San Juan, Puerto Rico
Bienvenidos al Viejo San Juan
Old San Juan is an enchanting, romantic, vibrant and gay friendly neighborhood of San Juan, Puerto Rico. The old town is lined with cobble stone streets, colorful colonial architecture, world famous cocktail bars, restaurants serving Caribbean cuisine and playing music during all hours of the day. It is rich in history, flanked by two fortresses and surrounded by a stone wall overlooking the North Atlantic.
After visiting several times over the past few years, the island has become a second home to us. We often fantasize about moving here, living in the old town and opening a bakery. This guide focuses primarily on Old San Juan (OSJ) and the surrounding neighborhoods in San Juan.
Neighborhoods & Streets
La Perla. A colorful seaside neighborhood located between the north wall of OSJ and the Atlantic Coast. Over the past years, the community in La Perla has turned their neighborhood into a destination filled with rustic bars, local hangouts and art.
Calle San Sebastián. This street is filled with colorful and vibrant colonial architecture and incredible nightlife. Multiple famous bars as well as a few gay bars can be found here.
Calle San Francisco. This street runs central through OSJ and is a good place to start exploring. There are plenty of restaurants, bars, cafes, shops, hotels, plazas and residences here.
Calle de la Luna. Though all streets in OSJ are flanked with beautiful architecture, this one is one of our favorites to walk down. There are many colorful buildings, colonial balconies, unique door knockers and abandoned buildings that have been retaken by nature.
Calle Fortaleza. This street is filled with shops, restaurants and usually has a shaded awning the block before reaching the Governor’s Palace, La Forteleza. It used to be hundreds of colorful umbrellas and most recently, the Puerto Rican flag.
Sights & Museums
Castillo de San Cristóbal. This is one of the largest colonial military fortress in the Caribbean and marks the entrance to OSJ. You can easily spend a half day here exploring the barracks, fortress walls, guard towers and grounds. One of the fort’s hidden gems is a surviving drawing of Spanish ships drawn on the wall of a former prison cell deep with in the tunnels.
Castillo San Felipe del Morro (El Morro). This is the oldest colonial fortress in the Caribbean and a great place to learn about the history and strategic importance of OSJ. Similar to San Cristobal, you can spend an afternoon here exploring the different levels and sections. The fort is perched on the NW side of the old town. It’s accessible after crossing a large lawn known for flying Chiringas or kites and food carts selling Piraguas, tropical flavored shaved ice.
(Pro tip: Your receipt from one fort gets you access to the other on the same day you visit.)
Paseo del Morro. A romantic seaside pathway that follows the old town’s wall. It is a beautiful place to walk, watch the sunset and look out towards the sea. It passes La Puerta de San Juan, the original entrance to the walled city and connects Paseo de la Princesa to the Maria Magdelana Cemetery.
Maria Magdalena Cemetery. A beautiful seaside cemetery located between La Perla and El Morro along the coast, a strategic place thought to carry the deceased souls across the ocean and into the afterlife.
Paseo de la Princesa. A palm lined seaside promenade along the south wall. There is a nightly market with salsa dancing, food trucks offering up fried foods and sweets, gazebos selling cocktails, and tented vendors selling homemade crafts.
Capilla del Cristo. A small but beautiful chapel dedicated to health and well being. People feed and pose with pigeons here…
Plaza das Armas. OSJ’s historic town square with performers, a fountain, statues and pigeons. It’s a favorite spot of ours to grab a coffee and mallorca from the green gazebo in the NW corner.
Museo de las Americas. This museum focuses on pre-colonial and modern art and artifacts, the colonization of Puerto Rico and the island’s African heritage.
Things to Do
Hire a Photographer. Hire a photographer to take photos of you around the old town during the morning or evening golden hours. There are a number of options available though Airbnb Experiences. We booked with Raul and couldn’t have been happier with the outcome!
Fly a Chiringa. The ocean breezes above the lawn in front of El Morro make it a great location and fun Sunday afternoon pastime. Kites can be bought from street vendors adjacent to the lawn on Calle Norzagaray.
Walk to the Beach
Playa Peña. The closest beach to OSJ, located on the other side of Castillo de San Cristobal. It is a cute sand and rock beach below the cliff in front of the capitol.
Playa El Escambrón. Less than 15 minutes from OSJ, it’s a popular beach for swimming, snorkeling, grilling and sunbathing.
Visit the Farmers Market. Located in front of the San Juan Museum every Saturday morning. It’s a great spot to purchase local produce, fresh baked breads and flowers.
The Food Scene
A huge part of the culture in Puerto Rico involves eating, drinking and getting together with others. With that in mind, there are so many great places to eat and drink.
Pro tip: It’s best to make a reservation whenever dining out in OSJ.
