Top St Augustine Private Sightseeing Tours

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.

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.

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.

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.

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.

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.

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.

Exclusive Private Experience PHOTOS INCLUDED! Skip the crowded trolley tours and experience St. Augustine in style with a private historic tour in an open-air, eco-friendly electric Moke! Enjoy a relaxed, intimate journey through the city as you visit iconic sites like the Castillo de San Marcos, Flagler College, and the scenic St. George Street. With the freedom to explore at your own pace and personal attention from your guide, this unique tour is the perfect way to soak in the charm of America’s oldest city—comfortably and crowd-free. The Moke’s design also allows for easy photo opportunities and a more relaxed pace through narrow streets and historic areas. Including a Rare Stop at the St. Augustine Lighthouse While many tours focus on the downtown area, we make a special stop at the St. Augustine Lighthouse.

Cruise through St. Augustine’s scenic waterways on Fury’s Historic Landmark Boat Tour. Choose a daytime narrated cruise or a romantic Champagne Sunset Cruise, both featuring 360° views of iconic landmarks like the Castillo de San Marcos and the St. Augustine Lighthouse. Hear engaging commentary spanning 450+ years of history while spotting dolphins and native birds. During the holiday season (mid-November–mid-January), enjoy dazzling Nights of Lights displays from the water. On July 4th only, experience a special Fourth of July Fireworks & Sunset Tour. Includes soda and water on all cruises, plus a complimentary champagne toast on the sunset tour. Perfect for families, couples, and groups. **Nights of Lights Viewing mid November - mid January Only ***Fourth of July Fireworks and Sunset Tour on July 4th Only

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.

Ghost Tours of St. Augustine's PRIVATE ORIGINAL Ghostly Experience Walking Tour is the very first ghost tour in the state of Florida, operating since 1994- we are the tour that started it all! We did all the initial research and cataloguing of St. Augustine's haunted history. We have been in operation longer than any other ghost tour company in the United States. This private tour is good for up to 15 people, and the time can be adjusted to meet your group's needs.

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.

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.

Experience our Private Excursion tailored exclusively for you! Embark on a serene journey through the picturesque landscapes of USA as you make your way to the heart of the city. Upon your arrival, meet your seasoned tour guide, ready to lead you on an enchanting tour of St. Augustine. Discover the awe-inspiring allure of St. Augustine, marvel at the grandeur of Lightner Museum, and capture iconic moments at landmarks like Cathedral Basilica of St. Augustine, and many more. Our excursions are meticulously designed schedule. We'll greet you directly at the hotel and ensure you return with ample time to relax and relish your day. Leave the details to us as we escort you on an extraordinary adventure, crafting memories that will stand the test of time!

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.

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.

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.

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.

Experience the historic charm of St. Augustine, Florida, in style with our luxury, 8-passenger including the guide, and golf cart tours. Discover the nation's oldest city from the comfort of your own personal golf cart, guided by knowledgeable local experts. Cruise through brick-lined streets, past centuries-old architecture, and along the scenic waterfront as you soak in the rich history and vibrant culture of this enchanting destination. During the holiday season, see one of the top ten holiday lights displays in the world on your own personal golf cart tour. Downtown St. Augustine glows with holiday magic as millions of tiny white lights that drape the city's unique Spanish Colonial architecture and glow from the downtown sidewalks to the rooftops, over the Bridge of Lions, along historic buildings, public spaces, hotels, restaurants, and approximately 20 blocks of the Nation's Oldest City's historic district. No long lines, no waiting, and a central pick-up location.

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.

Discover the history, haunts, and hangouts of the oldest city in the United States with this private electric golf cart tour of St. Augustine. You’ll cruise throughout the old Spanish city, including the oldest street in the country: 11 Aviles Street. Get familiar with the city, noting where the oldest schoolhouse, museums, and other points of interest are located.

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

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.