City Gate Old San Juan PR

The list of must see and do things while in Old San Juan, Puerto Rico is limited only by the length of time you have to spend in this exciting Caribbean city. To help you plan your visit we have put together a list of our top 10 favorites to get you started! Old San Juan is a colorful, vibrant Caribbean city full of life and activity. Stroll the streets, visit the forts, take a free trolley, shop, eat, drink and enjoy salsa music and dancing in this historic colonial city that is rich in old world European charm.

1) Stroll the Colorful Streets of Old San Juan

Brightly painted buildings Old San Juan PR

The brightly painted buildings along the streets of Old San Juan combined with the colorful tropical flowers are truly inspiring. Shopping and sightseeing are a great way to spend your day as you walk along these charming streets.

Tropical colors Old San Juan PR

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Tropical colors can be seen everywhere in Old San Juan. There are over 400 restored 16th and 17th century Spanish colonial style buildings in the 7 square blocks of this historic area. A free trolley service runs 7 days a week and makes frequent stops. You can hop on and off at any of the trolley stops.

Colorful Steep streets Old San Juan PR

The colorful streets in Old San Juan can be steep. It’s a good idea to start your sightseeing early in the day and pace yourself as it can get very hot in the summer. Be sure to wear a hat, drink plenty of water and use sunscreen.

Narrow cobblestone paved street Old San Juan PR

The narrow streets in Old San Juan are paved with blue cobblestones. The cobblestones were originally used as ballast for the trade ships arriving from Spain. The blue building at the end of the street is La Fortaleza. It is the oldest governor’s mansion still in use in the Western Hemisphere and part of the old city’s World Heritage Site.

2) Explore the Historic Forts of Old San Juan

Castillo San Felipe del Morro

Castillo San Felipe del Morro Fort Old San Juan PR

The Castillo San Felipe del Morro Fort was built by Spain to protect the city against attacks along the coastline. Construction of El Morro began in 1539 with many of the walls being added from the 1760’s -1780’s. The fort rises 140 feet above the sea and is made up of 6 massive levels. The different levels include the barracks, dungeons, ramps, towers and tunnels. You can explore the fort on a self-guided tour at your own pace. The forts are part of the San Juan National Historic Site and are administered by the National Park Service.

Castillo de San Cristóbal

Castillo de San Cristóbal Fort Old San Juan PR

Castillo de San Cristóbal Fort was built by Spain to protect the city of San Juan against land attacks. It is the largest fortification built by Spain in the New World. When it was completed in 1771 it rose 150 feet and wrapped around the entire city of San Juan. The views from both forts are incredibly beautiful. With more than 400 years of history, the forts are the oldest European style fortifications within the territory of the United States. You can take the free trolley between the two forts.

3) Enter the City Gate of Old San Juan

City Gate Old San Juan PR

This city gate to Old San Juan still stands proud today. There were originally 6 gates in the wall that surrounded the city to protect it from attacks; this is the last remaining gate. Centuries ago the huge wooden doors would be closed at sundown to protect the residences of the city. The path along the water to the left outside the old city gate will lead you to the Paseo de la Princesa. This lovely tree lined promenade has gardens, a restaurant and usually some vendors. Walking through the gate will lead you to the heart of Old San Juan.

4) View the Sculptures & Statues of Old San Juan

La Rogativa Sculpture in Rogativa Plaza

Plazuela de la Rogativa sculpture Old San Juan PR

Plazuela de la Rogativa is a small plaza featuring a bronze sculpture overlooking the Bay of San Juan. According to legend, the bishop and the women of the town formed a procession and frighten away British troops during the 1797 attack on the city of San Juan. Carrying torches, singing and ringing bells as they walked through the streets the British mistook them for large troop reinforcements and decided to sail away. The view of San Juan Bay and the city wall from the plaza are outstanding.

Raices Fountain & Sculpture Along Paseo de la Princesa

Raices sculpture fountain Paseo de la Princesa PR

Raices is a dramatic fountain and bronze sculpture located at the western end of the Paseo de la Princesa. The sculpture represents the islands heritage and cultural roots. It is an excellent spot to sit, relax and watch the sunset in Old San Juan with a beautiful view of the harbor.

Four Seasons Fountain at Plaza de Armas

Plaza de Armas City Hall Old San Juan PR

Plaza de Armas, located on San Jose Street, was designed to be the main square of Old San Juan. The fountain in the center of the square features four 100 year old statues known as The Four Seasons, each statue representing a different season. City Hall can be seen in the background. Plaza de Armas remains today as a central gathering place. Children love feeding the pigeons there.

