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.
More ways to explore the area's outdoor wonders
Hang tight — photos are loading
This usually takes just a second.
Difficulty
easy
Duration
2–3 hours
Fitness Level
No special fitness is required; the tour is mainly seated aboard the trolley with short walking around the stops.
Wildlife
History
Sarasota’s history blends Native American heritage with early coastal settlement, reflected in its architecture and cultural landmarks visited during the tour.
Conservation
Local efforts focus on protecting coastal habitats and marine wildlife, encouraging sustainable tourism practices throughout Sarasota.
Discover Sarasota Tours
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.
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.
Tours Offered
10 tours & events
Trolley tours, themed rides, and special events.
Typical Duration
75–90 minutes
Short, sightseeing-friendly itineraries.
Local Guides
Named local guides
Includes costumed and expert storytellers.
Year-Round
Seasonal & year-round events
Ghost tours, cabarets, and wine trips available.
Book online for specific dates, themed events, and named-guide tours — secure seats for history, art, ghost stories, and wine trips.
Arrive Early for Complimentary Drinks
Get settled and enjoy your complimentary drinks at the Trolley Cottage Tiki Bar before the tour starts to kick off the fun.
Bring a Light Jacket for Evening Breezes
Florida evenings can get breezy near the waterfront, so a light jacket will keep you comfortable during the sunset views.
Designate a Driver or Use Ride-Share
Since craft beer samples are included, plan your transportation accordingly to stay safe and compliant with local laws.
Stay Hydrated
Complimentary drinks and beer tastings can be dehydrating, so drink water throughout the tour to stay refreshed.
Light Jacket or Sweater
Keeps you warm during cooler evenings and waterfront breezes.
fall
Reusable Water Bottle
Helps you stay hydrated during warm Florida evenings and beer tastings.
summer
Hat or Cap
Provides sun protection before sunset during daytime waiting periods.
spring
Comfortable Footwear
Useful for short walks at the brewery and tiki bar stops.