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Opened in 2013, Andaz’s first and only Hawaiian property has four cascading infinity pools (plus many more private plunge pools) and an enviable location on Mokapu Beach, meaning guests are never more than a few steps from water.

The 290 rooms and suites are decked out in stylish, contemporary furnishings—some even come with Viking grills on private lanais—and 10 luxurious villas feature up to four bedrooms, with the largest maxing out at a sprawling 4,000 square feet.

The resort’s full calendar of activities offers everything from coconut leaf weaving to kayaking, outrigger canoeing, and stand-up paddleboarding—plus GoPro shooting and editing lessons to best capture it all. At Morimoto Maui, one of four restaurants on the property, renowned chef Masaharu Morimoto combines Japanese and Western influences in inspired dishes like yellowtail “pastrami,” served with a gin-spiked crème fraîche.

At the ‘Awili spa, where guests can choose locally sourced ingredients for a custom body treatment.

Pritzker Prize–winning architect Daniel Libeskind found inspiration in wind-filled sails and the waves off Haeundae Beach when he devised the curvilinear geometry of this 269-room hotel. The interior design includes French oak floors, granite bathrooms with soaking tubs, and floor-to-ceiling windows that afford views of the Gwangan Bridge. The biggest draw is the sun-filled spa. Guests can look out at the city from the indoor swimming pool or indulge in treatments that meld Korean and European beauty traditions. Doubles from $250. 51 Marine City 1-ro, Haeundae-gu, 82/(0) 51-990-1234. This appeared in the October 2013 issue.

One of Cape Town’s most picturesque corners, this small fishing harbor sees boats sail in daily with their catches (often trailed by hungry seals waiting for tidbits). Recently, however, the area has also become known for its antique stores, restaurants, and shops—one of the best collections of African curios, materials, and artwork for sale can be found at Artvark, on the edge of town. Expect to see everyone from hipsters to surfers to an old couple who’s lived here for 50 years. A seaside promenade connects Kalk Bay to the colorful beach cottages of St. James and to Surfers Corner in Muizenberg, another gem of an old-world suburb that is becoming a second Kalk Bay. Don’t miss Cucina Labia, a restaurant housed in a mansion built by an Italian who wanted to create a little Venice here.

This is a great place to spend a free day in Puerto Rico. There are many interpretative trails in this park, and all are free and open to the public. Some lead to caves, others lead to beautiful views.

There are also many covered areas for picnics. The trails are mostly leveled off and easy hikes, although some can be a bit more challenging. Be sure to bring lots of water, as it can be humid. Also, bug spray will be your friend! If you plan to take a trail that leads to a cave, be sure to have a flashlight with you as well.

The vibe in Waikiki is the most frenetic of all the spots in the islands, but there is an escape. The scene at the current iteration of the classic Hawaiian hangout, Duke’s, is a step back even by Oahu standards. Best approached via the beach to enhance the original feel and avoid the mall-like carnival from the street entrance, this is the kind of bar that welcomes sand on your flips. Slip in for happy hour and be prepared to jockey for a spot. Even with the crowd, the music, the food, the drinks are all designed draw you back to a simpler time when Duke was still riding the longboard. I’m partial to the beers and french fries, but will never refuse a fish taco. With a long relationship with the Kona Brewing brand, I opt for the Longboard larger or Fire Rock Pale ale. The umbrella drinks don’t disappoint, but neither do the gin and tonics. The local musical talent that ply the stage at Duke’s are traditional Hawaiian in style and like to keep the island theme front and center. There is a family vibe to the musical community, much like the rest of Hawaiian culture, and it’s not unusual to get a sibling or cousin to come up on stage and do some traditional Hawaiian dance or help out on a song or two. There was an 8 year old girl that got asked to come up on one of our visits and she blew the crowd away! The strip a Waikiki can be a bit daunting in terms of relaxation, but Duke’s remains my refuge from the madness. Aloha.

For those who aspire to travel as trendsetters in Jamaica, it helps to know that Port Antonio, way out on the eastern end of the island, is the destination to head for. And the address to shelter at is the Trident Hotel, whose 13 waterfront villas would not look out of place on South Beach. Nor would the crowd that hangs around its infinity pool or in its restaurant, Mike’s Supper Club, where local musicians and the occasional celeb sit down to knock out tunes on the 1917 Ferrari-red grand piano. The Trident Castle, a kind of fantasy annex, is a former private residence whose grand rooms, sea-view terraces, and dollhouse-size chapel make it ideal for destination weddings. A hard road to get there? Not for guests who avail themselves of the helicopter pad.

The centerpiece of a vast resort, golf club, and residential community complex, Rosewood Bermuda sits on 240 acres of waterfront land overlooking Castle Harbour, Harrington Sound, and the Atlantic Ocean. The recently refurbished resort is anchored by the Manor House, where 88 guest rooms blend classic cottage-style architecture and modern interiors that continue to set the standard for today’s luxury seekers: think canopy and four-poster beds, plantation shutters, and colonial-era antiques, all set against a cool white backdrop. Spring for a deluxe poolside room, which also has access to a private poolside daybed. Just don’t expect too much down time. Three on-site restaurants and two bars are beyond selfie-worthy, treatments at the spa incorporate local ingredients like cedar and juniper, and hotel guests receive membership to the 18-hole Roger Rulewich–designed golf course, tennis courts, and a beach club that sits on an exclusive stretch of pink sand for the duration of their stay.

