Best Spots for your Old San Juan Couples or Engagement Session in Puerto Rico


Old San Juan is probably the top destination in Puerto Rico for couples and engagement photography. If you are visiting you are more than likely already planning to stroll through the cobblestone streets and even enter the forts. Old San Juan is so extremely beautiful it’s the perfect spot for a mini session and even a 3 hour session if you are up to the walking. That’s why here I’m compiling what I consider the best spots for pictures. You can pic your top spots to narrow down your session path. Some of the locations require a permit, but most of them are complete free. Let me know in the comments section which are your favorite. The spots are listed in no particular order.

San Cristobal Fort (Permit needed)

The San Cristobal Fort dates back to 1783 and was built by the Spanish to help protect against invasions. This magnificent fort, not only is it beautiful inside but it’s exterior is surely impressive. Permits are needed to photograph inside, but the benefits outweigh the troubles. The inside of the San Cristobal Fort will be a memorable part of your trip to the Island and your couples or engagement photos.

Castillo San Cristobal, Puerto Rico

Castillo San Cristobal, Puerto Rico

El Morro Fort (Permit needed)

Who can say no to getting your pictures taken at a World Heritage Site. Just like the San Cristobal you need a permit to have your photos taken professionally inside the fort. This 18th century fortification is breathtaking and full of so much history. No trip to Old San Juan is complete without a visit to El Morro.

El Morro

El Morro, Puerto Rico

Caleta de Las Monjas

This colorful street connects easily to many beautiful attractions like Plazuela La Rogativa as well as one of my favorite spots, Callejón de las Monjas.

Caleta las Monjas

Callejón de las Monjas
Callejón de las Monjas

Callejón del Hospital

One of the few streets with built in steps. This spot has houses that merge colonial and contemporary architecture. If you are allergic to cats, I suggest you skip this part of town. But, if you are a cat lover like me, it will be an added bonus. 😊 You will find lots of cats at Old San Juan. Treat them with kindness and respect! They keep the city clean of rats and mice. The cats at Old San Juan are taken care of by Save a Gato, a non-profit organization dedicated to easing the suffering of Old San Juan cats through TNR. Get 10% off your session if you make a donation (restrictions apply):

Callejón del Hospital, Old San Juan

Calle Luna

This street is closet o sights like the San Cristobal Fort which I love specially for mini sessions, because we get a little taste of what Old San Juan architecture is all about.

Best Spots For Your Old San Juan Couples Or Engagement Session In Puerto Rico

Bastión de San Sebastián

This area is all about the ocean views as well as the amazing view of the San Cristobal Fort. Definitely a must!

San Cristobal Old San Juan

San Cristobal Old San Juan

Paseo La Princesa

This beautiful promenade takes you all the way to Las Puertas de San Juan or San Juan Gates.  It has gorgeous views of the San Juan Bay and has more of a natural landscape.

Paseo La Princesa

Plazuela La Rogativa

At the Plazuela La Rogativa you will find a sculpture that commemorates a women-led religious procession that took place in 1797. It has one of the best views of the San Juan Bay and as well as part of the Paseo La Princesa.

Plazuela La Rogativa

Casa Rosa

Also known as Pink House is a historic house that used to serve as a barrak for the Spanish troops. As the name implies it’s painted in a very cheerful pink color.

Casa Rosa Old San Juan

Calle de San Fracisco

Grab a piragua by la Puerta de San Juan and stroll through Calle de San Francisco. Old San Juan is full of cute doors and cobble Stone and this street doesn’t disappoint. Walk east to get to Plaza de Armas, one of the main squares at Old San Juan.  

Best Spots For Your Old San Juan Couples Or Engagement Session In Puerto Rico

Sentry Boxes

I can’t just name one. Sentry boxes or Garitas are an iconic symbol of our past. They are set all throughout the old city.

Best Spots For Your Old San Juan Couples Or Engagement Session In Puerto Rico

Old San Juan from the Ocean

If you can’t get enough of Old San Juan how about Old San Juan from the Ocean! Book a sunset boat tour and enjoy!

Best Spots For Your Old San Juan Couples Or Engagement Session In Puerto Rico

Puerta de la Bandera

Last but not least, this one is a classic. Like trip advisor best describes it’s a place of cultural appreciation for those who visit.

Puerta de la Bandera Old San Juan

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