Top 5 Instagram Worthy Spots in San Juan

March 16, 2022

Condado Ocean Club is the perfect choice for any traveler eager to explore Puerto Rico’s capital city for photogenic, historically significant, and eye-popping opportunities to grab the attention of friends and followers on Instagram.

Sure, just strolling through San Juan’s diverse, colorful sections and neighborhoods turns up myriad surprising sights you will want to grab for Instagram. You will encounter them all: gorgeous romantic beaches, lush tropical flowers, the Island’s stunning birds, San Juan’s style-conscious locals, and around the next corner, a facade of stunning old-world architecture.

From Spanish colonial homes to alluring cobblestone byways, the breathtaking surprises are waiting for you in the City of San Juan. For travelers who are on an Instagram “mission” to share their adventures and fun with people back home, here are our choices of San Juan’s five top Instagram-worthy sights:

Fortaleza Street

A high point of your Instagram tour of San Juan should definitely be the end of Fortaleza Street, which we are sure is the most instagrammable street in Old San Juan. Known as Paseo de Sombrillas, because of its first art installation a few years ago. Every once in a while the installation changes, usually in honor of an awareness cause. Currently you can find pink butterflies in honor of the women who have battled cancer, in collaboration with Susan G. Komen.

The Caribbean sunlight shining down around the multitude of bright colors makes for dazzling visual images. Try to make your visit to this street at an off-hour unless you want to cope with the considerable crowds drawn to this major tourist spot. For just you in your Instagram photo, try to arrive at the street early in the morning. Hey, if you arrive late. you can try for some colorful crowd scenes as Puerto Rican shoppers, as well as lots of tourists, explore this special byway of a unique city.

fortaleza street decorations in old san juan
Fortaleza Street in Old San Juan

Cobblestone Streets & Historic Architecture

Just strolling through the cobblestone streets and admiring the history in every step and the architecture makes it all worthwhile. This famous Drug Store is standing tall in Plaza de Armas since 1850, with a large inventory for everyone's needs.

Paseo de la Princesa

For a picturesque and Instagram-inspiring stroll along the bay, try the Paseo de la Princesa—the Path of the Princess. The walk itself provides gorgeous views at every turn and lots of history, too. You will find little stands selling food and snacks and some boat tours originate here.

Puerto Rican Flag

On the corner of Calle de la Virtud and Calle Imperial, you will find one of the many Puerto Rican flags painted all over the enchanting old town. This flag is one of our great pride and joys so local artists love to paint it all over town. Another famous spot is the "Puerta de la Bandera" in Calle San José, where you will find the white and black flag, in a mural accompanied by silhouettes of local artists.

Castillo San Felipe del Morro & Castillo San Cristóbal

Old San Juan’s two earliest military forts required more than two centuries to complete after construction began in the 1500s. These were the first fortifications erected by the Spanish to defend the island against invasion by the English or Dutch. Castillo San Felipe is named for King Phillip the Second of Spain, while Castillo San Cristobal is also known as Fort San Cristobal–the single largest Spanish fortification ever constructed in the New World. Note that when complete, this huge fortification essentially enclosed all of San Juan. Entry to the capital was through guarded gates.

Originally built on a hill and named by the Spanish "San Cristobal" in honor of their victories over the English and Dutch, both Castillo San Felipe del Morro and Castillo San Cristóbal are operated today by the U.S. National Park Service. For best views and photo ops, climb to the top level of each edifice to get sweeping views out over the Atlantic Ocean. Or show your Instagram followers the perfect frame you found for a photo of the Atlantic—the glassless windows located in the bathrooms of both forts!

castillo viejo san juan