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The Diamond Deluxe is a multifaceted property that offers a laid-back take on European upscale properties in paradise. The main feature of the place is a idyllic collection of large pools that cluster within its center. Bridges crisscross these expanses of blue leading the way to beautiful boxes basking under the bright Grecian sky. I recently stayed in one of the Diamond Suites which also comes with it’s own decent sized private pool. (Though gardeners were prone to passing by at odd times of day.) The room was well outfitted with spacious showers, plush beds, and competent air conditioning. (In contrast to the high temperatures outside, the internet was positively glacial. Pretty much unusable.) Being prone to typical Euro qualities, don’t expect the best dining experiences or consistent service. (Some employees were great! Others, not so much.) Alcohol is also best procured elsewhere if you’re hoping for a late night by the room. Oh and on some sites I’ve read it was “overlooking one of Kos’s best beaches.” This couldn’t be further from the truth. You will need to travel to get to a great beach. I recommend renting a car. Driving is easy on Kos. All that said, the property to beautiful, bright, blue, and best enjoyed with a laid-back attitude.

Not every celebrity who visits Harbour Island stays at the Pink Sands Hotel. Bill Gates, for instance, has his own home on the island. But Keith Richards has checked in here, as have Martha Stewart and Kate Moss. Since its opening in the 1950s, the 25-room hotel, like the island itself, has been a low-key enclave of the rich and famous, drawn not just by the like-attracts-like vibe (one of the previous owners was Island Records founder and Bob Marley “discoverer” Chris Blackwell), but by its location on Pink Sands Beach, widely considered one of the world’s prettiest. Accommodations are in plush one- and two-room cottages that have king beds and ocean or garden views; some have outdoor showers. Reserve a table at the British-colonial–inspired Malcolm 51 for island-style bouillabaisse and charred octopus salad, but don’t get too carried away with the sundowners. All manner of aquatic activities (snorkeling the nearby coral reef, bonefishing in the shallows, or merely swimming in the heated freshwater pool) await in the morning.

It’s easy to see why Jade Mountain is consistently ranked St. Lucia’s most romantic hotel. Rising high above the sea and offering an unparalleled view of the Pitons, the hotel features adults-only rooms with an open concept (the so-called “sanctuaries” are missing a fourth wall), equally dramatic alfresco baths, and private jewel-toned infinity pools with otherworldly vistas. (The resort was also the backdrop for a season finale of The Bachelor.) James Beard Award–winner Allen Susser prepares the food of love in the on-site restaurant using ingredients cultivated in the resort’s private organic farm, and a rotating schedule of weekly classes, from rum tastings to a tandoori cooking lesson, encourages shared experiences. Guests also have access to the rendezvous-worthy beaches and spa of sister property Anse Chastanet, located just down the hill.

From this 900-foot-high viewing platform—equipped with a telescope, map, and signage—you have a panoramic view of the majestic Mesopotamia Valley (“Mespo”), home to St. Vincent’s fruit, vegetable, and spice crops. A sea of green expands in every direction, bordered by the blue Caribbean far to the south and the mist-shrouded Grand Bonhomme Mountain to the north. It’s the perfect spot to soak up St. Vincent’s rich natural beauty—and to catch a cool breeze.

The Caribbean’s first long-distance hiking trail runs 115 miles south to north. Fourteen segments break Waitukubuli into manageable day hikes—important for rule-followers, as camping is tolerated but not technically legal in Dominica’s reserves and national parks. Brace for lofty peaks, precipitous valleys, and riotous tangles of rain forest vegetation on this trek, which bears the island’s original indigenous name, meaning “tall her body.” Consider hiring a local guide for expert advice on trekking the steep, corrugated landscape, which Christopher Columbus once described by simply crumpling up a ball of paper.

