Sunset Cabaret: Sarasota’s Iconic Evening Trolley Tour
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.
Overview
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.
Sunset Cabaret
120 minutes in peak season • Complimentary beer/wine • Ages 21+
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Adventure Photos
About This Adventure
Experience the vibrant Sunset Cabaret City Tour aboard Dolly the Trolley, led by the charismatic Steve McAllister. Enjoy complimentary drinks at the Trolley Cottage Tiki Bar, indulge in trivia and tales of Sarasota’s history, and savor stunning sunset views. This engaging adventure promises fun for both locals and visitors alike!
Enjoy A Cabaret City Tour and Craft Beer at Golden Hour
Duration
120 minutes in peak season
About
Hop aboard Discover Sarasota Tours’ air-conditioned Dolly the Trolley for a Sunset Cabaret with local tour guide, actor, songwriter and raconteur, Steve McAllister.
This engaging tour kicks off with free wine/beer at the Trolley Cottage Tiki Bar before boarding, and then heads on a trivia-filled adventure to 99 Bottles to enjoy a premium beverage from the Sunset Cabaret menu along the tour. Free parking and a charming gift shop add to the experience. Enjoy views of the sunset on the bay, entertaining tales about Sarasota’s colorful history, seasoned with cabaret-style songs, jokes, city history and trivia along the way.
This tour is fun for visitors or locals alike! You’re sure to learn something new about Sarasota, even if you’ve lived here all your life.
Fall Hours: Tour runs from 5 PM – 7 PM Spring Hours: Tour runs from 6 PM – 8 PM
Departure/Return Location
1826 4th Street in Sarasota (behind The Breakfast House off Fruitville)
Arriving
Please arrive at least 30 minutes before the tour leaves, to check in and visit our gift shop while you wait to board. Trolleys leave at your scheduled time. If you don't arrive within 5 minutes of departure time, we reserve the right to resell your ticket.
Parking
FREE on-site parking is available!
Things to Note
- This tour stops at 99 Bottles; otherwise you should expect to be seated for the rest of the trip.
- Includes complimentary wine or beer in the Trolley Cottage Tiki Bar before the tour.
- No coolers or personal alcohol are allowed on our tours. No alcoholic beverages are allowed on the trolley.
- Visit the Trolley Cottage Gift Shop, offering unique Sarasota merchandise while waiting to board.
- We also offer group tours of 20 or more for any regular tour—or let us create a custom tour for your group!
Adventure Tips
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.
Local Insights
Wildlife
- Great blue herons often seen near coastal wetlands
- Loggerhead sea turtles nesting seasonally on nearby beaches
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.
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Recommended Gear
Light Jacket or Sweater
Keeps you warm during cooler evenings and waterfront breezes.
fall specific
Reusable Water Bottle
Helps you stay hydrated during warm Florida evenings and beer tastings.
summer specific
Hat or Cap
Provides sun protection before sunset during daytime waiting periods.
spring specific
Comfortable Footwear
Useful for short walks at the brewery and tiki bar stops.