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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.

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.

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.

If you’re wondering what to by and where to buy it, don’t worry – you’ll quickly discover that you’re spoiled for choice when engaging in retail therapy on St Barths. St Barths is something of a shopper’s paradise. The island features dozens of upscale boutiques, shops, and handicraft stores—many in close proximity to great French bistros and cafes (for when you need a little pick-me-up).

It’s time to drink like a local in Antigua: the island plays host to stellar spirits & brews, with the majority coming from two local places: the Antigua Distillery Limited and Antigua Brewery Limited. From Antigua’s distillery you get national rums like Cavalier and English Harbour, while from the Brewery there’s Wadadli and also Wadadli Gold, which kicks up the manliness a notch. But if you really want to drink like a local, check out Bushy’s and get a taste before it’s gone!

Off the coast of mainland Malaysia, Langkawi is an expanse of sandy beaches, forested mountains, and unique wildlife. Socialize with the residents or find solitude on the shores of a private island for the day. No matter what you do, it’ll be a trip to remember.

While there are a growing number of beach resorts on St. Kitts, you can still find plenty of secluded sands around the island when you want to disappear for a few hours. Visitors can also look forward to sunbathing on the black sand of Dieppe Bay, spotting dolphins on Turtle Beach, or snorkeling over shipwrecks in White House Bay.

St. Lucia is home to incredible biodiversity, from dense rain forests in the heart of the island to dramatic volcanic landscapes by the sea. When visiting, be sure to explore beyond the beaches to discover lush botanical gardens, tropical forests full of birds, rushing waterfalls, and even a drive-in volcano.

Three days in San Sebastián leaves just enough time for the city’s essentials. Visit the hallowed bars of the town’s old part, eating, drinking, and repeating until you find your favorite pintxo, those small bites for which San Sebastián is known. Drink in the city’s views from the surrounding mountains, beaches, and islands. Whether hiking or splurging at the seaside spa, a visit to San Sebastián is a lesson in luxurious living.

Montego Bay and the west coast of Jamaica attract first-timers to the island, and it’s easy to see why: white-sand beaches, the most glorious sunsets in Jamaica, plush resorts, a wide variety of restaurants, and a lively music scene. But there’s also plenty to see and do in the west coast interior away from Montego Bay: rivers, cenotes, and waterfalls such as the stunning Mayfield Falls.

Food trucks filled with the best fish tacos and seafood dot the roadways around Honolulu and the Island of Oahu. From downtown to the North Shore, trucks serve up sweets, burgers, bentos, shrimp, and fish tacos. Some sit in a fixed spot in the capital; others roam around Oahu; and several function as the catering arm of a stand-alone restaurant.

Whether served from busy food trucks parked near the harbor or at waterside tables set with candles and white tablecloths, the foods of Tahiti—based on the local bounty of just-caught fish and shellfish, as well as fresh fruit—will be one of your fondest memories of the tropical island.

Doña Olga* is a large kiosk in Piñones, from which the smell of fritters wafts all the way to the beach. I often find myself getting a large order of bacalaitos (round cod fritters), empanadillas (turnovers), alcapurrias (dough of plantains or yucca and filled with meat), and piononos (deep-fried sweet plantain balls stuffed with meat and cheese). Halfway through the meal, I start thinking my eyes are bigger than my stomach, but the flood of Puerto Rican flavors in my mouth makes me devour every last morsel in front of me. Of course, there’s no way I’d be able to handle all that without a refreshing drink on hand. My drink of choice is coconut water. (It’s completely natural; an employee will chop off the top of the coconut with a machete and bring it to you with a straw.) After you drink the water, you can scoop out coconut meat (the white stuff), which serves as a pleasantly light dessert. A swim in the nearby beach (two minutes away walking) and a nice nap will perfect your day. *Doña Olga is my first choice, but this whole road is bursting with beachside kiosks selling fritters and other Puerto Rican fare.

San Juan Cemetery lies on the coast adjacent to El Morro (San Juan’s beloved fort) and nestled in the district La Perla, a rougher part of town. Its statues and tombs make it as beautiful as a New Orleans cemetery. Exiting El Morro, head down the grassy field to your left to catch this flustering overhead view. On this day, a powerful storm was rolling in, casting everything in gray.

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.