, but are also content to let guests do their own thing. Within walking distance, you can swim at four pristine beaches, explore red volcanic cliffs, kayak a river, and hike in a rainforest. Other area highlights include a fishing village, art gallery, and chocolate factory. Back at the hotel, savor the stunning coastal vistas, along with delicious food, in the terrace cafe and rooftop bar. If you’re a Pirates of the Caribbean fan, be sure to look for Treasure Island just offshore. Note: Unsuitable for guests with disabilities, the hotel welcomes children aged 12 and above.

This property is currently closed for hurricane-related repairs.

Peter Island is “an oasis of tranquility,” known as much for its five flawless beaches as its word-class spas and luxurious ocean view villas. The island is the largest of the private islands and the fifth largest of the 60 islands in the BVI. Visitors can hop a ferry to reach the island from Tortola or opt for booking a helicopter, water taxi, or private yacht.

Off the coast of Port Antonio is a small, uninhabited plot called “Pellew Island,” otherwise known as “Monkey Island"--there used to be a colony of imported monkeys here. To get here, you could first head to San San Beach, a beautiful and private stretch open daily (10 a.m.4 p.m daily, US$5). Rent a kayak and snorkel gear and make your way over to the small plot, within clear view ahead. The island is completely covered in vegetation, there’s a small white sand beach, and the waters are shallow. Rest your kayak on shore and snorkel around the island for as long as you please. Visibility is incredible and this is one of the best snorkeling spots in the area. Just watch your step if you’re barefoot, as there can be sea urchins on the seabed.

Once summer has arrived in all her glory, city folk yearn to escape the concrete jungle. The cheap and chic solution for locals is to pack a picnic and head for a beach day on the Toronto Islands, just a short ferry ride away. Of the three primary islands, all of which are connected by paths and bridges, Centre Island boasts the highest number of visitors; people head straight to its main strip to get to the beach and the amusement park. Ward’s Island offers more charm: In addition to the sandy shore, there are small summer cottages and gardens. Those intent on exercise can rent bicycles or paddleboats.

A tiny, man-made island in Clifton Harbour built with discarded conch shells, Happy Island is really just a small bar where you can tie up for a while and have a drink, a meal, and a conversation with Janti Ramage, the island’s joyful builder, owner, and operator. Just be sure to call ahead, as Ramage keeps flexible hours.