Old San Juan, Puerto Rico is one of the most historic islands in the Caribbean. Not only does it have rich history and beautiful architecture, but whether it’s day or night there is always something to do. Here is one way you could spend an entire day of fun in Old San Juan.

Flying Kites and Touring El Morro

El Morrow

photo via Wikipedia

El Morro is one of the most historic sites in Puerto Rico. Its full name being El Castillo San Felipe del Morro, this castle was named after Kind Philip II of Spain, and was designed to guard the entrance to the San Juan Bay to defend the Spanish colonial port city of San Juan from enemies. In the 1500s, Sir Francis Drake attempted to attack San Juan and failed. In the late 1800s, El Morro was attacked during the Spanish-American War by American Naval Forces, the most impacting being the Bombardment of San Juan on May 12, 1898. Now, this castle is not only a huge historic monument in Puerto Rico, but a beautiful spot to spend your morning. Locals and tourists alike can be found flying kites on the lawn of El Morro, which is a fun day activity to do before exploring the rest of the city.

Shopping  on Calle del Cristo

Calle Cristo

photo via Lonely Planet 

If shopping is what you want to get done during your time in Old San Juan, you can find almost anything on Calle del Cristo. This cobblestone street has high end stores like Coach, Ralph Lauren and Burberry, as well as Don Collins, a famous local cigar shop. It’s also a great place to get souvenirs all in one spot. This street is also lined with various restaurants, cafes, and art galleries that can make your shopping experience a full day event if you’re looking to have a relaxing day in this ocean side city.

Food and Drinks at Old Harbor Brewery

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Photo via photos1.blogger.com 

Old Harbor is the only microbrewery on the island, and crafts fine, unique beers. The food is also Puerto Rican cuisine that will be sure to satisfy. This restaurant is known for its seafood and beer, which is a perfect combination to enjoy after a long, warm day. I go to Old Harbor every year I go to Old San Juan, and it never disappoints. I recommend their Kofresi stout beer, which has notes of coffee, dark chocolate, and malt.

Sunset by The Raíces Fountain


photo via World Adventurer 

The Raíces Fountain is a monument in Old San Juan that celebrates the ” raíces” or “roots” of Puerto Rican Taíno, Spanish, and African heritage. The fountain is beautiful during the day, but worth a visit during sunset. It’s consindered one of the most romantic spots in all of Old San Juan.

Drinks and Dancing at the Rumba Cruise Tour


photo via San Juan Travel Guide 

The Rumba Cruise Tour is one of my favorite things to do for fun in Old San Juan. Tickets are usually pretty affordable, and you can buy drinks on board. There’s live music on the second level of the boat for some dancing, and you get a beautiful view of Old San Juan at night.

Stay at La Terraza Hotel


photo via Trip Advisor 

La Terraza is one of the most famous hotels in Old San Juan, known for it’s beautiful, traditional architecture and for being close to all tourist spots. It’s the perfect place to stay after a long day of travelling the city.

Where would you want to visit in Old San Juan?

Rebecca is (secretly Linda Belcher) a senior at Iona College, studying Mass Communications. She loves to travel, coffee, and her dog. Fan of boy bands, big hair, and everything bagels. Professional shade thrower and wearer of beanies.


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