Please support small businesses and consider booking us directly, just use a web search to find us: Pineapple Ride and Tour ***Nights Of Lights Tours are available on our website ONLY*** Our Historical Tour is informative, comfortable, and convenient. Our expert tour guides will take the time to get to know you and share many stories about the oldest continuously occupied european settlement in the continental United States. Our tours are conducted on an electric vehicle with open sides and seat up to 10 People. This is an excellent way to see where everything is, and to learn Saint Augustine's history in a fun and informative way. Three reasons to consider our tour: - FREE parking or get picked up anywhere downtown, Just call - We are pet friendly, all sizes and breeds welcome - This is THE MOST conveniently located and professional tour service available in Saint Augustine.

Our original walking tour combines St. Augustine history with relaxed stops at some of our favorite local pubs and restaurants. Led by a local guide who is part historian, part new friend, part drinking buddy, you’ll explore the city’s historic streets and architecture while hearing the stories and characters that shaped America’s oldest city. The route changes regularly, allowing us to highlight different partner establishments depending on the day and season. While beer lovers will feel right at home, each stop offers beverage options beyond beer, which may include wine, cider, cocktails, hard seltzers, THC-infused drinks, or non-alcoholic selections. Food is included during the experience, making this a fun, social, and well-paced way to enjoy St. Augustine’s history. If you’re looking for an exciting and unique way to experience St. Augustine’s history while discovering favorite local spots you might never find on your own, this is the walk for you.

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. Wander through historic districts, spotting architectural influences, and visiting iconic sites like the Ximenez-Fatio House and the Cathedral Basilica. Get unlimited use of this tour before your booking date and after it. You can use the virtual tour option at home, too. Once you have booked, you will receive instructions and a unique code to download the tour. The app displays directions to the starting point; when you’re in the right place, tap start.

Our tours at Casa de Vino 57 Historical Tours are personally tailored to each individual or party. We use a balanced mix of both primary and secondary sources in our research process for our tours. We employ the scientific method approach for the study of history in the development of our tours and their narratives. As we understand that history comes alive when it is relatable, we do our best to get to know as much as possible about our patron and their tour desires so we can provide a tour of Saint Augustine that is a truly enjoyable historical experience.

Explore the historic heart of St. Augustine, the oldest continuously inhabited European-founded city in the United States, on this self-guided walking tour through its most iconic streets, plazas, and landmarks. Starting near the Castillo de San Marcos, you’ll follow a route through Old Town, St. George Street, Aviles Street, and the city’s civic core. Along the way, you’ll uncover how Spanish colonists, Indigenous peoples, enslaved Africans, and later civil rights leaders shaped a city defined by survival, adaptation, and cultural exchange. This immersive audio experience is designed for independent travelers who want more than surface-level sightseeing. Stories unfold as you walk, connecting fortifications to daily life, power to resistance, and past events to the living city around you. Unlike a group tour, this experience lets you explore at your own pace—pause, rewind, or linger wherever you like.