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.

The coastal town of St Augustine is renowned as the oldest European settlement in the United States. On this private tour, benefit from the undivided attention of your guide and enjoy a tour itinerary tailored to your group’s interests. Traveling by electric vehicle, visit areas normally only accessible on foot, stop at historic landmarks and churches.

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.

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.

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.

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.

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.

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.

Delve into St. Augustine's eerie past with a personalized pub crawl that combines spooky history and vibrant nightlife. The Ghoul's Night Out tour takes you to the city's most thrilling bars while sharing tales of the paranormal, true crime, and haunted legends. Enjoy a complimentary mimosa at the starting location and choose your adventure between lively bar hopping or a more subdued exploration of dark history. This unique experience promises an unforgettable night of fun and frights in the nation's oldest city. - Private tour designed for groups of 6 or more - Explore haunted and historical sites while enjoying drinks - Choose between a lively bar crawl or a dark history itinerary - Complimentary mimosas at the starting point included

Saint Augustine is a proud part of our beautiful history here in the United States. The nation’s oldest city has the longest reigning carriage industry in America, dating back to 1877. Our tours are professional, authentic and comfortable and the memories last a lifetime. We provide fully narrated historical and ghost tours of our beloved 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

From its jaw-dropping Bridge of Lions to the resilient fortress of Castillo de San Marcos, St. Augustine is like a historical theme park where the exhibits are real, and the stories are legendary! On this walking tour, you‘ll take in more than 350 years of fascinating history with Context Travel expert and storyteller, Jennifer Geraghty. As you walk, she‘ll bring the city‘s colorful characters to life, recount epic battles, and point out the many historical firsts that shaped the city. Wander through historic districts, spotting architectural influences, and visiting iconic sites like the Ximenez-Fatio House and the Cathedral Basilica. Get unlimited use of this tour before your booking date and after it. You can use the virtual tour option at home, too. Once you have booked, you will receive instructions and a unique code to download the tour. The app displays directions to the starting point; when you’re in the right place, tap start.

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.

Our tours at Casa de Vino 57 Historical Tours are personally tailored to each individual or party. We use a balanced mix of both primary and secondary sources in our research process for our tours. We employ the scientific method approach for the study of history in the development of our tours and their narratives. As we understand that history comes alive when it is relatable, we do our best to get to know as much as possible about our patron and their tour desires so we can provide a tour of Saint Augustine that is a truly enjoyable historical experience.

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.

Gather 'round for an exciting new adventure that's sure to thrill and enrich your visit to St. Augustine. Join us for the Private guided walking history tour where you and your family can step back in time and learn about the swashbuckling pirates and brave colonial citizens who once roamed these historic streets. Our guided walking tour is the perfect way to immerse your family in the rich history of this fascinating city. As you stroll through the streets and narrow alleys, your guide will regale you with tales of daring pirates, brave settlers, and epic battles on the high seas. This is no ordinary history lesson. We believe that the best way to learn is by doing, so we've crafted a series of hands-on learning experiences that will make you feel like they're part of the action. They can hold a real cannon ball and imagine the power of a pirate ship's artillery, feel the weight of a nail from the blacksmith's forge, and examine ancient artifacts up close.

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

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.

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.

On this self-guided audio tour, you will dig up the good, bad, and ugly stories buried under St. Augustine's historic streets. St. Augustine is the oldest, continuously occupied city in the United States. On this walking tour, you’ll follow the journey of founding father Pedro Menendez de Aviles, and the many others who gave everything they had to settle this hostile land. From the original city gates to Plaza de la Constitución in historic downtown St Augustine, I’ll show you the scars around every corner. Along the way, you’ll hear good, bad, and ugly tales about what it took to build a perfect fort, and how it was attacked many times but never taken. St. Augustine’s history is long, and its twisted tales are endless. This is a storytelling adventure into the lives and times of those who built this city. Whether you’re visiting St Augustine for the first time or are a curious local, this tour will give you a greater appreciation for the city and its rich cultural heritage.

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.

Go at your own pace, anytime. This is a location aware smart phone guided walking tour. Get our app, put your phone in your pocket and let our patented technology guide you through St. Augustine and share stories written by tour guides, told by professional narrators and infused with music. On our historic adventure I’ll be guiding you to the historic sites linked to the history of the oldest city in America. You’ll see the Old City Gates, the narrowest street in America, the oldest schoolhouse, historic St. George Street, the old churches, shrines, forts, monuments, parks, statues and so much more. And along the way I’ll share with you the stories of the Spanish, Ponce De Leon and how he enslaved an island, Pirates of the Seas, The Red Coats, the Americans, the history of Slavery in Florida, The Oldest Market, the Greek shrine, the Minorcans, and we are just getting started. Want to listen later? No problem. Your tour never expires.