Welcome to the Old San Juan Tour
Embark on a walking tour of San Juan, full of majestic architecture, breathtaking views, and embattled history. Behold the largest Spanish-built fortification in the Americas. Hear stories of pirate battles, greed, and power, featuring figures like Sir Francis Drake. Stroll down ancient city streets rich with culture and history, then walk along this beautiful city’s old walls and enjoy some gentle ocean views.
About the Tour
Your self-guided walking tour begins at the Cruise ship pier, 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!
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Old San Juan Map
Where To Start?
We recommend Starting From: Cruise Ship Pier, FV7Q+H8W, San Juan, 00916, Puerto Rico
How Does It Work?
- Once you book a tour, you’ll get a text/email with instructions.
- Download the app (while in good wifi/signal) and use your unique password to access your tours. If there are multiple versions or entrances for your tour, be sure to download all audio guides.
- To begin touring, go to the starting point and launch the app.
- The audio starts automatically once you reach the starting point. Stick to the tour route and speed limit for the best experience.
- Please note that no one will meet you at the starting point.
Preview The Tour
Tour FAQs
The tour begins at the colorful La Corazon Steps, featuring a painted beating red heart.
The Teatro Alejandro Tapia y Rivera is one of the oldest drama theaters in the US and is rumored to be haunted.
Plaza Colon features a towering statue of Columbus, and you can learn about Columbus’s claim to the island and the origin of San Juan’s name.
The majestic Castillo San Cristobal is encountered, and you can discover its construction history and its connection to explorers seeking riches on the island.
La Perla is known as the filming location for the music video of the hit song “Despacito.”
The tour covers the story of Sir Francis Drake and his attempt to seize the island from Spain, as well as the Spanish General Sancho’s defense.
The tour delves into Dutch attempts to take power, including the torching of the city, and the Spanish efforts to prevent further defeat.
The tour visits Castillo San Felipe del Morro, and you can learn about its historical importance, including attacks and defenses.
The tour explains how the fall of El Morro marked a major turning point in world history.
The tour concludes just past the famous La Fortaleza, a towering fortress dating back to the 1530s, which played a crucial role in the island’s history.
Inclusions and Exclusions
App on your phone: A link to download the Action Tour Guide App and Password for your tours.
Easy to use: Stories play automatically by GPS. Hands-free. Get HELP all day: Call, Chat, or Email.
Flexible schedule: Use any day, any time. Valid for multiple visits up to 1 year after purchase.
Interactive audio stories: Experience local history and culture through clear, concise narratives from experienced narrators.
At your own pace: No group. Take breaks for photos, snacks, hikes. Go at your own pace.
Offline use: No cell signal or wifi required. Offline GPS Map & route. Stop-to-stop direction.
Don’t miss a thing: Full itinerary, travel tips, professionally narrated videos, text, and hidden gems.
Transportation, parking fees, food, and drinks.
Entry tickets or reservations to any attractions along the route.
Car Rental: Please arrange a rental car at the closest airport or train station.
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