San Juan, Puerto Rico, is the oldest continuously inhabited post-European contact city in United States territory and the second oldest in the entire Western Hemisphere. Since the Spanish founded it in 1521, San Juan has served as the capital city of Puerto Rico. Located in the western corner of the beautiful San Juan Islet, the Old San Juan Historic District is the historic core of the city. San Juan evolved from a frontier community to become an important Spanish outpost and port until the United States annexed Puerto Rico in 1898 at the end of the Spanish-American War.
Exploring Old San Juan, Puerto Rico as a local can be a delightful experience filled with history, culture, and stunning architecture. Below is a suggested itinerary for a day of exploration in Old San Juan.
You don't need a passport to visit Puerto Rico if you're a United States citizen. With a valid driver's license or ID, you can enter the country without a problem.
The best way to arrive in Puerto Rico is through Luis Muñoz Marin International Airport in Carolina. There you can rent a car or take an Uber or taxi to get to Old San Juan. If you rent a car there are plenty of options for parking lots in the historic city (La Puntilla, Doña Fela, and the one near the San Felipe del Morro fort).
Although Old San Juan is pretty hot, always check the weather to know beforehand what you need to wear, or if you need to carry an umbrella.
Let's dive into the Itinerary!
The best way to start your day is by having a nice breakfast.
El Mesón Sandwiches
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Local franchise with great options for sandwiches, coffee, breakfast, pastries, and more.
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St. Germain Bistro & Cafe
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Relaxed eatery serving local fare, fresh food, vegetarian dishes, and brunch.
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Paseo de la Princesa
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The promenade is lined with adorned lamp posts and extends for a quarter of a mile along the southern city walls of Old San Juan
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Puerta de San Juan
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The Puerta de San Juan is the most colorful and known of all the entrances to the walled city. It was the main gate through which the priests and governors made their entrance to their investiture ceremonies
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Catedral Basilica Menor de San Juan Bautista
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The Catedral de San Juan is the second oldest church in the Americas. The structure of this church is a rare example of medieval architecture during Spanish rule in the New World.
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Capilla del Santo Cristo de la Salud
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This small sanctuary was built at the top of the walls of the city, an unusual decision for colonial times. Its altar is made of embossed silver and the room is decorated with two José Campeche paintings.
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La Fortaleza
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La Fortaleza is the oldest state residence of the New World still in use. Originally built between 1533 and 1540, La Fortaleza has served as a fortress, a prison, and an arsenal, and is now the official residence of the Governor of Puerto Rico. This executive palace conserves traditions such as candlelit-only dining rooms and original Spanish objects from the colonial era.
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It's time for a treat:
Chocolato
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Local Italian Gelato shop, with great options for vegan, sugar-free, lactose-free, or regular gelato, coffee, cocktails, and more.
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Barrachina
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Home of the famous Piña Colada, a refreshing drink made of coconut cream, pineapple juice, and ice. This drink was invented in this restaurant by a Spanish bartender.
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Señor Paleta
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FRUITY ICE CREAM BARS. THEY HAVE FLAVORS SUCH AS NUTELLA AND STRAWBERRY CHEESECAKE.
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Have a stroll in the beautiful and colorful streets of Old San Juan and visit their stores.
Stop for some iconic drinks at:
La Factoría
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It's in the top 50 of the best bars in the world. Offers cocktails & classic bar bites dished up in a vibrant hangout with a rustic-chic vibe. Order the lavender mule.
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La Taberna Lúpulo
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Local draft beers, bites, and great ambience. Love their chicken wings with guava sauce and their sliders.
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El Callejón de la Tanca
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This street is full of fried Puerto Rican delicacies. You must try empanadillas, alcapurrias, local drinks and piraguas. Dance to the rhythm of the local music.
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At least visit one of these Historic Sites. You have to pay an entrance fee.
The perfect spot to watch the sunset, fly a kite, have a picnic, or rest.
Castillo San Felipe del Morro
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Better known as El Morro, this impressive citadel is one of the largest fortifications built by the Spaniards in the Caribbean during the 16th century. Made up of six staggered levels that integrate barracks, dungeons, and storerooms, this fortress was designed to protect the city from attacks made by sea, and it still has some of the original cannons facing the ocean. In its history,
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Casa Blanca
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This is the oldest residence in Old San Juan. Casa Blanca was built to be the home of Puerto Rico’s first governor, Juan Ponce de León. Sadly, Ponce de León died before he could occupy it, but it was left for his descendants to reside in. Have gorgeous gardens and gated areas.
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Castillo San Cristóbal
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Standing guard at the eastern gate, this fortress was built to guard the city from enemies approaching by land. Covering over 27 acres, this fortification is the largest one made by the Spaniards in the New World. This castle holds the famous Garita del Diablo, the center of many military tales and stories on the Island.
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The Old San Juan is packed with great places to eat. Here are some ideas:
Café Manolín Old San Juan
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Cafetín of local PuertoRican food.
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Pirilo
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Best Pizzeria in Old San Juan. Fusion of local Puerto Rican ingredients and Italian pizza. You must try "La Tripleta if you like the savory and sweet mix.
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Marmalade
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Fine dining restaurant featuring an international menu with creative plates, plus cocktails & wine.
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La Madre
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Modern Mexican restaurant with many margarita options and authentic dishes.
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If you're a Coffee lover you should visit:
Quimera, Holistic Boutique
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A cozy café boutique where literature and imagination take center stage.
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Café Cuatro Sombras
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Authentic Specialty Coffee from Puerto Rico
Their farm-to-cup coffee is grown following traditions that began in 1856.
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You can edit or adjust this itinerary according to your available time. My recommendation is to arrive early to enjoy most of your day in the city. There are many things and corners to visit in Old San Juan, you can plan according to your needs and expectations. I hope you enjoy this Itinerary and have a blast in this beautiful and iconic city.
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