Trolley Tours of Sarasota & Venice

18 Different Air-Conditioned Tour Themes!

OFFERING PRIVATE GROUPS ONLY IN AUGUST & SEPTEMBER.

During these months we are not open for public tours.
We resume all public tours starting October 8, 2025.

Don’t forget to book your Halloween and Christmas Tour tix now before they sell out!

Discover the history, culture, neighborhoods, and things to do in Sarasota and Venice on one of our many award-winning air-conditioned daytime or nighttime tours.

**To book your tour, check our FULL CALENDAR for the tours offered each day.**

The trolley is also available for Memorial Celebrations or Private Rentals. Contact [email protected].

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Most popular daytime tour!

90 minutes
Year Round

Sarasota City Sightseeing Tour

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!

NIGHTLY TOURS IN OCTOBER!

From $30.99 - $40.99

45 minutes
October

The BooMobile

A fun, interactive musical adventure for kids of all ages, featuring WitchyPOO and her Pumpkin too!

Ghost Stories, Mystery Guests & Spooky Fun!

75 minutes
October

Haunted Sarasota Tour

Step aboard the trolley for a thrilling and historical musical journey through Sarasota’s eerie past with Lady Melody & Mystery Spirits! Learn about Sarasota’s famous murders, haunted buildings, and unsolved crimes on this fun trolley tour. Keep an eye out for surprise guests along the way!

2 hours

Literature & Lattes

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.

3 hours

Sip & Stroll

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.

HOLIDAY FUN FOR ALL AGES

From $34.99 - $58.99

75 minutes
December

Christmas Carol Trolley: Letters to Santa

Hop aboard Dolly The Trolley to enjoy our holiday musical tour — fun for the whole family! Christmas Carol Trolley: Letters To Santa is a musical, holiday adventure tour featuring our singing cast members, The Trolley Troubadours.

Visit Pinecraft Amish Community

90 minutes
Nov-May

Amish Experience: Bridges To Understanding

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.

FUN FOR ALL AGES!

90 minutes
Year Round

Murder Mystery Trolley: Who Killed The Circus Queen?

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.

NEW TOUR

1.5 hours
Year Round

Sing-Along 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.

POPULAR TOUR!

90 minutes
Year Round

Circus Secrets of 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.

POPULAR TOUR

90 minutes
Jan-April

Venice City Sightseeing 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.

Explore Sarasota Architecture

90 minutes
Year Round

Architecture Tour

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.

FASCINATING HISTORY

90 minutes
Jan-April

Circus Secrets of Venice

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.

Explore Sarasota Art

90 minutes
March, April, February

Public Art Tour

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.

Sunset Musical Cabaret Tour!

120 minutes
Year Round

Sunset Cabaret

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.

Sarasota's Founding Women

90 minutes
Nov-Apr

Leading Ladies of Sarasota

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.

Spiritual

90 minutes
Year Round

Psychic Sundays Tour

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

Sip and See Art!

4 hours
Jan-April

Art Crawl Trolley

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.