San Juan Self-Guided Walking Tour

What your day looks like

Your self-guided walking tour begins at the colorful La Corazon Steps, which features a painted beating red heart! Next, stop by the Teatro Alejandro Tapia y Rivera, one of the oldest drama theaters in the US, and which is also supposedly haunted! Then you’ll come to the Plaza Colon, with its towering statue of Columbus. Hear how Columbus claimed the island and how San Juan got its name! As you stroll along these scenic streets, take in the majestic Castillo San Cristobal. You’ll unearth the story behind its construction and hear about the vast riches that brought so many explorers to this island Up next is the colorful and historic La Perla neighborhood by the seaside. You might recognize it as the music video filming location for the hit song “Despacito!” Then get to know Sir Francis Drake and revisit his fight to seize the island from Spain. Learn how his Spanish adversary, General Sancho pulled off a victory even though they were hugely outnumbered! You’ll also hear about the Second Battle of San Juan and find out why it was such a short-lived win for the English. Your historical journey takes even more twists and turns as you uncover subsequent Dutch efforts to take power. Learn how they torched the city and how the Spanish fought to prevent this defeat from repeating! As you keep walking, you’ll behold ancient walls and gunpowder magazines, then finally the awe-inspiring Castillo San Felipe del Morro itself! And speaking of attacks, hear about Puerto Rico’s struggles for independence and find out why the US got involved. Hear how the fall of El Morro marked a major turning point in world history. Also be sure to take in the breathtaking ocean views and give yourself a little respite! Pay a visit to the Cuartel de Ballaja, which now houses the Museum of the Americas, Then continue onto the Casa Blanca. Hear how it was meant for Ponce De Leon, and learn the story of the grandson who wrote one of Puerto Rico’s most critical historical texts! Also find out how Ponce De Leon himself met a poisonous end! The next stop is the historic Catedral Basilica Menor de San Juan Batista, the final resting place of Ponce De Leon. Learn how the oldest church in the Americas survived countless attacks over the centuries, including Dutch attacks and Hurricane Maria. As the journey winds down, stroll along lovely cobblestone streets to the Puerta San Juan, the only remaining gate from the old city. Your tour concludes just past the famous La Fortaleza, a towering fortress dating back to the 1530s!