Old San Juan, Puerto Rico
Bienvenidos al Viejo San Juan
Old San Juan is an enchanting, romantic, vibrant and historic 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 music playing 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.
A Second Home
Puerto Rico has become a second home to us. From quick weekend getaways to month long trips, we’ve spent time exploring the island and immersing ourselves in so much of what it has to offer from the nature, cuisine and culture. This guide focuses on our time visiting and staying in Old San Juan.
Neighborhoods & Streets
Calle San Sebastián. A cobblestone street is lined with colorful and vibrant colonial architecture. It’s known for its bustling nightlife scene, famed cocktail bars and lgbtq+ friendly atmosphere.
Calle San Francisco. This street runs central through Old San Juan 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 Old San Juan 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.
Plaza das Armas. Old San Juan’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 northwest corner.
Caleta de San Juan. A romantic tree covered street lined with colorful colonial buildings, hole in the wall restaurants and wine bars. The cobblestone street leads uphill from the Puerta de San Juan to the historic Basilica of San Juan.
La Perla. A colorful seaside neighborhood located between the north wall of Old San Juan 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.
Sights & Museums
Castillo de San Cristóbal. This is one of the largest colonial military fortress in the Caribbean and marks the entrance to Old San Juan. 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 Old San Juan. 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 tropical flavored snow cones called Piraguas.
Pro Tip. The receipt from one fort gets you access to the other on the same day you visit.
Paseo del Morro. A romantic seaside promenade that follows the old town’s wall. It is a beautiful place to walk, watch the sunset and look out towards the sea. We we’re incredibly lucky to see the Green Flash from here. 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.
La Casa Estrecha. A narrow house, measuring about 5 feet wide, with a vibrant yellow facade. Adorned with the Puerto Rican flag, the building is an iconic symbol of Old San Juan.
Calle Fortaleza. A street is filled with souvenir shops, restaurants and jewelry stores, ending at the Governor’s Mansion, La Forteleza. The end of the street is often decorated in an ever changing canopy of umbrellas, banners, flowers or lights.
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.
Plaza del Quinto Centenario. A plaza commemorating the 500 years since Columbus first voyaged to Puerto Rico. At its center is a tall totem made from fragments of clay pottery representing the violent first meeting between the indigenous Taino and European colonists.
La Puerta de la Bandera. A black and white painting of the Puerto Rican flag on the wooden door of a crumbling brick building. It symbolizes Puerto Rican resistance against injustice.
Parque San Francisco. A small and hidden park nestled between the crumbling brick and plaster walls of the surrounding colonial buildings. The park offers a quiet place to relax and take a break while exploring the old town.
Callejón de la Puerta con la Bandera. A large doorway at the end of a blue cobblestone alley with a vivid painting of the Puerto Rican flag. It’s a very popular photo spot for both tourists and locals. Recently an artist added a colorful mural of Puerto Rican artists Bad Bunny and Elizam Escobar to the adjacent door.
Maria Magdelana Cemetery. A beautiful seaside cemetery with above ground tombs, a large mausoleum and monuments dedicated to the dead. Its location between La Perla and El Morro along the coast is strategic to carry the deceased souls across the ocean into the afterlife.
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.
Capilla del Cristo. A small chapel built on the cliffside edge of the old town’s wall. It is dedicated to health and well being, commemorating the story of a man who plunged off the cliff while horse racing but survived.
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. We booked with Raul at Rolo Photo PR and couldn’t have been happier with the outcome!
Fly a Chiringa. The ocean breezes from 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.
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.
Sunset Harbor Boat Ride. A sunset cruise on a large pontoon style boat around the harbor of Old San Juan with historical info, snacks, rum punch and music. Book Here!
Vamos al la Playa
Playa Peña. A secluded beach in Old San Juan, located on the other side of Castillo de San Cristobal. It’s a cute sand and rock beach below the cliff in front of the capital. The water isn’t safe for swimming.
Playa El Escambrón. A sandy palm covered beach between Old San Juan and Condado. It’s a popular beach for swimming, snorkeling, grilling and sunbathing. The best place to snorkel is the protected cove next to the Caribe Hilton. Come here in the morning to spot sea turtles feeding in the seagrass and tropical fish swimming among the underwater sculpture garden. There’s also the ruins of a small fort, Fortín del Escambrón, nearby.
Places to Shop
Spicy Caribe. A spice store with hot sauces, spices and vanilla made from locally grown ingredients.
El Mundo Taino. A souvenir shop with locally made home goods, artwork, jewelry and coffee.
Hatian Gallery. A shop specializing in handmade artwork, sculptures and jewelry from Puerto Rico and other Caribbean islands.
Materia Prima. An organic grocery store with local farmed Puerto Rican produce, provisions and meats. It has a coffee bar and is connected to a wine bar in the Hotel Convento.
U Go Market. A grocery store with produce, snacks, beverages, alcohol, beach-ware and sunblock.
