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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.)

Set tight in the jungles around Hotel Casa Chameleon, at Las Catalinas, the restaurant Sentido Norte is 45 minutes from the Guanacaste provincial capital, Liberia. A hilltop restaurant helmed by Costa Rican chef José López, it showcases a mix of local tastes and other modern classics, from sunrise until sunset daily. French toast with plantains, and ceviche punta penca (shrimp, octopus, and avocado) are current top orders; don’t miss the liquid enchantment on offer at the bar, perfect for sunsets, and aguas de sapo, a sweet, spiky pop made with guaro aguardiente.

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.

The laid-back restaurant Carbon Caribbean Cuisine takes you on a culinary journey around the Caribbean. You can order typical dishes from Cuba, Jamaica, Puerto Rico, and, of course, the Dominican Republic. Popular with locals, Carbon offers a glimpse of island life beyond the beaches and resorts.

Old San Juan offers historically and culturally significant experiences including a walk through 500-year-old forts, visits to UNESCO sites, historic churches, museums, the second oldest cathedral in the Americas and Ponce de Leon’s mansion. Cobblestone streets and pastel buildings are perfect for exploration during the day and variety of restaurants and shops make for a complementary evening.

Looking for something really unique to bring back from your time spent in Puerto Rico? Grab a t-shirt from Uncharted Studio (or a trucker hat, a bag, some stickers...). Established in 2005, this place put custom silk screening shirts on the map for Rincon. They use 100% ringspun cotton tees for a nicer quality and feel. and their printing solvents are non-chemical, soy and citrus based. Talk about eco-minded! This is something you want to support! Your trip to Rincon is not complete without stopping here for a t-shirt!

To stay at the Verana, an eco-lodge outside Puerto Vallarta, guests take a 30-minute boat ride to the village of Yelapa. (Dolphins accompanied me on the journey.) Scattered on a jungle hillside are eight variegated cottages and stand-alone rooms. My cottage, Palapa, had no walls, which maximized the views of the Bay of Banderas. A gang of chatty wild parakeets provided my wake-up call. The hotel spa offers facials and massages, and you can relax by the pool, which is crafted from concrete tinted in the hues of the local trees, rocks, and clouds. —Karen Catchpole

Coco frios are sold on every corner during the high season (fall and winter) in Puerto Rico. Cold, fresh coconut water is the lifeblood of island living. Literally, if you were ever stranded on an island, you could sustain yourself on what’s inside a coconut (just ask Les Stroud). There is a difference between coconut water and coconut milk. Coconut water is clear to translucent and not as sweet—you harvest this from a fresh green coconut that has just fallen, or is ready to fall from the tree. It might taste unusual at first if you have never tried it, but this is actually the best form of natural electrolytes to replenish yourself after a workout or surf session. Watch the roadsides for the carts and folks with machetes—because this is your hint that coco frios await you!

The customary dessert of Puerto Rico, the brazo gitano (gypsy arm), can be found at Franco’s in Mayaguez. This place has been around for generations, preparing the rolls for local markets and grocers and also for their own store. The cake is rolled into a log shape and then pumped with a filling. This one is a zanahoria (carrot) cake with a cream cheese filling. You can find many types of rolls, with all sorts of fillings. The traditional ones contain fruit jams. When in Mayaguez, be sure to stop here for this delicious roll.

A new 16-bungalow beach retreat lures travelers to Mexico’s Pacific coast surf town of Puerto Escondido. When the sun goes down, locals and guests hit the underground dance club. From $213. This appeared in the January/February 2014 issue.

La Poza del Obispo (Bishop’s Pool) is a hidden treasure near the Arecibo Lighthouse in Puerto Rico. This beach is loved for its contrast. You will find a calm spot (though it can get rough in bad weather) where you may float, swim, or simply stand around talking to friends. This area is surrounded by limestone rocks. On the rocks and beyond them, as you near the open sea, large bursts of water spray into the air. The water is so clear that a fish and I once became friends. He kept swimming by my side and stopping when I stopped. The tiny silver and blue fish amused me for quite a few minutes. It’s a clean little area where you can sift through seashells and, if you snorkel, you can take a peek at coral on the rocks. Feel free to bring food and have a picnic, since there are a couple of tables and trashcans around.

When I first moved to the island, I joined a friend in the Old City for a tour and lesson on the history of Puerto Rico. When passing by this little section of town near Pigeon Park, my friend and native-turned-tour-guide said that this was the smallest house in Old San Juan. Wow, okay, so this little yellow portion is technically a house? I’ve visited this site several more times since then and have never actually seen anyone enter or leave this door. Whether it’s true or not, it makes for a cool story and great photo.

On Puerto Rico, horses roam the farms, the mountains, the town centers—and also the beaches. A couples’ horse ride at sunset is a perfect way to kiss the day good-bye. With Tropical Trail Rides, in the northwestern municipality of Isabela, you can take a two-hour ride through the forest and by the beach as the sun sinks down toward the water. Make sure you take the opportunity to break for a hike or a swim along the way. On the north side of the island in Manatí, Kerry’s Horses designs personalized sunset rides by the beach or through nature reserves.

Shop for an authentic souvenir in Everything but Match, a store inspired by a T-shirt line designed by the owners’ 6-year-old daughter. In this shop in Old San Juan, you’ll find original art, accessories, and children’s clothing made by local artists and artisans. From unique jewelry to brightly colored throw pillows, you’re sure to fall in love with something unique to bring home in your suitcase.

New York has Ellis Island; Buenos Aires has the Hotel de Inmigrantes. The huge waterfront building, located near the old port docks in what’s today known as Puerto Madero, served as the temporary home for waves of European immigrants arriving to Argentina between 1911-53. Today, the Hotel de Inmigrantes is an intriguing (and free) museum that few tourists see: come to see photos and memorabilia representing the many immigrant groups who came through the port of Buenos Aires, plus colorful advertisements for trans-Atlantic passages and model boats.