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In the heart of El Viejo San Juan, the Plaza Colón (Columbus Plaza) is so much more than a place honoring an important piece of San Juan’s history. Sure, snapping an Instagram photo in front of the bronze statue of Christopher Columbus, credited for the first discovery of the island, is definitely a “must-do.” Find a local and in your best Spanish accent say “Perdón, podría tomar una foto por favor?” Or play it safe and ask another tourist in English (they’re not hard to find!). Either way, stay and hang out. Explore the local artists’ tents (like this one, with rings and bracelets made from brightly colored ceramic beads and recycled aluminum, customized to fit). Pick out unique, inexpensive gifts for loved ones and, of course, something to remember the trip! And don’t ignore the ringing bell of the sorbet vendors selling “coco frio” for $1. Try a scoop of papaya y piña to help cool off in the heat of the Puerto Rican sun.

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!

A short drive outside the town of San Pedro de Atacama, Tierra Atacama has wonderful views of fields and Volvano Licancabur. The hotel is part of the Tierra hotel group owned by the Chilean-American Purcell family (who also own Tierra Patagonia, Tierra Chiloé, and Ski Portillo). The property originally served as a cattle corral, but Chilean landscape artist Teresa Moller has transformed the grounds, preserving the ancient algarrobo and chañar trees and restoring the adobe walls.

The bedrooms are decorated in natural colors, with local touches like ceramics marching along the sills of the extra-large windows. Animal-skin rugs and alpaca throws provide a touch of warmth for the cool desert nights. You can see the incredible silhouette of Volcano Licancabur from all the rooms, but the Poniente rooms are slightly larger and have better views. There is a friendly communal vibe at the hotel, and upon arrival guests meet with the head guide in the main lounge to choose from the range of group activities on offer each day.

Palo Verde National Park is the perfect escape for avid wildlife and bird watchers. The park is one of the world’s most important wetland sanctuaries and a vacation destination for many species of migratory birds. It is also home to crocodiles, monkeys, deer, coati, and jaguarondi. The best way to glimpse the wildlife is on board a boat ride through the fast-flowing Tempisque River.

What better way to rejuvenate than a yoga class and massage on the beach? Lorena at ReFLEXion Yoga Tamarindo is a gifted and soothing yoga instructor and healer. Besides the yoga classes (for all levels), she also offers an array of other healing therapies for the body and mind, including massage and reiki sessions. Sometimes being on vacation can start to get... well, stressful. This is the perfect solution.

La Isla de Guilligan (Gilligan’s Island, though not the one from the television show) is a popular hangout for Puerto Rican locals. I myself am only home for several weeks a year and I still go once or twice every year. The island is sometimes isolated and sometimes crowded. It boasts snorkeling (I’ve spotted many anemones, fish, crabs, starfish, and barracudas), calm water perfect for floating and swimming, and several trees from which you can jump into the water. It’s off the coast of Guanica, and there are two ways to get there. Either take a ferry (call 787-821-5706 for more information) or rent a kayak from Mary Lee’s by the Sea. If you choose to do the latter, you might want to take your kayak to Isla Ballena (see my highlight “Kayaking and Snorkeling and Hoping for Whales”). This tends to be a day trip, so I suggest you have some food. You can either pack up your own or, if you take the ferry, place an order before embarking and tell them when you’d like to have it delivered. There are picnic pavilions that you can claim if it’s a calm day or you get there early.

Suppose I told you there was a small, remarkably idyllic and fairly unpopulated island in the Caribbean just a short distance from the mainland United States, an island so immaculate, plans were in the works to make it a National Wildlife Refuge, an island with a beach rated one of the best beaches in the world, an island where you could basically do whatever you wanted along its iridescent shores with little chance of being interrupted by prying eyes.... What’s the first thing you’d do? Well, if you were the U.S. military back in 1901 and the destination in question was the island of Culebra, you’d blow it all to hell! For nearly 75 years, bombs pounded Flamenco Beach on Culebra, la “Última Virgen,” while the U.S. military used it for target practice. Protests drove the Navy away, but some relics remain on the once pristine sands as a reminder of how never to treat one of the best strips of beach in the world. During the weekends, Flamenco Beach can get fairly crowded with “mainland” Puerto Ricans taking the ferry over for a day in the sun, so I recommend you make time during the week for a more secluded experience. There are vendors nearby, but not too near, to make your stay a pleasant one with local cuisine and plenty of ice-cold beer.

