Discover Saint Augustine’s oldest streets one cocktail at a time. This 2.5-hour guided tour pairs rich local history with expertly crafted drinks at iconic historic bars. Get ready for a unique cultural and flavorful experience in Florida’s oldest city.
Discover Saint Augustine’s oldest streets one cocktail at a time. This 2.5-hour guided tour pairs rich local history with expertly crafted drinks at iconic historic bars. Get ready for a unique cultural and flavorful experience in Florida’s oldest city.
Verified experiences and guided adventures in the surrounding area.
Operated by Saint Augustine Transfer Company Inc · St. Augustine, Florida
easy.
2–3 hours.
Suitable for most fitness levels; requires walking on uneven historic streets for up to 2 miles total
Yes, non-alcoholic options are available at each stop to accommodate all guests.
Yes, booking in advance is recommended as tours often fill up quickly, especially on weekends.
Approximately 1.5 to 2 miles total on historic uneven surfaces, manageable at a leisurely pace.
Yes, please inform the guide ahead of time so that venues can prepare appropriate drink options.
All guests must be 21 or older with valid government-issued ID to participate.
Public parking garages and street parking are available within a short walk of the tour starting point.
Saint Augustine was founded in 1565, making it the oldest continuously inhabited European-established settlement in the continental U.S.
The city actively promotes sustainable tourism to protect its historic sites and coastal ecosystems, encouraging responsible visitation practices.
Saint Augustine Transfer Company Inc is a St. Augustine, FL-based tour operator offering a diverse collection of guided experiences across the historic district. The company presents food-focused walking tours, evening pub crawls, family-friendly activities, golf-cart dessert outings, focused history walks, and hands-on paranormal investigations — all operating within the Nation’s Oldest City. Tours include multi-stop food experiences such as the three-hour Feast of St. Augustine Walking Food Tour and The Ghoulish Gourmet Haunted Food Tour. Bar-focused experiences include two-hour pub crawls — Spirits with the Spirits Pub Crawl and Toast of St. Augustine Pub Crawl — each featuring a complimentary drink at every stop. Family-oriented programming includes the 30-minute Kids Krew Tour with authentic tools, historical artifacts, and a scavenger hunt. Short history options include the one-hour Story of St. Augustine walking history tour. The Haunting Hour Walking Ghost Tour runs about an hour and is recommended for guests aged 16 and older; pets are welcome on select walking tours. Specialty trips include Dessert À la Cart, a two-hour electric golf cart tour visiting four dessert stops with drinks and local stories, and Echoes of the Unseen, a two-hour paranormal investigation using tools such as K2 meters and dousing rods. Most tours note practical details such as recommended comfortable footwear and age guidance. All activity descriptions and durations are provided to help guests choose the right experience while exploring St. Augustine’s architecture, cuisine, and supernatural lore.
Book with Saint Augustine Transfer Company Inc