• Castillo de San Marcos National Monument - Experience the oldest masonry fort in the continental U.S. This impressive, star-shaped fortress has endured centuries of battles, sieges, and changing empires. Beyond its military significance, the coquina-built stronghold shares compelling stories of conquest, resistance, and survival that resonate through its walls.
• Oldest Wooden School House - Travel back to the 18th century at one of America’s oldest surviving wooden schoolhouses, featuring hand-forged nails and original materials. This modest landmark provides insight into colonial education and daily life in a city defined by perseverance and tradition.
• Tolomato Cemetery - Behind wrought-iron gates lies one of St. Augustine’s oldest burial grounds. Tolomato Cemetery is the final resting place for Spanish settlers, free Black Catholics, and early residents. Quiet and evocative, this sacred site reflects the city’s rich spiritual and cultural history.
• Flagler College - Once a luxurious Gilded Age resort for America’s elite, this architectural masterpiece—designed by renowned innovators Carrère and Hastings—now houses Flagler College. Step inside to admire soaring ceilings, Tiffany glass, and the opulence that transformed St. Augustine into a dream destination.
• Cathedral Basilica of St. Augustine - Admire the oldest Catholic parish in the U.S. The Cathedral Basilica blends Spanish mission roots with stunning stained glass, and bell chimes echo centuries of devotion. This tranquil landmark combines faith, resilience, and artistry in the heart of America’s oldest city.
• St. George Street - St. George Street is the vibrant heart of St. Augustine’s Old Town, bustling with charm, history, and local flavor. Stroll past centuries-old buildings, artisan shops, and hidden courtyards where the past and present intertwine with every step.
• Plaza de la Constitucion - This historic public square has witnessed triumph, tragedy, and transformation, from colonial rule to civil rights protests. Plaza de la Constitución, framed by historic landmarks and shaded by ancient oaks, is a poignant place to pause and reflect on St. Augustine’s evolving story.
• Government House Museum - Once the seat of colonial governors, this grand building has served many roles over the centuries, from royal court to post office. Today, the Government House Museum exhibits trace the city’s layered past, offering a glimpse into life under Spanish, British, and American rule.
• Lightner Museum - The Lightner Museum, housed in a former Gilded Age resort built by Henry Flagler, dazzles with its eclectic collections, from Victorian curiosities to fine art. Step inside to explore elegance, innovation, and the opulence of a bygone era.
• The Oldest House Museum Complex - The González-Alvarez House, known as the oldest house in Florida, is a well-preserved residence reflecting over 300 years of architectural and cultural evolution. Walk through its rooms to discover the daily lives of colonial families who once called this place home.
• Father Miguel O’Reilly House Museum - One of the city’s oldest surviving structures, this stone home belonged to Father Miguel O’Reilly, a pivotal figure in St. Augustine’s Catholic heritage. Today, it offers an intimate look at faith, education, and resilience in colonial Florida.
• Aviles Street - Walk along the oldest public street in the U.S., where centuries of history line a narrow, picturesque lane filled with art galleries, cafés, and hidden courtyards. Every cobblestone tells tales of Spanish soldiers, settlers, and stories long passed.
• The Ximenez-Fatio House - This beautifully restored boarding house reveals the lives of 19th-century women entrepreneurs and travelers in early Florida. Step inside the Ximenez-Fatio House Museum for a rare glimpse into the domestic and social world of a frontier city on the rise.
• Bridge of Lions - Guarded by marble lions and spanning the Matanzas River, this iconic drawbridge connects the historic district to Anastasia Island. The Bridge of Lions offers a scenic crossing with sweeping views. It’s both a practical link and a symbol of the city’s enduring grace.
• Monson Motor Lodge Pool - Civil Rights Monument - The Monson Motor Lodge Site witnessed protests that helped spark change nationwide. Once a segregated hotel at the center of the Civil Rights Movement, the owners made headlines worldwide when they poured acid into the pool to stop protestors. Though the building is gone, the location remains a powerful testament to courage and justice.
• Colonial Quarter - Journey back in time with this immersive living history experience, where costumed interpreters, blacksmith forges, and reconstructed buildings bring colonial St. Augustine to life. It’s part museum, part time machine, and entirely unforgettable.

• Flexible Usage (unlimited access)
• Audio Guide
• App and Tour Download

• Smartphone (bring your own)

Discover the historic core of St. Augustine, the oldest continuously inhabited European-established city in the United States, with this self-guided walking tour through its most renowned streets, plazas, and landmarks.

Beginning near the Castillo de San Marcos, the route takes you through Old Town, St. George Street, Aviles Street, and the city’s civic center. As you journey, learn about how Spanish colonists, Indigenous peoples, enslaved Africans, and later civil rights leaders influenced a city characterized by resilience, adaptation, and cultural exchange.

This engaging audio experience is crafted for independent travelers seeking more than just superficial sightseeing. As you walk, stories unfold, linking fortifications to everyday life, power to resistance, and historical events to the vibrant city surrounding you.

Unlike a group tour, this experience allows you to explore at your own pace—pause, rewind, or linger wherever you wish.

• Works entirely offline once downloaded—no cell service required
• GPS-triggered audio plays automatically based on your location
• Flexible - Buy once, use any day/time—access never expires
• Get the Drives & Detours app and download the tour ahead of time
• Children 10 and under are free

For a full refund, cancel at least 24 hours before the scheduled departure time.