Manifiesto Café is known for its wide-ranging menu of coffees and careful brewing methods. Order a cup with beans grown in Mexico, Colombia, Costa Rica, El Salvador, or a handful of varieties from Europe. No matter which coffee you choose, it will be freshly-roasted. Manifiesto doesn’t serve coffee that was roasted more than 48 hours earlier. But that’s not the owners’ only rules for the coffee they serve. They also prefer beans harvested at plantations that are about 4200 feet above sea level. If you’re looking for a quick cup of coffee, go elsewhere. Manifiesto takes its coffee very seriously and uses a variety extraction methods. The payoff? Quite easily the best cup of coffee you’ve had in a good long time.

Marino Las Baulas National Park is a protected area compising Playa Grande, Ventana and Langosta. Together they are the stage for one of the most magical occurrences in the animal kingdom: the nesting of the gigantic baula (leatherback turtle), an endangered species. The hatching of these turtles is a remarkable highlight each year as they make their way out to sea. The egg-laying season goes from October-November.

Among Playa Avellana’s numerous pleasures, the small-town, almost-no-cars vibe sets the scene for true relaxation—as well as fun. Look for Lola’s—perhaps the hippest spot in town—in the tiny business district and try out fresh, locally sourced pizzas, mahi-mahi tacos, and veggie burgers; smoothie lovers will go nuts. Locals and visitors pack in under the almond trees late mornings after surf excursions and other adventures. Be on the lookout for Lolita, the piglet daughter of the original Lola (sadly no longer with us) as she frolics in the sand or ranges across the property.

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.

This woman-owned artisanal aged-cheese producer was on the front wave of what is an increasingly vibrant local food movement. Wanda Otero, a microbiologist, decided to start her business in part to offer Puerto Ricans an alternative to expensive imported cheeses. She has since expanded into yogurt-making, and her products are now sold in supermarkets and found on the menus of the island’s finest restaurants. Travelers can visit the Vaca Negra facility for a tour, which includes the opportunity to make their own cheese.

Part dive bar under the palms, part reggae dance hall, and part DJ club. This is the place to come for a great night out with friends. All Pura Vida!

Guavate, a section of Cayey better known as the Ruta del Lechon (“Pork Highway”), bursts into a rush of food-infused ecstasy every Friday and Saturday. People from all parts of the island come to watch someone roast a whole pig over the open fire before chopping it with a machete. Side dishes abound. I recommend sorrullos (corn sticks), bacalaitos (cod fritters), alcapurrias (fritters made of plantain dough and stuffed with meat), and rice with different types of beans. The blood sausage is not for me, but my father and boyfriend devour it every chance they get. Here in the mountains, shacks of all sizes let you pick your poison—beer, piña colada, or mojito (made from lime, mint leaves, rum, and sugar)—and drink to the beat of salsa and reggateon music. This creates the euphoric atmosphere for which Puerto Ricans are so famous. The cherry on top of the piña colada: Guavate lets you absorb the laughter, music, and food for a reasonable price. If you want the pig, but not the rambunctiousness, take your food to El Yunque National Forest and eat it by a waterfall (see my “Swimming Under a Hidden Waterfall” highlight). To find it, get on Luis A. Ferre Expressway, take the exit toward PR-184, and follow the signs for Guavate. You’ll start seeing pork soon after you take PR-184, but wait about fifteen minutes (until you’re around km 27) before you stop to get all the real action.

It’s hard to believe you’re in the middle of the Costa Rican rainforest at Amor Loco, part fine dining restaurant and part swanky lounge at Nayara Springs, a resort located near Arenal Volcano National Park. Moody lighting, velvet chairs and an onyx-topped bar set the stage for such diches as pumpkin puree soup or a perfectly cooked steak. Ask for bartender Carla to whip you up a cocktail on the spot (just let her know what your favorite tipple is).