Sip & Stroll Trolley Tour in Sarasota, Florida
Difficulty
easy
Duration
2–3 hours
Fitness Level
Suitable for all fitness levels; the trolley provides a seated experience with minimal physical effort.
Overview
Enjoy an evening trolley ride through Sarasota with craft beer tastings, sunset views, and entertaining stories. Sip & Stroll is the perfect way to explore the city in a fun, relaxed setting.
Sip & Stroll
3 Hours • Complimentary beer/wine • Ages 21+
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Adventure Photos
About This Adventure
Embark on a delightful journey aboard the air-conditioned trolley to Fiorelli Vineyards for a unique wine tasting experience. Enjoy live music and a scenic tour while sampling exquisite wines. Enhance your visit with a delicious lunch amidst the beautiful gardens, making this a memorable outing for wine lovers and music enthusiasts 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, and then heads on a trivia-filled adventure to Sun King Sarasota brewery in the Limelight District for craft beer samples and a mini brewery tour. 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 Sun King Sarasota brewery; 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
Reserve your spot early
Tours fill up quickly, especially on weekends and during sunset hours, so booking in advance is essential.
Arrive 15 minutes early
Getting to the departure point ahead of time ensures a smooth check-in and boarding process.
Bring a light jacket
Even though the trolley is air-conditioned, evenings by the bay can get cooler, especially during winter months.
Plan transportation after the tour
Arrange a ride home or nearby accommodation as alcohol sampling is part of the experience.
Local Insights
Wildlife
- Great blue herons along Sarasota Bay
- Osprey soaring near the waterfront
History
Sarasota has a rich arts and cultural history influenced by early 20th century development and the Ringling family legacy.
Conservation
Local efforts focus on protecting the bay's delicate marine ecosystems and promoting sustainable tourism practices.
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Frequently Asked Questions
Recommended Gear
Light Jacket
Keeps you comfortable during cooler evening temperatures.
fall specific
Sunscreen
Protects your skin if you ride earlier before sunset when sun exposure is higher.
summer specific
Reusable Water Bottle
Stay hydrated alongside complimentary drinks throughout your tour.
Camera or Smartphone
Capture stunning sunset views and memorable moments on the trolley.