John Napoli. A kitchen supply store with a range of cookware and kitchen gadgets including Puerto Rican pilóns, calderos and large paella pans.
Puerto Rican Cuisine
Chillo Frito Entero. A fried red snapper served whole with crispy skin, tender meat and squeezed with lime. It’s usually accompanied by fried plantains like tostones, mofongo or amarillos.
Mofongo. Fried plantain mashed with garlic and butter. It’s often served plain or stuffed with an option of seafood. If prepared with bread fruit and yucca, it’s known as trifongo.
Empanadillas. Puerto Rican style fried empanadas stuffed with a range of fillings like octopus, conch, cod, shrimp, crap and pizza.
Pinchos. Grilled meats served on a stick often served at beaches or roadside kiosks. Our favorites are shark and shrimp.
Mallorca. A Puerto Rican pasty often shaped like a bun or swirled roll and dusted in powered sugar. Our favorite preparations are pressed with guava with cheese or egg and cheese.
Coco Frio. A cold and freshly opened coconut. Drink the coconut water inside then the sweet meat inside. Alternatively, enjoy it with coconut rum to create a tropical cocktail
Rum. Puerto Rico is unarguably the rum capital of the Caribbean with several distilleries and local brands served in bars across the island. Order it on the rocks, in a Pina Colada or other tropical cocktail.
Medalla. The island’s most popular local beer, recognizable by it’s small golden can. It has a light slightly nutty flavor and is served everywhere. Buy a 6 pack for the beach!
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. Having visited Old San Juan several times, we’ve been able to try out numerous restaurants, cafes and bars.
Pro Tip. It’s best to make a reservation whenever dining out in Old San Juan.
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.
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 tomatos).
Ladis. A famous seaside restaurant built into the cliff between OSJ and Condado. Come here for seafood, cocktails and ocean views.
Señor Paleta. A popular spot to buy fruit and dessert popsicles mid-day or after dinner.
Puerto Criollo. A Puerto Rican restaurant with classics like fried snapper, stuffed mofongo and octopus salad. They also service inventive tropical cocktails in unique glasses.
Al Fresco Rooftop Wine & Tapas. A quiet place with a rooftop patio in the middle of Old San Juan. Come here for lite bites and wine. We shared a cheese board and bottle of bubbly.
Otras Cosas. A large outdoor restaurant to come for lunch, dinner and live music. Try the whole Caribbean lobster and coconut filled with coconut rum.
Mar y Rosa. A rooftop restaurant with el fresco dining and an elevated menu. Come here for the panoramic views at sunset, tasty cocktails and seafood menu with Korean & Caribbean influences.
El Champi. A tapas restaurant offering Spanish style small plates, paella and charcuterie. It’s located on Caleta de San Juan, a romantic tree covered street. It’s adjoined by El Rincón del Vino, a small wine bar with a broad selection of wines all nestled within a small interior courtyard.
Atelier Rooftop Terrace. A rooftop bar and restaurant at the Hotel Palacio Provincial. It offers sunset views and overlooks the neighboring basilica.
Caleta del Vino. A charming wine bar, nestled on cobblestone street along the historic city wall. Come here for a romantic sunset to enjoy a curated charcuterie spread paired with wines by the glass or bottle.
Dos Lobos. A local chain specializing in nearly a dozen different types of baked Puerto Rican pastelillos (aka, empanadas). Order a pastelillos to go or enjoy one at the bar with a local beer or cocktail.
Cafes & Coffee Shops
Cuarto Estaciones. A green gazebo located in the Plaza de Armas serving coffee and pastries. We often come here for our first breakfast while in town, sitting under the shaded patio, surrounded by potted plants and chirping birds. Our usual order consists of iced lattes with canela and Mallorca with guava and cheese. They’re cash only.
La Carreta. Come here for the variety of sweet and savory breakfast dishes. Try an egg sandwich on Mallorca and a mimosa made from freshly squeezed OJ.
Caficultura. A good spot for breakfast and coffee, have the Mallorca con Guayaba (guava).
St Germain Bistro & Cafe. A vegetarian friendly brunch spot with pancakes, toasts, sandwiches and burgers.
Mallorca. A bakery specializing in its namesake, Mallorca. It’s unmistakable by its sign spelling out Mallorca in large red letters.
787 Coffee. A coffee shop brewing Puerto Rican grown and roasted coffee beans. We discovered them on the East Village of NYC and visited their location near Escambron Beach while in Old San Juan.
Pilao Bakery-Cafe. Bakery with large portion breakfasts and coffee.
Bien Papaya. A coffee shop with Mallorca, smoothies and smoothie bowls right by San Cristobal.
Don Ruiz. A cafe in the Museo de las Americas with fresh roasted coffee and bottled beer.
C.B Restaurant. A breakfast and brunch spot in plaza colon. Try the Boricua Morning Mallorca.