With its Spanish moss-draped oak trees and beautiful stucco buildings, the College of Charleston‘s campus is long on atmosphere and makes a great place for a stroll. Randolph Hall, a magnificent edifice built in 1828 and one of the six college buildings on the register of National Historic Landmarks, has appeared in movies from The Patriot to Dear John, and in the Civil War miniseries North and South. Also of note, the President’s House, once the parsonage of St. Philip’s Church, is the oldest building on campus.

Hotel Atarazana is a simple, airy, and clean hotel a stone’s throw from Plaza España at the north-east of Santo Domingo’s Zona Colonial. There is a cute walled courtyard where you take breakfast, and an open rooftop (with some shade) for sunbathing, reading, and rum; drinking water is included; and the staff are friendly and some speak English. All the Zona Colonial’s sights are within easy walking distance; the pedestrianized El Conde is a ten minute saunter south. (Note: The hotel is so close to the bars / clubs off Plaza España that it can get noisy at night.)

Located on the Samaná Peninsula, 300 feet above Playa Cosón and the Atlantic Ocean, this 18th-century, plantation-style home impresses with Victorian trim and wraparound terraces perfect for sipping cocktails in the shade. Inside, antiques from Asia, Europe, and Turkey; rugs from Istanbul; and details like Brazilian hardwood floors and French doors add further charm. The six guestrooms, all housed on the second floor, feature four-poster beds, mahogany soaking tubs, and private terraces—rooms 5 and 6 have the best ocean views.

Breakfast and dinner are served on vintage china in the main house, while lunch takes place a seven-minute shuttle ride away at the Beach Club. This is where you’ll also find the inn’s pristine beach, a nearly 90-foot stretch of sand that’s mostly empty, great for swimming, and considered one of the country’s best places for kiteboarding. When you’re not lounging here, visit the town of Las Terrenas (just 10 minutes away) or try to spot the humpback whales that migrate from as far off as Greenland and Iceland to mate and calve in the warm waters surrounding the Samaná Peninsula (every January through March).

White Elephant has been a Nantucket landmark for nearly a century, with more rooms than a typical inn but without sacrificing the intimacy and personal service of a small property. Located on the waterfront a short walk from Brant Point Light, the inn has a sprawling lawn with chaises for relaxing, as well as shuttle service to the area’s beaches. Accommodations range from king-bedded guest rooms (each with a private balcony or patio) in the main inn building to spacious garden cottages (some with kitchens and fireplaces) and penthouse-like lofts in downtown Nantucket. A small spa offers therapeutic massages, facials, and body treatments. A luxury resort that is truly family-friendly, kids and babies can get fully kitted out for bath time, mealtime, or beach time with a wealth of amenities and toys. The Brant Point Grill is a local favorite for an al fresco lunch, lobster dinner, or Sunday brunch (complete with Bloody Mary bar). The White Elephant also provides regular transfers on the 21-passenger boat, Lady Wauwinet, to the Wauwinet Inn’s restaurant TOPPER’S, which cultivates its own oysters.

Hugging the golden crescent of Playa Conchal on Costa Rica’s northern Pacific Coast, the 2,400-acre Westin Playa Conchal is an all-inclusive (Westin’s only one) that has put great care into navigating the needs of both families and guests who prefer a more peaceful experience. A kid-friendly club features designated suites, all-day assistance of a “family concierge,” and exclusive activities, while the adults-only Royal Beach Club is almost a resort-within-a-resort, with its own lounge and private pool. Both have access to the greater resort, including the huge lagoon-style pool with swim-up bar, Jacuzzi, 10 restaurants and five bars, and the fitness club. All of the rooms and suites have balconies or terraces, and the Royal Beach Club suites also have a large outdoor tub. Guests also have access to the par-71 golf course designed by Robert Trent Jones, Jr.

