Join Discover Sarasota Tours for a private 90-minute trolley ride through vibrant public art scenes featuring over 50 sculptures and murals, including the famous “Unconditional Surrender.” Experience the city’s rich arts culture with expert guide Jerome Chesley.
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 as the tour is primarily onboard the trolley with minimal walking.
Wildlife
History
Sarasota’s public art reflects its history as a cultural hub since the 1920s, influenced by the Ringling Brothers Circus legacy.
Conservation
Efforts are in place to preserve outdoor artworks and promote eco-friendly tourism practices within Sarasota’s city limits.
Discover Sarasota Tours
Join Discover Sarasota Tours for a private 90-minute trolley ride through vibrant public art scenes featuring over 50 sculptures and murals, including the famous “Unconditional Surrender.” Experience the city’s rich arts culture with expert guide Jerome Chesley.
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
Private tours fill up quickly, especially on weekends and holidays, so reserve your spot early.
Arrive early
Arriving 10-15 minutes before the tour start ensures a smooth boarding process and better seating options.
Wear sun protection
Florida sun can be strong even during short tours, so bring sunscreen and a hat for comfort.
Bring a camera
The tour offers unique photo opportunities of striking public art and urban landscapes—don’t miss capturing them.
Sunscreen
Protect your skin from Florida’s strong sun during the outdoor portions of the tour.
summer
Water Bottle
Stay hydrated throughout the 90-minute tour, especially during warmer months.
Camera or Smartphone
Capture stunning photos of Sarasota’s unique public art and vibrant murals.
Light Jacket
Comfortable for cooler mornings or evenings during the winter months.
winter