Top St Augustine Private Sightseeing Tours

Bring your sense of adventure, and up to 6 of your closest friends for a private tour that is second to none. Explore themes like Haunted History, Spanish Colonial, Flagler Era & Gilded Age, Civil Rights or just tell your first rate guide your personal interests to create a truly unique experience. The most luxurious and comprehensive way to see the Oldest City.

Experience the Nights of Lights in St. Augustine on a private electric golf cart tour. Travel through the historic streets with your group, viewing illuminated landmarks from a comfortable, open-air vehicle. The private format offers a more flexible and efficient way to see the lights compared to walking, with easy navigation through busy areas and space for up to seven guests.

Discover St. Augustine's historical sites with ease, without the hassle of research or figuring out transport, during this private guided tour. Ride in a vintage vehicle with guides dressed in 1920s fashion as you cruise past landmarks such Castillo de San Marcos, Flagler College, and St. George Street in the historic district, while learning more about the sites than you would on your own.

With hundreds of years of bloody wars, murders, and suspicious deaths, the oldest city in America has quite a haunted history. You’ll go bump in the night, too, as you cruise over the brick streets around St. Augustine’s historic district on this private electric golf cart ghost tour. Join your guide for a ride into the past where you’ll visit allegedly haunted sites like St. Augustine National Cemetery, Aviles Street, and St. George Street.

See St. Augustine's key landmarks—and enjoy a one-of-a-kind, environmentally friendly way of traveling—on a small-group electric golf cart tour. Choose a convenient morning or afternoon tour time, meet your guide in the city center, and hop on board. See St. Augustine landmarks, including the Castillo de San Marcos, Tolomato Cemetery, and Mission Nombre de Dios, and learn all about the city’s centuries of history.

Discover a new perspective on St. Augustine—and enjoy a relaxing trip out on the water—on this sightseeing boat tour. Pick from multiple start times, head to the marina, and hop aboard. See highlights like the Bridge of Lions, Castillo de San Marcos National Monument, and National Shrine of Our Lady of La Leche, and learn the stories behind the sights from your captain’s narration.

Enjoy a comfortable and flexible way to explore the best of St. Augustine on this narrated Old Town trolley tour. See dozens of points of interest, such as the Old Jail, Flagler College, and Spanish colonial neighborhoods. Along the way, discover more about America’s oldest city, founded in 1565, from your conductor, and listen as they share in-depth narration about St. Augustine's history.

Explore the freshwater tributaries along the scenic St. Johns River on a thrilling airboat ride that skims through a maze of shallow waterways. Watch for alligators, manatees, birds, and snakes as you speed through the watery Florida landscape, and learn the story of an infamous pirate ship that sank in the St. Johns River. This St. Johns River airboat tour includes personal headsets, so you won't miss a word of the captain's fun and informative commentary.

Experience a different side of St. Augustine on a horse-drawn carriage ghost tour through the city's historic streets. As you travel through the oldest city in the United States, your guide shares chilling ghost stories, local legends, paranormal theories, and firsthand accounts connected to some of St. Augustine's most intriguing locations. Pass by historic landmarks, centuries-old cemeteries, and atmospheric neighborhoods while discovering the mysteries that linger beyond the city's well-known history. This family-friendly tour combines storytelling, heritage, and a touch of the supernatural for an unforgettable evening adventure. - Ride through St. Augustine by horse-drawn carriage - Hear ghost stories, legends, and paranormal theories - Pass by historic cemeteries and iconic landmarks - Family-friendly experience with local storytelling

Experience St. Augustine from the water on a private boat tour for up to six passengers. Cruise past the city’s historic waterfront with a dedicated captain who manages navigation while you relax and enjoy the views. Choose a daytime outing or plan around sunset for softer light and cooler temperatures, making this a flexible and intimate way to experience the city.

Explore the stunning coastal waters of St. Augustine on a private dolphin tour. Encounter the intelligent bottlenose dolphins in their natural habitat, often seen feeding and socializing in pods. With a high success rate of over 90%, these two-hour excursions allow up to six passengers to enjoy an intimate experience while watching dolphins. Additional wildlife such as manatees, sea turtles and pelicans may also be spotted during the tour. Catering options are available for a personalized touch. Perfect for families and wildlife enthusiasts seeking a memorable marine adventure. - Private dolphin excursions lasting two hours for up to six guests - Exclusive for your group only, avoiding crowds - Observe dolphins in their natural habitat with a success rate over 90% - Catering options available for a customized experience - Additional wildlife viewing opportunities, including sea turtles, manatees and birds

St. Augustine’s original “frightseeing” tour provides an evening of fear and fun. Board Ghosts and Gravestones' Trolley of the Doomed for a spooky ride through St. Augustine's sinister past. Listen to stories of the ghosts and ghouls believed to still wander the town’s streets as you pass supposedly haunted hot spots, and visit Potter’s Wax Museum. Expect a tour so scary, it comes with a warning: not recommended for under-13s.

