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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 Sp…
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 Constit…
We hope to make this your favorite memory to your visit in St Augustine - sharing the history and nature of St Augustine are our favorite things. Being on our tour boat is like floating by the sights on a front porch - r…
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 frightenin…
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 ecosyste…
National Geographic has selected The Ancient City, one of the top-10 places in the world to see Christmas lights, for over a decade! Each year, more lights are added and the Nights of Lights Festival becomes more and mor…
Get lost with the glorious wonder of St. Augustine's attractions. Our Adults Only 21+ option on vessel GREAT BLUE HERON is specifically made for the adult crowd and welcomes anyone 21 and older. We have a beer and wine…
**IMPORTANT: If you are booking this tour after June 1st 2026, see Spyglass on this site to book our new improved experience** We take a unique approach to tours in St. Augustine, using the latest technology. Our certif…
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. Startin…
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 …
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 s…
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 informat…
Explore St. Augustine’s beautiful Intracoastal Waterway on your private floating tiki boat! This BYOB cruise is the perfect way to relax, take in scenic waterfront views, spot local dolphins, and enjoy good times with fr…
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 fro…
Best first way to see St. Augustine. See the highlights of St. Augustine the easy way on a small group golf cart tour. The best first way to see St. Augustine is with Explore Tours and PickUps, especially if it’s your f…
Beneath the charming facades and centuries-old cobblestone streets of St. Augustine lies a chilling truth: this city isn’t just the oldest in America—it’s one of the most haunted by history’s darkest deeds. Join us for t…
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 l…
We are family friendly and welcome children on our sunset tours. You are welcome to bring drinks snacks and adult beverages on board (small coolers allowed). We will search for dolphin as we travel and take in the sights…
The Haunted History Tour is taking a different approach for your paranormal experience. The tour is based in the complete and accurate history of the city of St. Augustine and the sites that are visited. All guides are f…
Embark on our breathtaking Sunset Cruise in the heart of historic St. Augustine, Florida! We will be partying, singing & dancing along the scenic Matanzas River while enjoying stunning views of the nation's oldest city f…
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…
Explore the oldest continuously occupied, European-settled city in the United States -- St Augustine -- your own way! There are several ways to experience St. Augustine's rich history and culture. With this pass, you a…
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-ne…
There isn’t a funnier way of Sightseeing in Saint Augustine, riding around in our unique vehicles are guides dressed up in 1920s fashion. You become one of our city's attractions as you often have your picture taken and …