Visit the oldest city in the United States and get your dose of warm Florida sun and fascinating history. St. Augustine is known for its gorgeous sandy beaches, breathtaking architecture, antiquated buildings and its significance to the shaping of our nation.

When you climb on board Old Town Trolley Tours of St. Augustine, you’ll have a chance to see the Ancient City in all its glory, from historical attractions like the site where Ponce de Leon first landed ashore, to unique attractions like the Alligator Farm. During the 90-minute tour, you’ll have the opportunity to get off and on the trolley as often as you wish, giving you a chance to stay at any of the stops for as long as you want.

Our local conductors make the tour even more entertaining by providing history and humor all rolled into one. Our conductors are recognized for their ability to captivate and entertain each of our guests. Local residents who come from various cities around the U.S., they share a common enthusiasm for history and talent to amuse folks. You’ll learn about the first settlers to the city and the powerful Spanish influence that still exists today. You’ll see the Castillo de San Marcos Fort that guarded the city against foreign invaders and is the oldest European fort of its kind still standing.

From museums to architectural masterpieces like The Ponce de Leon Hotel, now Flagler College, to the oldest wooden schoolhouse, you’ll see it all on the orange and green trolleys. Only Old Town Trolley Tours of St. Augustine offers the best of the city in one delightful tour.

Here are just a few reasons why Old Town Trolley is the best sightseeing tour in town:

St. Augustine was founded by the Spanish under Admiral Pedro Menéndez de Avilés in 1565.

• 100% Money Back Guarantee (No Questions Asked)

• FREE Admission to St. Augustine History Museum

• Over 100 Points of Interest

• Your ticket is good for three consecutive days of unlimited use

• FREE Beach Shuttle to Alligator Farm, the Lighthouse Museum, and the beach

Where does the past end and the present begin? In St. Augustine, one may never make that distinction as the ancient city has a history that spans back more than 500 years. Through wars, opposition and dominance by various countries, St. Augustine has had its share of colorful characters, military conflict and tumultuous events.

If you’re curious and courageous, take your seat on board the Trolley of the Doomed as St. Augustine’s Ghosts & Gravestones Tour transports you on a ride to another reality - a time when people feared being buried alive and when amputations and gruesome medical practices were commonplace. Step into the world that the original St. Augustine settlers lived in day after day and see why so many spirits of the past have never truly rested…in peace.

On the Ghosts & Gravestones Tour you’ll enter into three of the city’s spookiest places and most well known sites for supernatural occurrences.

Take a tour through the Spanish Military Hospital and stay close to your group as a stroll down the corridor is enough to frighten even the bravest of souls. Once inside, your Gravedigger Guide will enlighten you about the many strange and horrible ways the hospital staff handled medical emergencies in that era. You’ll also get a chance to hear the real story about what happened to Chief Osceola’s head.

Exercise great care as you walk through the Old Drug Store…the tales of burials in St. Augustine will shock and amaze you. And once inside the Old Jail, listen quietly for voices in the night; guests have reported hearing cries for help as they walked through the hallways. Be extra careful not to run into resident ghost Charlie Powell, an inmate who served his time, yet was never set free.

Be wary of weird noises and lights as we pass by two of the city’s oldest cemeteries. Both are home to long lost residents whom many believe still linger about. Is St. Augustine really haunted? Only you can answer that question for yourself. Embark on an adventure like no other as you journey through to the other side on the Ghosts & Gravestones Tour.

RESERVATIONS ARE REQUIRED!

Home to prisoners for over 60 years, the Old Jail in St. Augustine looks more like a resort than a maximum-security facility. The original structure was built in 1891 by Henry Flagler, and although it has been restored and renovated throughout the years, it looks very much the way it did when it opened over a century ago.

Today, visitors to the Old Jail can take a guided tour, learn about the many prisoners and practices that took place here and see where the Sheriff and his wife and family lived— adjacent to where the prisoners were housed.

Meet Sheriff Joe Perry who had a reputation as being a harsh and strict warden – one of the toughest in the South. Walk through the men’s and women’s cells and see where executions took place in the gallows. Discover the history behind judicial practices in the 19th century and see an array of weapons and artifacts.

Adults and children are thoroughly entertained by our costumed actors who portray deputies from the early days and everyone gets a chance to try and escape! The Old Jail is one of just a few prisons of its kind still standing and makes for a great sightseeing and history adventure.

In addition to being a national tourist destination and the continental United States' oldest city settled by Europeans, St. Augustine was also a pivotal site for the civil rights movement in 1963 and 1964.

Gain a greater understanding of the evolution of Florida, the people who helped shape its future and the rich past that it represents at the St. Augustine History Museum.

Stroll through a myriad of displays and exhibits to learn how four different nations ruled over this quaint beach town and how each one made an indelible mark on its culture and personality. In the St. Augustine History Museum, a Spanish treasure room showcases a magnificent collection of items found on actual sunken ships. A Timucuan Indian Village and Florida Cracker trading post provide an up-close look at how the earliest settlers lived and made a living.

Visitors will learn the amazing facts about the different periods of St. Augustine’s history where the British, Spanish and French dominated the city and how it came to be a part of the United States of America. More than four centuries of war, government and heritage are featured throughout the museum’s various displays.

Discover Henry Flagler’s undeniable influence upon the city, from his stunning architectural masterpieces that still stand throughout St. Augustine, to his historic triumphs in the railroad industry.

Florida was a United States territory until 1845 when it became a U.S. state

The St. Augustine History Museum is an ideal stop for guests of any age - an educational and enlightening experience that offers an in-depth look at Florida’s amazing history.

For school children, there’s no better way to learn Florida’s history than reliving it during one of our extraordinary field trips. Our educational tours offer visits to many of St. Augustine’s most significant historical sites, an assortment of choices for itineraries and much more.

Bring your students to see first-hand the places you’re discussing in your history lessons. Let them witness the magnitude of the Castillo de San Marcos, the largest Spanish Fort in America and one of the few structures of its kind still in existence. They’ll enjoy a guided tour of this imposing Castillo and gain a perspective of how the soldiers during that era lived and fought to defend St. Augustine. Also included are visits to The Old Jail and the St. Augustine History Museum as well as a fully- narrated Old Town Trolley Tour that showcases 100 points of interest throughout the city.

Our field trips can also include stops at the Oldest Wooden School House, the Fountain of Youth, The Lighthouse & Museum, Alligator Farm and more. And the best part? You can design your own adventure to suit the needs of your students—our experienced planners will assist you in customizing your excursion so it is most beneficial to you and the children.

Adhering to the educational standards set forth by the state, each of our field trips is designed to bring your history curriculum to life. Teachers receive a 16-page activity booklet that provides fun and educational activities to be performed before, during and after the field trip. These booklets are developed by curriculum specialists who are diligent in keeping with Sunshine State Standards and are committed to enhancing your in-class learning activities.

If you’re looking for an unforgettable way to teach Florida’s fascinating history, our tours are ideal. Spend a couple of hours or an entire day exploring all the glorious historical sites in the ancient city. Your students will be delighted, entertained and most importantly—enlightened!