Step aboard Sarasota’s trolley to experience history, mystery, and culture through engaging guided tours with Discover Sarasota Tours. From family shows to haunted streets, these rides offer an entertaining and insightful way to see the city.
More ways to explore the area's outdoor wonders
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Difficulty
easy
Duration
1.5 hours
Fitness Level
Suitable for all fitness levels, minimal physical exertion required since tours take place on seated trolley rides.
Wildlife
History
Sarasota was a magnet for artists, architects, and circuses since the early 20th century, giving rise to its unique blend of cultural influences.
Conservation
Local efforts focus on preserving Sarasota’s historic downtown structures and public art, alongside protecting Gulf Coast natural habitats from overdevelopment.
Discover Sarasota Tours
Step aboard Sarasota’s trolley to experience history, mystery, and culture through engaging guided tours with Discover Sarasota Tours. From family shows to haunted streets, these rides offer an entertaining and insightful way to see the city.
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.
Book in Advance for Popular Tours
Tours like the Murder Mystery Trolley and Sing-Along Trolley fill quickly, especially on weekends and holidays.
Prepare for Florida Weather
Trolleys feature windows that open or close, but sunscreen and hydration are recommended during warm months.
Bring a Camera with a Zoom
Large windows provide excellent photo opportunities, including architectural details and scenic waterfront views.
Arrive Early for Gift Shop Browsing
The charming check-in cottage offers unique local souvenirs and postcards worth checking out before your trip.
Light Jacket or Sweater
Evenings on the trolley can get cool during Sarasota’s winter months.
winter
Sunscreen
Protect skin from sun exposure during open-window tours in warm seasons.
summer
Camera or Smartphone
Capture vibrant street scenes, architecture, and fleeting moments along the route.
Reusable Water Bottle
Stay hydrated during warm weather tours.
summer