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A stroll of St. Kitt’s capital, whether started at Port Zante Marina or the centrally located Independence Square, is an entertaining way to learn more about the island’s past. While the French named Basseterre (it means “low land”), the British are responsible for the town’s most recognizable landmark—the green, cast-iron Berkeley Memorial Clock in the center of the Circus, where several streets intersect. Make sure to visit the area, as well as Independence Square, St. George’s Anglican Church, and the Old Treasury Building, which now serves as the National Museum of St. Kitts. Along your walk, you’ll also find duty-free shops and local boutiques, plus a lively produce market by the waterfront if you come on the weekend.

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.

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.

Built between 1914 and 1916 on an octagonal base, this stone, double-lens lighthouse is Aruba’s marquee landmark. Standing tall at 98 feet, it’s the highest structure on the island and offers the best views in its respective area. It gets its name from the SS California, a British steamship that sank in nearby waters in 1891 and now functions as a fantastic dive site. Adjacent to the lighthouse, visitors will find a beloved Italian restaurant and the California White Sand Dunes, a hot spot for dune surfing.

Many islands have laws with steep fines against wearing beach wear when not on the sandy shoreline and while you may have heard of folks going au-naturel on St. Martin, that’s certainly not the norm throughout the region. On St. John, however, things were a little different. About a mile walk from a parking lot on the edge of Cruz Bay along what’s called the Lind Point Trail, through typical island bush and over a hill and down through more bush past a fork (where either choice gets you to the same place) intrepid travelers are rewarded with a tiny strip of sand, only around 25 yards long, unofficially known as the island’s only nude beach: Salomon Beach. I’ve been to this secluded sandy alcove a number of times and without fail the maximum number of sun worshipers was never above four or five. In fact, most times, the beach was deserted. So, for years this is where those with a passion for enjoying nature to the fullest could go to let it all hang out in relative privacy… Until recently. Since my last trip to Salomon Beach back in 2007, there’s been a crackdown on this unofficial naturist haven. Suddenly being a free spirit isn’t so free due to the stiffness of fines—around $110 for those caught with their pants down (so to speak). But, hey, doesn’t mean you can’t press your luck!

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.

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.

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.

Wherever your travels may take you around the world whenever you ever see anyone sporting this distinct hook bracelet, you’ll know they possess a special place in their heart occupied by the island of St. Croix. There are many, many imitations and evolutions of the Crucian hook bracelet (some better than others), but this is the original and, in my opinion, only truly authentic version. Pick one up and Sonya’s, wear it wherever you go and you’ll be surprised how many new friends you make.

Located in the middle of New York harbor, less than half a mile from Manhattan (and even closer to Brooklyn), 172-acre Governors Island feels like a world unto itself, far from the bustling city. It has played a key role in the defense of New York at various points and two fortifications here, Fort Jay and Castle Williams, reflect that history. From 1966 to 1996, the island was a Coast Guard station; since it closed, the city, state, and federal governments have discussed various plans for the island’s development. In the meantime, it is open to the public for six months each year, from May 1 to October 31, when it is possible to wander among the Coast Guard barracks, visit the commander’s house, and bike around the mostly car-free island. Ferries depart from both Manhattan and Brooklyn starting at 10 a.m. and running until 6:15 p.m. on weekdays and 7 p.m. on Saturday and Sunday. During many weekends in the summer, art fairs, food festivals, and other events help draw visitors to the island, but even if you go on a day without anything special scheduled, a journey here provides a refreshingly different perspective on New York.

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.

Mandarin Oriental’s first Caribbean resort has all the amenities you’d expect from the luxury brand—with the price tag to match. Nestled within lush greenery overlooking the white sands of Godahl Beach, the 26 suites and villas, which sit on the grounds of a 1,200-acre estate on the island of Canouan, are elegantly appointed with modern furnishings, marble baths, and rosy accents befitting the hotel’s name. Here, though, it’s all about the public spaces, including a Jim Fazio–designed golf course overlooking sparkling blue waters, a hilltop spa specializing in island-themed treatments, and four elegant restaurants serving every kind of cuisine, from pan-Asian to Italian. At Turtles, a cocktail lounge straight out of the Hamptons, opt for the Pepper Bliss, made with rum, bell pepper syrup, and pineapple juice.

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.

Opened in 1962, Curtain Bluff is Antigua’s oldest luxury resort, and one of the island’s finest. It is the kind of place guests return to through the generations, with the same expectation of timelessness they’ve experienced for as long as they can remember. Located at the southern end of the island on a promontory that divides an often roiling Atlantic from a much calmer bay, the resort offers sea views from every room, two beaches, a top-notch tennis center, a pair of restaurants that can boast one of the Caribbean’s most outstanding wine cellars, and a staff whose commitment has often been passed from parent to child. And except for spa treatments, a premium bottle of wine, and the occasional Cuban cigar, there is little that’s not included in the rate, making a stay a better value than the price might at first indicate.