Explore Sarasota by Trolley — History, Ghosts, Art & Wine

Discover Sarasota’s haunted past on a private guided tour that brings eerie stories to life. Perfect for history buffs and thrill-seekers alike, this experience offers a spooky twist on Sarasota’s rich heritage.

Discover Sarasota’s vibrant history and architecture on a fun, 90-minute trolley tour. Perfect for first-timers and history lovers alike, this guided ride unveils the city’s hidden stories and scenic spots—comfortably and conveniently.

Explore Sarasota’s history from the perspective of its most influential women on a 90-minute costumed trolley tour. See the city’s top historical sites and hear captivating stories that bring the past to life.

Join the Sunset Cabaret City Tour in Sarasota for a lively evening aboard Dolly the Trolley. Enjoy drinks, craft beer samples, local trivia, and stunning sunset views all in one unforgettable trip.

Join Discover Sarasota Tours for a private 90-minute trolley ride through vibrant public art scenes featuring over 50 sculptures and murals, including the famous “Unconditional Surrender.” Experience the city’s rich arts culture with expert guide Jerome Chesley.

Experience Sarasota's haunted past on the Sing-Along Trolley, a fun and musical ghost tour that brings history and mystery to life. Join Lady Melody & Mystery Spirits for a night you won't forget!

Enjoy an evening trolley ride through Sarasota with craft beer tastings, sunset views, and entertaining stories. Sip & Stroll is the perfect way to explore the city in a fun, relaxed setting.

Join the Trolley Bash! this November in Sarasota for a festive celebration filled with food, fun, and live entertainment. Explore local shops and toast to community spirit aboard a vibrant trolley tour.

Join a private trolley tour to explore Sarasota’s famous architectural treasures. Experience historic neighborhoods and iconic designs in a relaxed, intimate setting.

Explore Sarasota’s Amish and Mennonite cultures on a 105-minute trolley tour through Pinecraft. Savor local pies, shop unique crafts, and gain genuine insights into a treasured community.

Step aboard the Murder Mystery Trolley in Sarasota, Florida, and help solve the Circus Queen’s murder. Dress up, sip drinks, and enjoy 90 minutes of interactive fun and suspense!

Hop aboard The BooMobile for a Halloween trolley adventure in Sarasota! Enjoy a musical quest, costume contests, and historic sights on this family-friendly 45-minute tour.

Experience Sarasota’s dynamic art districts on the Art Crawl Trolley, a hop-on/hop-off tour connecting six vibrant gallery hubs across downtown. Enjoy local brews, diverse artworks, and the city’s cultural heartbeat from 4 PM to 8 PM daily.

Explore Sarasota's rich circus history on a private 90-minute trolley tour with expert guide Bob Collins. Discover hidden stories of the legendary Ringling Bros. Circus as you visit iconic landmarks and historic neighborhoods.

Enjoy a festive 75-minute trolley tour through Sarasota's holiday-lit downtown. Sing carols, hear magical stories, and see real Letters to Santa in a family-friendly experience everyone will love.

Dive into Sarasota’s mystical side with a scenic trolley tour guided by a psychic. Experience tarot readings, sound healing, and local spiritual sites in this unique water-linked adventure.

Step aboard a 90-minute trolley tour in Venice, FL, and uncover the hidden stories of the Ringling Bros. Circus. Discover Sarasota Tours guides you through landmarks and a unique museum stop that reveal the city’s circus past.

Take a 90-minute deep dive into Venice, Florida’s rich history and landmark scenes with Discover Sarasota Tours. Perfect for visitors aged 10 and up, this engaging coastal town tour delivers memorable insights alongside free parking.