Restaurants
La Garita . A restaurant and bar serving Puerto Rican dishes and rum cocktails with a view overlooking La Perla. Ask for a Pina Colada made with a double shot of Don Q, Puerto Rico’s most popular rum.
El Jibarito. Another restaurant serving Puerto Rican dishes. Come here for the whole fried fish and mofongo.
T•tuan. A lively restaurant on the wall with live bands and drag shows on the weekends. Try the mahi mahi sliders, crab empanadillas and coconut grilled shrimp.
San Se Marisquería. Close to the bars on San Sebastian, this is a great spot to eat before or while enjoying the nightlife.
La Madre. A Mexican restaurant with delicious tacos. Eat outside on the pedestrian tree-lined street.
Cayo Caribe. A small local chain of restaurants serving Caribbean seafood. Try the Salmorejo (stewed land crab and tomatoes)
Ladis. A famous seaside restaurant built into the cliff between OSJ and Condado. Come here for the food, cocktails and ocean view.
Señor Paleta. A popular spot to buy fruit and dessert popsicles mid-day or after dinner.
Cafes
La Carreta. Come here for the variety of sweet and savory breakfast dishes. Try a mimosa made from freshly squeezed OJ.
St Germain. A creative and vegetarian friendly breakfast spot.
La Bombonera. A historic restaurant and diner known for their Mallorca, soft, buttery sweet and fluffy bread rolls often dusted in powdered sugar. Try them alone or pressed in a sandwich grill.
Caficultura. A good spot for breakfast and coffee, have the Mallorca con Guayaba (guava).
Pilao Bakery-Cafe. Bakery with large portion breakfasts and coffee
Bars
La Factoria. A famous cocktail bar great for music and dancing Salsa. It’s cash only and be prepared to order several drinks.
La Cubanita. Connected to La Factoria, this bar is offers equally as good and unique cocktails. Our favorite section is the hidden bar up the stairs and though a door to the right.
El Batey. The definition of a dive bar and open late. The walls and lights are covered in graffiti, notes, cash and napkins left behind from past visitors.
La Casita. A pink house and outdoor cocktail bar serving rum and tiki drinks overlooking the bay. It’s a nice escape from the busy streets or to end the night.
La Verguenza. This multi-level bar overlooks La Perla is the center of nightlife in OSJ. The nightly party spills out into the streets and continues early into the morning.
La 39. An unofficial roof top bar past the basketball courts in La Perla serving Medalla an inexpensive local beer served everywhere across the island. People often flow between here and La Verguenza.
La Terraza De San Juan. This hotel has a large rooftop bar with 360 views of Old San Juan. Buy a drink from the street level bar and walk up the flight of stairs then sit back and relax in one of the lounges or tiny infinity pool.
Cannon Club. A dueling piano bar with live parrots, multiple levels and eclectic decor. This place is more about the drinks and unique atmosphere than the food.
Explore San Juan!
Though we love Old San Juan, it’s fun to venture outside of the old town and experience life and culture beyond its historic walls.
Neighborhoods & Streets
Santurce. A trendy and gritty area of San Juan. It’s an affordable place to stay, admire the graffiti & murals, visit art museums and experience local culture, cuisine and nightlife.
Condado. Popular for hotels, restaurants, bars and beaches. It’s a nice place to relax during the day before going out at night.
Ocean Park. A trendy yet local neighborhood popular with the LGBTQ+ community and younger crowds. Come here for the variety of restaurants, nightlife and beach.
Miramar. A residential neighborhood with historic homes and buildings built in The Spanish Colonial Revival style. It’s central to Old San Juan, Santruce and Condado.
Calle Loíza. Ocean Park’s main street for restaurants, food halls and bars. A good street to walk for breakfast and lunch options. Loíza Brinca. Famous corner building featuring the Puerto Rican flag
Calle Cerra. A gritty street in Santurce with many large murals and graffiti works. The street and surrounding neighborhood has many cafes & bars to grab a coffee or drink while exploring.
Sights & Museums
Fortín San Jerónimo de Boquerón. A small fort at the mouth of the Condado Lagoon. The visiting hours are infrequent due to repairs post Hurricane Maria. It’s worth visiting if open.
Puente Dos Hermanos. The bridge crossing the Condado Lagoon connecting to Old San Juan. It’s beautiful to walk across with great views. There is also a ledge making it easy to jump from into the lagoon. The Condado side has a small sandy beach, Playita del Condado.
Museo de Arte de Puerto Rico. A well curated and diverse collection of Puerto Rican art and history. After touring the galleries, walk through the sculpture garden.
Museo de Arte Contemporáneo de Puerto Rico (MAC). A contemporary art museum with rotating galleries specific to social movements, local artists and Puerto Rican heritage.
Things to Do
SUP or Kayak in Laguna de Condado. Tour companies based around the lagoon offer SUP and Kayak rentals for $20/hour. The lagoon is a boat free place to spot eagle rays, star fish and sea turtles. We booked though VIP Adventures Puerto Rico.
Dance Salsa. Take a beginners salsa class before dancing in the clubs. We took an Airbnb Experience with Angelina in the Plaza Antonia Quiñones
Visit a Rum Distillery. The two distilleries to visit are the Bacardi Factory or Ron del Barrilito. Both offer similar experiences. Bacardi is large scale production while Ron de Barrilito is small batch and higher end. Arrive to a welcome drink, learn about the history of each distillery, their processes of rum making and afterwards take a mixology class, sample aged vintages or simply order cocktails from the bar. Either way, expect to leave tipsy.
Beaches
Atlantic Beach. A sandy beach great for swimming nearby the hotels in Condado. There are no public amenities (restrooms or showers) though vendors rent umbrellas and chairs for negotiable prices. There is frequently a gay section in front of The Tryst Hotel.
Ocean Park Beach. This vast beach is probably the most popular in San Juan. Everyone from locals, tourists, families and couples come here. There are plenty of restaurants, marine sports and activities, chair and umbrella rentals and vendors selling drinks on the beach.
Restaurants
Café Comunión. A coffee shop and breakfast spot. Come for the coffee, open faced sandwiches and fresh sugar glazed donuts
Tostado - Calle Condado. A coffee shop breakfast spot. Come for the coffee, tropical fruit French toast and egg dishes.
Tresbé. Open air restaurant with multiple menus. Come for tacos, sushi, sliders and cocktails.
La Marqueta. An open air food hall with ocean views and palm trees. It’s a great spot to grab a bite or drink after visiting the lagoon or beach.
Paulina Escanes-Gourmandize. A locals restaurant in plain site. Innovative and creative Caribbean inspired dishes, cocktails and deserts.
Wicked Lily. The beach front bar at The Tryst Hotel. Come here for brunch, rent a pink umbrella and join the other gays soaking up the sun.
Bottega. We came for the inventive cocktails and music. We had the Safe Flight, Ritmo Tropica, El In-Muerto and shared the octopus salad. Lucha Libre DJ really added to the vibes of the night.
Food Truck Parks. Quite popular across Puerto Rico, two go-tos in San Juan are Lote 23 and Miramar Food Truck Park.
La Placita
La Placita is a cultural hub. It is a place to buy local produce during the morning, where elderly locals gather during the day and an energetic place to meet people, drink late into the evening and dance Salsa. The plaza is surrounded by lively restaurants and bars.
The Produce Market. Located inside the Plaza de Mercado in the center of the plaza. We used a machete to cut plantains from the bunch, picked out limes to make our own cocktails and selected a ripe papaya for lunch.
La Tasca del Pescador. The place to go for seafood. We ordered the snapper, squid Ink rice & grilled prawns.
Asere Cubano Kitchen and Bar. A fusion of Cuban and Puerto Rican cuisine with a roof top bar overlooking the plaza.
La Alcapurria Quemá. A hole in the wall for Puerto Rican street food, as the name suggests they’re known for their Alcapurria.
Jungle Bird. Tiki bar with tropical cocktails
Getting Around
On Foot. Old San Juan is best explored on foot! You can walk straight from end to end in less than 20 minutes. Spend time walking though the streets, admiring the architecture, discovering bars, dancing in the plazas and finding neighborhood gems.
By Shuttle. There is a free shuttle or multi row golf cart that weaves through the streets southern streets of Old San Juan and along the perimeter towards El Morro.
On Scooter. As of late 2020, there are rental scooters available around the streets of San Juan. Download the Bird app and scan the scooter’s QR code to ride.
By Uber. Ubers are the best way to get to/from the airport and throughout San Juan. If you request an Uber in the old town, the best place to request one is along Calle Norzagaray or Plaza Colon.
By Car / Parking. Rent a car if you plan on exploring outside of San Juan. Though expensive, it’s still the most affordable way to get around. Traffic gets congested in and around Old San Juan. The best place to park in Old San Juan is Dona Fella, garage on the south side of the Old Town. Parking typically costs $1 per hour.
For Next Time…
Whether a spontaneous weekend trip or planned vacation, we will certainly be back to Puerto Rico many more times!
Piñones. East of the airport is the town of Pinones. It is a food hub known for it Puerto Rican and Caribbean cuisine. The Main Street is lined with dozens of restaurant, bars and kiosks.
Take a Sunset Sail. Several tour companies offer sunset boat tour around OSJ, often cruising from the inner bay around the walled city and turning around at La Perla.
Explore more of the Island. Visit Rincón, Aguadilla and Poncé to the West and the island of Vieques to the East.
