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Musicians Aimee Mann, Joe Henry, and Loudon Wainwright III gather in Louisville to indulge in raw oysters, dry martinis, and unscripted conversation.

From roast pork, empanadillas, and plantains to street snacks, seafood, and freshly-made ice cream, Puerto Ricans enjoy many hearty local flavors. To really experience local culture and customs, you must take time to try each region’s culinary specialty. These foodie delights could be a unique twist on non-Puerto Rican food, or a delicious concoction of fruit and juices, to sandwiches stuffed with three kinds of meats. Locals love the flavors, and you will too!

The vivid flavors and colors of Puerto Rico cannot be ignored. Wander San Juan’s candy-colored streets, explore El Morro and the trails of El Junque, and linger on the inviting beaches: A weekend is just long enough to fall in love with this island.

AFAR chose a destination at random—by literally spinning a globe—and sent writer Ryan Knighton to Egypt’s sprawling capital with just 24 hours’ notice.

Any trip to Puerto Rico must include at least one perfect day in the old city of San Juan. The island overflows with a rich culture and history that you can first experience here in San Juan right after stepping off the plane. Spend a day roaming the old city, exploring cobblestone streets with hidden gems and restaurants, art galleries and shops. These are the must-see places to complete your perfect day in San Juan.

Love architecture? Then you’ll want to know about these hotels.

Mexico’s Pacific Coast beach town Puerto Vallarta is all about fun. Not sure what to do while in Puerto Vallarta? We’ve got you covered. Puerto Vallarta has fabulous nightlife, a charming downtown, a long malecón, or boardwalk, great al fresco dining options, and the best sunsets of the West. Visit the beach where the Richard Burton-Ava Gardner flick “Night of the Iguana” was filmed, eat fresh, delicious seafood, and then dance until dawn in one of Puerto Vallarta’s many neon nightclubs.

At Mosquito Bay Beach—also known as Starfish Beach—on Vieques Island in Puerto Rico, you’ll find tons of colorful starfish. While the beach itself is small, it’s still beautiful and perfect for a scenic walk. You won’t get bored searching for sea creatures in the water.

We were lying in the sand in Vieques. We’d been told to watch out for horses, but nothing could prepare me for this. What a majestic experience to see wild horses free on the sands of Sun Bay Beach.

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.

Mexico’s Pacific Coast is where Mexican beach tourism began. Acapulco, Puerto Vallarta, Mazatlán-- the names hark back to bygone eras of mid-Century Hollywood royalty and the Golden Age of Mexican Cinema. The allure of Mexico’s Pacific Coast has not vanished. Old town Mazatlán overlooking the beach, Sayulita surfing and fish tacos, fun-loving Puerto Vallarta, Acapulco in all its cliff-diving glory--these magical places and more await the visitor to Mexico’s Pacific Coast.

This is my favorite hike by far. Cueva Ventana (“Window Cave”) is a beautiful, scenic hole in the side of a mountain that opens up to a lush, green valley down below. You’ll trample through mud, hunker down under low-hanging stalactites, dodge around stalagmites, and never look up (there are bats, of course) while wandering through the cave. All this winding around through two caves leads you to one of the most spectacular views in all of Puerto Rico (but I may be biased). The hike to this cave is half the fun. You climb down into a small opening under enormous, ancient tree roots, and you get the feeling of a tomb raider. But, if you’re claustrophobic or don’t feel up to lowering yourself down a cave wall, there’s an additional path that bypasses the first cave and leads you straight to the easier hike to Cueva Ventana. There’s something for everyone! I’m pretty sure I saw one Puerto Rican woman doing the whole thing in heels. This is a must-visit site for anyone touring the northwest central part of Puerto Rico. Another tidbit is that it’s practically free! You can find the directions on PuertoRicoDayTrips.com, park at the adjacent Texaco gas station. UPDATE (2014): There is now an easier way to access this awesome view! There are now boardwalks for ease of access, and you must pay $11 to tour the site. You get a flashlight and hardhat for safety.

This is a great place to spend a free day in Puerto Rico. There are many interpretative trails in this park, and all are free and open to the public. Some lead to caves, others lead to beautiful views.

There are also many covered areas for picnics. The trails are mostly leveled off and easy hikes, although some can be a bit more challenging. Be sure to bring lots of water, as it can be humid. Also, bug spray will be your friend! If you plan to take a trail that leads to a cave, be sure to have a flashlight with you as well.

Descended from horses brought over in the 16th century by Spanish conquistadors, hundreds of wild horses rule the little island of Vieques. The horses, an attraction in their own right, dot the landscape wherever you go. With every encounter, I couldn’t help but slow down and admire their beauty. They are naturally intelligent and curious, so don’t be surprised if they approach you or your vehicle looking for little treats. For a guaranteed encounter, look no further than Sun Bay—where I snapped this picture. Here, they graze, take frequent sand baths, and (if you’re lucky) cool their hooves in the blue waters of the Caribbean.

Designed by Fuster + Architects, an award winning firm located in San Juan, Puerto Rico, El Blok takes its visual cues from the surrounding light, land and sea. In addition to being a playful structure, it is highly functional and built to withstand storms and hurricanes (a big plus anywhere in the caribbean!). It is located at the beach, at the start of Esperanza’s sleepy malecon, with its low-key seaside huddle of restaurants, bars, and stores, most of them back open after hurricane Maria’s devastating sweep of the island.

I loved my room, one of the spacious corner suites. The way the space captured the light was uncanny, every time I got back to my room, a new play of light beams and shadows was waiting for me. The restaurant downstairs serves up amazing food, hands down the best I had on island. Executive Chef, Carlos Perez. brings to the table a delicious, fresh take on Puerto Rican cuisine, centered around their bayahonda mesquite fired grill and Rotisol rotisserie. Just don’t expect much of a breakfast at the hotel. I took a short walk each morning to some cafés nearby, to grab a coffee and omelet. El Blok’s rooftop bar was ‘the’ place to hang in the evenings with locals and travelers alike, while listening to amazing music. When we were there, the duo Más Que Dos was playing and it made for an all around perfect sunset.

El Blok currently has 22 rooms and is adding another 11, slated to open in summer 2019. We were warned about construction noise between 8am and 2pm, but I can honestly say it didn’t interfere at all with my stay. It’s of course when you’re supposed to be out and about anyways, exploring the island!

Rates start at $140 per night plus tax.

A heartfelt thank you to Discover Puerto Rico (@DiscoverPuertoRico) for 3 days in beautiful Vieques and a fun stop-over in San Juan, Puerto Rico.