Top Florida Trolley Tours

Explore the best that Key West has to offer on this narrated, hop-on hop-off trolley tour. Visit more than 100 points of interest among Key West’s top attractions, with an expert guide who takes you through the history of the city. Select from an unlimited 1- or 2-day pass to suit your schedule.

Sarasota's BEST City Sightseeing Trolley Tour, a wonderful way to learn more about Sarasota's interesting past, whether you are a longtime resident, a newcomer, or a visitor.

Explore the best of St Augustine on this narrated Old Town trolley tour. See more than 100 points of interest such as the Old Jail, Flagler College, and Spanish Colonial neighborhoods. Discover more about America’s oldest city, founded in 1565 by Pedro Menendez de Aviles, from your friendly and informative conductor who shares interesting narration about St. Augustine's history.

When arriving at the Port of Key West, explore the best this island city has to offer on an independent, narrated, hop-on hop-off trolley tour. Visit more than 100 points of interest among Key West’s top attractions—like Mallory Square, Southernmost Point, and Key West Aquarium, to name a few. With this 1-day pass, board at any of the conveniently located stops and get to know the city in customized fashion, with live onboard commentary from a professional tour conductor.

Discover some of Key West’s deepest, darkest secrets on a 90-minute ghost-themed trolley tour. The Trolley of the Doomed explores the darker side of one of the most haunted cities in the country. Experience Key West’s frightening past while traveling down the narrow, dark streets of Old Town, lined with 19th-century wooden houses that still bear the secrets of their former inhabitants. This tour is narrated by a 17th-century gravedigger guide who’s almost as scary as the stories being shared.

Pedal a 4-wheeled party bike through West Palm Beach's downtown during this lively activity. With your driver/guide and up to 15 passengers, stop your bike, also known as a pedibus, at local hot spots to sample some of the city's best libations. Listen to your guide's engaging commentary about the night life, culture and history of West Palm Beach as you ride.

Explore the best that St Augustine has to offer with admission to three historic attractions plus a hop-on hop-off trolley tour of the city. Visit the Old Jail, the St Augustine History Museum and the Oldest Store Museum Experience, plus more than 100 other points of interest among the city’s top attractions. Board the trolley at any of the 22 stops. It's a great way to see everything St Augustine has to offer.

This is a one of a kind historical haunted pub crawl. Although one may find haunted pub crawls all over the world, this one is unique as the guides use magic to enhance the presentation. A portion of all ticket sales go to the Estero Island( Ft. Myers Beach)Historic Society.

St. Augustine’s original “frightseeing” tour is 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 streets of the town as you pass haunted hot spots. Feel your blood run cold as you visit the Old Jail, the site of countless strange occurrences over the years, and keep an eye out for malicious spirits at the Old Drug Store. The frights continue at Potter’s Wax Museum’s Chamber of Horrors, where retellings of gruesome executions are sure to lead to shivers. Expect a tour so scary, it should come with a warning.

Getting to Key West from Miami on your own can be such a hassle, but this nearby city has so much to offer. Don’t miss out—this day trip includes round-trip transport from your hotel, so you can enjoy a stress-free ride without worrying about navigating through a new area. Plus, you’ll have plenty of free time to plan solo explorations, and multiple upgrade options are available for add-on activities.

The Greatest Show on Wheels! Our tour guide, circus historian Bob Collins, has loads of great stories about how the Big Top helped to shape Sarasota's quirky arts and culture scene.

Hop onboard our fun-filled Sarasota trivia tour, with local performer and guide Steve McAllister. Show off your love of Sarasota trivia, win bar and restaurant gift certificates during trivia games and sing along to your favorite Florida-inspired songs during the 90-minute air-conditioned tour. Enjoy a stop at the Bahi Hut, the oldest tiki bar in Sarasota, for samples of their world-famous Mai Tai that are sure to spice up your night. Includes free beer or wine at the Trolley Cottage Tiki Bar before boarding.

