The hop-on hop-off trolley tour of Key West is a fantastic way to explore this historic island. Sit back and relax while your expert tour guide turns back the pages of history to the days of Indians, pirates, wreckers and the Civi... More

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 neig... More

Explore the darker side of the Nation’s Oldest City and let our Ghost Host be your guide. Climb aboard our Trolley of the Doomed as we journey to St. Augustine’s most haunted locations. Be Warned! Experience a frightening stop... More

Join your gravedigger guide aboard the Trolley of the Doomed for a journey through Key West's darker side! Take an evening trolley ride down the narrow, dark streets of Old Town and hear stories from your guide about the island’... More

Climb up into the Safari truck, fasten your seatbelt and get ready for the Around the Island Safari Truck Tour! Your tour guide driver will be showing you historical sites, celebrity neighborhoods, mega mansions and more. We'll ju... More

When you arrive in port in Key West, take an independent, hop-on hop-off trolley tour shore excursion for the best way to explore the island. While you’re off your cruise ship, simply sit back and relax while your expert tour gu... More

Experience the vibrant spirit of Downtown St. Petersburg like never before with our Mixer Tour. Jump aboard this unique, mobile pub and join a lively crowd for a 2-hour adventure that feels more like a parade through the heart of ... More

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, comfo... More

Get ready to discover Miami in Style on Flamingo Bus Miami Tours! 2-Hour Private city tour experience through Miami Beach Art Deco, Design District, Star Island, Wynwood Walls Murals, Historic Downtown & VIP Food Stop at Michelin ... More

Experience one of the country’s most famous cemeteries at your own pace on this hop-on hop-off trolley tour of Arlington National Cemetery in Washington DC. Visit the most notable graves and memorials and learn about the cemeter... More

Join the only official mural tour curated by the SHINE Mural Festival organizers and Star Trolley, showcasing stunning murals by internationally renowned artists with over 2 million followers combined. This 2-hour tour on an open-... More

Visit the only place in the world that the Amish and Mennonite communities come to vacation en masse and learn about their culture with your tour guide. On this tour, the goal is to create a “bridge of understanding” about the... More

Fun, interactive murder mystery theater on the trolley! Someone has murdered the Circus Queen...and suspects abound among the circus folk on board. Everyone seems to have a motive. Wear a circus costume if you wish, find yourself ... More

Explore the vibrant spirit of Tampa on this 90-minute guided city tour. Travel through iconic districts like Ybor City and the Riverwalk, discovering both historical landmarks and contemporary cultural gems. From the city's rich c... More

Sarasota is home to an amazing architectural legacy. On this 105-minute air-conditioned tour, guests will visit some outstanding examples of architecture and design, with tours featuring three of the city’s most distinctive styl... More

Discover Circus City USA’s secret places and charming stories on this unforgettable tour! It is a tour of the circus history in Sarasota and provides a wonderful historical perspective of the impact the circus has had in our are... More

Join us on Tuesdays January-April for our NEW Venice, FL Tours! Experience a full day of fun on our 10 AM Venice City Sightseeing Tour or our 1 PM Circus Secrets of Venice tour. Discover the history, landmarks, neighborhoods, n... More

The 2nd Annual Art Crawl Trolley tour runs Jan 10, Feb 14, Mar 14, & Apr 11, 2025. Book your boarding time (every 15 min) on one of 3 trolleys that visit 6 art district locations on a 45-min tour route in downtown Sarasota. Arts d... More

Sarasota has an outstanding collection of public art pieces. On this 90-minute tour aboard our enclosed, air-conditioned trolley, visit more than 50 of the city’s public art sculptures, monuments, and murals in charming neighbor... More

Christmas Carol Trolley: Letters to Santa is a holiday tour of music and lights! This holiday favorite is a 75-minute family-friendly show filled with downtown lights, caroling down Main St., holiday stories, and heartfelt perform... More