A collection of rambling beach bars, The Strip on South Frigate Bay is the best “lime” on St. Kitts—a beach bash by day that transitions to an open-air dance party, moveable feast, and pub crawl by night. The area is within walking distance of the St. Kitts Marriott Resort, but it’s a popular nightlife destination for locals and visitors from all over the island. Don’t miss Mr. X’s Shiggidy Shack, the most famous bar on St. Kitts, where you can enjoy grilled lobster alongside an ever-changing lineup of live entertainment, from karaoke to fire-eaters. Also worth visiting are Vibes (St. Kitts’ closest thing to a sports bar), ChinChillas (for Mexican food), and The Dock Bar, which offers a more relaxed scene and, as its name suggests, its very own dock. Wherever you land, expect live bands and DJs to keep the dance floor hopping well into the wee hours. If you get tired, cool off and then rev up with a “Ting with a Sting,” a popular drink of local CSR rum mixed with grapefruit soda.

Straddling Cancun’s sandy beach in the heart of the Hotel Zone, the CasaMagna Marriott Cancun Resort features 450 re-modeled rooms and suites with balconies with ocean views. The AAA Four Diamond-award winner houses a wide selection of restaurants and bars, offering Argentine, Japanese, Southwestern, Italian or Thai cuisine. La Isla-Pool Bar serves poolside snacks and drinks in a family setting, while Bahia dishes up fresh seafood on the beach. Las Ventanas Lobby Bar is the place to meet for drinks and appetizers and enjoy nightly entertainment, while Las Ventanas Gift and Coffee shop offers “grab and go” and late night snacks. A full-service fitness center, pool and onsite tennis and water sports complete the recreational package. The Marriott Kid’s Club offers entertainment for the younger guests. High speed Wi-Fi is available in rooms and public areas throughout the resort.

Being a guy from the Jersey Shore (which has nothing to do with that television show!), I love the sea front. The seaside resort of De Panne in Belgium is a place worth visiting. Sure, Belgium is usually rainy and cold but there are hot sunny days too, so it is advisable to hit the coast and check out De Panne. Its a typical Belgian seaside resort with lots of cafes and restaurants and a very big sandy beach. What I like about De Panne is the old style mobile cabanas, which were once popular along the Jersey Shore going back a century. The town was also the home of Belgium’s King Albert during WWI, since it was the only area that was not occupied by the Germans.

While pensions in French Polynesia are often touted as overpriced accommodations with no amenities, Fare Pea Iti proves this is not always true. In fact, this family home pension is downright luxurious, with an in-ground pool, well-manicured grounds and a mix of beach and garden bungalows featuring sumptuous amenities and whimsical touches. The beach bungalow is particularly opulent. While in the bathroom you’ll find Monoi oil body products and an over-sized walk-in tiled shower, the enclosed porch features beautiful views, self-catering kitchen with barbecue and mini-bar. In the room, the bed is adorned with tropical flowers and canopied with delicate baldaquin. Moreover, the garden bungalows offer comfortable beds, televisions, Monoi oil tiki soaps, a walk-in shower, mini bar and table and chairs in the garden for scenic relaxing. Don’t miss the fantastic homecooked meals in their open-air restaurant and bar. In the morning there’s an artisanal breakfast of hot beverages, fresh juices, fresh tropical fruit, homemade vanilla yogurt, fluffy bread and housemade jams with large chunks of fruit. Moreover, at night guests can enjoy a 3-course candlelit dinner featuring fresh local ingredients.

This sprawling resort features three luxury properties on one Nusa Dua site: the Mulia, the Mulia Resort, and the top-tier Mulia Villas. Choose a full board or half board package for an all-inclusive experience, complete with butler service (at the Mulia and Mulia Villas) and access to nine different dining venues and bars; there are also beach-level pools—one of them resembling a statue-lined Roman bath—and rows of umbrellas on Bali’s eastern shore. The villas feel like traditional Balinese homes, with indoor-outdoor living rooms that have hydrotherapy pools as well as views of colorful gardens or the Indian Ocean. And the spa is one of the most outrageous wellness temples in Bali, featuring a Finnish wood sauna, aroma steam room, and the region’s only ice fountain.