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Built in 1919, the Condado Vanderbilt Hotel is a Spanish Revival landmark, perched majestically above the Atlantic Ocean. From its opulent lobby to its luxurious guestrooms, the property fuses its storied past—it’s hosted everyone from European and Hollywood royalty to captains of industry—with distinctly modern amenities, making for one of San Juan’s best stays. Spread over a historic building and two towers, the 212 guestrooms feature stone-topped vanities, French windows, and ocean views, while the 107 suites include separate sitting and dining areas, L-shaped balconies, and 24-hour butler service. At the beach club and four pools, guests can also look forward to cabanas, personal butlers to bring refreshments, and assistance from a tanning and hydration specialist.

When hunger strikes, the Vanderbilt is prepared with three different dining options. Hit Tacos & Tequila for escabeche pork tacos and Patron margaritas; Ola Oceanfront Bistro for Puerto Rican cuisine and water views; or, if you’re in the mood to splurge, 1919 Restaurant for sophisticated fare by Michelin-starred chef Juan Jose Cuevas. Also on-site is VC Lounge for expertly mixed cocktails, Marabar Martini Bar and Lounge for live jazz, Veritas Wine and Cognac Bar for rare vintages, and Avo Lounge for fine cigars. When you need to detox, head to the spa for indoor–outdoor treatments, rainforest showers, and hammam rituals.

Chef Peter Schintler’s San Juan restaurant remains one of the capital’s top fine dining destinations after more than a decade in operation. Marmalade, located in Old San Juan, has allowed Schintler to experiment with international flavors and techniques picked up at previous stints in kitchens around the world, including one at New York’s fabled Le Cirque. While beloved by omnivores and travelers who will jet-set for cocktails, vegetarians especially appreciate Schintler’s menu, which includes a spiced cauliflower meze and hand-rolled black truffle pappardelle. Reservations are definitely recommended.

One of my favorite places in the whole world—Vieques! I’m actually a little apprehensive to share, because I’d love to keep it the semi-secret it is. If you time it well, you can have this beach all to yourself.

Scrub Island is one place where being shipwrecked might actually be a good thing—pity that dockside boat slips abound. Located on a volcanic speck just 75 miles east of Puerto Rico, Scrub Island Resort is the ultimate tropical idyll, with a spa, marina, and three restaurants. Its 52 suites and villas sit on 230 pristine acres, complete with neutral, colonial–style interiors (think four-poster beds, marble baths with soaking tubs, and floral curtains) that intensify the ocean views. Charter a boat to explore hidden coves or test your nautical skills at the resort’s sailing school. You can always forget what you know once the time comes to lift anchor and head for the mainland.

Genuine Magallanes fare such as open-flame, spit-roasted lamb is what you find on the menu at this bucolic oceanside estate on the Eberhard Fjord in Patagonia. Aperitifs in hand, visitors can watch how the flavor-packed food that just keeps coming is prepared, and the service is a paean to Patagonia’s renowned hospitality. Connoisseurs recommend ordering the matambre, an especially tasty cut of beef. Tables hold parties of six or more, and individual diners are seated with whatever group can accommodate them. Reserve on the restaurant’s website (and remember that mobile service can be intermittent in this corner of the planet). Open mid-September to late April.

At the neighborhood’s eastern extreme, on Rue Dante, this traditional Italian bakery is renowned as the purveyor of the city’s best cannoli, though it’s a hotly debated issue. They are blindingly scrumptious, that’s for sure, and they come in chocolate, vanilla ricotta, vanilla ricotta with tiny chocolate chips, vanilla custard or mocha. They’re just one of the many sweet treats on offer though, so wander over after a day at the market and let yourself be tempted by the cornetti, the million-layered sfogliatelle, the flaky, cream-filled lobster tails or the dozens of varieties of cookie.

When the directions to El Huacatay lead you from an unassuming street into an overgrown garden, you may be surprised. When you taste the food here—at what is one of the top gourmet dining rooms in Cuzco and the Sacred Valley—you’ll be equally surprised. Whatever you choose from the menu, you’re unlikely to be disappointed, from the melt-in-your-mouth beef tenderloin to the delicious and fresh valley trout. Share appetizers like the ricotta cheese croquettes with tree-tomato sorbet or the alpaca carpaccio. The drinks are excellent as well, with top marks for the coca sour, made with coca-leaf-infused pisco. Reserve to assure a table in this tiny boîte.

Puerto Rican plazas are laid-back gathering spaces where locals buy snacks, watch shows, play dominoes, and chat with friends. Take a seat on a bench to give your feet a break and soak up some of the everyday comings and goings. At the Plaza de Armas in San Juan, buy the kids traditional treats like sesame-seed lollipops or coconut candies and check out the fountain with the four statues symbolizing the seasons. The Plaza las Delicias in Ponce is made up of two squares divided by a cathedral—one has a statue of journalist and governor Luis Muñoz Marín, while the other is home to the Lions Fountain from the 1939 World Fair.

