How To Spend The Ultimate Long Weekend In San Juan, Puerto Rico

Celebrating its 500th anniversary, the city is booming, so it helps to know where to stay and what to do.

When it comes to the subject of clapping on an airplane, there are two camps. There are the clappers: those who clap the moment the plane goes wheels down on the tarmac. And there are the non-clappers, who sit in silent judgement of those clapping around them. 

Whatever camp you're in, you can pretty much guarantee that people will be clapping upon touchdown at Luis Muñoz Marín International Airport in San Juan.

"It's just a Puerto Rican thing I guess," my driver (and long-time San Juan expat by way of Chicago) Benny said as we made our way from the airport to the Fairmont El San Juan. "But when you get to paradise, why wouldn't you clap?" 

He makes a fair point.

Nicknamed The Island of Enchantment thanks to the array of beautiful white sand beaches, bioluminescent bays, mountainous jungles, and tropical El Yunque National Forest, Puerto Rico and locals like Benny have always seemed to embrace the best that life has to offer. 

Sandwiched between the Dominican Republic and the British and U.S Virgin Islands, Puerto Rico has seen its fair share of adversity over recent years as a result of Hurricane Maria in 2017, followed by the crippling effects the pandemic has had on tourism and local businesses.

Fortunately, the tides finally appear to be turning here, and between the convenience of dozens of direct flights from major US and international hubs, getting to paradise has never been easier.

This year marks the 500th anniversary since San Juan's founding (technically making it the oldest U.S city), and on a recent visit it was a delight to find the beach clubs bumping, hotels, cafés, and bars bustling, and the general joie de vivre that makes Puerto Rico such a singularly wonderful destination the perfect place for a post-pandemic holiday.

Here's where to stay, eat and play on your next visit to paradise. Just don't be afraid to clap when you get there. 

Where to Stay

Long considered one of San Juan's most iconic hotels, the Fairmont El San Juan Hotel is shining brighter and better than ever thanks to recent addition of 13 reimagined oceanfront Banyan Villas. 

Set directly on Isla Verde Beach about a five-minute drive away from the airport, the El San Juan blends all of the old-world charm with modern amenities you could hope for and, today, this beloved locale's legacy as an entertainment hub and hotspot continues to serve an allegiance of locals and visitors. In addition to a Foxwoods Casino on property, at the center of it all, the hotel's Chandelier Bar still is the perfect place to post up and people water, especially on a Friday or Saturday night when the party is in full swing here. Do yourself a solid and book a cabana by the pool where you can gorge on freshly grilled langoustines and passionfruit mojitos from the El San Juan Beach Club and Bar.


Home to a stretch of some of the San Juan's top beach resorts, restaurants, and nightlife, life over in Condado has always been teeming with activity, starting with the adults-only Condado Ocean Club and La Concha Resort, both of which offer coastal-chic luxury and beachfront access. Condado Vanderbilt Hotel is another reputable five-star stay with one of the island's best fine dining experiences at 1919 Restaurant.

For those who want to soak in some local history, Old San Juan boasts a contingent of charming hotels and inns, starting with the recently opened Palacio Provincial. Offering 43 sumptuous rooms and suites and a signature restaurant, Consular, the spacious rooftop and bar serves up some of the best pink mojitos and infinity pool views over the old city.

El Convento
Guests at this popular boutique hotel are in for quite a memorable history lesson. | El Convento

Originally built in the 16th century as the country's first convent run by Carmelite nuns, Hotel El Convento's reputation for being one of San Juan's most elegant boutique hotels still stands. This summer, the hotel is offering guests a History & Gastro experience, which includes a tasting tour of Old San Juan for two adults, as well as a pitcher or sangria or mojito and full American breakfast for two during their stay.

