Sit back as the talented Old Town Trolley conductors share the history, attractions and sights of America's oldest city. Founded by Pedro Menendez de Aviles in 1565, St. Augustine is a unique city filled with colonial Spanish neighborhoods, magnificent buildings and a charm all its own. The hop-on hop-off tour with 21 stops, features live narrations including 100 points of interest. Your ticket also includes admission into the St. Augustine History Museum.

Ranked #8 in the U.S.A. on TripAdvisor, our award-winning Wine, Cocktail & Food Experience is the ultimate way to discover why St. Augustine was named Southern Living’s #1 Small Town Food City. In a relaxed, small-group setting, you’ll explore the city’s historic streets with a local guide who quickly becomes a new friend, stopping at some of our favorite restaurants, bars, and boutique spots along the way. Indulge in handcrafted cocktails, boutique wines, and dishes worth talking about, carefully selected to highlight the best flavors this foodie city has to offer. Each stop is thoughtfully chosen to complement the next, creating a journey of taste, story, and history. From savory bites to perfectly paired drinks, laughter to insider tips, this tour isn’t just about tasting, it’s about discovering the city through its flavors. By the end, you’ll understand why locals and visitors alike keep coming back.

A 'Progressive Style', Seated Food Adventure (Strolling): This tasting experience takes you to four (4) handpicked venues — with each stop offering a dish featuring bold flavors, unique pairings, and unforgettable hospitality. From savory beginnings to sweet endings - you will enjoy one bite, one sip, and one story at a time. Highlights: CULINARY DELIGHTS: Each dish is thoughtfully paired with an exquisite wine or artisanal cocktail (pairings are subject to vary). INSIDER INSIGHTS: Get the scoop from a local culinary insider who'll be your guide throughout the journey. LEISURELY EXPLORATION: Stroll through St. Augustine's charming streets, soaking in its beauty and vibrant food scene, at casual pace. Note: Pairings are included. 24-HOUR ADVANCE NOTICE REQUIRED FOR ANY FOOD ALLERGIES. Age 21+ only. Sorry, NO pets of any kind. 4-person min to depart. Primary focus is on the culinary scene with a bit of history and sightseeing sprinkled in.

Rated #22 in the USA on TripAdvisor, this is one of the most exciting tours in St. Augustine! Perfect for families, foodies, and anyone who loves a little indulgence. On this small-group walking tour, you’ll explore historic downtown St. Augustine with a local guide who feels more like a friend, sharing fascinating stories from the city’s 460-year history. Along the way, you’ll stop at some of our favorite partner establishments to enjoy hand-selected pastries, chocolates, and other local sweets. The best part? Each guest receives a take-home insulated bag filled with extra treats collected on the tour at our partner establishments, so the experience keeps on giving long after your walk ends. You don’t have to eat it all at once! With small groups, personable guides, and a perfect mix of history and sweets, this tour is designed to delight every sense while giving you an insider’s view of St. Augustine.

This tour down dark bricks roads just might be the tour you are looking for. You may; See, Hear, Smell and Feel strange occurrences as witnessed by the Night Watchman whose kind have kept watch over the Nation's Oldest City since 1565. Walk down ancient streets, past historic buildings, while submersing yourself in the paranormal world. We tell the stories of St. Augustines ghostly past; such as Ida Alice, the strange occurrence with a murder (Black crows) and the spirit of the little girl living in the Pablo Sabate Home on 76 Spanish Street. Join us But remember its more than 500 years of history and ghosts...

Maybe you've taken one of the many tours offered in the wonderful city of St. Augustine previously. Would you like to hear about things you have NOT heard before? Learn something new for a change? Little secrets not usually talked about? Perhaps you will know some of them but pretty certain not all of them. This is not your typical "history" tour. You will hear about, and be shown, things on a variety of topics from history, crime, our many dead, buildings, plans, myths and truths. Group size limited to 12 for a more personal, intimate experience. This will take you little over a mile of walking, in the historic downtown area, and last about an hour. Tour takes place rain or shine.