Anywhere breakfast is served all day usually scores in my book. At Caficultura in Old San Juan, the food is “farm to table” and is as delicious as the creative menu sounds. In addition to the mostly healthy options, the highlight is the maple syrup made with rum, and coconut milk–dipped french toast topped with coconut shavings. The atmosphere was pretty cool—large black chandeliers hang from large wooden beams, and the picture windows face Plaza Colón outside.


Definitely a cool local place to stop into and grab a coffee or brunch while sightseeing throughout Old San Juan’s historic district.

Kaplash is located on the curve of Road 115 as you head toward the town of Rincon. The little unassuming orange and blue building boasts a beautiful view of the ocean and—in the opinion of myself and others—the best empanadillas on the whole island. Kaplash was featured in an island-wide food photography book by a local writer who ventured to all the great known local spots. That’s how I decided to try them, and I wasn’t disappointed. They are now the only place I stop for empanadillas (turnovers) and the only place I take family and visiting friends. Try all of them—they specialize in seafood—but I can’t get enough of the pizza one.

Locals love the Sunday Supper at City House, when chef-owner Tandy Wilson serves his highly creative Italian-influenced menu, but you really can’t go wrong any night here. Wilson, a 2016 James Beard Award winner, is a Nashville native who spent time in Italy and California before opening his restaurant in the former home of a sculptor in the trendy Germantown neighborhood. Since then, he’s been drawing visitors and locals alike with his belly ham pizzas, corn bread gnocchi, and main dishes like roasted chicken and corn meal–crusted catfish with peppers, garlic, anchovy, lemon, and parsley. Those in the know bookend their visits with a perfectly crafted cocktail at the bar and a dessert from pastry chef Rebekah Turshen, like the almond ricotta skillet cake with lemon marmalade and lemon ricotta gelato.

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.)

Harry’s Roadhouse, a favorite haunt of locals and visitors, is conveniently open seven days a week. The massive breakfast menu melds regional Mexican and New Mexican fare with items like huevos rancheros and hearty chilaquiles (eggs any style with salsa and cotija cheeses). For your sweet tooth, try the french toast or lemon ricotta pancakes, washed down with a cup of joe.

The mallorca (“my-your-cuh”) is the iconic Puerto Rican sandwich that’s typically eaten at breakfast, washed down with a cup of coffee. When I was in Old San Juan, I had more than my fair share at Cafeteria Mallorca. The mallorca is a soft, buttery bun that’s classically sliced in half, both sides generously buttered and then the sandwich is pressed between the hot steel plates of a griddle. Before serving, it’s generously dusted with powdered sugar. Oh yum! How can you go wrong with butter and sugar? It took me one bite to get hooked and before you know it, I had ordered another one but this time – jamon y queso….ham and cheese. It too came with a generous dusting of powdered sugar. Ham, cheese, sugar. I know, it sounds like an odd combination but don’t knock it til you try it because it’s good, so good, it’s addictive! The bread was slightly crunchy on the outside, soft on the inside. The mallorca was warm, buttery, sweet and savory, every bite made my tastebuds sing with joy! If you decide that mallorcas are not your cup of tea, the menu also offers up eggs, pancakes and cereal along with coffee, tea and juices. Conveniently located in the heart of Old San Juan, Cafeteria Mallorca is a homey and unpretentious place that’s a throwback to the simple cafeterias of days gone by. Great place to bring the kids!

The Heladería de Lares, a 45-year-old family business, sells about 50 unusual flavors of ice cream up in the mountains. Salvador Berreto, known to the locals as Yinyo, founded the shop to commemorate the Grito de Lares, a battle for freedom that had taken place exactly one century before. Yinyo started with corn, a flavor at the heart of the Puerto Rican diet and the current bestseller. Other flavors are cod, coquito (the Puerto Rican version of eggnog), and rice and beans. Fortunately, you can taste two flavors before deciding what to buy, and the ice cream is cheap, so you can stock up. Every weekend, people form what locals like to call lines, but are really boisterous blobs extending half a block down from the shop’s entrance. While eating, people skim through newspaper clips about when Denise Quiñones, a girl from Lares, won a Miss Universe pageant, or study photos of the 1945 Fuego de la Candelaria (a fire in Lares). After reading about the history behind Lares’s anthem and running their hands over the guiro (a musical instrument played by scraping its serrated surface), people often wander outside to the Plaza de la Revolucion. Here, on a typical Sunday, artisans sell paintings of the three magi (the Puerto Ricans’ second Santa) and of flamboyanes (the national trees with orange flowers). If you have doubts as to whether it’s worth it, just ask Bill Clinton and his daughter Chelsea. In 2008, Clinton forced $100 into the hands of Yinyo’s son for a mango ice cream.