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  • Mongoose Jct, St. John, VI 00830
    The home of St. John Brewers, among the leaders of the recent craft-beer revolution in the Caribbean, is a must-stop for all beer lovers visiting St. John. At the Tap Room, you can sample the brewery’s very latest beers, sometimes even while they’re in mid-development. Look for a plain black tap among the lineup of more colorfully ornate ones behind the bar. New beers in development are often available there. Feedback from customers goes into finalizing the brews.
  • 1000 El Conquistador Avenue
    As of May 2018, El Conquistador Resort and Las Casitas Village are closed indefinitely, due to damage sustained during Hurricane Maria.

    Situated atop a 300-foot bluff on the eastern tip of Puerto Rico, El Conquistador Resort, a Waldorf Astoria Resort, spreads across 500 acres overlooking the converging waters of the Caribbean Sea and the Atlantic Ocean. A stay at El Conquistador is a transformative experience. Guests can relax at the Eucalyptus steam room, enjoy exotic cocktails while gazing at the El Yunque Rainforest, or even kayak around a private island. Guestrooms and suites are divided into five villages, and feature ocean views, 23 restaurants, an 18-hole golf course, a state-of-the-art aquatic playground/water park for families, and the resort’s private island, Palmino Island, featuring water sports and white sand beaches.
  • John Hodge Rd, Meads Bay 2640, Anguilla
    Straw Hat, on quiet Meads Bay, is an established favorite with over 20 years to its name. Its creative menu of Caribbean cuisine with a twist will have you returning to this beautiful indoor-outdoor beachfront restaurant. It’s the perfect spot for a meal and an afternoon on the sand, or for watching sports. Try the ceviche of red snapper, the bigeye tuna flatbread, or the grilled crayfish with Anguillan rice and peas, among many other picks.
  • Southwest of Anguilla is one of the island’s top three beach areas: the two-mile-long brilliantly white stretch at Rendezvous Bay. Its long shore, steady breeze, and calm Caribbean waters provide a break from the crowds at Shoal Bay and Sandy Ground. The western end does offer some fun daytime beach-bar action, which grows rowdier at night and on the weekends, when the famous Bankie Banx’s Dune Preserve venue attracts residents and visitors for live music. You can view St. Martin, across the channel, from shore.
  • The colonial town of St. Pierre, on Martinique’s west coast, has a colorful past. Rich from the earnings of the sugar and rum trades, it was once considered the Paris of the Caribbean—until 1902, when it was destroyed by the violent eruption of the island’s largest volcano, Mount Pelée. A volcano museum in St. Pierre displays items plucked from the rubble and historic photos of the town before and immediately after the eruption. Today, the fine church with historic displays bears testament to the town’s comeback.

  • North Hill Village 2640, Anguilla
    If you’re a major foodie, or if you just want a romantic dinner night, Veya is one of the best picks on Anguilla. Set above Sandy Ground, this home-turned-restaurant serves up Caribbean fusion food in a Moroccan-style lounge, and outdoors on a veranda. The breeze, the candlelit atmosphere, the live music—not to mention the menu (which the restaurant describes as “cuisine of the sun”)—more than make up for not being directly next to the sea. Expect unusual dishes like Moroccan-spiced shrimp “cigars,” grilled jerk-spiced tuna with a rum-coffee glaze, and risotto with basil goat cheese, or try the five-course chef’s tasting menu. Veya is also known for whipping up the best desserts on Anguilla, and the list of options is long.
  • 5218 Sandy Ground, Sandy Ground 2640, Anguilla
    Sailing is Anguilla’s national sport, but it’s also the best way to explore the island’s dreamy Caribbean shores—and the best way to explore its marine life while in transit. Spend the day with Tradition Sailing Charters, gliding across iridescent blue waters on a 1978 50-foot sloop, drifting from one cay to another. You’re welcome to watch and learn how to sail if you’re a newbie, or to participate if you have experience. After a lunch stop at the only restaurant in Prickly Pear Cays, get underwater to check out this reef-protected bay where sea turtles, blue tang, and numerous other tropical critters thrive. There’s also a brown booby colony on land here.
  • Perched high above the sea on the east coast of St. Kitts is Brimstone Hill, a massive stone fortress built by African slaves for the British during the 17th and 18th centuries. Now a UNESCO World Heritage Site, the military stronghold, which took 100 years to complete, is considered one of the best-preserved fortifications in the region. From the top, you can see six neighboring islands on a clear day.

