Trolley Tours of Sarasota & Venice

Hop aboard Dolly the Trolley to enjoy our holiday musical tour – fun for the whole family! Christmas Carol Trolley is a musical, holiday adventure tour featuring your guide, Christmas Carol, and our singing cast members, The Trolley Troubadours. 

On this classic Sarasota City Sightseeing Tour, learn where to tour, dine, shop or visit! Get an entertaining overview of Sarasota’s rich history, culture, and neighborhoods. Wonderful for visitors and locals alike!

POP UP Experience: Discover the rich literary history of Sarasota on this fun NEW tour, Literature & Lattes, with our partners at Bookstore1 and Jessie’s Café located at The Reserve.

POP UP Experience: Hop onboard the air-conditioned trolley to visit our own Fiorelli Vineyards for wine tasting, live music, and a tour. Learn about the wine made at Fiorelli, sample several of their wines and add on a lunch option to eat while you enjoy the music in the gardens.

Learn about Amish & Mennonite cultures in Sarasota from tour guide Kendra Cross. Stops at Alma Sue’s Quilt Shop, The Carlisle Inn & Der Dutchman Amish Kitchen Cooking Restaurant for a pie shooter.

On this 90-minute interactive tour, solve the mystery of the Circus Queen’s murder in a fun, circus-themed theatrical show aboard the trolley.

Join our talented cast members for an interactive group sing-along tour to your favorite 70’s & 80’s top hits with trivia and a bar stop at 99 Bottles in downtown Sarasota.

Learn about the Circus Secrets of Sarasota by visiting key landmarks and hearing stories of the colorful cast of circus characters, showmen, and performers who called Sarasota home.

Step aboard the trolley for a fun historical musical journey through Sarasota’s eerie past with Lady Melody & Mystery Spirits! Hear stories about haunted buildings, intriguing ghosts, and spirited sightings during this 75-minute, musical Halloween tour.

Discover the history, landmarks, neighborhoods, natural beauty, and things to do in Venice, Florida on our Venice City Sightseeing Tour! Offered in partnership with Venice Florida Tours guides. Tours depart from the Venice Area Chamber of Commerce.

Hop aboard our air-conditioned trolley to learn about Sarasota’s distinctive architectural styles. Tours feature Mid-Century Modern, Art Deco, and Mediterranean Revival buildings, homes, and structures.

Join the Circus Secrets of Venice tour with Bob Collins, exploring Ringling Bros. history and the Historic Train Depot. Proceeds support the Venice Area Historical Society.

Hop aboard our air-conditioned trolley to see more than 50 pieces of public art in downtown Sarasota neighborhoods on our Public Art Tour led by painter Jerome Chesley.

Enjoy stories of Sarasota’s history, music, jokes, trivia, gorgeous setting sun driving by Lido Beach and a stop for beer and wine at 99 Bottles.

An Historical City Trolley Tour led by one of Sarasota’s Founding Women: Mable Ringling, Marie Selby, and Bertha Palmer, as portrayed by actress and guide Kathryn Chesley.

Learn about the psychic history of Sarasota with a sound healing immersive experience, a visit to Elysian Fields, and a walk along the labyrinth. Add a tarot card reading to your tour!

Explore Sarasota’s vibrant public art downtown & neighborhood gallery locations. Hop on, hop off at the art gallery and studio locations. Enjoy free beer/wine before boarding, and at galleries while you browse. Art Crawl with us on select Fridays, January-April.

Discover the Sarasota Opera House from the inside out with exclusive access to its private costume vault, a guided tour of the historic hall, and a family-style Mediterranean lunch.