America‘s Oldest City: A St Augustine Walking Tour With Context

From its jaw-dropping Bridge of Lions to the resilient fortress of Castillo de San Marcos, St. Augustine is like a historical theme park where the exhibits are real, and the stories are legendary! On this walking tour, you‘ll take in more than 350 years of fascinating history with Context Travel expert and storyteller, Jennifer Geraghty. As you walk, she‘ll bring the city‘s colorful characters to life, recount epic battles, and point out the many historical firsts that shaped the city.

Starting in front of the Governor‘s House Cultural Center and Museum, you‘ll hear how the city began as a humble Spanish outpost and blossomed into a glittering jewel of the Gilded Age. From there, you‘ll make your way around St Augustine‘s Historic District, and see several sites listed in the National Register of Historic Places. You‘ll see the Ximenez-Fatio House, the Sanchez House, and St Augustine‘s oldest house, the Gonzalez Alvarez House, and learn to spot Spanish and British influences in the architecture. Going up St George Street, Jennifer will also show you the Prince Murat Cottage and the Stanbury Cottage, known as the Gingerbread House. You‘ll see where the city walls once stood and pass through the Old City Gates. In Plaza de la Constitución, the oldest public space in the US, you‘ll hear the secrets behind the square‘s obelisk, like why it‘s the only one of its kind globally.

Along the way, you‘ll:

• Relive the first pirate attacks, which ransacked the town and captured several members of the local population
• Explore the Cathedral Basilica of Saint Augustine, the oldest parish church and the birthplace of Christianity in the US
• Trace the fascinating transformation of the Governor‘s House, serving as a historical treasure trove
• Learn how massive flooding caused the citizens of St. Augustine to build and rebuild a new sea wall
• Stroll down St. George Street, the historical heart of St Augustine
• Discover how the Oldest Wooden Schoolhouse survived a hurricane
• Find out why Castillo de San Marcos, a marvel of military defense took 23 years to complete and how its ”cheese-like“ walls made the fort impenetrable to the English
• Listen to the legendary stories of Biassou, the nation‘s first Black general
• Be captivated by the ghostly legends and astonishing stories that surround the Spanish Military Hospital, and the Oldest Wooden Schoolhouse
• See where the city was rebuilt after harrowing fires scorched it
• Follow the origins of the Yellow Fever epidemic
• Meet the lucky parrot who inherited millions of dollars

Experience the triumphs and tribulations that are etched into St. Augustine, from its resilience against invasions, and fires that tested their mettle, to its unyielding spirit of rebuilding against all odds.