As far as capital cities are concerned, San Juan, Puerto Rico is a unique destination that offers an array of experiences, including stunning beaches, a historic center adorned with architecture from the 16th century, a dynamic arts scene, a diverse population, and 18 neighborhoods each with distinct flavors and sights to explore.
Having grown up in the metropolitan area, San Juan transcends being merely my place of residence; it has become an integral character in my life narrative.
This city has imparted lessons on finding tranquility within the breezy atmosphere, embracing the vibrant chaos of its streets, and appreciating neighborhoods often overlooked.
San Juan merges urban sophistication with the distinctive appeal of the Caribbean. Despite its compact size, a few days may not suffice to fully experience its offerings. Below are some essential tips for maximizing your long weekend stay.
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When to arrive: It is advisable to arrive on Thursday morning to benefit from lighter traffic at the main beaches or to settle in and enjoy a meal. Avoid landing during rush hours — specifically from 6 am to 8 am and 4 pm to 7 pm — as extensive traffic jams can occur when exiting the airport.
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How to get from the airport: Public transportation is available from the airport; however, it may not be the most convenient for leisure travelers. It is suggested to rent a car, utilize rideshare services, or take an authorized taxi from the Puerto Rico Tourism Company.
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Getting around town: Once in San Juan, there are various options for exploring the area, depending on your location. Old San Juan is pedestrian-friendly, whereas other parts of the city may necessitate a rental car or rideshare services. You may also consider using Skootel for short trips between neighborhoods.
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Where to stay: A wide array of accommodations are available, ranging from luxury options to more budget-friendly choices. For a more upscale experience, consider a boutique hotel such as El Convento located in central Old San Juan or the historic Condado Vanderbilt. More economical lodgings include the Verdanza Hotel, situated just steps from Isla Verde beach, or the Doubletree in the lively Condado district.
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What to pack: Comfortable attire such as t-shirts, shorts, sneakers, and jeans are recommended. Include beachwear and sunscreen, but note that some venues may have dress codes that prohibit entry with only a bathing suit. When planning for nightlife, check for specific dress requirements and have some formal shoes and clothing readily available.
Friday
Morning: The mornings in Old San Juan provide a stunning backdrop, as the walled city begins to stir. Rise early and visit Chocobar Cortés for a sumptuous breakfast. Their chocolate grilled cheese is a notable dish, reminiscent of a traditional Puerto Rican comfort meal — hot chocolate accompanied by cheddar cheese. It’s worth experiencing firsthand.
For those preferring brunch, a visit to La Carreta Mercado Local is recommended, where the Bandeja Jibara – a hearty plate of roast pernil, rice and beans, fried sweet plantains, avocado, and bacon – awaits.
How to spend the day: Equip yourself with sunscreen and a hat as you ascend the steep, cobblestone streets to El Castillo San Felipe del Morro, a UNESCO World Heritage Site and the most iconic fortress on the island. This six-level structure, ensconced within a 140-foot wall, was designed to repel impacts from the British and Dutch armadas during the era of Spanish colonization. It serves as a significant site for understanding Puerto Rico’s historical narrative.
Take time to visit its counterpart, Castillo San Cristóbal, which commenced construction in 1634 and was completed after 150 years. This Vauban-style fortress was constructed to safeguard the island against land assaults. Managed by the National Parks Service, the entry fee is $10 per fortification, though this is waived with an America The Beautiful pass.
Dinner: Stroll down to La Perla via the passageway adjacent to the cemetery to find La Garita Yaz, an ideal rooftop venue to enjoy cocktails and dinner while overlooking the lively community and San Juan Bay.
The prices at this straightforward restaurant are reasonable, allowing you to sample local delights such as fried plantain tostones stuffed with octopus, shrimp, or conch. Also, be sure to try a mofongo filled with options ranging from churrasco to lobster.
If you wish to further discover the city, take a trip to El Champi for a selection of Spanish-style tapas like pimientos de padrón in their open-air patio. Popular choices here include the Serrano ham croquettes and the patatas bravas, accompanied by the restaurant’s specialty drink, sangría. Reservations are advisable, as it can become crowded during dinner hours.
After dark: Enjoy a lively evening while bar hopping along Calle San Sebastián, a renowned street rich with history. Experience innovative cocktails at La Factoría, which has been recognized among The World’s 50 Best Bars for its inventive drinks and speakeasy atmosphere.
The lavender mule, a delightful twist on the classic, is a popular choice, crafted with lavender, spiced rum, citrus, ginger tea, and vodka, alongside the scrumptious espresso martini. La Factoría houses six distinct themed bars with DJs creating a dynamic nightlife experience.
