Top Sarasota Trolley Tours

Holiday Music + Light Tour! This beloved holiday tour runs nightly from Dec. 7-23 with live musical performances by professional singers, trivia, jokes, stories, caroling down Main St. and a view of many holiday lights in downtown Sarasota and its neighborhoods. Perfect for the whole family!

Learn about Sarasota’s history of gruesome murders, unexplained happenings, and supernatural events—and immerse yourself in the city’s spooky ambiance—on this haunted trolley tour. Grab a wine or beer, hop aboard the air-conditioned trolley, and set off as your costumed guide regales you with creepy stories. Discover the city’s most supposedly haunted landmarks as you go—and even witness reenactments of macabre past events.

This high energy, highly entertaining tour is the perfect way to celebrate date night, girls night out, birthdays, date night anniversaries or group events. Each tour offers guests the chance to sing their hearts out as a group led by talented singers as we drive by points of interest that relate to the songs' themes. A bar stop mid-way through offers the chance to meet other guests and have fun together. Come in 70'sor 80's costumes for even more of a themed fun tour.

For something different than beaches, discover one of Sarasota's most unique communities on an insider’s tour of Pinecraft, an Amish vacation enclave right on the outskirts of town. Led by a guide with personal connections to the local Amish and Mennonite communities, learn about their roots in Florida, traditional customs, and beliefs. You’ll also have the chance to shop for handmade gifts and sample famous pie at an Amish cafe.

Discover some of the finest examples of Sarasota architecture and design in a comfortable, air-conditioned vehicle on this tour of the city. Hear about styles like Art Deco, Mediterranean Revival, and Mid-Century Modern with the help of your local tour guide. It’s a great experience for locals and tourists alike to learn more about Sarasota.

Combine a trolley ride with drinks and live entertainment on this interactive murder mystery trolley experience in Sarasota. Audience participation encouraged: get into the spirit by donning a circus costume and reading lines from a script, and see if you can help solve the mystery of who killed the circus queen. Includes alcoholic beverages.

Discover the highlights of Venice City, Florida, in comfort and without getting footsore, on this guided morning sightseeing trolley tour. Sit back in air-conditioned comfort as the trolley makes its way around the city, and learn about the city, its neighborhoods, history, landmarks, and things to do from guided commentary onboard.

Guests will begin with an exclusive visit to the state-of-the-art production and rehearsal facilities at the Asolo Repertory Theatre's Robert & Beverly Koski Center to see exactly how stage magic is made. Traveling on Dolly The Trolley to the Van Wezel Performing Arts Hall, guests will step onto the stage where a Van Wezel guide will get to peek behind the curtains to learn about the many hands that create thrilling shows for your enjoyment. You will see the ropes and pulleys that "fly" the scenery on and off the stage, the movable orchestra pit, star dressing room, and loading dock where traveling shows back up their 18-wheelers load into the theater. All the while you'll be dazzled by stories and anecdotes around the colorful world of show business. The final stop is a chance to see improv performance and try out your improv skills at the Florida Studio Theater.

Spend some time appreciating the artistic side of Sarasota during this public art tour. Did you know that there are more than 60 sculptures, murals, and monuments throughout the city? Hop on a trolley, or in a van for smaller groups, and cruise around to view them. Your group will roll through St. Armands Circle and other areas as your guided art expert tells you the history and tales of Sarasota’s art culture.

Sarasota has a history unlike most cities—one that’s embedded with tales of the circus and its special performers. Avoid guidebooks and book this Sarasota Circus Secrets History Tour led by a circus historian. