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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.

Step off the beaten path that leads to Jim Morrison’s grave at Père Lachaise and head instead to the lesser-known, yet extraordinary Montparnasse Cemetery. Locals bring metro tickets to leave on Serge Gainsbourg’s grave in honor of his song “Le Poinçonneur des Lilas (The Lilas Ticket Taker).” Nearby rest the poet Baudelaire and eternal lovers Jean-Paul Sartre and Simone de Beauvoir. A married couple by the name of Pigeon share a tomb that is as surprising as their family name. Susan Sontag opted for a minimalist grave, while artist Niki de Saint Phalle chose a rainbow-colored mosaic cat for the grave of her assistant Ricardo. Brancusi’s The Kiss sculpture stands at the head of his grave. Stop at a guardian’s kiosk when you enter the tranquil space and ask for a map of the luminaries who have made this their eternal resting place.

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!

Just a mile off Messinia’s coast is the beautiful Proti Island, which is said to resemble a crocodile in shape, and is a haven for history buffs. On land, you’ll find archeological sites and ruins from ancient temples and citadels. Additionally, Proti Island is great for diving due to its clear visibility, 15 dive sits and mix of reef, cave, wall, wreck, canyon, and drift diving. As you swim through turquoise Mediterranean waters, keep your eyes peeled for blue-spotted rays, painted combers, damselfish, sea turtles, and myriad colorful corals and sponges. One company that can take you diving off Proti Island is Navarino Sea by Aqua Divers Club, a Padi Five-Star IDC Resort.

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.

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.

Besides Poás’s impressive volcano, this beautiful region is home to cozy down-home restaurants. One standout is Freddo Fresas, named for the strawberries (fresas) that constitute the region’s principal crop. Diners here enjoy tasting local specialties such as hand-thrown tortillas, chorreadas (a sweet-corn pancake iteration), tamales, bean empanadas, and other rustic yummies. Their strawberry-based desserts—fashioned from fruit just picked from the restaurant’s garden—are a must. Never too acidic or overly sweet, the perfect berries are like nothing you can get at your hometown supermarket. Try fresh strawberry juice or eat the fruit in the Costa Rican mode, i.e., with condensed milk or melted chocolate.

The Bardini Garden is one of Florence‘s best kept secrets. It was built in the 12th century as part of a large estate owned by the Mozzi family. During the 20th century it was closed for many years and only reopened in 2005 after significant restoration. The garden is small and easy to walk through in about an hour and its hillsides offer spectacular views of Florence. Wandering among the terraces and flowers is an excellent way to escape from the touristy historic center and instead feel part of what this old city once was. During the off-season and in the morning or late afternoon, you may be the only visitor! The Bardini Garden can be accessed in two ways. One is by going into Boboli Gardens and exiting on the left side—this can be hard to find, but is marked on the Boboli Gardens map you receive on admission. The second way is via street da Costa San Giorgio 2. The garden opening hours vary according to season. It is closed the first and last Monday of each month. Admission is included in the Boboli Gardens ticket, or can be purchased separately for around 10 euros (and includes admission to the villa). There is also a restaurant with beautiful terrace views.

With its striking white facades and terra-cotta rooftops, you might mistake Cap Maison for a Mediterranean villa on the Costa Brava. However, this all-inclusive resort set on a former sugar plantation on St. Lucia’s north coast offers more than meets the eye. The pastel-hued interiors are matched by the sunny dispositions of the superb staff, who cater to every request, whether it’s finding a shady spot by the terraced pool area, booking a paddleboarding excursion off the private beach on Smuggler’s Cove, or arranging for the house yacht to take you to the neighboring island of Martinique for the day. Don’t miss the sunset views at the Cliff at Cap restaurant, where locally sourced dishes like reef conch ceviche and passion fruit soufflé are topped off with some of the resort’s house-made rum.

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.

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.

Gonçalo Alves and his wife, Marta Fonseca, spent eight years turning an abandoned chicken farm on Portugal’s wild Costa de Prata into their dream retreat. “We wanted a big house to share with people,” says Alves. Their hotel, located a 45-minute drive north of Lisbon, is a whimsical escape with a hippie vibe. Each night Alves and Fonseca invite guests to join them for wine and traditional folk music around a bonfire. The architecture is modern, but the interiors have a fashionable flea-market feel. Inside the 10 rooms and four villas you’ll find bedding, rugs, and light fixtures from Morocco and India, driftwood-frame beds, and fireplaces that hang from the ceiling. Doubles from $345. 351/2-6193- 6340. This appeared in the October 2013 issue.

Looking for a great afternoon or evening hike, high above the clouds of the East Bay? Need a few good labyrinths and a volcano to make it desirable? It so happens, I’ve found your place. Located on the border of Oakland and Contra Costa, the parking for Sibley is on Skyline Boulevard. This is a Regional Preserve and is managed by the East Bay Regional Park District. All the perks of hikes in this part of the Bay are here and include a great network of trails, soaring views and many a grassy vista. It also claims an extinct volcano and at least four or five labyrinths for potential meditation. You have two major continental plates to thank for the geological grandeur and a few thoughtful locals for the peace of mind, found within.