For something truly extraordinary, The Gallery Inn holds a special place in this travel writer's heart and is a memorable experience you won't soon forget. No two rooms are the same in this quirky 27 key boutique, and from the eclectic art-filled rooms and public spaces, every nook and cranny of the former 19th century mansion has been accounted for. Don't be surprised if you hear opera singers or piano music bellowing out from one of the rooms here. The balcony views directly overlooking the Atlantic, walled in pool lined with giant busts and patios are perfect for drinking in this little slice of paradise.

Where to Eat

Before we dig in here, a disclaimer: Dinner reservations should be made in advance of traveling to San Juan, especially on the weekends if you plan on going to Old San Juan. 


Wherever you're staying, there's no better way to start your morning than with some freshly baked quesitos and coffee. Quesitos are a delightful Puerto Rican pastry and whether you find them on the menu at your hotel or in one of the local panadería (bakeries) they are delightful local delicacy.

Kaffe Haus in Old San Juan lays claim to being "the best brunch in town" and while that's certainly a bold statement, this quaint coffee house has the croquetas, chocolate, and coconut coffee, along with tapas and cocktails to back it up. Stroll a bit further along Calle de Tetuán and you'll find Spiga, whose menu includes breakfast sandwiches and freshly baked sourdough along with an assortment of coffee.


There's no shortage of charming restaurants, cafés, and bars starting with Barrachina which has long maintained themselves as the birthplace of the piña colada. While the jury's still out on that, it's a charming place to sit in the courtyard and sip delicious frozen bebidas nonetheless.

La Fortaleza is the main artery of Old San Juan, and when it comes to fine dining in the old city, it doesn't get much better than Marmalade where chef/owner Peter Schintler continues to turn out the best five-course tasting menu and wine pairing in town.

If you happen to be visiting on a Saturday and can manage to tear yourself away from the beach, Mercado Agrícola de Viejo San Juan is the local farmers market and a great place to poke around and support local growers.

Ranked on The World's 50 Best Bars list, La Factoría and La Cubanita reign supreme when it comes to their signature lavender mule and boozy rum punch. A block over, El Batey Bar is a cool local dive with a long list of mezcals and mixed drinks. Right next door, Pira Rum is a fun tapas bar to keep the cocktails, piraguas (shaved ice), and food flowing.

Over in Condado, Mario Pagán serves up some of the city's most inventive Puerto Rican inspired dishes. Just next door, The Oyster Shack is shucking up some of the area's best crudo, crabs, and cold plates in a convivial setting. 

For traditional Puerto Rican home cooking with an elevated twist, José Enrique in Condado, CAÑA by Juliana Gonzalez at The Fairmont El San Juan, and Café El Punto for some mofongo (plantains) and tostones in Old San Juan are all excellent spots to check out on your next visit.

What to Do

Whether or not you're staying in Old San Juan, you'll want to carve out plenty of time to just amble around here. The blend of Spanish and African influence can be found everywhere you look, just be sure to take extra care on those cobblestone streets. 


If you really want to dig in to the local history, there are plenty of excellent walking tours in the old city, and a beautiful sunset sail around the bay. El Castillo San Cristóbal and San Felipe El Morro are two fortresses that date back to the 16th century and are great for walking around and snapping some pics.

Of course, shopping is a requisite activity in San Juan and there's no shortage of charming local boutique and galleries. Stop at Ole Puerto Rico to get fitted for a handmade Panama hat and spend some time chatting with the shop owners who will get you fitted for a one-of-a-kind souvenir that will last for years to come. 

Once you're donning your new hat, head outside and take a short stroll over to the "Umbrella Path" at the end of La Forteleza just in front of the Governor's Mansion is a popular spot for snapping a few San Juan selfies.


Finally, it's worth paying a visit to San Juan Cathedral. The second oldest cathedral in the Americas is the final resting place of the country's first governor and seeker of the fountain of youth, Ponce de León. From the cathedral, walk down the leafy and oh so pretty Caleta de San Juan. If you time it right, there's no better place to catch the sunset than Puerta de San Juan. 

No matter what camp you're in, don't be surprised if you find yourself clapping by the time the sun goes down in this beautiful piece of Puerto Rican paradise.