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Before Columbus arrived in the West Indies, indigenous tribes had lived on Puerto Rico for at least 2,000 years. The Igneri were the oldest recorded inhabitants, followed by the Taino, and artifacts from both peoples have been found at the Tibes Indigenous Ceremonial Center, a settlement just outside of Ponce that flourished from roughly 400 C.E. to 1000 C.E. Many of the artifacts are on display at the on-site museum, and a replica Taino village shows how native Puerto Ricans lived in the pre-colonial era.

Ponce is Puerto Rico’s second-largest city and is nicknamed the “Pearl of the South.” Life here seems to move at a slower pace than San Juan, and that’s the way locals like it. For them, there’s nothing better than an evening or weekend stroll around Plaza Las Delicias, the main square, which is full of history and entertainment. Stop by the unmissable red-and-black–wooden firehouse (now a museum) to learn more about the central roles that fire and firefighting have played in Ponce’s history. Then work your way around the square to see Ponce’s symbol, the lion, anchoring each side of the plaza, the church, the fountains, and finally, Kings Cream, a no-frills emporium that sells small cups of ice cream—with flavors such as passion fruit, peanut, guava, and coconut—at bargain prices.

Though the DR isn’t traditionally known for its surfing, the little town of Cabarete (a 30-minute drive from the Puerto Plata airport) is fast becoming a hot spot for newbies and those wanting to take their board skills to a new level. Cabarete boasts several surf camps including SWELL, “a purpose-built surf camp” that attracts surfers and wannabe surfers from all corners of the globe. A cross between a hostel and a just-the-basics boutique hotel, the camp has co-ed quad dorms and private rooms accommodating some two dozen travelers of all ages — a healthy mix of singles and couples, mostly urban professionals. Days here start really early, but what does it matter when you’re on the water catching waves? (There’s always the rest of the day to make up for that lost shut-eye.) Once you’re done with your surfboard, wander into Cabarete to grab a cerveza and a bite. Be sure to check out the town’s other favorite pastime, kitesurfing. Just look to the sky.

Is Bar Agricole the best bar in the city? It’s certainly in the top five, based on the groundbreaking cocktail program developed by bartender and owner Thad Vogler; the award-winning architecture and interior design by local favorite Aidlin Darling; and a daring menu centered around produce from nearby organic and biodynamic farms. Vogler used to bartend in Tokyo, and his obsession with Japanese precision shows. You’ll see influences of that in the hand-cut ice cubes he uses, and in Agricole’s glassware and aprons (all from Japan). The bar stocks a limited selection of 20 or 30 spirits, almost all small batch, and with a special focus on rum. Come for drinks, come for dinner, or come for brunch: the midday menu highlights include ricotta doughnuts with quince marmalade and a chicory salad with fuyu persimmon and house-made vinegar. Pro tips: In winter, book the private dining room (nicknamed the Grotto) for a seated, though still laid-back, dinner for up to 32 people; for an outdoor event, Bar Agricole’s covered and heated patio is perfect for larger, more casual groups. For lessons in liquor, check out the private spirits tastings that Vogler offers through IfOnly.

San Juan’s Condado neighborhood is Puerto Rico’s version of Miami Beach. It’s a great place for beach-lounging and people-watching, with a multitude of bars, cafés and resorts along the sand. Be aware that the water can get rough in places, so use caution when swimming. La Ventana al Mar Park sits right on the beach, and the footpath along the jetty offers great views up and down the waterfront.

I think the most appealing aspect of Old San Juan is the architecture and design of the city. Residential apartment buildings have been converted to designer boutiques or little B&Bs, and interior courtyards invite hungry guests to relax and unwind in the shade.... I’ve been to this area multiple times and still I manage to find a street I’ve never wandered down. Some are more popular than others, in particular Calle San Sebastian, which hosts eateries, bars, and shops, and Calle San Francisco. At the corner of this street is my particular favorite, Franky’s antiques. It’s in a four-story building, loaded with vintage goodies. There’s so much to see, one trip is not enough. If you want to shop, consider wandering all morning and into the early afternoon. You’ll be delighted by all the unique shops. Then, take a break at my favorite restaurant, Triana, for Spanish-style tapas and their famous sangria. It’s a must-stop place any time I’m in the old city. You don’t need a car to get around. Just park at one of the garages and explore by foot. There’s lots to see and do in Old San Juan.

Lago Dos Bocas is a perfect place to take the family to spend a day. This man-made lake is situated behind a dam in the Utuado/Arecibo region of the west/central part of Puerto Rico. There is small park that is freely open to the public and is operated by the Department of Transportation. There are ferry rides around the island that leave on the hour, and these 20 minute rides are free of charge. The main draw of this area are the restaurants situated along the shoreline, to which the boats can bring you to for an meal of local comida criolla. Be sure to head there on the weekend to catch these places during open hours! photo by chelsea harms

“For those folks who enjoy camping, Hix is the Four Seasons. And for those who stay only at the Four Seasons, at Hix they will think they are camping.” So goes the saying of the owners of Hix Island House, located on remote and beautiful Vieques Island. Puerto Rico’s first sustainable lodging facility, the hotel caters to guests who know that going green and living luxuriously are not mutually exclusive. Rooms come with See Design bedding as well as Frette robes and towels. Solar panels provide power, and wastewater from each room supplies the lush gardens. Canadian architect John Hix is responsible for the hotel’s striking concrete exterior, which stands in stark contrast to the surrounding hills, yet provides guests with both privacy and sweeping views out to sea.

