Sing along, sip cocoa, and see Sarasota's holiday lights from Dolly the Trolley
75 mins
Up to 29 people
Music, cocoa, beer/wine
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.
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
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.
Trolley Cottage, 1826 4th St, Sarasota, FL 34236
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.
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.
Katrina Schreiber
August 1, 2026
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.
Katrina Schreiber
August 1, 2026
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