Cocktail Bars & Nightlife
La Casita de Rones. 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 Factoria. A famous cocktail bar, once ranked in the Top 50 in the World. The bar is in a dimly lit old world interior, connected to multiple other bars. One of our favorite drinks to order here is the El Peligroso, made with Ron de Barillito, Campari, spices and lime.
Antiguo 26. A high end cocktail bar, set inside a former soda factory. Mixologists craft innovative cocktails using homemade sodas as a nod to the building's history. Its distinctive yellow and blue tiled facade makes it easily recognizable among the colorful buildings of Old San Juan.
The Mezzanine. A cocktail bar offering a variety of tropical drinks made using local ingredients and spirits. Try the Coqui Coqui, a modern take on the classic Piña Colada, awarded best at the annual Piña Colada Festival or the Rum Sunset and Borikén Breeze for fruity and refreshing rum based drink.
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 Desvio. A candle lit cocktail bar hidden within the passageways of La Factoria
El Batey. A late night dive bar with graffitied walls, a pool table and lights covered in notes, cash and napkins left behind from past visitors.
Colmado Cocteleria Tropical. A bar on Calle de San Sebastián designed like a traditional Puerto Rican colmado (a local convenience store) with shelves of faux and vintage groceries and plantain decor. Sip on a cocktail while playing dominos or taking pictures in the photo booth.
La Grieta. A dimly lit cocktail bar specializing in mezcal and mezcal cocktails. There is limited seating inside however the bar spills out onto the cobblestone street with small tables and sofas.
La Sombrilla Rosa. A popular gay bar on Calle San Sebastián. Bartenders serve in inexpensive drinks while Reggaeton music echos out onto the street.
Barrachina. The location where the Piña Colada was invented. Come here for the classic cocktail and stay for lunch or dinner in their courtyard.
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.
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.
Scryer Rum Barrelhouse & Rooftop. A small batch rum distillery and cocktail bar in Old San Juan with a wall of barreled rum. We drank cocktails here made exclusively from their house distilled rum under candle light during a city wide black out.
Cafe Darsenas. A blue gazebo on the Paseo de la Princesa with affordable drinks and light bites. We often come here for a frozen sangria to-go.
El Vino Crudo. A hidden wine bar tucked away on Callejón Gambaro. They pour natural wines and serve Spanish tapas late into the night.
Places to Stay
We’ve stayed at a range of places in Old San Juan including apartments overlooking the ocean, a private room in a rum baron’s mansion, a ruin style apartment and a boutique hotel.
Casa Luna. A boutique hotel with range of apartment rentals and a rooftop terrace. It’s located in the middle of Old San Juan on Calle de la Luna. Book Here!
Cozy Historic Ruin Apartment. A small apartment built within the ruins of a crumbling building.The space has character and charm that exemplifies the old town. Book Here!
PH Apt in Old San Juan w/ Terrace. A comfortable and spacious apartment with a large private terrace overlooking the old town’s cobblestone streets and colorful buildings. Book Here!
Live Like a Rum Baron in a 200 Year Old Mansion. An elevated apartment with private rooms and cozy communal spaces in a renovated colonial building. Book Here!
Getting Around
On Foot. Old San Juan is very walkable and by far the best way to see the city. Be careful of the narrow sidewalks and cobble stones.
By Uber. Use Uber to get to/from Old San Juan from the airport or San Juan proper. Ubers are typically inexpensive. The best place for pick up and drop off is Plaza Colon at the entrance of the old town.
Free Shuttle. There is a free “shuttle” aka a large golf cart the shuttles people a loop in the old town.
By Car / Parking. 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.
Elsewhere in Puerto Rico
Having visited Puerto Rico nearly 20 times, we’ve experienced many places across the island. Though we don’t live here, we consider ourselves non-local experts and one day hope to call this beautiful island our home. Experience Puerto Rican culture in the capital city of San Juan. Head to the southern coast of Caribbean Puerto Rico. Participate in Carnival during the Festival of Masks in Puerto Rico’s second city, Ponce. Hike the El Yunque Rainforest in Eastern Puerto Rico. Visit the surf towns along Western Puerto Rico. Head to the Caribbean Coast of Southwestern Puerto Rico. See the indigenous Taino sights of Central Puerto Rico. Get off the mainland to visit the islands of Culebra and Vieques.
For Next Time…
Whether a spontaneous weekend trip or planned vacation, we will certainly be back to Puerto Rico many more times! We have our eyes set experiencing things we’ve missed during past trips around Old San Juan including:
San Sebastian Festival. A massive festival and street party held throughout Old San Juan in January to mark the end of the holidays with performers, a parade, street food, music and dancing.
Tomb of Juan Ponce de León. The tomb of the decisive conquistador credited with founding San Juan. His tomb is located inside of the Catedral Basilica Menor de San Juan Bautista
Casa Blanca. A 500 year old house in Old San Juan built for Ponce de Leon. It was converted into a museum with Spanish colonial artifacts.
