The ultimate weekend in San Juan

As far as capital cities go, San Juan, Puerto Rico is a rare gem that has it all – beautiful beaches, a historic center with architecture dating back to the 16th century, a vibrant arts scene, an increasingly diverse population, and 18 neighborhoods with unique flavors, sounds and sights to discover. 

Born and raised in the metropolitan area, San Juan is more than just the place where I lived, hung out, worked and played. In all of my stories about Puerto Rico, the city itself is a character that shaped me.

The place that taught me how to find calm in the sea breeze, to embrace the chaotic nature of its streets, and to love places and neighborhoods that had been deemed unlovable.

It’s a place that combines big city allure with the unique charm of the Caribbean. Don’t be deceived by San Juan’s size. It's a small city, but a few days isn’t always enough to see everything it has to offer. Here are a few quick tips to help you pack as much as possible into a long weekend.     

• When to arrive: Arrive on a Thursday morning so you can take advantage of the slow traffic on the main beaches for the day or get settled and grab a bite to eat. Avoid arriving during rush hours – 6am to 8am and 4pm to 7pm – as you may get stuck in endless traffic jams exiting the airport.  

• How to get from the airport: While there is public transportation from the airport, it is not recommended for casual travelers. Plan on renting a car, using rideshares or grabbing a taxi authorized by the Puerto Rico Tourism Company.

• Getting around town: Once you’re in San Juan, there are several ways to explore the island, depending on the area. Old San Juan is a walkable city, but other parts of the town may require the use of a rental car, rideshare or, alternatively, you can use Skootel for short distances between neighborhoods. 

• Where to stay: The world is your oyster when it comes to high-end, mid-range and budget accommodations. For a more posh experience, choose a boutique hotel like El Convento in the center of Old San Juan or the historic Condado Vanderbilt. For budget-friendly stays, check out the Verdanza Hotel, steps from the Isla Verde beach, or the Doubletree in the buzzy Condado district. 

• What to pack: You’ll never go wrong with packing comfortable clothes like t-shirts, shorts, sneakers and jeans. Beachwear and sunscreen are a must, but be advised that some places may not let you in when wearing just a bathing suit. When it comes to nightlife, check for dress codes and bring some nice shoes and more formal wear, just in case.  

Friday 

Morning: Mornings in Old San Juan are a sight to behold, as the walled city is at its quietest. Wake up early and head over to Chocobar Cortés for a decadent breakfast. Their chocolate grilled cheese is highly sought after for its resemblance to a traditional Puerto Rican comfort food – hot chocolate with a piece of cheddar cheese inside. Don’t knock it ‘till you try it!

If you’re more the brunch type, walk to La Carreta Mercado Local, where you can try the Bandeja Jibara – a hearty plate full of roast pernil, rice and beans, fried sweet plantain, avocado and bacon.      

How to spend the day: Grab some sunscreen and a hat and walk up the steep, cobblestoned streets to El Castillo San Felipe del Morro, a World Heritage Site. It is undoubtedly the most iconic fortification in the islet, built inside a 140-foot wall meant to protect the island from attacks by the British and Dutch armadas during Spanish colonization. This six-level fortress has many stories within its walls, and it’s an important stop to learn about Puerto Rico’s history of colonization and displacement. 

Take some time to visit its sister fortification, Castillo San Cristóbal, which started construction in 1634 and took 150 years to complete. The Vauban-style fortress was meant to protect the islet from land attacks. The National Parks Service manages both sites and the entry fee is $10 for each fortification or free with an America The Beautiful pass.       

Dinner: Walk down to La Perla through the passageway beside the cemetery and you’ll find La Garita Yaz, a perfect rooftop restaurant to grab sunset cocktails and dinner overlooking the vibrant community and the San Juan bay.

The prices at this no-frills restaurant bar aren’t steep for the area, and you can feast on local favorites like fried plantain tostones filled with octopus, shrimp, or conch. Try a mofongo as well, filled with anything from churrasco to lobster. 

If you want to further explore the city, head down to El Champi and enjoy Spanish-style tapas like pimientos de padrón in their open-air patio. My favorite tapas here are the Serrano ham croquettes and the patatas bravas with a sangría, the restaurant's specialty drink. Reservations are recommended as it gets full around dinner time.  

After dark: You’ll have the most fun bar hopping through Calle San Sebastián, a mythical street with lots of history. Enjoy a cocktail at La Factoría, voted one of The World’s 50 Best Bars for innovative cocktails and speakeasy vibes.

You can’t go wrong with their famous lavender mule – a twist on the classic made with lavender, spiced rum, citrus, ginger tea and vodka. Their espresso martini is also a delight. La Factoría itself has six different themed bars with DJs inside the building – dance your way through them all as the night unfolds.

