Old Town Trolley Tours

10/26/2026

Halloween week is here, and night tours are filling up fast! Reserve your evening seats aboard Ghosts & Gravestones St Augustine today. Experience eerie tales in the spookiest city in Florida! https://bit.ly/4gZoxl9

10/23/2026

Tomorrow is race day at the historic Old Jail! Lace up your sneakers for the Jail Break 5K, benefiting St. Johns County students through INK! Race across the Vilano Bridge to the Atlantic Ocean, wear your best Halloween costume for a chance at $500 in prizes, and enjoy a ride back aboard our trolley.

Secure your spot online today! https://bit.ly/4gZoxl9

10/22/2026

Ready to cross the Vilano Bridge this weekend? 🌉 🌴

The 10th annual Jail Break 5K is almost here on Saturday, October 24, at 8 a.m. We are taking off from 167 San Marco Ave through uptown St. Augustine, heading out to the beach, and catching a shuttle back for the official post-race party and medals.

Not a runner? Come cheer from the sidelines! All proceeds benefit Investing In Kids (INK!) classrooms.

Secure your spot before registration closes at the link below!
https://bit.ly/4rM4ziO

10/19/2026

Uncover the lingering spirits hiding in America's Oldest City. Ghosts & Gravestones St Augustine takes you through the city's ominous history and haunting legends.

Click the link to claim your spot on the Trolley of the Doomed now! https://bit.ly/4gZoxl9

10/16/2026

Are you brave enough to walk through dark jail cells late at night? Step inside the historic 1891 Old Jail and experience paranormal activity at one of the most haunted buildings in Florida.

Book your night investigation tickets online! ⬇️
https://bit.ly/4gZoxl9

10/15/2026

Only 10 days left until the 10th annual Jail Break 5K hits St. Augustine on Saturday, October 24 at 8 a.m.! 🏃‍♀️ Run, walk, or jog your way from the Old Jail all the way to the Atlantic Ocean while supporting Investing In Kids (INK!) classrooms.

Register your crew or grab your spot at the link below!
https://bit.ly/4rM4ziO

10/15/2026

Centuries of dark colonial legends linger around every cobblestone corner in St. Augustine!

Read more about top haunted places in St. Augustine here: https://bit.ly/4cGJIr6.

10/10/2026

Autumn weather is here, and our conductors have your seats ready! Hop aboard our open-air tram to visit the Castillo de San Marcos, the Lightner Museum, and historic St. George Street without parking hassles. Reserve your day pass! 🎟️ https://bit.ly/4gZoxl9

10/09/2026

Weekend plans? Start thinking about your breakout gear! ⛓️ 🏃‍♂️

The 10th annual Jail Break 5K is coming up on Saturday, October 24 at 8 a.m. Escape from the historic Old Jail, head over the Vilano Bridge to the beach, and cross the finish line for a post-race party and medals.

Costumes are heavily encouraged, and every step supports Investing In Kids (INK!) classrooms.

Grab your crew and register at the link below!
https://bit.ly/4y7HXeu

10/06/2026

Embark on a chilling adventure, hearing tales of lingering residents while traveling through dark historic streets! Book your Ghosts & Gravestones St Augustine tour online now! https://bit.ly/4gM9RqV

02/23/2026

03/28/2025

Ready to explore Charleston's hidden charm? ✨ Our NEW Charleston City Tour takes you off the beaten path to uncover the city's unique stories. Come see what you've been missing! 💚 🧡

Book your adventure today ➡️ https://bit.ly/3QB5DV6

03/19/2025

From hidden gems to must-see attractions, you're now able to explore a wealth of information that reveals the fascinating history and lore of Charleston with the Charleston City Tour.

Book today! ➡️ https://bit.ly/3QB5DV6

03/14/2025

✨ OPENING SOON ✨ We're thrilled to announce that Old Town Trolley Tours® is expanding its magic to its ninth city — the charming Charleston! Hop on to experience its beautiful views and fascinating history with a Charleston City Tour. 🚌✨🧡

Book your adventure today ➡️ https://bit.ly/3QB5DV6

03/11/2025

Get ready for a new adventure in one of America's best-hidden gems aboard the new Charleston City Tour! 🤗 💚 🧡 Book now for April tours!

Book today ➡️ https://bit.ly/3D5YbOJ

03/06/2025

Ready to embark on a captivating journey? Let's uncover the charm of South Carolina aboard the historical Charleston City Tour. Your Charleston dream is just a step away! 🤗🧡

Check us out ➡️ https://bit.ly/4hhimr7

03/02/2025

Coming soon! Discover South Carolina charm aboard the Charleston City Tour, our upcoming tour of this great city. 🤗 🧡

Check us out ➡️ https://bit.ly/3CYTeHx

09/04/2023

From our Old Town Trolley Tours family to yours, we hope you have a safe and happy Labor Day. 🤗 🧡

02/20/2023

Today we salute all the great presidents that helped lead our nation — Happy Presidents' Day! 🏛
📸: on Instagram