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Designed by Oscar de la Renta, who was also a guiding force in the original vision for Puntacana Resort, Tortuga Bay Hotel has 13 freestanding villas comprising 30 suites, each with Frette linens, a kitchenette, and a balcony or terrace with views of the Caribbean or La Cana Golf Club. Hotel guests landing at Punta Cana International receive fast-track passage through customs, pickup by a private driver, personal concierge check-in, and keys to a golf cart for getting to the resort’s Oscar de la Renta Tennis Club, two golf courses, and Six Senses Spa.

On the Dominican Republic’s northern coast, near the tip of the Samaná Peninsula, this unpopulated Atlantic beach stretches three miles from Cape Samaná to the cliffs of Cape Cabrón. To get here, you’ll need to take a four-wheel-drive vehicle or a boat charter from the small fishing village of Las Galeras, but once you arrive, you’ll find a nearly empty stretch of sand. The west end of the beach features calm waters ideal for swimming and snorkeling, while the east end has great waves for surfing. You’ll also find spots to rent kayaks, snorkeling gear, chairs, and umbrellas, as well as a few food vendors serving rice, beans, and seafood cooked over an open-hearth fire. This is the place to go when you want to get away from the crowds.

Both charming and affordable (it doesn’t charge a resort fee), this intimate 37-room property also has an unbeatable central location—near the heart of Old Town and just a few blocks from Duval Street and Mallory Square. Part of the Historic Key West Inns collection, the Key Lime Inn features classic Key West style with a 19th-century main house highlighted by a double-height colonnaded entrance and green shutters. Rooms follow suit with high ceilings and classical proportions, and beds are done up in crisp, white linens; most have sitting areas and private walkouts or porches to encourage lingering. Though short on amenities, the grounds are shaded by tall palms and dotted with Caribbean-style clapboard cottages painted in cheery colors with gingerbread trim, and all offer free WiFi. And if the beach doesn’t call you, a large wood deck surrounds the heated outdoor pool, and hammocks and porch swings are placed around the property for maximum relaxation.

South of San Pedro is the award-winning luxury resort of Victoria House. The plantation style property is unlike any other on Ambergris Caye, offering some of the best views of the Caribbean Sea. Despite being one of the larger properties with 42 rooms spread out over 10 acres, Victoria House is one of the most intimate resorts. A majority of the staff at Victoria House have been there for years and it shows. Their love for Victoria House and its guests is genuine and evident throughout every part of the resort. Look for several dining options on property, including the more casual Admiral Nelson Bar, perfect for daytime dining, and the more high-end Palmilla, an ideal spot for a romantic dinner. Meal plans are available for guests looking for a more all-inclusive experience. Victoria House offers a range of room styles, from staterooms and plantation rooms to private suites and villas. Rates start at $195 for staterooms all the way up to $1,775 for a five-bedroom villa.

Near the pontoon bridge in Handelskade in Willemstad, wooden boats from Venezuela dock alongside the canal, and vendors here sell just-caught fish and tropical fruits and vegetables (plantains, citrus, papayas, avocados) directly from the quay under the shade of tents. Mornings are the best time to visit, for the finest selection of produce, the cooler temperatures before the midday sun shines, and the pleasant ambience of the hours before the crowds arrive.

The Caves, just west of Negril, is aptly named. While the 12 cottages and one villa sit atop honeycombed cliffs, the Blackwell Rum Bar, a private dining venue, and the massage table of the hotel’s Aveda Concept Spa are actually in underground grottos open to the sea. The setup is very Treasure Island, and the flicker of candlelight and the echo of waves off cave walls make it uniquely romantic. Each of the thatch-roofed cottages is as colorful as a paint box, and each gives a sense of being alone at the end of the land. This is one of music mogul Chris Blackwell’s Island Outpost properties, so the vibe at the Jacuzzi, sauna, or salt-water swimming pool is hip but relaxed. Although famed Seven Mile Beach begins almost where the cliffs end, the hotel itself has no beach, which is why a tradition at the Caves is to begin the day by jumping from the cliffs into the usually calm Caribbean below—or at least thinking about it.

This open-air bar and restaurant is right at the ferry dock in the heart of Cruz Bay. It’s a great spot to have lunch between island adventures, or just to grab a drink and enjoy some people-watching along the dock. The menu lists barbecue ribs, fish tacos and Caribbean-style roti, as well as a variety of sandwiches and salads.

Creamy travertine floors and castle brick walls of pearl-stone tiles fuse with Asian antiques and dark teak furniture in the Caribbean-meets-Indonesian design at Villa Balinese, on an elevated crescent fronting Providenciales south shore. From the original local art to the antique Moroccan vases and curved bamboo chairs, it makes a bold and seductive statement throughout -- and best of all, every piece of furniture in this villa rental is hand-picked and meticulously placed by its owners. With just three bedrooms, but 4,200-sq-ft of space and 30-foot vaulted ceilings, it’s impossible not to be transfixed by the Alice-in-Wonderland dimensions and sexy stark vibe encountered here. Entering the grand entrance foyer, the eye is drawn almost immediately to the impressive sunken living room, where a wall of floor-to-ceiling glass windows slides open onto a grand marble pool terrace with panoramic ocean views. The infinity pool running the length of the house was constructed with emerald-colored tiles, creating a vibrant contrast with the turquoise-hued sea it disappears into. A 50" plasma TV, which can be raised with a remote click from a recessed hiding place and swiveled to face the pool, is another one-of-a-kind design example. There is no beach access on-site, but the crystal-clear sea running parallel to the property can be reached via a ladder dock. Please note that children under 12 are not allowed, but this property works great for couples or older families.