5) Visit Capilla del Cristo

Capilla del Cristo chapel Old San Juan PR

Capilla del Cristo, located at the end of Calle Cristo, is a small chapel built in 1753. Inside the chapel is a small silver altar which was dedicated to the Christ of Miracles. The wrought-iron gates are usually closed but you can view inside the chapel through the gates. There are many versions to the legend that led to the construction of the chapel. One version states in 1753 a young horseman raced down Calle Cristo and fell to his death plunging over the steep cliff. Another declares that he miraculously survived the fall and yet another version tells that the horse amazingly stopped just before tumbling over the cliff. Maybe we’ll never know the true story behind this legendary chapel.

To the right of the chapel is Parque de las Palomas (Pigeon Park). You can purchase food to feed the pigeons there or just sit and enjoy the magnificent view of the harbor and mountains in the distance.

6) Enjoy the Food of Puerto Rico

Food Dinner San Juan PR
Pastry Dessert San Juan PR

Food in Puerto Rico is a treat and good food can usually be found in small cafes and street vendors for a very reasonable price. Some of the more traditional foods are roast pork, mofongo, plantains, yucca, rice and beans. Try them all if you have the opportunity…I bet you will walk away happy! Don’t forget to try some of the amazing bakery treats you will find in almost any restaurant in Old San Juan.

“SOFO” Culinary Fest on South Fortaleza Street

Culinary Fest Old San Juan PR

The Culinary Fest held on South Fortaleza Street in Old San Juan is an event not to be missed! We try to plan our trips to Puerto Rico around the announced date for this event although it can be hard to get an exact date well in advance.

Culinary Fest South Fortaleza Street Old San Juan PR

During the Culinary Fest Fortaleza and nearby streets are closed to traffic so dining and dancing in the streets can be enjoyed. It’s a culinary street party that’s hard to beat.

Culinary Fest Parrot Club Fortaleza Street Old San Juan PR

The Parrot Club along with approximately 40 other participating restaurants set up booths offering their specialty dishes and drinks. Drinks are made to order and food can be sampled sitting down or taken with you to enjoy as you walk along checking out the next booth! This is a great way to taste the food from some of Old San Juan’s trendiest restaurants. There’s live music, dancing in the streets, lots of eating and an all around good time during the “SoFo” Culinary Fest.

7) Visit Cathedral of San Juan Bautista – San Juan Cathedral

Cathedral of San Juan Bautista Old San Juan PR

Cathedral of San Juan Bautista in Old San Juan is the second oldest Cathedral in the Western Hemisphere. Built in1540, it is over 450 years old. The medieval architecture and exquisite artwork on the ceilings are outstanding. Ponce de Leon, the Spanish explorer, which we referred to in our post St. Augustine Florida Celebrates 500 Years of History, was the first Governor of Puerto Rico and is entombed here. The Cathedral is open daily and Mass is still held here.

8) Visit Santa Maria Magdalena Cemetery

Santa Maria Magdalena Cemetery Old San Juan PR

Santa Maria Magdalena Cemetery in Old San Juan is the most beautiful cemetery we have ever seen. It is located just outside the walls of Fort San Felipe del Morro fort directly on the Atlantic Ocean. Constructed in 1863, it is the final resting place of many of Puerto Rico’s most prominent natives and residents. The headstones and sculptures in this cemetery are exquisite works of art. It’s amazing to see the way the artisans were able to convey emotions in their sculptures. The cemetery is open to the public although we have found the gate to the entrance sometimes closed. You can still view the statues through the fencing.

9) Try a Hand Made Cigar in Old San Juan

Try a hand made cigar while you are in Old San Juan, Puerto Rico and be sure to bring some home to share! This vendor sells hand made cigars made from Puerto Rican and Dominican tobacco leaves.

Hand made cigars Old San Juan PR

10) Enjoy Local Music & Dancing in Old San Juan

Salsa Dancing at Nuyorican Café

The Nuyorican Café is the place to go in Old San Juan for live music, salsa dancing and a true taste of Puerto Rican culture. Popular with locals and tourist alike the atmosphere here is lively and fun! The café is tucked away in an alleyway off San Francisco Street just below Da House hotel which adjoins the cafe. Da House hotel is where we always stay when we are in Old San Juan.

Nuyorican Cafe Old San Juan PR

Live Music and Dancing Along Paseo de la Princesa

Paseo de la Princesa music singing dancing Old San Juan PR

Paseo de la Princesa near the cruise ship docks is where you can find live music on most weekend nights and holidays. The band plays local music, singers entertain and couples enjoy dancing. The street is lined with vendors selling food, drinks and souvenirs. It’s a great way to end your day in beautiful Old San Juan.

Puerto Rico day trips from Old San Juan:

Arecibo Observatory in Puerto Rico Celebrates 50 Years
Rio Camuy Cave Park
Guavate, Home of the Lechon
Culebra Island – Puerto Rico’s Little Paradise

We’d like to hear from you!

Have you visited Old San Juan? What gets your vote for the best things to see and do while there? Let us know in the comments below.

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