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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.

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.

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.

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.

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.

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.

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.

Yo, ho, ho and oh, my! Up on Government Hill, this watchtower, built circa 1678, is known as Blackbeard’s Castle and is literally the stuff of legends. Although it’s open for debate whether the notorious pirate ever used the five-story tower as a lookout, one thing is for certain: Its views are tops. Nearby the flower-lined 99 Steps (technically there are 103), built in the 18th century of ship-ballast brick, lead from historic Kongens Quarter to some more terrific views of the island.

For nearly three centuries, workers serving the nobility at Castello Banfi in Tuscany lived in a small hamlet within the castle grounds. In 2007, however, the stone houses within their tiny village were completely renovated under the direction of Italian interior designer Federico Forquet, catapulting Castello Banfi into a new era of grandeur. Today, the property welcomes guests from November through March in two guest rooms and 12 suites, each with wood-beamed ceilings, countryside views, and bathrooms stocked with “vinotherapy” products made from the estate’s Sangiovese Brunello. A central garden with a pergola, a heated outdoor pool, secluded lounging spaces, and alfresco massage tents offer plenty of ways to take in the surrounding vineyards. If you’re feeling more active, take a cooking class with the chef (held a short drive away at the estate farmhouse), tour the Banfi winery, or venture out to nearby historic towns like Montalcino and Siena.

Checking out the famously preserved mummies at the world’s oldest public museum is on many London wish lists, but there’s much more to the British Museum than ancient Egypt. Other must-sees include the Elgin Marbles and the African masks, both part of an enormous collection that spans ancient Iran to modern Sweden. The Great Court, which was cleverly revamped with a geometric glass roof by Foster + Partners in 2000, is a spacious gathering area with a shop and a café—and a sight worth seeing in itself.

Chef Peter Merriman’s flagship restaurant in Waimea is known for some of Hawaii’s best farm-to-table foods. At the forefront of the local menu movement, his award-winning dishes include Bulogogi Spiced Kauai Prawns, Hirabara Farm Earth Grown Lettuce, and an Original Wok Charred Ahi that can be paired with a carefully selected wine from a global list of vineyards. But, for the most authentic flavors, check out seasonal Hawaiian choices that could include a Waipio Taro Enchilada or mahi mahi served with mushrooms from the Hamakua region on the Big Island. No matter what you choose to indulge in, it feels good to eat at Merriman’s when you know the restaurant sources ingredients locally, gives back to the Island community, and even offers a culinary scholarship. After you’ve enjoyed the beautiful meal, be sure to pick up the Merriman’s Hawaii Cookbook so you can indulge your palate at home as well.

On Tahiti’s rocky east coast, the volcanic Lava Tubes of Hitiaa are underground channels and eroded sections of rock in caves that have been penetrated by water. Although you can visit solo, it is really best to visit with a guided 4WD tour. Check with Marama Tours, which also does a range of other island tours from encounters with dolphins to 4WD trips across the Papenoo valley that is rich in waterfalls and archeological sites.

Battery Point was one of the first lighthouses on the California coast, and today its unique island spot makes for a historical visit that doesn’t have to be boring. The Del Norte County Historical Society operates the lighthouse and its accompanying museum—open daily during the summer, but strictly on weekends from October to March. Notably, the lighthouse is accessible to the public only during low tide. Guests have to make their way across the land bridge, which can quickly go underwater when the tide comes in. Once on the small rocky island you can check out the lighthouse keeper’s home, which has been memorialized as a museum with vintage odds and ends from the days when the lighthouse was operational. Many people also come out simply to admire the natural beauty.