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 neig... More

Explore the darker side of the Nation’s Oldest City and let our Ghost Host be your guide. Climb aboard our Trolley of the Doomed as we journey to St. Augustine’s most haunted locations. Be Warned! Experience a frightening stop... More

A unique view of St Augustine available only from the water. Since the 1900’s St. Augustine Scenic Cruise has been giving visitors to St. Augustine a unique view of the city and a way to enjoy St. Augustine’s historic land ma... More

Support small local businesses by looking us up directly on the web; ExploreToursAndPickUps.'com' This is an extensive and educational tour of St. Augustine. Explore the cultural events that made St. Augustine a key component in w... More

Experienced Naturalist on board as your guide, you will be sure to leave with a new passion for our marine life. This part of Florida is beaming with estuary delights, all of which come together to form quite an ecosystem. We regu... More

Get lost with the glorious wonder of St. Augustine's attractions. Our vessel OSPREY is specifically made for the adult crowd and welcomes anyone 21 and older. We have a beer and wine bar on board, with a fantastic selection, and... More

There are only a few places in the world where you can encounter the West Indian Manatee and St. Augustine is one of them! Come join us for a once in a lifetime experience that is great for all skill levels. Everyone from 6 year o... More

The best way to reach all areas of the Oldest City in search of ghosts without the need to walk. Embark on a fun adventure to experience the dark side of St. Augustine. You will meet your guide at the Plaza de la Constitucion to s... More

Step into 460 years of history on the most popular walking tour of St. Augustine. On this engaging small-group experience, explore America’s oldest city with a knowledgeable local guide who is part-historian and part-new friend... More

Taste and sip your way through the rich and fascinating history of the Ancient City, using its cuisine as your guide. Enjoy perfectly curated food selections paired with adult beverages and dessert thoughtfully chosen by our Cert... More

Bring your own beverages, kick back, and relax with a cold one and let us show you St. Augustine from OUR point of view! As the shadows get long and the sun sets behind the skyline, you'll feel the stresses of the week slipping aw... More

Ideal for families, this ghost tour of St. Augustine’s spookiest sites combines light-hearted fun with spine-tingling tales of the city’s past. Alongside a costumed guide, you visit cemeteries, the ground of the Old Fort, and ... More

Start your evening out by winding down on the water! Let us take you on an adventure to the bay-front, where our experienced guides will give you a tour on nature, wildlife, and famous historic landmarks. We are lucky to see a ple... More

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. ... More

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,... More

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, comfo... More

Unique opportunity to see the Old City from the water and land. Choose from two departure times daily: morning or sunset. Your guide will greet you at the Plaza de la Constitucion, for an introduction of the City of St. Augustine ... More

There is not a better way to witness the sunset of St. Augustine, then on our boat tour. Our tour guides will educate you on some of the historic sites in Saint Augustine. While we’re on the water, hopefully we will see dolphins... More

• Enjoy a personalized experience with up to 7 people. • Get closer to attractions such as Lightner Museum, Ponce de Leon , Old Jail and more for photo opportunities • Explore Historic Lincolnville with last remaining slave... More

**45' Corinthian Power Catamaran will be operating this tour from January 13th - April 2nd, 2026.** Sailing Catamaran tours will resume on April 3rd. Cruise through the historic harbors near Vilano Beach, as we seek out some of S... More