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Expanded Fall 2020 Tour Schedule

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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.

A weekends-only schedule continues through October with our most popular 90-minute air-conditioned tours, City Sightseeing, Circus Secrets of Sarasota, and Psychic Sundays, running on weekends and the spooky Haunted Sarasota Tour running nightly October 23-30 for Halloween.

A full schedule of 10 tour themes resumes November 1, including the four tours mentioned above, along with Amish Experience Tour, Art Crawl Trolley, “Infamous Sarasota” Happy Hour Tour, Public Art Tour, Tiki Trivia Trolley Tour, plus special seasonal tours—Holly Jolly Trolley in December, Love Stories of Sarasota in February, and Irish Hooley on the Trolley in March.

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 now offering a new half-day small group option for 12 or fewer guests who prefer to tour with family and friends, allowing them to explore various Sarasota museums and attractions.

YEAR-ROUND TOURS

CITY SIGHTSEEING TOUR
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.

CIRCUS SECRETS OF SARASOTA
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.

HAUNTED SARASOTA TOUR
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!­­­

PSYCHIC SUNDAY TOUR
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.

 

SEASONAL TOURS

AMISH EXPERIENCE TOUR
Learn why Sarasota is the ONLY place in the world the Amish come en masse to vacation. Learn about our vibrant Amish and Mennonite cultures in Sarasota from tour guide Kendra Cross. 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 (November-April).

ART CRAWL TROLLEY
Hop on board our air-conditioned trolley to visit three local art galleries during your 90-minute tour. Each gallery will provide wine and appetizers while you browse. 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.

HOLLY JOLLY TROLLEY
Join guide Jenny Jingle for our special daytime holiday tour with cocoa, carols & Christmas stories of Sarasota. Visit city spots with Christmas story connections, hear about our Sarasota traditions during the holidays & sing along to your favorite Christmas songs. Prizes for best Ugly Sweater on all tours! Includes FREE cocoa at the Trolley Cottage before boarding.
Ages 21+ $34.99; Under 12 $18.99. Special December tour leading up to Christmas.

“INFAMOUS SARASOTA” HAPPY HOUR TOUR
Relive the glory days of Sarasota’s sunny and scandalous 60s, 70s, 80s, and 90s with tour guide Jonny Mac! Hear stories of growth booms, legendary bars and the fascinating people who frequented them, and stop at the Bahi Hut for a sample of their world-famous Mai Tai! Includes FREE wine or beer in the Trolley Cottage Tiki Bar before boarding.
Ages 21+, $39.99. Fridays at 5:30 PM (October-June).

PUBLIC ART TOUR
Visit more than 50 of the city’s public art sculptures, monuments, and murals in charming neighborhoods and downtown Sarasota. Sit back and relax as painter and public art expert Jerome Chesley helps you see the city through new eyes!
Ages 8+, $34.99. Thursdays at 1 PM (October-April).

TIKI TRIVIA TROLLEY TOUR
Show off your knowledge of Sarasota, sing along to your favorite Florida-inspired songs, and play to win bar and restaurant gift certificates during fun-filled trivia games led by local performer and tour guide Steve McAllister. Enjoy a stop at the Bahi Hut, the oldest tiki bar in Sarasota, for samples of their world-famous Mai Tai! Includes FREE wine or beer in the Trolley Cottage Tiki Bar before boarding.
Ages 21+, $39.99. Weekly on Sundays at 4 PM.

To 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 to shop for holiday gifts, and enjoy cool treats from The ChillMobile, our vintage ice cream truck parked onsite.

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

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ABOUT US:

Discover Sarasota Tours offers 15 entertaining, interactive, and informative air-conditioned trolley tours about the most interesting people, intriguing places, and amazing stories that have shaped Sarasota’s rich cultural past.

All tours depart from our 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.

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