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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.
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.
Book with Discover Sarasota Tours
Verified experiences and guided adventures in the surrounding area.
Operated by Discover Sarasota Tours · Sarasota, Florida
Discover Sarasota from a unique perspective with the Sip & Stroll private trolley experience offered by Discover Sarasota Tours. This enchanting evening tour combines the charm of a comfortable, air-conditioned trolley ride with the excitement of sampling craft beers at Sun King Sarasota brewery. As you cruise through the city during sunset, you'll enjoy stunning views paired with lively cabaret performances and engaging trivia that reveal fascinating stories about Sarasota's history and culture. The complimentary drinks served onboard add a delightful touch, ensuring you stay refreshed while soaking in the beautiful Florida sky. Perfect for groups and individuals who appreciate casual entertainment mixed with a touch of local flavor, the Sip & Stroll promises a relaxed yet memorable adventure. Whether you're a first-time visitor or a local looking for fresh ways to explore Sarasota, this guided trolley tour offers an ideal blend of sightseeing, socializing, and craft beer tasting all in one charming package. The tour’s relaxed pace means it’s suitable for nearly all ages and fitness levels, making it an inclusive experience worth booking.
easy.
2–3 hours.
Suitable for all fitness levels; the trolley provides a seated experience with minimal physical effort.
Yes, the Sip & Stroll is family-friendly, but alcoholic drinks are only for guests 21 and over.
Complimentary drinks, including craft beer tastings, are included on the tour.
Transportation is not included, so plan to arrive at the departure location independently.
Outside beverages are not allowed, but the tour provides complimentary drinks.
Cancellations made 24 hours before the tour receive a full refund; shorter notice may incur fees.
Pets are not permitted on the trolley except for certified service animals.
Sarasota has a rich arts and cultural history influenced by early 20th century development and the Ringling family legacy.
Local efforts focus on protecting the bay's delicate marine ecosystems and promoting sustainable tourism practices.
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.
Book with Discover Sarasota Tours