Steeped in over five centuries of history, the walled city of Old San Juan stands as a testament to Puerto Rico’s rich colonial heritage and architectural splendor. From imposing fortresses to intimate chapels, and grand plazas to narrow cobblestone streets, Old San Juan offers a visual feast—if you know where to look. For those planning their San Juan travel itinerary, this Old San Juan architecture and design guide spotlights 10 must-see places in this historic district, along with Old San Juan hotels.

Castillo San Felipe del Morro Begin your Old San Juan architecture and design tour at Castillo San Felipe del Morro, better known as El Morro. Once the most feared of all the Spanish colonial fortifications, the imposing 140-foot walled citadel has guarded the entrance to San Juan Bay since the 16th century. 

Castillo San Cristóbal Complementing El Morro’s seaside defenses, Castillo San Cristóbal protected Old San Juan from land attacks. Covering 27 acres, this massive fort is the largest built by the Spanish in the New World. With its intricate network of tunnels, sentry boxes, and casemates (large vaulted, bombproof rooms), it’s also a masterclass in 18th-century military architecture and engineering.

Plaza de Armas At the heart of Old San Juan lies Plaza de Armas, the city’s main square since the 16th century. Surrounded by significant buildings including the City Hall and Puerto Rico Department of State, it exemplifies Spanish colonial urban planning and design.

Calle del Cristo Any architecture guide to Old San Juan would be remiss to not include Calle del Cristo, the city’s oldest street. This picturesque cobblestone lane is lined with beautifully restored 16th and 17th-century buildings, showcasing the characteristic features of Spanish colonial architecture: ornate balconies, wooden doors, and vibrant facades in a palette of pastels. It also serves as Old San Juan’s shopping street, with an array of boutiques, restaurants, and cafés.

Capilla del Santo Cristo de la Salud At the end of Calle del Cristo, you’ll find this tiny, one-story 18th-century chapel. Its ornate altar in gold and silver leaf, oil paintings by renowned Puerto Rican painter Jose Campeche, and intriguing legend surrounding its construction make it a fascinating stop for those interested in the intersection of art, architecture, and local folklore.

La Fortaleza This beautiful executive palace has housed more than 170 governors of Puerto Rico and is the oldest state residence of the New World still in use. Although public access is limited, guided walking tours cover the lush Moorish gardens—as well as inside the building when the government isn’t in session.

Calle Fortaleza Stretching out from La Fortaleza is this iconic Old San Juan street, also known as “Umbrella Street” for its multicolored umbrellas that form a dazzling canopy. The hanging display changes throughout the year, ensuring a fresh experience each time.

Casa Blanca Venture to Casa Blanca, Old San Juan’s oldest residence. Constructed in 1521, it was meant to serve as the main home of Juan Ponce de León, the Spanish explorer and Puerto Rico’s first governor. He never got to occupy it, but the building remains a quintessential example of early colonial architecture, and is now home to a museum of 16^th and 17^th-century artifacts. Catedral de San Juan Bautista This Gothic-style cathedral, whose structure dates back to 1540, is recognized as the oldest church on U.S. soil. Come for the stunning stained-glass windows, centuries-old, clay-colored walls and columns, faded murals—as well as Ponce de León’s tomb. 

Puerto de San Juan With its striking red hue and imposing scale, the most boldly colorful of all the entrances to the walled city is on every design lover’s bucket list when visiting Old San Juan.

Top Places to Stay in Old San Juan Puerto Rico

Some of the best Old San Juan hotels offer a unique blend of historical charm and architectural character, reflecting the rich heritage of the city. 

Hotel El Convento Old San Juan hotels don’t get any more historic than this 81-room boutique hotel featuring wooden beams and handcrafted tiles in a former Carmelite convent dating back to 1651.

Decanter Hotel This 20-room hotel and restaurant is situated in a meticulously restored 1881 building, with a stunning rooftop terrace. 

Top Design-Centric Places to Stay in San Juan Puerto Rico

For those planning their San Juan travel and wishing to be closer to the island’s famed beaches or Santurce’s buzzy art, restaurant, and nightlife scenes, it’s a good idea to look beyond places to stay in Old San Juan Puerto Rico. Dreamers Welcome provides laid-back luxury stays for design-focused alternatives to staying in one of the Old San Juan hotels. Below, five highlights from the Dreamers Welcome hospitality group that are either within walking distance to Ocean Park Beach or situated in San Juan’s cultural hotbed of Santurce.

Dreamcatcher by DW

Nestled in Ocean Park just a block from the beach and ten minutes by car to historic Old San Juan, this design guide mainstay features 19 rooms and suites, each with its own distinctive personality and private tropical terrace. Whether you choose the Romantic, with its lush green private terrace, swaying hammocks, and custom polished-concrete soaking tub, or any other room or suite, every element has been thoughtfully considered. An added bonus: The award-winning full-service property holds the honor of being San Juan’s only vegetarian hotel.

APT by DW

Just outside historic Old San Juan in colorful Santurce, this collection of eight apartment-plus accommodations each feature two bedrooms, a full kitchen, a large private garden, and thoughtful design touches from woven artwork to pops of vermilion.  

Tropicalia by DW

Art and design lovers take note: These minimalist-cool vacation rentals in buzzy Santurce are within walking distance of the Puerto Rico Museum of Art, which boasts the most comprehensive collection of art in the Caribbean, and Ocean Park Beach. Ranging from a studio to a three-bedroom, all feature full kitchens, private outdoor space, and clean lines.

Noa by DW

Located just a 10-minute walk from Ocean Park Beach, these modern vintage-inspired vacation rentals range from a spacious studio apartment with a sleek kitchenette and light-filled terrace to a sprawling four-bedroom retreat complete with an oversized private rooftop deck with a hot tub, loungers, and BBQ offering expansive views over the city.

Verde by DW

These spacious studio and one-bedroom apartments in vibrant Santurce combine retro-chic charm, minimalism, and photo-ready terraces. A hidden door in two of the four accommodations lead to a secret room inspired by the infamous Andy Warhol Factory.