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    5. Sing-Along Trolley Tour in Sarasota
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    Sing-Along Trolley Tour in Sarasota

    Sing 70s & 80s hits on a trolley with a bar stop at 99 Bottles

    4.8 stars• 1.5K reviews
    From$71/ personincl. taxes and fees

    Duration

    75 minutes

    Includes

    Songbooks, props, bar stop

    Highlights

    Hop onboard a Sarasota trolley and join an interactive group sing-along to 70s and 80s pop hits. Warm up with a complimentary beer or wine before boarding, then stop at 99 Bottles during the tour.

    • Sing along with cast members to 70s and 80s top hits
    • Play trivia as you ride through downtown Sarasota
    • Stop for a premium beverage from the Sing-Along menu at 99 Bottles
    • Browse the Trolley Cottage Gift Shop before you board
    • Park for free on-site at 1826 4th St in Sarasota

    What's Included

    • Trolley ride
    • Songbooks
    • Props
    • Complimentary beer or wine at the cottage tiki bar before boarding (21+)
    • Premium beverage from the Sing-Along menu at 99 Bottles

    Things to know

    Guests must be 21+. No alcohol is allowed on the trolley. Video, audio, and film recording of any performance by patrons is prohibited.

    Cancellation Policy

    Tours run rain or shine. If you cancel at least 24 hours in advance, they will try to move you to another tour based on available space or offer a gift certificate. All sales are final and no refunds are provided for no-shows or missed tours.

    FAQs

    Yes. Guests must be 21+ and children are not allowed.

    No. No coolers or personal alcohol are allowed, and no alcoholic beverages are allowed on the trolley.

    Yes. Every guest must have a paid ticket to board. You will check in at the Trolley Cottage by last name (no physical tickets).

    Meeting details

    Discover Sarasota Tours - 1826 4th St, Sarasota, FL 34236

    Experience provided by Discover Sarasota Tours
    Experience provided by Discover Sarasota Tours

    How can we help?

    We are here to assist with special requests, large groups, last minute needs, and any questions you may have.

    Call or text (650) 414-7338

    Report an issue

    Reference #VU64UT

    Adult

    $71.23

    Ages 21+

    0

    Why book through Greetwell?

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      No booking or service fees, ever

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    • Free Cancellation Available

      Most experiences can be cancelled for a full refund

    Discover what we've curated for you

    Review summary

    4.8
    Excellent
    1.5K reviews•Google Maps

    Visitors consistently rave about the engaging guides and entertaining theatrical elements that make these tours memorable. Steve, Jon, and Deni get special shoutouts for their knowledge of Sarasota's history, architecture, and local culture, while the costumed actors who appear on themed tours like the Haunted Sarasota experience bring impressive talent and energy. The variety of offerings is notable—from singing trolley rides and psychic tours to circus routes and Amish experiences—giving people plenty of reasons to return for multiple adventures. The interactive nature really stands out. Guests sing along with provided songbooks, enjoy props, and often make stops at local spots like bars or boutiques. Owner Tammy is described as an entrepreneurial spirit focused on customer experience, and the gift shop full of local products adds a nice touch. One reviewer mentioned the owner's heavy involvement during a tour came across as micromanaging the staff, which distracted from the experience. Still, the overwhelming majority describe fun, informative outings perfect for newcomers wanting to learn about Sarasota or locals looking for a unique night out with friends.

    What people are saying

    Review 1 of 5
    5/5

    We have been to Sarasota many times and were excited to accept the invitation of some friends to take a trolley tour to learn some of the history of a specific area of the city - the Amish people in Pinecraft. The trolley itself was comfortable and the driver was expert (smooth ride). What really stood out was our guide, Kendra. She has a personal connection to the Amish and the stories she shared helped to grow our understanding of their culture and customs. We rode through the neighborhood and saw the homes and a park - the hub of recreation. There was a stop where we saw multiple points of interest including a hotel geared to Amish families, though anyone can stay there. There was also a quilt shop where ladies were quilting and a bakery that smelled amazing (several people purchased bags full of goodies). It was a most enjoyable tour - infotainment for sure!

    Photo of Tracie Carley

    Tracie Carley

    March 20, 2026

    Review 1 of 1
    5/5

    We have been to Sarasota many times and were excited to accept the invitation of some friends to take a trolley tour to learn some of the history of a specific area of the city - the Amish people in Pinecraft. The trolley itself was comfortable and the driver was expert (smooth ride). What really stood out was our guide, Kendra. She has a personal connection to the Amish and the stories she shared helped to grow our understanding of their culture and customs. We rode through the neighborhood and saw the homes and a park - the hub of recreation. There was a stop where we saw multiple points of interest including a hotel geared to Amish families, though anyone can stay there. There was also a quilt shop where ladies were quilting and a bakery that smelled amazing (several people purchased bags full of goodies). It was a most enjoyable tour - infotainment for sure!

    Photo of Tracie Carley

    Tracie Carley

    March 20, 2026

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