Old San Juan Trolley and Sightseeing Tour

Plaza Colón is one of Old San Juan’s most iconic squares, rich in history and culture. Named after Christopher Columbus, whose statue stands proudly at its center, the plaza was built in the late 19th century on the site of the old city gate, Puerta de Santiago. The area became a bustling hub as the city expanded beyond its original walls, and it continues to serve as a social and cultural gathering place today. Surrounded by historic theaters, cafés, and shops, the plaza reflects San Juan’s colonial past and vibrant present.

Plaza Colón is also the meeting point and starting location for your tour, making it a perfect place to take in the history and energy of the city before your adventure begins.

The Antiguo Casino de Puerto Rico is one of San Juan’s most elegant landmarks, located in the heart of Old San Juan. Built in 1917, this historic Beaux-Arts building once served as an exclusive social club and now functions as a premier venue for weddings, galas, and cultural events. Its grand marble staircase, dazzling chandeliers, and ornate ballroom make it a favorite spot for visitors to admire and photograph. The Antiguo Casino beautifully reflects Puerto Rico’s architectural and cultural heritage.

Casa de España is a stunning Moorish Revival building located near the entrance to Old San Juan. Built in 1934 as a social club for the Spanish community in Puerto Rico, it showcases exquisite Andalusian-inspired architecture, with arched doorways, colorful tiles, and a picturesque courtyard featuring a beautiful fountain. Today, Casa de España serves as a venue for weddings, cultural events, and private gatherings, while its striking façade makes it a favorite spot for visitors to admire and photograph.

El Paseo de los Presidentes in Old San Juan, Puerto Rico, is a small but meaningful outdoor monument featuring life-sized bronze statues of all U.S. presidents who have visited the island. Located near the Capitol building, the statues stand side by side, offering a unique glimpse of history and the political ties between Puerto Rico and the United States. It’s a popular stop for visitors exploring Old San Juan, combining culture, history, and striking photo opportunities.

Plaza Rafael Hernández Marín is a charming public square in Old San Juan dedicated to Rafael Hernández Marín, one of Puerto Rico’s most beloved composers and musicians. Known as “El Jibarito,” Hernández is celebrated for his timeless boleros and patriotic songs that have become part of Puerto Rico’s cultural identity. The plaza features a bronze statue of the composer, inviting visitors to reflect on his contributions to music while enjoying the tranquil setting. Surrounded by local shops and cafés, it’s a peaceful spot to pause and appreciate Puerto Rican heritage during your visit.

The Monument to Lamento Borincano is a poignant tribute located in San Juan, honoring one of Puerto Rico’s most iconic songs, "Lamento Borincano," written by composer Rafael Hernández Marín. This beloved canción tells the story of the struggles of a humble jíbaro (farmer) and reflects the economic hardships faced by Puerto Rico in the early 20th century. The monument features a bronze sculpture of the jíbaro with his mule, symbolizing resilience and the island’s rural heritage.

It is a meaningful stop for visitors who want to connect with Puerto Rico’s history and music, offering a moment of reflection on the island’s cultural identity.

Puente Dos Hermanos (Two Brothers Bridge) is an iconic bridge in San Juan that connects Condado with Old San Juan. Built in 1910, it was named in honor of the Behn brothers, German engineers who helped modernize the city’s infrastructure in the early 20th century. The bridge offers scenic views of San Juan Bay and the Atlantic Ocean, making it a favorite spot for photographers and those enjoying a stroll between the two districts.

Today, Puente Dos Hermanos stands as both a vital roadway and a historic landmark, symbolizing the connection between the old colonial city and the modern Condado area. It’s a great place to pause for photos and appreciate the contrast between historic and contemporary San Juan.

entana al Mar is a beautiful oceanfront park located in the heart of Condado, San Juan. This open plaza features lush gardens, fountains, and plenty of seating areas, making it a favorite spot for both locals and visitors to relax and enjoy the sea breeze.

It’s also a perfect spot for pictures of the ocean and beach, with sweeping views of the Atlantic and Condado’s sandy shores. Whether you stop by during the day or at sunset, Ventana al Mar offers a peaceful setting and a great backdrop for memorable photos.

Escambrón Beach is one of San Juan’s most popular and family-friendly beaches, located just minutes from Old San Juan. Known for its calm waters protected by a natural coral reef, it’s perfect for swimming, snorkeling, and even beginner scuba diving. The beach is part of the Escambrón Marine Park, making it an ideal spot to observe tropical fish and other marine life.

With picnic areas, shaded spots, and nearby walking trails, Escambrón Beach is ideal for relaxing, enjoying the sun, and taking in stunning views of the Atlantic Ocean and San Juan’s coastline. It’s also a fantastic location for photos, especially at sunrise or sunset.

The Capitolio de Puerto Rico (The Capitol of Puerto Rico) is one of San Juan’s most impressive landmarks, located at the entrance to Old San Juan. Completed in 1929, this neoclassical building serves as the home of Puerto Rico’s Legislative Assembly. Its grand marble façade, soaring columns, and iconic dome make it an architectural treasure and a symbol of Puerto Rican democracy.

Inside, visitors can admire stunning mosaics, murals, and exhibits that depict the island’s history, including a detailed copy of the United States Constitution carved in marble. The Capitol grounds also feature monuments and memorials, making it a great place to learn about Puerto Rico’s political and cultural heritage.

Our final stop is Plaza Colón, one of Old San Juan’s most historic and lively squares. This is where your tour will conclude and where you’ll be dropped off. Take a moment to enjoy the plaza’s beautiful surroundings, snap some last photos, or grab a coffee at one of the nearby cafés before continuing to explore on your own.

Thank you for joining us — we hope you had a wonderful time!