St. Augustine Old Jail

Sit back as the talented Old Town Trolley conductors share the history, attractions and sights of America's oldest city. Founded by Pedro Menendez de Aviles in 1565, St. Augustine is a unique city filled with colonial Spanish neighborhoods, magnificent buildings and a charm all its own. The hop-on hop-off tour with 21 stops, features live narrations including 100 points of interest. Your ticket also includes admission into the St. Augustine History Museum.

Ideal for families, this ghost tour of St. Augustine’s spookiest sites combines light-hearted fun with spine-tingling tales of the city’s past. Alongside a costumed guide, you visit cemeteries, the ground of the Old Fort, and other haunted locations to discover the little-known legends that surround the romantic venue. This small-group tour is limited in order to maintain an atmosphere suitable for the ghost walk. • Haunted ghosts walk around historic St. Augustine • Ideal for families, the tour combines humor with spooky stories. • Visit allegedly haunted spots such as the Old Fort and local cemeteries. • Keep your eyes peeled for restless souls in two cemeteries.

Located on San Marco Avenue in St. Augustine’s Uptown District, the Old Jail Museum offers an educational and intriguing look into what it would have been like to be a prisoner in the Nation’s Oldest City. Take a guided tour led by the “jailers” for a compelling look at the cells where imprisoned men and women once lived, the maximum security area reserved for the most nefarious criminals and a collection of weapons.

Beneath the charming facades and centuries-old cobblestone streets of St. Augustine lies a chilling truth: this city isn’t just the oldest in America—it’s one of the most haunted by history’s darkest deeds. Join us for the Blood on the Cobblestones Pub Crawl, a true crime walking tour that pairs cold cocktails with even colder cases, taking you through the shocking, scandalous, and unsolved murders that still echo through the Ancient City. As you sip your way through some of St. Augustine’s finest bars, we’ll guide you to the scenes of five unforgettable crimes—each more twisted than the last. From colonial secrets to 20th-century tragedy, this tour reveals the blood-stained underbelly of a city better known for its beauty.

Explore the oldest continuously occupied, European-settled city in the United States — St Augustine — your own way! There are several ways to experience St. Augustine's rich history and culture. With this pass, you are able to visit the Old Jail, engage in the Oldest Store museum experience, take the Old Town hop-on hop-off trolley tour – with 21 stops – and spend time at the history museum!

Our tour takes a unique approach to tours in St. Augustine. We limit our groups smaller to create a more personal experience. Our certified guides offer the most experienced and entertaining historical narrative of the city of St. Augustine, locations of historic events and the citizens who helped create and maintain the oldest city in the nation. We will cover the founding of the city, the first Spanish period (1565-1763), the British Period (1763-1784), the second Spanish period (1784-1821), the American territorial period (1821-1845), and the Flagler Era (Gilded Age, 1884-1913). This is a walking tour which covers a 1.7 mile route over the 90 minutes of the experience. It takes place during the day in Florida, so plan accordingly. Wear comfortable walking shoes, bring water, sunscreen and maybe an umbrella as well. There will be restrooms available at the beginning, end, and at the midway point as well. This is the perfect tour for the history enthusiast!

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.

A 'Progressive Style', Seated Food Adventure (Strolling): This tasting experience takes you to four handpicked venues — with each stop offering a dish featuring bold flavors, unique pairings, and unforgettable hospitality. From savory beginnings to sweet endings – you will enjoy one bite, one sip, and one story at a time. Highlights: CULINARY DELIGHTS: Each dish is thoughtfully paired with an exquisite wine or artisanal cocktail. INSIDER INSIGHTS: Get the scoop from a local culinary insider who'll be your guide throughout the journey. LEISURELY EXPLORATION: Stroll through St. Augustine's charming streets, soaking in its beauty and vibrant food scene, at casual pace. Note: Pairings are included. 24-HOUR ADVANCE NOTICE REQUIRED FOR ANY FOOD ALLERGIES. Age 21+ only. Sorry, NO pets of any kind. 4-person min to depart. Primary focus is on the culinary scene with a bit of history and sightseeing sprinkled in.

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.

Prepare yourself for a night you’ll never forget at The Old Jail After Dark. The 2 hour and 30-minute paranormal experience allows you to participate in an actual paranormal investigation of St. Augustine’s most haunted building, the Old Jail. Before your investigation begins, the experienced guides will share their investigative techniques to prepare you for any strange and peculiar phenomena that you may encounter. You will be provided with and trained to use an array of traditional and state-of-the-art ghost hunting equipment or feel free to bring your own. A cell phone can be a very helpful tool during a paranormal ghost hunt. Immediately following the conclusion of your investigation, the experts will help you to rule out any logical explanations from your findings and to help you understand any paranormal or psychic phenomena that you may have just experienced. You, the investigator, will then be left to decide whether or not you believe the Old Jail is truly haunted!