Afterward, continue your night at Taberna Lupulo, where you can select from a broad array of local and international beers on draft, including the seasonal Ocean Lab Oktoberfest beer.
Seize the chance to navigate the cobblestoned streets of San Juan, marked by intriguing alleyways, Spanish-style mosaics, and myriad nightlife venues. A stroll down Paseo de la Princesa leads you through an artisan night market on weekends, culminating at the Puerta de San Juan, the initial entry point in Puerto Rico during the Spanish colonial period.
Saturday
Morning: Commence your day with a leisurely walk through the Miramar neighborhood, making your way to Lucía Patisserie Café, led by French-trained chef Lucía Merino.
The menu varies each day, but if you spot the Hot Honey Buttermilk Biscuit with sausage and Gouda, it is highly recommended, paired with a cortadito or fresh seasonal juice. The café opens Thursdays and Fridays from 7:30 am to 2 pm, and Saturdays from 8 am to 12 pm, so it is advisable to arrive early given its popularity.
If Lucía’s has an extensive wait, opt for Tostado and savor a Lolita bowl, a hearty meal consisting of root vegetable mash, roasted vegetables, scrambled eggs, and pan sobao toast. Their innovative version of traditional quesitos, featuring bacon, is also a delightful treat.
How to spend the day: A vehicle is necessary to navigate the Miramar-Condado-Santurce area, which is well worth the visit. For local shopping, check out Santurce POP, a collective market featuring pop-up stores showcasing local products and handmade crafts. The vendors rotate monthly, but be sure to stop by Oye Records, renowned among vinyl collectors.
Additionally, a short drive will lead to Calle Cerra, noted for its public arts initiative, Santurce es Ley. This project features murals created by both Puerto Rican and international artists, recounting the rich history of the El Gandul community where Calle Cerra is situated.
A map is available for details on artist contributions and corresponding murals or art installations. While exploring, do exercise caution, as this area can be rugged; finding parking on main streets is advisable. For further exploration, Calle Loíza in neighboring Condado boasts a variety of trendy restaurants, bars, and boutiques.
After dark: Calle Cerra is a vibrant spot for locals, owing to its art installations and fantastic bar-hopping opportunities. Options range from the laid-back ambiance of Esquina Watusi, where one can enjoy a refreshing Medalla (Puerto Rico’s national beer).
As you reach the end of the street, consider dining at El Carey. It is recommended to order shared plates to sample diverse local flavors such as carne frita, conch salad, fried cheese with guava sauce, and fried plantains. Don’t forget to try their coconut mojito for a perfectly balanced drink.
Nearby, Machete serves exceptional craft cocktails, including the Post Melón, which blends fruit flavors with citrus, melon, salsa macha drops, and vodka. Conclude your evening at La Disquera, a bar specializing in Japanese whisky and featuring vinyl DJs in an intimate setting.
Sunday
Morning: Ideally, you should not be recovering from a hangover; however, brunch at Bistro Café in Isla Verde is a must-visit. Renowned for its generous portions, family-style dining is an excellent option here. The French Toast and Monte Carlo Scramble are unforgettable.
For a quick takeaway, you cannot go wrong with Panadería España, which offers delectable sandwiches and traditional Spanish dishes, including paellas. A Choripan (chorizo sandwich) or a Media Noche, filled with roast pork, ham, and cheese, are highly recommended.
How to spend the day: Dedicate your Sunday to unwinding at any stretch of beach along the Atlantic coast. Note that most beaches in Isla Verde may lack lifeguards or facilities.
For clean restrooms and gazebos, consider Balneario de Carolina, a Blue Flag beach, which operates from 8 am to 5 pm daily and provides ample parking. I particularly recommend the rustic allure of Pine Grove, where you can swim while watching surfers maneuver smaller waves.
If you enjoy beer, indulge in the artisanal selections at Ocean Lab Brewery and its rooftop dining. It’s an ideal locale to capture the sunset while savoring an Ocean Mambo – a passion fruit Witbier. The Crispy Whole Red Snapper with tostones is worth indulging in at $40, while the Guava BBQ Glazed Chicken Wings and various appetizers elegantly cater to those on a budget.
Leaving Puerto Rico may be challenging; nonetheless, Isla Verde’s proximity to Luis Muñoz Marín airport facilitates a smooth departure. Should you have extra time, take the opportunity to explore the northeastern region of the island, stopping at Luquillo kiosks for fresh seafood.
