Support small local businesses by looking us up directly on the web; ExploreToursAndPickUps.'com' This is an extensive and educational tour of St. Augustine. Explore the cultural events that made St. Augustine a key component in world history. The tour is conducted on our electric golf carts in the downtown area of St. Augustine passing by all the main historical structures and areas. Between The Mission Nombre de Dios, Castillo De San Marcos, The Ponce De Leon Hotel (now Flagler College), The Cathedral Basilica, The Tolomato Cemetery, The Saint Francis Barracks, and The Plaza De La Constitución...there are endless adventures waiting to be discussed. The driver is your guide and you are welcome to ask questions. During the historical tour your guide will point out historical attractions and places of interests while discussing the history of charming St. Augustine. We stay seated on the vehicle for the duration of the tour. *Please read your receipt/ticket for directions and details*

Guided Historical Tour of St. Augustine Per Person

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-new friend and brings the streets, buildings, and stories to life. Discover how five different flags once flew above the Castillo de San Marcos and shaped the city's unique past.

Walk along the historic harbor, take in views of the oldest masonry fort in the United States, and explore the oldest grid street system in the country. Along the way, you'll learn about the people who left their mark on St. Augustine, including Juan Ponce de León, Pedro Menéndez de Avilés, Henry Flagler, and Dr. Martin Luther King Jr.

Designed to orient you to the city, this tour gives you the context and confidence to explore St. Augustine on your own after the walk, and we also highlight our favorite spots to eat and drink along the way in the "Best Food Town in the South"!

History Walking Tour in St. Augustine

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.

St Augustine Shared Golf Cart Tour

Join local guides on a tour of St. Augustine's walled city featuring the city's 450-plus-year history. This 90-minute, personally narrated tour occurs on the comfort and ease of an electric cart. This private tour is for groups of 1 to 7 people, ages 7 and up. Your group will not be combined with other people. Seatbelts and no alcohol permitted per regulations.

This tour is a detailed and educational tour of historic St. Augustine. Focusing on the colonial walled city of St. Augustine, highlights of the tour include the Castillo de San Marcos, Flagler's Hotels and Churches, the Oldest House, the Plaza, and Aviles St. 

During the tour, your guide will share the interesting and storied history of St. Augustine.

Private Guided Historic Electric Cart Tour of St. Augustine

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 informative, comfortable, and convenient. Our expert tour guides will take the time to get to know you and share many stories about the oldest continuously occupied european settlement in the continental United States. 
Our tours are conducted on an electric vehicle with open sides and seat up to 10 People. 

This is an excellent way to see where everything is, and to learn Saint Augustine's history in a fun and informative way. 

Three reasons to consider our tour:
- FREE parking or get picked up anywhere downtown, Just call
- We are pet friendly, all sizes and breeds welcome
- This is THE MOST conveniently located and professional tour service available in Saint Augustine.

1 Hour Historical Tour of Saint Augustine Florida & FREE Parking

Support small local businesses by looking us up directly on the web; ExploreToursAndPickUps.'com'This is an extensive and educational tour of St. Augustine, Florida. Explore cultural events that made St. Augustine a key component in world history. The tour is conducted on our electric golf carts in the downtown area of St. Augustine passing by all the main historical structures and areas. Between The Mission Nombre de Dios, Castillo De San Marcos, The Ponce De Leon Hotel (now Flagler College), The Cathedral Basilica, The Tolomato Cemetery, The Saint Francis Barracks, and The Plaza De La Constitución...there are endless stories waiting to be discussed. The driver is your guide and you are welcome to ask questions. During the tour your guide will point out historical attractions and places of interests while discussing the history of charming St. Augustine. We stay seated and on the vehicle for the duration of the tour.

Private Historical Tour of St. Augustine

Unique opportunity to see the Old City from the water and land. Choose from two departure times daily: morning or sunset. Your guide will greet you at the Plaza de la Constitucion, for an introduction of the City of St. Augustine then we will drive you to the Marina were you will board the Victory III for the 75 minute narrated boat tour. Upon returning to the dock, your guide will meet you to show you around downtown St. Augustine for a one hour city tour on a golf cart. For larger groups please call us.

