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  • 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.
  • Calle principal, Cabarete 52000, Dominican Republic
    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.
  • 54 Calle Fortaleza, San Juan, 00901, Puerto Rico
    Have you been here? Tell us about it below!End your day in Old San Juan with a pre-dinner stroll along the water, alongside the Old City Walls. It’s that time of day when everything seems to slow down, even the waters of the Caribbean Sea begin to ease into a glassy stillness - perfectly reflecting the midnight blue sky and the incandescent glow of the street lamps. Start from Paseo de la Princesa, at the Raices Fountain, and wind your way around the walls. Take in the views of the setting sun from the benches that line the walkway. Reminisce about the day and linger. There’s no need to rush into the night and tomorrow will come soon enough.
  • 151 Calle del Cristo, San Juan, 00902, Puerto Rico
    Dating to 1521, the Cathedral of San Juan Bautista isn’t just one of the oldest buildings in San Juan—it’s the second-oldest cathedral in all of the Americas. Go inside to see the tomb of Spanish explorer Ponce de León, who founded the first settlement on Puerto Rico and in 1509 was named the island’s first governor. The remains of St. Pio, a Roman martyr, can also be seen in the cathedral—the saint’s mummy has been displayed here in a glass box since 1862.

  • San Francisco, San Juan, 00901, Puerto Rico
    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.
  • PR-115, Añasco, 00610, Puerto Rico
    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.
  • Rincon, 00602, Puerto Rico
    Behind one of the most popular surf spots in Rincon is a breathtaking view of the northwest coast of PR. Domes Beach during fall/winter will be packed with surfers, but if you want to enjoy the location without being slapped by boards or crowds, then take the short dirt walk behind the “dome” (old nuclear center) and hike along the raised seawall for a gorgeous and unobstructed view of the rugged, lush, tropical cliffside and the waters below. You can take this trail all the way to Pools Beach (in Puntas, the upper part of Rincon) and watch more surfers pick off waves in another great surf spot. This photo was shot with my iPhone 4S, and edited as HDR.
  • José María Morelos SN, Villa de Etla, 68200 Villa de Etla, Oax., Mexico
    In Oaxaca, religious celebrations leading up to Easter tend to be quite somber, which is appropriate considering what the days commemorate. Although a lot of people take advantage of the two-week school break to go to the beach, those who stay in town partake of these somewhat mournful observances. Silent religious processions and passion plays are commonly held on Good Friday. Easter Sunday is generally a quiet day, but there are some festive celebrations that take place. In front of the church in Etla people carry religious images draped with flowers. Bands play music, and the people carrying the images dance around as they balance the weight on their shoulders.
  • Bahía Dorita s/n, Cisnes, Región de Aysén del General Carlos Ibáñez del Campo, Chile
    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.
  • Km 5, 5 Norte S/N, Natales, Región de Magallanes y de la Antártica Chilena, Chile
    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.
  • Esperanza is located on the southern side of Vieques island with a laid-back vibe reminiscent of Key West. This small town has an main street that runs parallel to the ocean called “El Malecón” that is dotted with friendly guest houses, funky bars and even gourmet restaurants. It makes a great base for exploring the island’s treasures: it’s walking distance to Playa Esperanza and Sun Bay and only a 10-20 minute drive to the secluded beaches in the wildlife refuge.
  • San Juan-Caguas-Guaynabo, PR, Puerto Rico
    Cuevas del Indios (Indian Caves) of Arecibo offers a tidbit of ancient history of a lost people. An easy-to-find natural wonder, with a simple $2 fee for parking, this you won’t want to miss. Bring some sunscreen and your camera. Begin your hike up sharp and spiky cliff sides (no worries, I was able to do it all in sandals). Work your way up to the top of the cliff and enjoy the fantastic view below. Ocean spray from the massive waves breaking against the side of the rocks will cool you off with a little salty mist. Dare to look over the edge to see a landscape of arches and tunnels, burrowed below your feet. Climb down into the rocks to find a wonderful—and surprisingly well-preserved—variety of Taino Indian petroglyphs. A small climb down a somewhat sturdy, handmade ladder lands you at the base of the cave with stone carved images surrounding you. Now is your chance to experience some history. Wander through the smaller tunnels, and listen to the ocean making its way inside the cave with every massive wave crashing outside.
  • Mercado del Puerto, Rambla 25 de Agosto de 1825 228, 11000 Montevideo, Uruguay
    Convenient to Montevideo’s cruise ship terminal, the Mercado del Puerto was first inaugurated in 1868 and long served as the city’s principal meat and produce market. The clock here is almost as famous as the building itself. Constructed, like the entire market, in England and then shipped to Uruguay, it dominates the central hall of the cast-iron building. The Mercado del Puerto no longer operates as a market and today houses a number of popular restaurants serving typical Uruguayan dishes.
  • Porfirio Díaz 115 esquina con Morelos Calle del General Porfirio Diaz
    Oaxaca’s Casa de la Ciudad is housed in a big yellow building just a couple of blocks from the Zocalo. On the ground level you’ll find the Andres Henestrosa memorial library which contains over 50,000 volumes, and some rooms that are used for temporary exhibits. Make your way across the central patio and up the steps to the second floor, where you’ll find, among other things, a room that has two very large aerial photos (about 12 square feet) of Oaxaca city on the floor. One of the photos was taken in 1990, and the other in 2006. They call this the “foto-piso” (photo-floor). It’s fun to walk over it and pick out landmarks and see how Oaxaca has changed over time. The Casa de la Ciudad often has exhibits dealing with urbanization and architecture, and it also hosts workshops, concerts and other events. It is open daily from 9 am to 8 pm, and admission is free.
  • Limón Province, Puerto Viejo de Talamanca, Costa Rica
    This surfer town draws tourists keen to catch a wave, so it’s little wonder that it’s chockablock with folks who want to sell their wares to the visitors. From New Agey shops to a farmers market, there are lots of opportunities to shop and support the local economy. Be sure to bring cash, as many vendors don’t accept plastic.