After La Factoría, walk over to Taberna Lupulo for a big array of local and international beers on draft, including the seasonal Ocean Lab Oktoberfest beer. 

Don’t miss the opportunity to explore San Juan’s cobblestoned streets, full of interesting alleyways, Spanish-style mosaics, and a plethora of nightlife options. Paseo de la Princesa is a beautiful promenade that leads straight through an artisan night market on the weekends and towards the Puerta de San Juan, the first official entry point in Puerto Rico during Spanish colonization. 

Saturday

Morning: Begin your day with a stroll through the Miramar neighborhood and get an early morning breakfast at Lucía Patisserie Café from the French-trained pastry chef, Lucía Merino.

Their menu changes every day, but if you happen to catch the Hot Honey Buttermilk Biscuit with sausage and gouda, don’t hesitate to try it, accompanied by a cortadito or a fresh seasonal juice. The shop opens Thursdays and Fridays from 7:30am to 2pm and Saturdays from 8am to 12pm. It’s a local favorite, so arrive as early as possible. 

If the line is too long for Lucía’s and you don’t want to wait, go to Tostado and order yourself a Lolita bowl – a hearty plate full of root vegetable mash, roasted veggies, scrambled eggs and pan sobao toast. You’ll thank me later. Their twist on traditional quesitos is also a delicacy, featuring bacon.  

How to spend the day: You’ll need a car to move around the Miramar-Condado-Santurce area, but these are areas of San Juan you don’t want to miss. Up for some local shopping? Head over to Santurce POP, a collaborative market with pop-up stores selling local products and handmade goods. The shops change monthly but mainstay Oye Records is a must for vinyl lovers. 

Within a short driving distance you can check out Calle Cerra, home to one of the biggest public arts projects in the metro area – Santurce es Ley. The murals were done by a mixture of Puerto Rican and international artists, and a good chunk of them tell the rich history of the El Gandul community, where Calle Cerra is located.

There’s a map where you can find information on all of the artists and their respective murals or art installations. This part of Santurce can be a bit rough, so exercise caution and try to find parking on the main streets. If you’re up for more adventures, Calle Loíza in neighboring Condado has plenty of restaurants, trendy bars and boutiques.    

After dark: Calle Cerra is a very popular hangout for Puerto Ricans, not only because of its art projects but because it is a great bar-hopping destination. There’s everything from the super laid back Esquina Watusi, where you can enjoy an ice-cold Medalla (Puerto Rico’s national beer).

Walk towards the end of the street and have dinner at El Carey. I suggest ordering plates to share so you can try a variety of local dishes like carne frita, conch salad, fried cheese with guava sauce and fried plantain. Top it off with a coconut mojito for a perfect combination. 

Nearby Machete has excellent craft cocktails like the Post Melón, a fruity fusion of citrus, melon, salsa macha drops and vodka. Finish your night at La Disquera, a Japanese whisky bar with vinyl DJs and a speakeasy atmosphere. 

Sunday

Morning: Hopefully, you’re not nursing a hangover but regardless, brunch at Bistro Café in Isla Verde is where you need to be. This restaurant is famous for its gigantic portions, so family-style dining is a great option. The French Toast and Monte Carlo Scramble are life-changing. 

If you’re looking for something to go, Panadería España has excellent sandwiches and traditional Spanish fare like paellas. You cannot go wrong with a Choripan (chorizo sandwich) or a Media Noche, a sandwich full of roast pork, ham and cheese.   

How to spend the day: Spend a relaxing Sunday at any stretch of beach along the Atlantic coast. Keep in mind that most beaches along Isla Verde don’t have lifeguards or facilities.

However, if you do need access to bathrooms and gazebos, go to Balneario de Carolina, a Blue Flag beach. It’s open from 8am to 5pm daily and there’s ample parking. I’m a big fan of the more rugged Pine Grove, where you can bathe and also watch the surfers practice on smaller waves. 

If you’re a beer fan like me, you’ll delight in the artisanal variety at Ocean Lab Brewery and rooftop restaurant. It’s a great place to watch the sunset with an Ocean Mambo – a passion fruit Witbier – in hand. Get the Crispy Whole Red Snapper with tostones – it's worth the $40 price tag. If you’re on a budget, the Guava BBQ Glazed Chicken Wings are delectable, as are any of the appetizers on their menu. 

Nobody wants to leave Puerto Rico – trust me, I know. But if you must leave, Isla Verde is conveniently located right next to the Luis Muñóz Marín airport for a smooth exit. If you’re staying for longer, explore the Northeastern part of the island, and stop at the Luquillo kiosks for fresh seafood.