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    1. Local experiences
    2. /Things to do in Sarasota…
    3. /Specialty Tours
    4. /Seasonal and Holiday
    5. /Sarasota Holiday Lights Trolley Tour
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    Sarasota Holiday Lights Trolley Tour

    Sing along, sip cocoa, and see Sarasota's holiday lights from Dolly the Trolley

    4.5 stars• 261 reviews

    Duration

    75 mins

    Ideal For

    Up to 29 people

    Includes

    Music, cocoa, beer/wine

    Highlights

    Celebrate the season aboard Dolly the Trolley with holiday songs performed by entertaining cast members, jingle-bell caroling down Main Street, and views of Sarasota neighborhood lights. Start with a cocoa bar before boarding, then settle in for a festive ride through the city.

    • Sing along with holiday songs performed by cast members
    • Carol down Main Street with jingle bells
    • See Sarasota neighborhood lights from the trolley
    • Sip from a cocoa bar before boarding

    What's Included

    • Cocoa bar before boarding
    • Complimentary beer and wine before boarding
    • Jingle bells

    Important details

    • No outside alcohol or drinks are allowed onboard

    Cancellation Policy

    Tours run rain or shine. All sales are final; no refunds are provided for no-shows or missed tours. If the operator cancels a tour, refunds are issued within 30 days.

    Product ID: ENKYP2

    FAQs

    Arrive at least 30 minutes before departure. Boarding begins about 10 minutes before the tour, and the trolley leaves on time.

    Ages 0–20 are eligible for the child ticket. Infants and children under 10 are not allowed on this tour.

    No outside alcohol or drinks are allowed onboard. Food and drinks are not allowed on the trolley.

    Meeting details

    Trolley Cottage, 1826 4th St, Sarasota, FL 34236

    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 1-877-GREET-WELL

    Report an issue

    Adult 21+

    $74.09

    Ages 21+

    0

    Child

    $45.59

    Ages 0-20

    0

    Why book through Greetwell?

    • No Added Fees

      No booking or service fees, ever

    • Concierge Support Included

      Real humans ready to help with timing, questions, or special requests

    • Free Cancellation Available

      Most experiences can be cancelled for a full refund

    Discover what we've curated for you

    Review summary

    4.5
    Excellent
    261 reviews•Google Maps
    204
    20
    7
    4
    21

    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 4
    5/5

    This experience was the perfect activity to dive into Sarasota, FL. The length was perfect and comfortable, while having many landmarks. I moved here 6 months ago, and was surprised there was so much to learn about my own city and its gems! I strongly encourage going to the Ringling Museum before or after this trolley tour - we had just gone to Ringling Museum the day before, and it made it that much more special to learn how interwoven the Ringling family is to the fabric of this city.

    Photo of Katrina Schreiber

    Katrina Schreiber

    August 1, 2026

    Review 1 of 1
    5/5

    This experience was the perfect activity to dive into Sarasota, FL. The length was perfect and comfortable, while having many landmarks. I moved here 6 months ago, and was surprised there was so much to learn about my own city and its gems! I strongly encourage going to the Ringling Museum before or after this trolley tour - we had just gone to Ringling Museum the day before, and it made it that much more special to learn how interwoven the Ringling family is to the fabric of this city.

    Photo of Katrina Schreiber

    Katrina Schreiber

    August 1, 2026

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