One of the Dominican Republic’s finest museums can be found in its second-largest city, Santiago de los Caballeros. Centro León, a philanthropic project run by the Grupo León Jimenes tobacco company, focuses on Dominican culture, showcasing everything from historical displays to contemporary art. Learn about the island’s ecosystem, history, and people, then browse work by noted Dominican artists. In a separate building is an exhibition about the founder of Grupo León Jimenes and his family business. For a souvenir, be sure to stop by the excellent gift shop, which features a wide selection of books on Dominican history, art, culture, and food.

Remote and difficult to access, this three-mile beach on the Dominican Republic’s southwestern Caribbean coast (15 miles from Pedernales and close to the Haitian border) is also blissfully uncrowded. Playa Bahia de las Águilas, which translates to “Bay of Eagles,” can only be reached via a four-wheel-drive vehicle on an unpaved road, or a 15-minute speedboat ride from the little village of La Cueva at Cabo Rojo. Once there, however, you’ll discover a pristine beach, bordered by rocky cliffs and free of any hotels or restaurants—the beach is located in the Jaragua-Bahoruco-Enriquillo Biosphere Reserve, so building is forbidden. Turquoise water laps the white sand, while well-preserved coral reefs wait just offshore. Don your mask and snorkel to see starfish, sand dollars, and maybe even a manatee. Also remember to bring water and sunscreen as there’s virtually no shade, and pack lunch or plan to eat in nearby La Cueva.

Just a few blocks from the bustle of Old Town and Duval Street, this Caribbean-style resort is a serene retreat with a swath of white-sand beach, a pool concierge, and a private pier for fishing or gazing out over clear turquoise waters. All of the contemporary rooms and suites are generously sized and have private balconies with views of the pool, courtyard, or ocean, but the real draw remains right outside your door. Guests can snorkel off the shore, face off on the giant chess board, or simply sway between two palms in one of the beachside hammocks. They also have privileges at sister resort Casa Marina, just up the beach, including at the oceanfront Spa al Mare. Have kids in tow? The hotel offers a full roster of activities, plus babysitting services for parents who want to hit the town.

Though it lacks a beach, this family-owned and professional diver–managed resort on the rocky coast just south of George Town has direct ladder access into the Caribbean. Grand Cayman’s two famous underwater sites, Eden’s Rock and Devil’s Grotto, are just a short swim away, and boat trips offer the option of two daily dives (including night dives). Images by some of the world’s most respected underwater photographers decorate many of the tiled and comfortable smoke-free rooms, some of which have kitchens and private balconies or terraces. The vibe is laid-back; post dive, guests sit by the pool or swap stories at the palapa bar, which has the island’s best sunset vista. Managers Anne Briggs and Lisa Evans, the granddaughters of Sunset House’s founders, make sure everything runs smoothly and ensure visitors explore the best of Grand Cayman both on shore and underwater.

By law, every beach in Antigua is public. But at this all-inclusive resort surrounded by 140 acres of undeveloped land on the island’s west coast, guests feel “their” beach belongs almost exclusively to them. The hotel is a 35-minute drive from the airport, and it’s accessed by an unpaved road. Seclusion is a big part of the appeal at this adults-only (except in July and August) hideaway. Its 27 minimalist but spacious cottage suites begin on the beach and are scattered up a hillside that overlooks a picture-perfect bay. All the cottages have outdoor showers, king-size beds with mosquito netting, and at least a partial view of the sea. Expect to see a lot of honeymooners and other romantically inclined couples here, but don’t expect to see much of them, except at meal times, when the foodie-approved mix of European, American, and Caribbean dishes draws out even the most recently married.

Barefoot Bar is a place that’s known for just that: bare feet. Located on the shores of the Caribbean Sea, Barefoot is a Placencia staple where locals and visitors mingle, drink, and eat great Belizean food. The bar is known for the lobster grilled cheese—a huge grilled cheese sandwich stuffed with catch-of-the-day lobster. Buy two: one to eat now, and another to bring home for later. Barefoot also makes perfectly crispy salbutes, which are a great tacolike light lunch to go with your $3 drink special.

The moment you walk into Buba’s, you feel like family. It’s easy to understand why when you consider that surrounding this blink-and-you’ll-miss-it hillside restaurant are Buba’s house, Buba’s sister’s house, and Buba’s Brother’s house across the street. Buba’s own two daughters, nephews, cousins, and other miscellaneous family either host, help in the kitchen, play dj, man the bar, or simply greet visitors from their porches with welcoming, West Indian waves. This homegrown approach extends beyond hospitality to deliciously impact the food as well. Nearly every fruit, vegetable, and herb used in the dishes at Buba’s are all grown on the sloping overgrown gardens surrounding the restaurant. The result is a quintessential island restaurant with no real set menu. Instead, expect the freshest ingredients of the day lovingly coaxed into a collection of authentic Caribbean fare like rice and peas, stew chicken, steamed veggies, salad, and more.