Discover the Sarasota Opera House from the inside out with exclusive access to its private costume vault, a guided tour of the historic hall, and a family-style Mediterranean lunch.

POP UP Experience: Hop onboard the air-conditioned trolley to visit our own Fiorelli Vineyards for wine tasting, live music, and a tour. Learn about the wine made at Fiorelli, sample several of their wines and add on a lunch option to eat while you enjoy the music in the gardens.

Join our talented cast members for an interactive group sing-along tour to your favorite 70’s & 80’s top hits with trivia and a bar stop at 99 Bottles in downtown Sarasota.

Join the Circus Secrets of Venice tour with Bob Collins, exploring Ringling Bros. history and the Historic Train Depot. Proceeds support the Venice Area Historical Society.

Discover the history, landmarks, neighborhoods, natural beauty, and things to do in Venice, Florida on our Venice City Sightseeing Tour! Offered in partnership with Venice Florida Tours guides. Tours depart from the Venice Area Chamber of Commerce.

Experience the world-famous Sarasota sunset on this Tiki cruise! Enjoy 2 hours of scenic beauty along Sarasota’s stunning coastline, capturing unforgettable moments. Book now for an enchanting evening on the water!

Embark on a 2-hour kayak and paddleboard rental adventure! Safe for all ages, they provide equipment and brief lessons. Explore the bay’s calm waters, possibly spotting dolphins and manatees. Experience nature at its finest!

Ready to ride the waves? Learn to surf in Sarasota with their experienced coaches. Enjoy uncrowded breaks and smaller waves ideal for beginners. They ensure safety and fun, providing equipment and flexible scheduling. Dive into the surf adventure today!

Experience the magic of Florida’s mangrove tunnels with their knowledgeable guides. Journey through Little Sarasota Bay for 2 hours, exploring diverse wildlife. Don’t forget your camera for unforgettable encounters with manatees, dolphins, and more.

Discover the captivating history and flavors of Downtown Sarasota on their lunch tour. With a passionate local guide, indulge in culinary delights from 4 top restaurants while soaking in the city’s art and heritage. Join a group or bring a friend for a unique experience!

Discover the convenience of exploring with their 4-seat electric golf cart rental. With premium features, eco-friendly design, and easy charging, it’s the perfect way to navigate your destination. Book now for a seamless adventure!

Experience the magic of Sarasota’s waterways with their Clear Kayak Tour. Paddle through mangroves, spot wildlife like dolphins, and dip into secluded beaches. Perfect for beginners and nature lovers alike. Book your adventure now!

Experience Gulf Water Tours’ Private Sunset Cruise in Sarasota, Florida. Set sail on the tranquil Gulf of Mexico and Sarasota Bay for a picturesque sunset. Enjoy the serene atmosphere, dolphin sightings, and romantic ambiance. Unforgettable moments await.

Enjoy stories of Sarasota’s history, music, jokes, trivia, gorgeous setting sun driving by Lido Beach and a stop for beer and wine at 99 Bottles.

On a tight schedule but want to learn about all the areas that make Sarasota so unique? This tour explores some of the top 10 places in the Sarasota County area.

Sip on free beer & wine while you shop! We’ll also have Gift Certificates, Stocking Stuffers, Raffles, Discounts & a jolly good time!

Join us and hop through history on our annual, week-long celebration of Sarasota County history! History Hop Trolley is brought to you in partnership with the Lemon Bay Historical Society (of Englewood), Venice Area Historical Society, Sarasota County’s Historic Phillippi Creek Estate, and Venice Florida Tours.

Hop aboard our air-conditioned trolley to learn about Sarasota’s distinctive architectural styles. Tours feature Mid-Century Modern, Art Deco, and Mediterranean Revival buildings, homes, and structures.

Come celebrate our anniversary at our customer appreciation event, the annual Trolley Bash! Includes complimentary beer, wine, food, Trolley Cottage Gift Shop discounts and mini-tours.

Hop aboard Dolly the Trolley to enjoy our holiday musical tour – fun for the whole family! Christmas Carol Trolley is a musical, holiday adventure tour featuring your guide, Christmas Carol, and our singing cast members, The Trolley Troubadours. 

A fun, interactive musical adventure for kids of all ages, featuring WitchyPOO and her Pumpkin too!

On this 90-minute interactive tour, solve the mystery of the Circus Queen’s murder in a fun, circus-themed theatrical show aboard the trolley.

An Historical City Trolley Tour led by one of Sarasota’s Founding Women: Mable Ringling, Marie Selby, and Bertha Palmer, as portrayed by actress and guide Kathryn Chesley.

On this classic Sarasota City Sightseeing Tour, learn where to tour, dine, shop or visit! Get an entertaining overview of Sarasota’s rich history, culture, and neighborhoods. Wonderful for visitors and locals alike!

Explore Sarasota’s vibrant public art downtown & neighborhood gallery locations. Hop on, hop off at the art gallery and studio locations. Enjoy free beer/wine before boarding, and at galleries while you browse. Art Crawl with us on select Fridays, January-April.

Hop aboard air-conditioned Dolly The Trolley to discover Sarasota’s best food, flavors, and history with local chef and tour guide.

Grab your girlfriends for a personal shopping experience, visiting local boutiques on each tour offering clothing, accessories & gifts, home décor, or unique vintage finds.

Celebrate Saint Patrick’s Day early! This festive tour leads to one of Sarasota’s lively Irish pubs for beer tasting and music, with jokes, songs, stories, and laughs along the way!

Make someone’s day with a gift certificate from Discover Sarasota Tours!

NEW Valentine’s Tour! Learn about the love stories of Sarasota’s leading couples, and enjoy their favorite love songs. Free champagne/beer/wine before boarding!

Learn about Amish & Mennonite cultures in Sarasota from tour guide Kendra Cross. Stops at Alma Sue’s Quilt Shop, The Carlisle Inn & Der Dutchman Amish Kitchen Cooking Restaurant for a pie shooter.

Hop aboard our air-conditioned trolley to see more than 50 pieces of public art in downtown Sarasota neighborhoods on our Public Art Tour led by painter Jerome Chesley.

Learn about the psychic history of Sarasota with a sound healing immersive experience, a visit to Elysian Fields, and a walk along the labyrinth. Add a tarot card reading to your tour!

Learn about the Circus Secrets of Sarasota by visiting key landmarks and hearing stories of the colorful cast of circus characters, showmen, and performers who called Sarasota home.

Step aboard the trolley for a fun historical musical journey through Sarasota’s eerie past with Lady Melody & Mystery Spirits! Hear stories about haunted buildings, intriguing ghosts, and spirited sightings during this 75-minute, musical Halloween tour.