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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.

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.

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.

In 1911, American star jockey Tod Sloan took a bar in Manhattan, dismantled it, and shipped it to Paris. At the time, American tourists and members of the artistic and literary communities were beginning to visit the City of Light in ever-increasing numbers, and Sloan wanted to capitalize on his fame and make the place a spot where expats would feel at home. Over the years, Harry’s New York Bar has been frequented by a number of famous Americans and international celebrities, including Sinclair Lewis, Ernest Hemingway, Coco Chanel, Jack Dempsey, Rita Hayworth, Humphrey Bogart and the Duke of Windsor. Whether or not you have star status, you can still settle in on a stool with a drink and soak in the history.

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 city within a city, Makati is Manila’s poshest shopping, business, and nightlife district. At the Makati Shangri-La, guests have amazing access to—and respite from—all of the above, including the malls that have made the neighborhood a retail pilgrimage site. After settling in, walk over to Glorietta, where you’ll find everything from high-end beauty boutiques to a family-run pawn shop and multiple Starbucks for good measure. Some of Manila’s best restaurants are also located in Makati, but the Shangri-La’s own Shang Palace is so beautiful and beloved, you won’t want to miss the experience if you have even the slightest interest in Cantonese food. As for the aforementioned breathing space on the guest floors, it starts with the waterfall you’ll pass en route to your room and ends with the custom-appointed bed in your plush, spacious surroundings. Go for one of the Deluxe Suites and you’ll also enjoy panoramic views of the bustle you’ve just left behind.

The undisputed grande dame of Filipino hospitality, the Manila Hotel has so many tales to tell that even Hemingway was impressed. “If the story’s any good,” he’s reported to have said, “it’s like Manila Hotel.” The Nobel laureate was but one in a series of visiting dignitaries, from military brass (General MacArthur took up residence in 1935 and left shortly before Japanese troops occupied the property in the ’40s) to Hollywood A-listers (including Douglas Fairbanks, Jr. and Sammy Davis, Jr.) to rock stars (when the Beatles notoriously snubbed Imelda Marcos by accident in 1966, they stayed here). The hotel has had plenty of cosmetic work done as well, including a dramatic renovation for the 2012 centennial festivities. So while you can still stay in, say, MacArthur’s quarters (known as the MacArthur Suite), the bathrooms now come with Bulgari toiletries and the bedrooms with HDTV. There was little the hotel could do to improve upon the already amazing bay views, as you’ll see from the suite’s dining room windows.

The soft, gold sand of Batibou Beach stretches along Dominica’s northeast coast, where the Atlantic is calm enough for swimming. Visitors and locals alike come here to relax in the shade of towering coconut trees, or sip rum punch in a hammock at the tiny, rustic beach bar. To reach Batibou, walk 20 minutes down a rough, often muddy trail, or hire a roundtrip ride from the Hampstead Country House. If you’re seeking solitude, avoid Sunday afternoons, when the barbecue scene is particularly lively.

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.

San Diego’s first food hall is housed in the city’s former naval training center, a 361-acre site in Point Loma that now features a lively business district with wide lawns, a waterfront park, and historic Spanish Revival–style buildings. Here, vendors serve everything from coconut-curry chicken sausages to ahi tuna poke bowls, providing the makings of a casual lunch or dinner. Take your food to the patio, or sit inside at the high-top tables near the bar and enjoy the untouched murals that line the upper walls. Painted by naval recruits in the 1950s, they depict various vessels, from a late 18th-century sailing ship to a World War II aircraft carrier.

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.

Lime Cay, an uninhabited island about two miles off of Port Royal, is a favorite destination of Kingstonians for white-sand beaches, sunbathing, and swim time. This is an ideal deserted escape on weekdays, and weekends are usually only a bit busier and bring a few vendors. Don’t count on the vendors, though: Bring your own food, water, sunscreen, and snorkeling gear. Wear water shoes, as there can be urchins. To arrange a trip over, ask at your hotel, or inquire at the bar on Morgan’s Harbour called the Y-Knot—they’ll help you find a boat ride or fisherman willing to take you to the island for no more than US$20.

Snorkel, fish, relax and recover while you’re in Panama on Contador Island, in the Pearl Islands Archipelago. These beautiful boats are ready for hire (in hugely affordable fashion) once you’ve left Panama City and landed on this enchanting island. With Air Panama there appear to be two or three short (45 minutes) flights a day that will get you there from Panama City. Be sure to pack your swimsuit, a good book and some sunscreen. This is a very small island and you can explore land on foot or by a rental scooter to see it all. In Spanish, Contador means ‘the one that counts’, and it’s easy to make your day on the island count with a local rental boat. Your captain (that will inevitably also be fishing while you’re moving) are a reliable way to go and find nearby remote snorkel locations. Be sure to agree on the price before you head out for your big day on the water.