Despite its size (10 square miles) and population (fewer than 170 permanent residents), Little Cayman enjoys a worldwide reputation among serious divers. The island is renowned for its exceptional underwater visibility and vertigo-inducing walls, especially north-shore Bloody Bay. Dive boats flock to Three Fathom Wall, where bulbous coral heads teeming with fish rise to within 10 feet of the surface. Snorkelers are likely to encounter schools of blue tang and stoplight parrot fish, as well as hawksbill turtles and nurse sharks.

This tiny island is north of Isla Mujeres and Cancun and is only 26 miles long and offers visitors in search of a “Robinson Crusoe” experience the perfect escape. Long, sweeping beaches beckon with water sports, snorkeling, sport fishing, and total R&R. A shallow lagoon gives sanctuary to thousands of flamingos, pelicans and other exotic birds and creatures, allowing visitors the perfect spot in which to commune with nature. Several good restaurants and hotels are available and tours to area attractions can be arranged by ferry and small plane. Getting around the island is via bicycle or golf cart.

One of the few hotels on picture-perfect Grace Bay Beach that can work for both honeymooners and families, Seven Stars sits on 22 acres of lush grounds at the edge of Princess Alexandria National Park and has studio to four-bedroom plantation style suites available. All feel very private. Besides wraparound terraces with awesome ocean views, the rooms here all feature full kitchens, making it easy to cook your own lunch or make snacks for the kids. That said, the house restaurant, aptly named Seven, is very good, so plan on dining here at least a few times. The spa is also excellent - perfect for honeymooners - and there is a dedicated activities concierge that will arrange all sorts of water sports and even a kids’ camp.

While not as large as other ancient Mayan cities in the region, Tulum draws in visitors for its stunning setting of centuries-old temples perched on a cliff by the Caribbean Sea. You’ll pass a large market with souvenirs, a casual Mexican restaurant, and even a Starbucks before reaching the entrance, where a train can take you to the site if you’re not up for the 10-minute walk. It’s advisable to hire a guide to fully understand each structure’s significance and the history behind the ruins; informative signage is all but nonexistent. Don’t forget to bring your swimsuit, as the site encompasses a white-sand beach with soothing waves and beautiful rock formations that’s reached by a long wooden staircase.

From the porte-cochère entry at the Westin Puntacana Resort & Club, you’ll catch an inviting first glimpse of coconut palms, manicured grass, and a long swimming pool that seems to end at the sea. The view only gets better upstairs, where all 200 rooms—including 16 suites—offer swoon-worthy ocean vistas. On the hottest of days, the high-ceilinged, open-air lobby is a great place to hang with a cold one while catching the ocean breezes. When it’s cooler, have lunch by the pool or at the beachside La Palapa, and plan for dinner at the open-air Brassa. As a guest at the Westin, you also have access to Puntacana Resort & Club’s eight restaurants, two golf courses, tennis center, Six Senses Spa, aquatic center, and Grupo Puntacana Foundation activities.

Of the many draws of this upscale property on 26 pine-clad acres, the biggest is arguably its beach, one of the longest private stretches on Lake Tahoe, where guests can relax in cabanas and lounge chairs, rent jet skis, boats, or kayaks, and even stay in one of the 26 luxury beachside cabins. The lobby, with its massive timbers, flagstone walls and fireplaces, and huge windows, recall some of the great National Park Lodges; the rooms, however, are modern and spacious, swathed in soothing neutral colors. (Rooms on the upper levels of the 12-story tower have the best views.) And because the resort resides on the Nevada side of the North Shore, there’s a 20,000-square-foot casino. Other amenities include a spa, fitness center, and an indoor/outdoor swim-out pool that—along with a lazy river and water fountains—is heated year-round, as well as a kiddie pool and two large whirlpools. And no need to leave Fido behind: the resort accepts your furry friends, too.

This 12-cottage luxury hotel, 3,100 feet up in the Blue Mountains, is Jamaica without the beaches. It is the Jamaica of misty mornings, cool, cuddle-worthy evenings, and a musical heritage recognized worldwide. First as a private estate belonging to music producer Chris Blackwell and then as part of his Island Outpost collection of hotels, Strawberry Hill has been a creative refuge for performers including Bob Marley, the Rolling Stones, and Willy Nelson. After Hurricane Gilbert destroyed the estate’s great house in 1988, Blackwell commissioned Jamaican architect Ann Hodges, who specializes in historic reconstructions, to build the cottages, a restaurant, and a pool, which were opened in 1994. Yet despite the rock and roll history, and the hanging with like-minded souls up in the mountain mists, what guests seem to remember most is the far-below views of Kingston, especially at night, when the lights glow and sparkle from what must certainly be another world.

An intimate gem whose only shortcoming (in some eyes) is that it does not sit on Pink Sands Beach, the Rock House Hotel & Restaurant was a labor of love for the late Wallace Tutt, an interior designer to the stars who was best known for designing Gianni Versace’s Miami mansion. Ten individually decorated rooms in the 1940s private home turned boutique hotel echo that property’s grandeur with king size beds and seaside motifs, as well as sumptuous linens and stone lion heads mounted on the walls in the restaurant. But the real story here is the service: There is always a picnic basket on-hand in every room, a library of games and books is available for perusal on rainy days, and the concierge is happy to arrange in-room pampering treatments if the walk to the neighboring spa feels like too much trouble.