Explore St. Augustine’s paranormal hotspots on a private golf cart tour led by a local investigator. Designed for small groups of up to five people, this experience includes a hands-on introduction to paranormal investigation equipment and techniques. Travel between outdoor locations efficiently while hearing historical background and reported encounters, offering an interactive alternative to traditional ghost tours without entering buildings.

See St. Augustine from a new perspective with this leisurely sunset cruise. Climb aboard a boat for a scenic cruise including views of Castillo de San Marcos National Monument, the Bridge of Lions, and the St. Augustine Lighthouse. Sip beer or wine from the on-board bar with the Osprey, 21 and older option, or select the Island Breeze option for a family-friendly experience.

The uniqueness of this tour will provide you with visiting sites and discussing all that began to construct our Country. This tour is merely a City overview which will give you the knowledge to proceed with visiting our local sites. Our Cities History, founding Religion, and continued Spanish Architecture will be discussed. This is a walking tour so please wear suitable walking shoes. Our City has many streets that are extremely old, any personal accidents occurring on tour from improper footwear and issues concerning the streets are not the fault of our tour and will be hold harmless.

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.

See popular places in St. Augustine like the Cathedral Basilica of St. Augustine and St. Francis Barracks all in one day during this St. Augustine Private Historical City Tour. This tour is perfect for history buffs or anyone wanting to get more acquainted with the city. It takes you and your private group of up to nine around as you learn about St. Augustine’s interesting past from a private guide.

This is a MINI version of the regular Photo Adventure -Having lots of fun while creating special memories of St Augustine with great keepsakes (digital images). You will be captured at locations that can be iconic but also ones that are obscure, hidden gems or interesting views/aspects. It's whatever you like. It's a personalized experience, so we will set route and locations/areas of interest with you personally. In addition, it is not a stuffy, formal experience [unless you want it to be. lol] You are encouraged to be yourself! Whether that be silly, fun, serious, dramatic . . .or MIX it up! Being a MINI version, it is basically half the original: half the price is $75, half the time (is up to 45 minutes) and includes up to 12 edited digital images. [delivered to you electronically, taken on a Pixels device designed for great photos] [Contact for special circumstances or accommodations]

This is a self-guided ghost hunt where you'll be catching ten restless spirits in the old town of America's oldest city, with the app as your scanner. Every ghost is stuck on a mystery it left unfinished. Solve it and the ghost is caught. One of the ten is lying to you, and your job is to work out which one. The route takes you from Granada Street past the Plaza de la Constitucion, down St George Street and around Flagler College, in about 2 hours. You'll uncover stories like the senator lured onto a rainy road by a fake call about her daughter, the doctor who died of guilt, and the librarian who never came home. Each stop has its own puzzle: a magic-square blood test, a code hidden in a monologue, a shelf of antiques with one fake among them. Best after dark with your phone torch on. About 1.3 miles of walking, with unlimited breaks. Hints and 24/7 support if you get stuck. Perfect for Halloween or any night you're in the mood for creepy ghost stories.

Please support small businesses and look us up on the web to book directly. Just do a search for: Pineapple Ride and Tour ***Nights Of Lights tours are available directly on our website ONLY*** See Saint Augustine like you never have before on one of Pineapple Ride and Tour's Electric Vehicle. Our Historical Tours are guided by only the best and most informative local guides. Join us to see an hour or more of St. Augustine’s most incredible views and historical landmarks. Our tour is informative, comfortable, and is a great way to get to know where everything is, making your stay easier and more relaxing. We will take the time to get to know you and share our knowledge of our beautiful little town. Leave our tour with a new understanding of Saint Augustine and its history. We also offer FREE PARKING at our location if you book a tour, and we have a very nice waiting area by the edge of the San Sebastian River, that is both accommodating and scenic.

If you’re brave enough to stroll the streets of St. Augustine alone, this self-guided audio tour will take you through the haunted history of the country’s first city. Explore the historic alleys in search of the most haunted hotels, cemeteries, restaurants and homes surrounding the old city. Walk by the Oldest Wooden School House, the Old Powder House Inn Bed and Breakfast, and many more sites, some dating back hundreds of years.

See the side of St. Augustine that predates the city’s settlement during this inshore fishing charter. Explore the waters of the Matanzas River, Salt Run, and Tolomato River as you try to reel in cobia, flounder, spotted sea trout, and more. A certified captain will provide all fishing and safety equipment; all you need to do is enjoy this private charter in St. Augustine’s inshore waters.

Sail along St. Augustine’s picturesque coastline—and indulge in a number of generous wine samples—during this two-in-one tour. Make your own way to the dock, hop aboard the pontoon boat, and get comfortable: as you set off, you’ll see landmarks like the Castillo de San Marcos, the Bridge of Lions, and more. You’ll also taste six different wines, and will have access to the on-board bar.