Step onboard our Holly Jolly Trolley with guide Jenny Claus for our special daytime holiday tour with cocoa, carols & Christmas stories of Sarasota. Visit city spots with Christmas story connections, hear about our Sarasota traditions during the holidays & sing along to your favorite Christmas songs. Includes FREE cocoa at the Trolley Cottage before the tour!

See why Sarasota is often called "Sedona by the Sea," for its ley lines and unusual levels of psychic energy. Our tour guide, Michael Newton-Brown, offers personal Tarot readings following the tour, for an additional fee.

Grab your girlfriends and join us for a personal shopping experience aboard our air-conditioned trolley. Sip on complimentary champagne while browsing through our cute Vintage Sarasota gift shop at the Trolley Cottage. Then enjoy a mini neighborhood tour, guided by Discover Sarasota Tours owner Tammy Hauser, a certified shopping expert, and stopping along the way at three local boutiques offering unique and beautiful clothes, purses and gifts, home decor, or unique vintage finds—plus wine and treats at each stop!

Our Rainbows & Unicorns tour starts with cookies and lemonade at The Trolley Cottage before embarking on a 75-minute scavenger hunt tour looking for rainbows & unicorns in Sarasota’s magical places. Sing songs while you see the Children’s Garden, Marietta Museum of Art & Whimsy, the little people’s houses, and many other whimsical places with your guide, Princess Jenny. Prizes for best fairy costumes awarded on each tour! For families with kids ages 4 and up.

Pedal your way to seeing Daytona's most historic pubs and bars while enjoying the company of friends. Our tours offer a unique experience to learn some history and drinks some brews in an open air pedal bike. Great for birthday parties, bachelorette/bachelor parties, team building, group tours and more.

Tour guide, bon vivant and raconteur Jonny Mac has loads of juicy first-hand stories about visiting Hollywood stars and the Sarasota literati set.

Sarasota has an outstanding collection of public art pieces. Our tour gives a wonderful overview of the sculptures and murals that make the city a true arts mecca.

Looking for a fun and unique way to tour Daytona Beach? Get a group together and hop on the Hopcycle! This two hour pedal bus tour travels to 2-4 local pubs while giving a historical tour of Daytona Beach. Guests will receive a beer or wine included at our first stop and can purchase additional drinks at other stops (drink specials available at most stops for Hopcycle guests). Our pub crawling tour is a great way to see the town and learn about our heritage. Stops may change or vary per tour based on traffic. Minimum 8 participants, maximum 15.

The highest heights in Florida can be found on this high-flying aerial adventure that takes you soaring through our Sky High Canyon! This newest addition to our park packs huge thrills into a small budget. All three zip lines on this tour tower above our other lines! The longest line stretches out across the entire Sky High Canyon at a staggering 1,150 feet long and 155 feet off the ground! The final zip of this tour will have you soaring over Gator Lake at an incredible speed!

Hop on board our air-conditioned trolley to visit three local art galleries during your 90-minute tour. Each gallery will provide wine and appetizers while you browse. Each tour has a specific art medium or style focus, so book all four to experience all that Sarasota galleries have to offer! In between gallery stops, enjoy a public art neighborhood tour with artist and guide Jerome Chesley. Tour includes complimentary beer or wine at the Trolley Cottage Tiki Bar before boarding!

Guests will enjoy complimentary prosecco and chocolate upon arrival in our Trolley Cottage Tiki Bar while browsing through our Vintage Sarasota Gift Shop full of fun old-time treasures. Then they will board the trolley to travel around Sarasota hearing about the legendary love stories of John and Mable Ringling, William and Marie Selby, the Unconditional Surrender statue icons, Owen Burns and his wife Vernona, and many more. A selection of romantic songs, performed on the trolley by Lilian Moore and Richard Caldwell, completes the night of love!

Hop on board for a spellbinding narrated adventure! Hear stories of Sarasota’s famous murders, haunted buildings, and unsolved crimes from your ghost guide and surprise visitors!