St Augustine Boat and Golf Cart Tour

The Wicked St. Augustine tour delves into the unwritten history of the nation's oldest city. You will hear stories of the illicit industries that made the town a financial success, all while avoiding the reputation of a sinful city. From its founding St. Augustine had a thriving tavern, gambling and prostitution industry, even while portraying a city founded on religious principles. See the locations of high stakes gambling, speak easy taverns, and private clubs which skirted around the laws of the day, like prohibition. Learn how the political powers knew of these activities, secretly supported their providers, all while keeping a squeaky clean image.

Wicked St. Augustine: Bootleggers, Brothels & Gambling in the Ancient City

Enjoy a leisurely walk through the ancient streets of the nation's oldest city. A more intimate and in-depth telling of the history of the people and events that led the city through the trials and tribulations of the past. Learn the complete history of our Oldest City, from its founding by the Spanish, through the various colonial periods, into the territorial period and statehood and finally into the revitalization of the Gilded Age Renaissance of the city as an exclusive tourist destination.
 Groups are kept small by design, tours are interactive, ask all the questions you would like, and hear the a complete history not just a few blurbs of stories as you pass by. Let us introduce you to the real history of the Nation's Oldest Continuously Occupied European Settlement, or as we say, the Oldest City.

Walking Guided History Tour of Old St. Augustine

Support small local businesses and see more availability by looking us up directly on the web at 'ExploreToursAndPickUps' dot com. Personable tour of the holiday light display with a twist of history throughout the Historic District of St. Augustine! Venture down the smaller streets with our unique carts that others can not pass through! We venture off the beaten path which display beautiful holiday decorations at the famous bed & breakfasts.

Private Nights Of Lights Tour

Support small local businesses and see more availability by looking us up directly on the web at 'ExploreToursAndPickUps' dot com. Personable tour of the holiday light display with a twist of history throughout the Historic District of St. Augustine! Venture down the smaller streets with our unique carts that others can not pass through! We venture off the beaten path which display beautiful holiday decorations at the famous bed & breakfasts!

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. 

St. Augustine Free Walking Tour

St Augustine at Sunset History Golf Cart Tour

St. Augustine, renowned as the oldest city in the United States, is more than just a historical destination; it's a vibrant community offering a unique blend where the past and present seamlessly intertwine. The history and charm captivate every visitor. 
A day spent strolling its historical streets is not just a walk-through time, but an opportunity to make lasting memories. Begin your journey with some of the city's most iconic landmarks. 


St. Augustine Walking History Tour

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.

ST. Augustine Historic Founding to Gilded Age Walking Tour

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. 


Historic St Augustine Audio Self Guided App GPS Tour

This tour offers the opportunity to view the most important landmarks in the entire city. This is a private tour only for your group. Slow moving vehicle allow for a better experience. Easy to get in and out of the vehicle. Covers downtown as well as the north side of St Augustine.

St. Augustine Private Golf Cart Tour

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.

America's Oldest City: An Audio Tour of St Augustine

Embark on a self-guided walking tour of St. Augustine, the nation's oldest city! Start your journey at the historic Castillo de San Marcos, exploring centuries-old fortifications. Next, uncover swashbuckling tales at the St. Augustine Pirate & Treasure Museum. Continue to Flagler College, marveling at its Gilded Age architecture. Conclude your adventure with a stroll across the iconic Bridge of Lions, witnessing breathtaking views and vibrant marine life. This tour connects you with the rich tapestry of St. Augustine's past and present.

After booking, check your email/text to download the separate Audio Tour Guide App by Action while connected to WiFi or mobile data. Enter the password, download the tour, and enjoy it offline. Follow the audio instructions and route from the designated starting point.

New, Lifetime access, no expiry. Use it anytime, on any trip, as many times as you want.

This isn't an entrance ticket. Check opening hours before your visit.

St. Augustine City Self-Guided Walking Audio Tour

This entertaining, informative, and engaging walking ghost tour will take you to multiple haunted and historic locations, where your experienced local tour guide and haunted history expert will tell you of the hauntings that persist at iconic buildings surrounding St. Augustine's historic district. 

