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Discover Sarasota Tours

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Jul 26, 2023

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Florida - Sarasota, Bradenton & Charlotte Counties

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Trolley & Van Tours Around Sarasota, Florida

Discover Sarasota Tours offers fun, entertaining, interactive, and informative air-conditioned trolley and van tours of the most interesting places and stories that shaped Sarasota’s rich cultural past. We offer many different daytime, nighttime, or holiday trolley tours exploring the history, culture, and unique aspects of Sarasota.

If you are looking for a fun activity for your next group outing, look no further! Our tours are perfect for groups. Check out our private Group Tours page.

Our tours run year-round, but during the hottest months of the summer, we don’t run all tours every day, so please check the calendar. If there is a date not listed when you would like a tour, please email us at info@discoversarasotatours.com.

Our comfortable, air-conditioned trolley (or van) embarks from our Trolley Cottage, a charming 1930s bungalow at 1826 4th Street, with easy, FREE on-site parking behind the Breakfast House off Fruitville Road.

See the All Tours page for a full listing of current offerings.

Discover Sarasota Tours’ Trolley Cottage Gift Shop features curious collectibles and memorabilia curated to complement our trolley tour themes. The Trolley Cottage is also home to our groovy vintage 1979 ice cream truck, The ChillMobile, selling cool locally-produced ice cream, popsicles & novelty treats.

Please allow extra time for traffic and plan to arrive 30 minutes in advance of your tour. We leave the Trolley Cottage at the regularly scheduled tour times.






Hop aboard our air-conditioned trolley or passenger van to hear entertaining stories of fascinating people, interesting places, and intriguing events that shaped Sarasota’s rich culture on one of our many Daytime Sightseeing Tours or Nighttime Theatrical Shows.

Due to limited availability, advance reservations are highly encouraged! Generally tours that begin on the hour run in the trolley and those that begin on the half hour run in the van. Both vehicles are enclosed and air-conditioned. We cannot accommodate wheelchairs.

Check our FULL CALENDAR for the tours offered each day.

Tours that are running are listed on our calendar. If a tour is not listed, it is not running on that day or time, is already sold out, or is booked for a private event. All available tours and seats are listed on the website.

Private Group Daytime Tours generally run on Mondays; Private Group Evening Tours can run other days of the week.

The Trolley Cottage Gift Shop is open:
Mondays-Sundays 9 AM – 5 PM


  • MOST POPULAR DAYTIME TOUR!
$48.99

City Sightseeing Tour

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

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  • EXPLORE SARASOTA ARCHITECTURE
$48.99

Architecture Tour

Hop aboard our air-conditioned high-top van to see outstanding examples of Sarasota architecture. Tours feature three distinctive styles: Mid-Century Modern, Art Deco, and Mediterranean Revival.

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  • HALLOWEEN FAMILY FUN!
FROM$24.99 -$39.99

The BooMobile

A Fun Interactive Musical Adventure for kids of all ages with Miss WitchiPOO and her Magic Pumpkin. Enjoy FREE apple cider and cookies at the Trolley Cottage before boarding.

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  • FUN FAMILY HOLIDAY SHOW!
FROM$29.99 -$49.99

Christmas Carol Trolley: Letters from Santa Family Show

A fun-filled holiday music and light tour for the whole family aboard the trolley, with holiday sing-along and stories, real letters to Santa, jokes and trivia. Book now!

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  • POPULAR TOUR!
$48.99

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.

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  • A TASTE OF SARASOTA!
$99.99

Dine Along Trolley

Hop aboard air-conditioned Dolly The Trolley to discover Sarasota’s best food, flavors, and history with local chef and tour guide.

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  • POPULAR NIGHTTIME TOUR!
$52.99

Haunted Sarasota Tour

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!!

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  • ADVANCE RESERVATIONS REQUIRED!
$52.99

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.

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  • SUNSET MUSICAL CABARET TOUR!
$52.99

Sunset Cabaret

Enjoy stories of Sarasota’s history, music, jokes, trivia, a gorgeous setting sun driving by Lido Beach and a stop for craft beer at the new Sun King Brewery.

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  • VISIT PINECRAFT AMISH COMMUNITY
$48.99

Amish Experience Tour: 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 sample of delicious pie!

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  • SARASOTA'S FOUNDING WOMEN
$48.99

Leading Ladies of Sarasota

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

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  • EXPLORE SARASOTA ART
$48.99

Public Art Tour

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

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  • EXPLORE SARASOTA COUNTY HISTORY!
$48.99

History Hop Trolley - Englewood, Sarasota, Venice

Join us for History Hop, our annual week-long celebration of Sarasota County history in partnership with the Lemon Bay (Englewood), Sarasota & Venice Historical Societies.

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Local Services By This Author

Discover Sarasota Tours

Senior Activities 1826 4th Street, Sarasota, Florida, 34236

Explore the vibrant cultural past of Sarasota with Discover Sarasota Tours, a locally owned tour company offering entertaining, interactive, and informative experiences. Step aboard our air-conditioned trolley or van tours and embark on a journey through Sarasota's most intriguing people, fascinating places, and captivating stories.What We OfferVariety of Tours: Choose from a variety of tours that highlight Sarasota's rich cultural heritage.Group Outings: Looking for a fun activity for your next group outing? Our tours are perfect for groups of all sizes. Check out our private group tours and nonprofit programs pages for more information.Tour AvailabilityOur tours run year-round, but during the hottest months of summer, we may not run all tours every day. Please check our calendar for availability. If there's a date not listed when you'd like to tour, feel free to email us at info@discoversarasotatours.com.Get in TouchDon't miss out on the opportunity to discover Sarasota's hidden gems and fascinating history. Contact Discover Sarasota Tours today to book your tour and create lasting memories with friends, family, or colleagues.