Photo Worthy Locations in San Juan, Puerto Rico

I travel to San Juan, Puerto Rico frequently for work, and while I’m usually indoors being industrious, sometimes I get the opportunity to venture out. During those instances I’ve both stumbled upon, and been led to the most charming photo worthy crevices/places in the city. I still have plenty of spots to visit, so this list isn’t exhaustive.  I anticipate it will grow as I explore more places in the future, but for now keep scrolling if you want to see my top San Juan photo-worthy spots.

1. The Umbrella Sky Project/ Paseo de Sombrillas

The most recent addition to San Juan, featured on this list, and probably the most primed for Instagram, the umbrella sky project was installed on Calle Fortaleza as a symbol of hope after the devastation caused by Hurricane Maria in 2017. The art installation represents the determination of Puerto Ricans and their ability to recover. The storms may have dimmed the vibrancy of the island temporarily, but Puerto Rico and its people are resilient and brighter times are ahead.

Where to find it: Fortaleza street, just in front of “La Fortaleza” the Governor’s residence.

2. El Convento

El Convento prides itself in being one of most unique hotels in world, and for good reason. Its history dates back to 1646 and still retains some of its old world charm. El Convento features an open interior courtyard with tiered balconies throughout the property. The buttery yellow is a constant throughout the property and a perfect backdrop. You don’t have to be a guest at the property to roam the Spanish style corridors, and in fact one of the most picturesque spots (there are several) in the property is right at on the ground floor, to the right of the concierge.

Where to find it: 100 Cristo Street, Old San Juan

3. Condado Vanderbilt

While El Convento is an ode to San Juan’s historic past, Condado Vanderbilt is one of Puerto Rico’s contemporary crown jewels, honoring both San Juan’s past and its potential for glitz. The Condado Vanderbilt is newly renovated, its stylish and the ambiance is unmatched. One of my favorite ways to unwind at the hotel is to sip mojitos while looking at the hotel’s infinity pool. The views from this area of the hotel are surpassed by none in the city.

4. El Morro

What’s a trip to Puerto Rico without visiting Castillo San Felipe del Morro, or el El Morro for short. El Morro is a 16th-century citadel that has played a critical role during various conflicts. The U.S. Army officially retired El Morro in 1961 and it became a part of the National Park Service. Visitors are now welcomed and its position provides the best view of the San Juan Bay.

Where to find it: Castillo de San Cristobal Avenida Muñoz Rivera, San Juan Puerto Rico 00901, Puerto Rico

5. Streets of Old San Juan

The streets of Old San Juan are scenic and delightful. Pastel and sherbet-hued homes line the cobbled street roads, making every corner Instagram worthy. The most astonishing part, people actually live in these homes. So be respectful when you are posing in front of them! Though almost every street in Old San Juan is beautiful my favorite is Calle Caleta de las Monjas.

Where to find it: Old San Juan


Hi! I’m Jenny, a millennial HENRY. I practice law in Washington, D.C. where I live with my husband. Like most HENRYs, when I am not at toiling away at work, I enjoy travel, new experiences, and a good outfit. My obsession with all the above led me to create this blog. I yearned for a creative outlet to air out my thoughts on the HENRY lifestyle, and the headaches that sometimes accompany it. I invite you all to join the conversation with me! Sit down, scroll, and let’s discuss HENRYing it up, the Jenny way.


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