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Join the Sunset Cabaret City Tour in Sarasota for a lively evening aboard Dolly the Trolley. Enjoy drinks, craft beer samples, local trivia, and stunning sunset views all in one unforgettable trip.
Join the Sunset Cabaret City Tour in Sarasota for a lively evening aboard Dolly the Trolley. Enjoy drinks, craft beer samples, local trivia, and stunning sunset views all in one unforgettable trip.
Book with Discover Sarasota Tours
Verified experiences and guided adventures in the surrounding area.
Operated by Discover Sarasota Tours · Sarasota, Florida
Experience Sarasota like never before on the Sunset Cabaret City Tour aboard Dolly the Trolley. Led by the charismatic Steve McAllister, this private guided tour offers a unique blend of history, entertainment, and local flavor. Start your adventure with complimentary drinks at the cozy Trolley Cottage Tiki Bar, setting the tone for a relaxed and fun evening. Then, enjoy a lively trivia journey as you travel to the Sun King Sarasota brewery, where craft beer samples await. While savoring local brews, learn fascinating stories behind Sarasota’s cultural and historical landmarks. The tour culminates with breathtaking sunset views that perfectly capture Florida’s coastal charm. Whether you’re a history buff, beer lover, or sunset chaser, the Sunset Cabaret is an evening full of spirited discoveries made even better by the personal touch of a small group and a passionate guide. It’s an unforgettable way to enjoy Sarasota’s vibrant night scene while making meaningful connections and memories.
easy.
2–3 hours.
No special fitness is required; the tour is mainly seated aboard the trolley with short walking around the stops.
Yes, complimentary drinks at the Trolley Cottage Tiki Bar and craft beer samples at Sun King Sarasota brewery are included.
The tour is best suited for adults 21 and over due to alcohol tastings, but younger guests are welcome with prior arrangement.
The tour generally lasts between 2 to 3 hours, including stops and travel time.
Yes, the tour is conducted aboard Dolly the Trolley with all transportation between stops included.
Wear comfortable clothing with a light jacket for evening breezes, and shoes suitable for brief walking.
Please inform Discover Sarasota Tours in advance so they can accommodate dietary needs when possible.
Sarasota’s history blends Native American heritage with early coastal settlement, reflected in its architecture and cultural landmarks visited during the tour.
Local efforts focus on protecting coastal habitats and marine wildlife, encouraging sustainable tourism practices throughout Sarasota.
Discover Sarasota Tours operates guided trolley tours and special events in Sarasota, Florida, offering history, haunted stories, public art, architecture, and themed experiences. The company runs multiple scheduled trolley routes and curated excursions that range from 75- to 90-minute guided rides to winery visits and evening cabaret-style tours. Tours are led by named local guides and entertainers such as Lady Melody, Kathryn Chesley, Jerome Chesley, Steve McAllister, and Tammy Hauser, who bring local stories and expertise to each route. Guests can choose from a Haunted Sarasota Tour, a Sarasota City Sightseeing Tour, the Leading Ladies of Sarasota history tour, a Sunset Cabaret, a Public Art Tour, a Sing-Along Trolley, Sip & Stroll winery trips, seasonal Sip & Shop and Trolley Bash events, and a focused Architecture Tour. Several trolley experiences specify air-conditioned vehicles and family-friendly formats; the Sing-Along and Haunted tours feature year-round and October costume programming respectively. The company emphasizes engaging narration, accessible meeting points in Sarasota, and a mix of daytime and evening departures designed for both visitors and residents. Discover Sarasota Tours maintains clear, tour-specific descriptions, consistent trip durations, and named guides to help guests select an experience that matches interests and mobility needs. Booking information, event schedules, and accessibility notes are provided with each tour listing. For travelers looking to explore Sarasota’s cultural heritage, public art, and local stories, Discover Sarasota Tours offers specialized, docent-style trolley experiences that highlight the city’s landmarks and characters. Reservations and gift certificates are available online and at the trolley cottage.
Book with Discover Sarasota Tours