This property is closed due to damage sustained during Hurriance Maria.

The W Vieques Island is a luxury boutique waterfront hotel located on pristine Vieques Island, located eight miles off the southeast coast of mainland Puerto Rico. What’s interesting about the island is that despite being so close to the mainland, it still has a very raw, untouched feel, with tourism weaving itself into the landscape instead of taking it over. Guests of the hotel can explore ecotourism on the island through kayaking tours of the bioluminescent bay, beach trips, scuba diving, mountain biking, fishing, horseback riding, outdoor yoga, farm-to-bar social hours at sunset, and visits to the the local farm to see where the restaurant’s ingredients are sourced and even to create a meal for themselves. There’s also a sumptuous spa. Inspired by the holistic nature of the surroundings, the spa seems to blend into the landscape, with rivulets and canals flowing throughout the space, front-row views of the Atlantic Ocean, vine-covered treatment rooms, a reflection pool, and a spa pavilion surrounded by lush gardens.

Feel instantly cool when you slip through the unmarked wooden doors and enter La Factoria. Garden lights hang from the graffiti-covered walls (designed to look artsy-shabby with a stylish restraint), seductive music plays, and the liquor bottles behind the bar are lit from beneath to add to the glow. The flattering amber light in this neighborhood bar invites whispered conversations and lingering glances. La Factoria, which introduced San Juan to the craft cocktail when it opened in 2013, encourages experimentation. Take your time enjoying your drink of choice, but be sure to wander a bit further into the sprawling building where you’ll come upon separate spaces with different moods: a wine bar, a speakeasy, a dance floor.

It may be only 22 miles west of San Juan, but Dorado Beach, a Ritz-Carlton Reserve feels a world away. The resort has a spectacular location on a three-mile stretch of beach on Puerto Rico’s north shore, where Clara Livingston once ran a sugar plantation—and Amelia Earhart visited before departing for her fateful world tour. In 1958, Livingston sold the property to Laurance S. Rockefeller, who turned it into the first of his legendary Rock Resorts. Known for his green streak, he designed the hotel to respect the local beauty, mandating that buildings could not be taller than the surrounding palm trees.

The Ritz-Carlton—which reopened in October 2018 after a meticulous restoration following Hurricane Maria—pays homage to that original vision. Here, every room is beachfront, with floor-to-ceiling sliding doors that disappear into ocean views, plus deep soaking tubs, outdoor showers shaded by gardens, and either spacious balconies or private plunge pools. As part of the property’s renovation, rooms were refreshed with a color palette that amplifies the natural beauty just beyond the doors. Additionally, the grounds showcase 3,000 new plant species, the spa is offering new locally inspired treatments and cuisine, Encanto Beach Club Bar & Grill features a refreshed dinner menu, and the Positivo Sandbar debuted an omakase and ceviche bar directly on the sand. There’s even an entirely reimagined signature restaurant, Coa, which serves farm-to-table fare cooked on the grill. Still standing strong on the verdant, 1,400-acre grounds are the five 18-hole championship golf courses. The biggest challenge is pulling yourself away from the luxury of the resort to tee up a shot.

Reachable only by boat, Puyuhuapi Lodge & Spa has incredible views of virgin forest, mountains, and water. The Aysén region is one of the least accessible, less touristy areas of Chile, and it’s really worth going the extra mile. The hotel was created by businessman Eberhard Kossmann, who in 1986 sailed with his family through the fjords south of Puerto Montt. He fell in love with this spot and by a stroke of luck was offered to buy the plot of land a few years later—and so began his first venture into tourism.

Built from local wood, Puyuhuapi Lodge & Spa sits alongside the Termas de Puyuhuapi (Puyuhuapi Hot Springs), and all the hotel’s hot water and heating is sourced from the thermal waters. Guests spend days exploring this beautiful part of Chile on excursions that range from hiking and kayaking to bird-watching and trips to glaciers. Evenings are spent soaking in the hot springs and relaxing in this picture-perfect wooden lodge on the waterfront.

If there were ever a hotel with history, it’s the Singular Patagonia. Opened as a hotel in November 2011, the original building once served as a post-Victorian cold-storage factory built by the British in 1915 for the purpose of processing sheep’s wool and meat to be shipped back to England. Overlooking the waters of Last Hope Sound, the long, red-brick building is located just outside the town of Puerto Natales. After operating for almost 70 years as a factory, it was declared a national historic landmark before being transformed into a luxury hotel.

History is by no means forgotten. The hallways are still stocked with brightly colored machinery—from steam condensers to boilers and forges—all stamped with the name of the British city in which they were built: Derby, Birmingham, London, or Glasgow. Designed by Chilean interior designer Enrique Concha and local architect Pedro Kovacic, the 57 bedrooms stretch along a new wing that was added to the original buildings, and these rooms are furnished with Victorian-inspired furniture.

If you want to meet the kindest cheesemonger in Rome, visit Roberto at Antica Caciara in the ‘you-must-cross-the-Tiber’ Trastevere section of town. Stock up on Pecorino Romano (that amazing hard grating cheese used in the standard Roman fare Cacio/Pepe pasta) and sliced cured meats. And if you are still hungry, you can grab a bag of handmade pasta before Roberto kisses you ‘buonasera’.

San Juan’s oldest restaurant has been serving up Puerto Rican and Spanish flavors since 1848. La Mallorquina, set right in the heart of Old San Juan, is known for rustic, home-style dishes like salt cod fritters, arroz con pollo (chicken with rice) and pasteles (similar to tamales).