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Seasonal Tour Schedule Resumes!


Discover Sarasota Tours resumes its seasonal tour schedule January-May, including the Amish Experience Tours, Public Art Tours, a new Centennial City Tour in honor of Sarasota’s Centennial Celebration, “Infamous Sarasota” Happy Hour Tour, Tiki Trivia Trolley Tour, and the popular Art Crawl Trolley.

Year-round tours continue: City Sightseeing Tour, Haunted Sarasota Tour, Boutiques & bubbles, Rainbows & Unicorns, Psychic Sunday Tour, and Circus Secrets of Sarasota.

Holiday Tours include the upcoming Irish Hooley on the Trolley running March 12 and 13.

Discover Sarasota Tours offers entertaining, interactive, and informative air-conditioned trolley tours of the most interesting places and stories that shaped Sarasota’s rich cultural past.

All tours depart from DST’s charming Trolley Cottage (behind the Breakfast House, off Fruitville in downtown Sarasota). The Trolley Cottage features ample FREE parking, a fun Vintage Sarasota gift shop, and The ChillMobile, a vintage ice cream truck.

Discover Sarasota Tours is also offering NEW half-day tours with lunch options in its 12-person passenger van, as well as private tours for small family groups.



Learn from tour guide Kendra Cross why Sarasota is the ONLY place in the world the Amish come on vacation en masse. Enjoy tour stops at Alma Sue’s Quilt Shop and The Carlisle Inn, and sample the delicious pie at Der Dutchman Amish Kitchen Cooking Restaurant!
Ages 21+ $34.99; Under 12 $18.99. Thursdays at 10 AM

Hop on board our air-conditioned trolley to visit three local art galleries during your 90-minute tour. In between gallery stops, enjoy a public art neighborhood tour with artist and guide Jerome Chesley. Includes wine and light appetizers at each gallery and FREE wine or beer in the Trolley Cottage Tiki Bar before boarding.
Ages 21+, $39.99. Thursdays at 6 PM.

Join guide Kathryn Chesley, AKA Rose Wilson, Sarasota’s first newspaper publisher, as you tour the city and learn about its 100-year history.
March/April/May. Ages 21+ $34.99; Under 12 $18.99

Relive the glory days of Sarasota’s sunny and scandalous 60s, 70s, 80s, and 90s with tour guide Jonny Mac! Includes FREE wine or beer in the Trolley Cottage Tiki Bar before boarding.
Ages 21+, $39.99. Fridays at 5:30 PM

Visit more than 50 of the city’s public art sculptures, monuments, and murals in charming neighborhoods and downtown Sarasota with watercolor artist Jerome Chesley.
Ages 8+, $34.99. Thursdays at 1 PM.




All Aboard the Classic Sarasota Trolley Tour
Circus lore, Amish culture, real estate developments, and colorful stories about Sarasota’s founders give a true overview of Sarasota’s rich and amazing history.
Ages 12+, $34.99; Under 12, $18.99. Most days at 10 AM & 1 PM and during season also at 3 PM.

The Greatest Tour on Wheels!
Learn about the rich circus history of Sarasota on an unforgettable trolley tour with seasoned guide, Bob Collins, who shares personal stories about the colorful cast of circus characters, showmen, and performers who called Sarasota home.
Ages 8+, $34.99. Wednesdays or Saturdays at 1 PM.

Mummies, Mayhem, & Murder in Sarasota!
Hear stories about famous murders, visit spirited buildings, explore unsolved crimes, and enjoy surprise guests along the way!! Includes complimentary beer or wine in the Trolley Cottage Tiki Bar before boarding!
Ages 12+, $39.99. Friday nights at 8 PM year-round with more dates in October. Prizes awarded for BEST MASK and BEST COSTUME!­­­

Learn why Sarasota is called “Sedona by the Sea” with psychic and medium Michael Newton Brown. Explore a metaphysical shop, Siesta Key Beach, and a labyrinth, and experience a mini tarot and spirit gallery reading during the tour. Includes FREE orange or pineapple mimosas in the Trolley Cottage Tiki Bar before boarding.
Ages 12+ $34.99. Monthly on Sundays at 1 PM.


a man and a woman standing in front of a storeTo accommodate COVID-19 requirements, DST staff and guests will have their temperatures checked when they arrive. All guests must wear masks. We will be selling up to 30 seats on each tour.

Visit the Vintage Sarasota gift shop for souvenirs, and enjoy cool treats from The ChillMobile, our vintage ice cream truck parked onsite.

To book your tour online, go to To book The ChillMobile for a neighborhood visit, driveway happy hour or corporate event, go to

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Discover Sarasota Tours is a locally-owned specialty tour company offering 14 entertaining, interactive, and informative air-conditioned trolley or van tours about the most interesting people, intriguing places, and amazing stories that have shaped Sarasota’s rich cultural past.