  • You’ve likely seen the main attraction of Tulum in a travel ad, a postcard, or a friend’s Instagram feed, but there’s still nothing like witnessing first hand the only Maya site that overlooks the Caribbean Sea. Standing before the 13th-century structures will leave you feeling awed by the Maya’s archaeological achievement and its resilience—still standing after being hundreds of years of being buffeted by salty water and wind. True, it’s the main attraction here, but it’s not the only one. With a quirky backstory and a lot of international press, more and more foodies are making their way to Hartwood, a restaurant that lacks electricity. The chef prepares all dishes—made with local ingredients—on an open fire.
  • Calle 6 Norte, Centro, 77710 Playa del Carmen, Q.R., Mexico
    Fusion, one of Playa del Carmen’s oldest and best-loved beach bars, has an indoor restaurant area, but it’s most famous for its outdoor lounge, right on the sand, under palm trees, and hard by the Caribbean. Fusion’s central location in the busiest part of the downtown area makes it ideal for enjoying a day under a palapa’s shade, or a night out on the town with live music and fire shows. The menu offers a variety of international cuisine, so you can find almost anything you’re craving, whether it’s tacos, Argentine empanadas, or classic pub grub à la burgers and wings.
  • The Bahamas
    The Exumas are a stunning archipelago of remote islands and cays strung between Nassau and Long Island, and around a dozen of these tiny islands are protected within the Exuma Cays Land & Sea Park. Established in 1958 as a preserve where no fishing is allowed, it was the first marine protected area in the Caribbean. It has been highly successful at maintaining the fragile beaches and marine life found in the area. Visitors can take boat tours to the park to go diving and snorkeling on the many healthy reefs and to explore the secluded tropical islands, where endangered Bahamian iguanas roam the beaches. On Big Major Cay, you can go swimming with the pigs at Pig Beach and give them fresh water, as their water supply is limited.
  • Calle Isabel La Católica, Santo Domingo 10210, Dominican Republic
    Historic Santo Domingo offers a unique look at how the New World was settled in the years following Christopher Columbus’s arrival in the Caribbean on his first voyage in 1492, as well as subsequent expeditions. The Colonial Zone sits along the Ozama River, where the settlement’s original layout, walls, forts and other buildings remain much as they were 500 years ago. With its wealth of colonial architecture, the area has not surprisingly been recognized by UNESCO as a World Heritage Site. Among the historic buildings is the first cathedral built in the Americas, the Basilica Cathedral of Santa María la Menor (also known as the Catedral Primada de América, recognizing its historic significance). The ornate church once housed the remains of Christopher Columbus until they were moved to the Columbus Lighthouse, in the eastern part of the city.

  • Tulum, Quintana Roo, Mexico
    As is the case with many hotels in the Tulum section of Riviera Maya, Casa de las Olas shies away from the “luxe” label, preferring to promote itself as a simple, eco-friendly retreat where intimate spaces and five-star service are more important than linen thread counts and extra amenities. Bright white walls, mosquito nets, private balconies, and canopy beds are what guests can expect in their rooms. This doesn’t mean that Casa de las Olas is skimpy in any way. The staff are known for their thoughtful attention to guests, and the small size of the hotel—just five suites—ensures they are never overwhelmed by guests’ requests or needs. Plus, each room has views of the Caribbean Sea, and the hotel’s private beach is never more than a few steps away.
  • Ross Blvd Portsmouth, Portsmouth, Dominica
    Why we love it: A stunning eco-resort where style meets sustainability

    Highlights:
    - Villas attendants who double as adventure concierges
    - A treehouse-style spa
    - A reputation for balancing nature and luxury

    The Review:
    An award-winning boutique resort, Secret Bay serves exquisite style, service, and seclusion just a 10-minute drive from Portsmouth on Dominica’s northwestern coast. The luxury property has no communal spaces, beyond the decks, beaches, a riverside yoga pavilion, and the Zing Zing restaurant. Instead, guests retreat to six elegant villas and bungalows, fully stocked with their choice of goodies. Conceptualized by Venezuelan architect Fruto Vivas, villas fuse high design, local craftsmanship, and sustainably sourced materials like Guyanese hardwood. Guests can look forward to plunge pools, gourmet kitchens, pillow hammocks, and furniture carved from red cedar, along with high-tech touches like Apple TVs and Sonos Bluetooth speakers.

    Committed to sustainability, owner Gregor Nassief helped site Secret Bay’s villas to preserve the rainforest and oversaw construction of the entire resort without any heavy machinery. The property also plants vetiver to strengthen its cliff location and has applied to create a marine reserve in the waters below, where parrotfish flit among the coral. Explore them with the complimentary kayaks, stand-up paddleboards, snorkeling gear, dry bags, and GoPros on offer, or head to the treehouse-style spa, which gazes down on the cove and offers treatments like massages with custom-blended local oils. Guests can also opt to create their own culinary masterpieces or have the chef’s choice delivered by their attendant, who also serves as their housekeeper and adventure concierge.

    Over the next few years, Secret Bay will slowly expand to 50 villas, hidden among the neighboring 27-acre valley and ridge. In the meantime, swim to the resort’s waterline cave or paddle a kayak to the soft, golden Secret Bay beach. Though open to the public, like all Dominica’s coast, the beach sees very few visitors, meaning you might very well be the only one there.
  • Cayman Islands
    Hit Seven Mile Beach, a beautiful and—as the name would suggest—long stretch of shoreline to see why it’s one of the Cayman Islands’ most fabled features. Facing out to sea, you’d be forgiven for thinking you were beholding a life-size Rothko installation, with bands of the palest aqua, the richest cobalt and every gradation of blue-green in between. Also keep an eye out for the schools of fish that sprint along the water parallel to the shore.