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A Weekend Guide To Puerto Rico — Where To Play, Eat, And Stay

Puerto Rico is the birthplace of some of the world’s most prized masterpieces – the piña colada, sexy salsa music, Bad Bunny. Where would we be without them? While I’ve long been a lover of these party-centric cultural contributions, what I learned on my recent trip to the little Caribbean island is that its charm goes far beyond just the hits. Puerto Rico is also home to a vibrant community, lush landscapes, and pristine beaches — as well as a food and drinks scene that’s rooted in history while rapidly evolving. The best part? You don’t even need your passport to get there!

One of the best things about Puerto Rico is that it feels like you’re in a far-out tropical paradise even though you’re still in a United States territory. And with the infamous passport delays and international airport nightmares over the past year, staying somewhere closer to home can be the most reliable option for travel as fall weather starts turning cold on the mainland. All you really need is a few days in Puerto Rico to enjoy your time there, too. I only spent a long weekend in town and was able to adventure in the outdoors, relax by the beach, and indulge in the local delicacies.

If you’re in the market for a tropical island vacation without the hassle of international crossings, Puerto Rico should be your go-to destination. Read on for my top recommendations on where to play, eat, drink, and stay.

Puerto Rico
Chloe Caldwell

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PART I — Where to Play

Visit El Yunque National Forest

El Yunque National Forest
Chloe Caldwell

All I can say about Puerto Rico’s tropical landscape is wow. The island’s mountainous and hilly terrain, in many places, is covered in lush flora that looks especially bright green in contrast to the crystal blue sea and sky. The best place to experience and learn more about Puerto Rico’s stunning natural scenery is by visiting El Yunque National Forest. It’s the only tropical rainforest in the US, making it a must on your itinerary.

Much of the public forest area is still closed due to lasting damage from Hurricane Maria, but there is still plenty of land and trails to explore. To start, stop by the visitor center for a guided informational tour. This is a great way to get familiar with the different plants and animals you might see before exploring on your own. From there, you can drive up the winding two-lane road that takes you to various trailheads, observation points, and historic sites throughout the forest. You’ll stumble across natural waterfalls, doable hikes (there are also overnight hikes for the avid adventurers), swimming holes, and awe-inspiring views.

My favorite stop along the way, which had what I believe might be one of the best accessible views on the entire island, was at the Yokahú Tower. It’s an old lighthouse-looking building in which you can climb up a winding staircase to the top. What you’ll find once you make your way up is an unobstructed sweeping view of the forest and the island beyond. You can see for miles, from the luscious rainforest canopy to the distant Caribbean waves.

Learn more about El Yunque National Forest here.

Go for a Sunset Sail

What’s a trip to the Caribbean without some boating? The best way to wind down after a long day of exploring and feasting on fried Puerto Rican food (more on this later) is by going for a sunset sail with Sail Old San Juan. The sunset tour fits up to six people, so grab your travel crew, throw on your nicest vacation getup, and celebrate by toasting with complimentary bubbly. It’s nothing but carefree, laidback vibes out there on the water.

Your US Coast Guard licensed Captain will take you through the San Juan harbor and past the city of Old San Juan. You’ll get a glimpse of the area’s famous historic sites, such as the Castillo San Felipe del Morro, a citadel built between the 16th and 18th centuries and a UNESCO World Heritage site. The sail lasts for about two hours, so you’ll have plenty of time to soak in the cool ocean breeze (savor it — Puerto Rico is hot) and gawk at the sun setting over the horizon. Overall Sail Old San Juan is an excellent way to take in the historical monuments from the water, admire the stunning sunset views, and relax at sea. Your captain might even let you steer the boat!

Book a sunset sail or another boating excursion with Sail Old San Juan here.

PART II — Where to Eat & Drink

Kioskos de Luquillo

Kioskos de Luquillo Puerto Rico
Chloe Caldwell

If you want to indulge in the goodness that is authentic Puerto Rican food, you need to make a trip to Kioskos de Luquillo — but be prepared for a serving of fried everything. Kioskos de Luquillo is a long street side row of about 60 family-owned kiosks selling food, drinks, and souvenirs. Some traditional Puerto Rican meals include mofongo, tostones, arroz con gandules, and coquito. Mofongo is one of the most recognized Puerto Rican dishes, made with plantains as its main ingredient — the plantains are typically fried and then mashed with salt, garlic, broth, and olive oil in a wooden pilón. Being that Puerto Rico is surrounded by clear Caribbean waters, there’s an abundance of good seafood options (for the most part, these are also fried).

Kioskos de Luquillo is an ideal lunch spot, especially if you spent the morning exploring El Yunque, as it’s only a short drive away from the forest. Plus, you’ll need to burn off some energy and get hungry before coming here. Like I said, there are 60 food stalls, bars, and shops to explore, so it’s best to come with a big appetite.

Learn more about the many family-owned food stalls here.

La Factoría

La Factoría
Chloe Caldwell

If you’re looking for a place to party it up on a weekend in Puerto Rico, head back to Old San Juan. There are tons of bars on the heavily trafficked San Sebastian Street, all located within walking distance of each other. The best place to start is at La Factoría. This low-lit, speakeasy experience has been named one of the world’s 50 best bars numerous times, and for good reason.

Beyond the main entrance, which appears to be more of a small dive bar, there are “secret” doors and passages to six other bars with their own unique ambiance and drink menus. I stayed in the main “Facto” bar area and ordered the Lavender Mule, a tart and tasty concoction made with Ketel One, ginger tea, lavender, and citrus.

Whether you want to sip on craft cocktails, dance late into the night, or just chill with your squad for a quick nightcap, it’s safe to say you can find what you’re looking for on a night out at La Factoría. You can basically start and end your night here exploring the different rooms, or bar hop down the lively and colorful stretch of Old San Juan.

View the full Facto menu here.

PART III — Where to Stay

Margaritaville Vacation Club

Margaritaville Puerto Rico
Chloe Caldwell

I know, Margaritaville. But seriously, it’s well worth staying here on your trip to Puerto Rico. The Margaritaville Vacation Club at Wyndham Rio Mar offers oceanfront suites, apartment-style accommodations (since it’s a timeshare property that’s available to book for short-term stays), poolside restaurant and bar service, and easy access to the beach — it’s just steps from the sand and sea. It’s pretty much what you’d expect from most “resort” properties, but that might be exactly what you want and need for a relaxing and somewhat secluded weekend away (as opposed to the bustle of Old San Juan). It’s definitely what I needed, and nothing helped me unplug and relax more than savoring a cup of fresh coffee on my oceanview balcony each morning.

The best part is the property’s proximity to El Yunque National Forest and Kioskos de Luquillo. It’s right down the street from both, so if these are top activities on your Puerto Rico to-do list, you can’t beat Margaritaville Vacation Club’s location.

Book your stay at Margaritaville Vacation Club at Wyndham Rio Mar here.

Margaritaville Puerto Rico
Chloe Caldwell

Hotel El Convento

If you’re looking for a more boutique yet still luxury experience, book a room at Hotel El Convento, a historic hotel in the heart of San Juan. It’s located just steps away from the historic landmarks and nightlife of the city, so this is ideal if you’re looking to be immersed in the action. Built in 1646, this property offers old-time charm combined with modern amenities and comfort — including high-end, vintage-inspired rooms, an open-air restaurant, courtyard bar, fitness center, and a pool with an ocean view.

Book a stay at Hotel El Convento here.


Uproxx was hosted for this story by Puerto Rico Tourism. However, they did not review this story. You can learn more about the Uproxx Press Trip policy here.

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