A 'Progressive Style' Foodie Adventure (ROLLING): This unique food tour invites you to explore the vibrant neighborhoods BEYOND the historic core. Satisfy your appetite with four progressive style stops, each offering a seated tasting experience in one of our city’s hidden gems. From savory starters to sweet finishes, every course is paired with a boutique wine or artisanal cocktails. Bonus: arrive via the comfort of our chauffeured vehicle. Highlights: ELEVATED EXPERIENCE: Delve into St. Augustine's culinary scene with exclusive tastings at four top-tier venues. LOCAL INSIGHT: Benefit from insider knowledge shared by a local culinary guide. CHAUFFEURED COMFORT: Explore the city's charm in comfort aboard our open-air electric vehicle. Note: Pairings are included. 24-HOUR ADVANCE NOTICE REQUIRED FOR ANY FOOD ALLERGIES. Age 21+ only. Sorry, NO pets of any kind. 4-person min to depart. Primary focus is on the culinary scene with a bit of history and sightseeing sprinkled in.

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.

If you are looking to see ghosts this tour is not for you. It is EXTREMELY rare to see a Ghost on tour. You would need to stay in a haunted location and that is not promising either. The small cobblestone streets, old homes and businesses of St.Augustine at night add to the reality of the ghostly past giving a unique experience.

Beer. History. Do we need to say more?! Take a fun and fascinating step back into Florida history with our St Augustine Beer & History walking tour! On this uniquely curated experience, you and your licensed, knowledgeable guide will stroll around the charming streets of St. Augustine, the oldest city in the nation, discovering some of our favorite Florida craft beers, all while discovering 450 years of amazing St. Augustine history.

At the St Augustine History Museum, a combination of historical displays and private collections bring over 400 years of Florida history to life. Guests can visit the Spanish sunken treasure room, a Timucan Indian Village and a Florida Cracker trading post.

IMPORTANT DETAILS: Reservations must be made by ROW – NOT BY PERSON. This is a private row that will accommodate a maximum of 4 people (1-4 people in your party only need a Qty of 1 Row/Traveler). Please enter the Quantity of Rows you desire to purchase in the "number of travelers" Box. You can purchase up to 2 rows per booking. Experience St. Augustine’s World-Famous Nights of Lights in the warm cozy comfort onboard Old Town Trolley. St. Augustine’s most beloved holiday tradition is back and is all aglow for the most wonderful time of the year. Over 3 million sparkling white lights adorn every corner of the city, stretching for nearly 20 blocks, creating an enchanted wonderland that will put a smile on your face and warm holiday memories in your heart. Your reservation secures you an entire row on the holiday trolley! Each row can accommodate up to 4 individuals. Please choose just 1 traveler for 1-4 people and 2 travelers for 5-8 people.

We will investigate the spirits that linger near the Oldest Wooden School House on St. George Street with exclusive access to both the gardens and the School House itself. This building is documented on tax rolls since 1716 and was bought by Juan Genopoly in 1780. Genopoly was an indentured person who came to the Turnbull Plantation to grow and process indigo. He became a merchant and his family lived in the building. In 1788 the school was started with teaching both boys and girls. The last graduating class is believed to have ended in 1864. Come and explore the grounds carefully, using all of the tools paranormal investigators use. You can bring your own or select one from our assortment of tools available. Make sure you bring your camera and take photos! We are determined to solve why those who have departed this life refuse to leave the area! This is a real paranormal experience. There are no jump scares, it isn't a haunted house type attraction.

Hit the road and experience the best of St. Augustine in the ultimate open-air ride—a custom 4-seater Polaris Slingshot! Cruise with your family or friends through Florida’s oldest city and discover iconic beaches, crystal-clear natural springs, and centuries-old historic landmarks. With the freedom to go where you want, when you want, this adventure combines comfort, style, and unforgettable sights. Renter needs to be 25+ and will need to present a valid driver's license, proof of insurance, and a credit or debit card for the refundable damage deposit at check-in. What’s Included Custom 4-seater Polaris Slingshot (automatic, easy to drive) Full tank of gas Safety briefing and driving overview Bluetooth sound system Route map featuring must-see beaches, springs, and historic stops Phone mount & charger Optional booster or child car seats

Who, other than the Guardian Angels, could convert the most incredulous stories of St. Augustine's past? Stories that went from battles, epidemics, yellow fever, fires, and pirate raids, to enchantment and kindness. Guardian Angels have been a rich part of the city's history for 455 years, and now you can explore the folklore, divine interventions, and history in Saint Augustine. This exquisite tour offers history, mystery and paranormal.

Parasailing in St. Augustine is unique because it combines thrilling ocean views with the rich history of America's oldest city. As you soar above the Atlantic, you may spot iconic landmarks like the Castillo de San Marcos and the Bridge of Lions, blending centuries-old charm with coastal beauty. The waters below are alive with dolphins, sea turtles, and even manatees, adding a wildlife-spotting bonus to your adventure. Calm breezes and clear skies make for ideal flying conditions, and the laid-back, friendly vibe of local tour operators ensures a relaxed, memorable experience. It's the perfect mix of history, nature, and adrenaline—all in one flight.