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The past two decades have seen the dozens of islands scattered across Boston Harbor transformed from barely noticed dots on the horizon to one of the city’s most popular attractions. The Boston Harbor Island National Recreation Area, established in 1996, has propelled them into prominence, with ferries carrying day-trippers and overnight campers from downtown Boston, Hingham, and Hull to eight of the islands (19 more are accessible by private boat or charter excursions). Most visitors head to Georges Island, home of the Civil War–era Fort Warren, or the beaches and hiking trails of Spectacle Island, the one closest to downtown Boston. (Don’t skip the concession stands here: The food is from James Beard Award–winning Boston chef Barbara Lynch.) You can also camp on Peddocks, Grape, and Bumpkin islands, or take a tour to Little Brewster Island to witness the 300-year-old Boston Light, the nation’s oldest lighthouse.

The Caramoan area, on the eastern tip of the Caramoan Peninsula in Bicol, is a rugged and remote landscape of white-sand beaches, rich woods, swampland, lakes, and caves. Numerous seasons of the reality TV show Survivor have filmed around this region, including at Gota Beach. Most travelers explore the pristine Caramoan Islands by small outrigger boat. There are too many to scope out in one trip, but don’t miss famous Matukad Island with its pure white sands, exotic rain forest, limestone rock formations, and even a hidden lagoon. Another must-visit is Manlawe Island, a one-kilometer-wide sandbar surrounded by ankle-deep water. Other highlights include Cotivas Island, Gota Island, and Sabitang-Laya, a triangular landmass with powdery sand, caves, and superb snorkeling. Accommodations in Caramoan include family-run inns that are equipped with modern amenities but rustic enough to accentuate the region’s remote and unspoiled ambience.

Among the three Cayman Islands, Brac is the most topographically endowed, thanks to its distinguishing feature: the Bluff, a limestone cliff rising along the length of the island and topping out at about 140 feet at the eastern end. Between that and the island’s densely forested interior, the local hiking options have a lot to offer—one of the best cases in point being the Lighthouse Footpath, a trail that runs two and a half miles (one way) along the bluff’s edge and that serves up endless sea views and likely encounters with the absurdly adorable brown boobies and soaring frigate birds. Try to go in the morning or late afternoon, and of course, take along plenty of water: You’re looking at a two-hour outing to the most beautiful of boonies.

Retail therapy takes on new significance at this nonprofit, where the vintage-inspired dresses, jackets, and bags are designed and handmade by the inmates of the women’s prison on Giudecca island as part of a skills training program. Fortuny and Bevilacqua donate some of the more sumptuous fabrics, and colors tend to be bold and cheery.

If you want to eat like a local, try heading to Potter’s Cay—an enclave of modest fish shacks tucked beneath the bridge to Paradise Island. The most famous of these is Twin Brothers, which serves up paper plates full of deliciously authentic cracked conch, conch fritters and citrus-marinated conch salad.

In the southwest of Providenciales, this national park encompasses the tranquil Chalk Sound lagoon, a large expanse of shallow water connected to the ocean by a small channel. Check out the fringe of jagged limestone, called ironshore, along the shorelines of the lagoon and its small islets. You can rent a car and explore scenic Chalk Sound Drive, or you can stop at Las Brisas Restaurant to rent kayaks for a paddling adventure. See if you can spot stingrays and small sharks finning through the water, or the local rock iguanas foraging on the islands.

Old San Juan may look, at first glance, like a few other charming cities built during the height of Spanish colonialism—Havana or Santo Domingo, for example—but what sets it apart is the extent to which its architectural infrastructure from that era remains visible. It’s the only city that has its original colonial wall almost entirely intact, and both of its principal forts are in excellent condition, remain accessible to the public, and offer panoramic views of the Atlantic Ocean (so bring your camera). Both El Morro and Fuerte San Cristobal are run by the National Park Service; guided tours will leave you with greater knowledge about the era, as well as the forts’ construction and their role in Puerto Rican history. (There are other, smaller forts in and around the capital, next to the Caribe Hilton, and in Luís Muñoz Rivera Park, plus Fort San Juan de la Crúz in the nearby town of Cataño.)

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.

Hogfish Bar and Grill, under a thatched palapa roof with open sides, is tucked in among the boats and gulls of Safe Harbour Marina in Stock Island. In short, a meal or a drink there makes you feel like an insider, a salty local far from the crowds downtown. That in-crowd feeling is burnished on weekends, when local bands play sets, or during one of the events held by Hogfish during the season, like shrimp boils. The simple food is served generously on plates crowded with side dishes. The hogfish sandwich, served fried on Cuban bread, is the stuff of late-night-post-beer legend.

Formerly the residence of the Maharajah of Jaipur, and now one of Jaipur’s most elegant luxury hotels, the 19th-century Rambagh Palace has had a front-row seat to history—and has hosted a long list of royals, dignitaries, and celebrities along the way. As an homage to those regal roots, the hotel’s fine-dining restaurant spotlights the cuisine of four of India’s former princely states: Rajasthan, Awadh, Punjab, and Hyderabad. In what used to be the palace’s banquet hall—still dripping with gilded mirrors and Italian frescos—enjoy dishes like laal maas (a Rajasthani spicy lamb curry), chicken cooked with raw mango and saffron, skillet-grilled lobster, and apricot-stuffed cheese dumplings simmered in tomato gravy. Cap off the night with a drink in the nearby Polo Bar, which serves fine spirits and cocktails inspired by the royal equestrian sport.

Store Bay, just outside Scarborough, is one of Tobago’s most popular beaches. Reserve some time after your swim for a visit to the dozens of bright and cheery craft shops and food stalls that make up the Store Bay Beach Facility. Need souvenirs? Browse for island crafts like batik, sandals, jewelry and items carved from wood and coconut shells.

This 1763 plantation house has an interesting tale to tell. It never employed slave labor, and its owners—descendants of Carib Indians—are commemorated with statues and figures spread throughout the rooms and gardens. Visitors can take tours of the house, gardens, and old overseer’s house, then enjoy beautiful views of the neighboring island of Nevis.

The 20 de Noviembre market has a variety of food stalls where you can sample many Oaxacan specialties, but carnivores flock to the one corridor that’s known as “El Pasillo de las Carnes Asadas” (the grilled meats aisle). Follow your nose to find it: smoke and the smell of meat grilling are thick in the air. You can select the raw meat that looks best to you and have it grilled to your specifications as you watch on. Find a spot at one of the long tables with benches and order salsa and guacamole to accompany your feast. Buy some tortillas from one of the passing vendors, and enjoy!

Negril, or the “Capital of Casual” as it’s known in Jamaica, is everyone’s favorite getaway, from locals to the visitors who return year after year. The buzz of activity on Seven Mile Beach’s powdery white sands is tempered by the breathtaking, serene views of the West End’s cliffs towering over the Caribbean. Lots of bars, hotels, and restaurants line Seven Mile Beach, and local eateries and smaller boutique resorts are perched up on the cliffs. While there’s more hustle and bustle and throngs of tourists on this end of Jamaica, the region still offers many secluded spots and unique experiences.

Jambe de Bois is an unpretentious food escape set idyllically in Pigeon Island National Park. The café—made of stone, driftwood, and thatch—serves up a beach view, an island atmosphere, and a simple menu that will keep you happy for hours. Sit on the deck at one of the picnic tables, and snack on sandwiches, salads, or local dishes like rotis, curries, or fish fillet with rice and peas at lunch and dinner. Come for happy hour or join the locals for live jazz on weekend evenings. The local art on display inside is for sale.