Hop aboard Dolly the Trolley and let Discover Sarasota Tours unveil the stories, secrets, and colorful characters that shaped Sarasota and Venice. This locally owned company blends comfort—think cushy seats and cool A/C—with livel...
Hop aboard Dolly the Trolley and let Discover Sarasota Tours unveil the stories, secrets, and colorful characters that shaped Sarasota and Venice. This locally owned company blends comfort—think cushy seats and cool A/C—with livel...
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.
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!
Tracie Carley
March 20, 2026
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!
Tracie Carley
March 20, 2026