Top St Augustine Cultural Tours

Discover the United States’ oldest city as you embark on a historic walking tour through St. Augustine. Join a small group and visit top landmarks such as the oldest masonry fort in the US, the oldest grid system, and Flagler College. While you explore, your guide sheds light on the tumultuous history of the 450-year-old city.

Discover the oldest city in the nation and meet other visitors during this shared golf cart tour of St. Augustine. Hop into the cart with your certified guide and learn all about the history, culture, and architecture of this beautiful city. You’ll hear haunted stories at the Huguenot Cemetery, view the 1695-built masonry fort, and make a stop in the Lightner Museum.

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.

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.

Enjoy a 90-minute walking tour through the nation’s oldest city, exploring centuries of history, architecture, and hidden stories that shaped St. Augustine. From the Castillo de San Marcos to charming colonial streets, and the beautiful waterfront, this tour hits all the highlights—perfect for first-time visitors or anyone looking to truly understand the city. The beauty of a free walking tour is that you get to decide what it's worth to you personally. Your licensed local guides receive no salary of any kind other than what they receive from guests on a tip basis. If you have a group larger than 6, please contact us in advance to make sure we can accommodate.

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.

Some claim St. Augustine is one of the oldest cities in the US, but unless you see its sights and hear its history, you may not understand or agree. This St. Augustine Boat and Golf Cart Combo Tour lets you see main landmarks of the city by both land and water, for a well-rounded introduction. First, go on a boat tour, and then cruise the city in a golf cart.

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.

Discover the rich history of St. Augustine, the oldest city in the U.S., on an immersive 2-2 1/2 hour fully guided walking tour. This tour features personal audio devices which allow you to hear every detail of the tour without dealing with noise pollution, other guest conversations or any of a number of distractions. Ideal for history buffs and curious travelers, this tour offers insights into the city's colonial past, well up into the Gilded Age and included architectural wonders, including the famous Castillo de San Marcos. Explore the historic district with an experienced guide who brings the stories of this vibrant city to life. A great introduction to St. Augustine before your lunch plans. And yes, WE ARE ALWAYS PET FRIENDLY!

A golf cart tour is the best way to experience the entire downtown area and visit the sites on the north of the colonial city. Golf carts allows easy access to get off and take pictures; feel the breeze and provide uninterrupted views of the sites. For larger groups, please contact us.

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.

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.

Climb aboard your zero-emissions EV cart and discover the crimes and murders through the history of beautiful St. Augustine. This 60-minute ride will take you through the oldest city’s winding streets, from the storied north side to the charming south end. Along the way, you’ll hear chilling tales of notorious crimes, unsolved murders, bloody battles and pirate attacks- the kind of history you won’t find in any textbook. The bloody legends that still haunt this cobblestone streets are rarely heard by other tour companies and will leave you questioning every shadow. Are you brave enough to face what the darker side of the Ancient City has to offer? Come for the sights. Stay for the stories. Book today - if you dare!

This relaxing cruise is great for nature lovers, families, or those who simply enjoy being out on the water. Cruise the Intracoastal Waterway—an inland waterway that runs parallel to the coastline—for a calm ride exploring St. Augustine’s estuaries. Keep your eyes peeled for marine life such as dolphins, manatees, sea turtles, pelicans, osprey, and spoonbill. Along the way, you’ll spot landmarks including the Bridge of Lions, Castillo de San Marcos, St. Augustine Lighthouse, and more.

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.

Have only a short amount of time to explore St. Augustine? Beat the crowds—and see most of the city's top highlights—all in one private, open-air electric vehicle tour. Meet your guide downtown, and hop aboard. You'll see highlights like the Mission Nombre de Dios, Castillo de San Marcos, and Cathedral Basilica of St. Augustine, and will learn all about the city's history.

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.

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.

Learn more about one of the oldest cities in the US while enjoying a frightfully good time on a family-friendly ghost tour of St. Augustine. Combine visits to spooky sites with light-hearted fun and spine-tingling tales. Your costumed guide takes you to cemeteries, the ground of the Old Fort, and other haunted locations to discover the little-known legends that you wouldn’t learn any other way.

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.

Whatever history you know of St. Augustine, this tour will teach you about the dark, unwritten side you might not know. The Ancient City has centuries worth of colonial era history and many more predating it, making it ripe for tales that are less than honorable. From the prostitution industry to the secret speakeasy taverns, you’ll learn about the seedy underbelly of St. Augustine’s past and which political powers allowed it to thrive.

Explore St. Augustine’s past on this small-group historical walking tour around Old St Augustine. Learn the comprehensive history of the city, from its Spanish origins through colonial periods to modern times as you follow your guide around, from the Bridge of Lions and Castillo de San Marcos National Monument to Memorial Presbyterian Church and Flagler College.

If you're into all things creepy and spooky, this 'beyond the grave' tour of St. Augustine is ideal for you. You'll be taken to a number of locations of interest to the Savannah Ghost Research Society. These include cemeteries and buildings where ghosts have been sighted and paranormal activity recorded. Your guide will dig beneath the urban legends in an attempt to uncover the true stories that lie within.