St. Augustine survived wars and disease to claim the title of the oldest city in America. Experience the terrors lurking in the shadows of this quaint Florida town. Old City Ghosts offers an unflinching look at St. Augustine's harrowing history and startling stories of real-life hauntings experienced by tour-goers, visitors, and locals alike. Join us to unveil what makes the Old City of St. Augustine one of the most haunted locations in the country.

Tour stops are subject to change. This is a walking tour and we do not go into the museums / private homes. The duration of the tour takes into account walking time to and from the historic sites.

St. Augustine: Old City World of Pirates Experience

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!

St Augustine True Crime History Tour by GA

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.

A Self-Guided Audio Tour of St Augustine's Twisted History

Scary, fun, affordable. This is the most responsive, low-bandwidth audio ghost tour on the market. No app. No data harvesting. No bloated code. Just streamlined, lightning-fast access—even in high-traffic zones. Scary, fun, and built for performance where others fail. Before booking any audio tour app, look at their App Store reviews.

St. Augustine Ghost Tour

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. 

Casa de Vino 57 Historical Tours The British Period 1763-1784

Our Tales of the Past History Tour is an hour and a half walking tour that has been fully researched at the St. Augustine Historical Society. Join us as we walk down Aviles Street, the oldest street in America, and visit the old Alcazar Hotel and Ponce de Leon Hotel. We will also visit the Old Slave Market, the Governor's House, and several stops along St. George Street. Come learn about the oldest city in America, and Henry Flager's contributions to this amazing city. 

Tales of the Past History Tour

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.

Walking History Tour of St Augustine Historic District

Set sail on a delightful 90-minute cruise aboard the Great Blue Heron, where culinary indulgence meets wildlife exploration. Enjoy an in-depth Dolphin Talk while sipping a mimosa from your onboard bar and savoring a curated Brunch Box filled with fresh seasonal fruits, cheeses, and more. As you glide through the scenic waters of St. Augustine, take in stunning views of historic landmarks like the Castillo de San Marcos and the St. Augustine Lighthouse. Perfect for travelers aged 21 and over, this brunch cruise offers a sophisticated escape on the water.

- 2-hour cruise exploring St. Augustine's waterways
- Expert-led Dolphin Talk to learn about local marine life
- Enjoy a complimentary mimosa and a delicious Brunch Box
- Scenic views of famous sites including the Bridge of Lions and more

Brunch and Bottlenose Dolphin Cruise in St Augustine

In a town full of tour activity, this one is unique and rare. 
We will follow the footsteps of victims, sometimes at the spot they actually fell. We will discuss cases that are not common knowledge or discussed elsewhere (that we know of lol)
True Crime fanatics, come get your fill! 

Torrid Tales Two More True Crime in St. Augustine

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

Cultural Tours in St Augustine

Guided Historical Tour of St. Augustine Per Person

History Walking Tour in St. Augustine

St Augustine Shared Golf Cart Tour

Private Guided Historic Electric Cart Tour of St. Augustine

1 Hour Historical Tour of Saint Augustine Florida & FREE Parking

Private Historical Tour of St. Augustine

St Augustine Boat and Golf Cart Tour

Wicked St. Augustine: Bootleggers, Brothels & Gambling in the Ancient City

Walking Guided History Tour of Old St. Augustine

Private Nights Of Lights Tour

Private Nights Of Lights Tour

St. Augustine Free Walking Tour

St Augustine at Sunset History Golf Cart Tour

St. Augustine Walking History Tour

ST. Augustine Historic Founding to Gilded Age Walking Tour

Historic St Augustine Audio Self Guided App GPS Tour

St. Augustine Private Golf Cart Tour

America's Oldest City: An Audio Tour of St Augustine

St. Augustine City Self-Guided Walking Audio Tour

St. Augustine: Old City World of Pirates Experience

St Augustine True Crime History Tour by GA

A Self-Guided Audio Tour of St Augustine's Twisted History

St. Augustine Ghost Tour

Casa de Vino 57 Historical Tours The British Period 1763-1784

Tales of the Past History Tour

Walking History Tour of St Augustine Historic District

Brunch and Bottlenose Dolphin Cruise in St Augustine

Torrid Tales Two More True Crime in St. Augustine

Ghoul Night Out Haunted Pub Crawl in St. Augustine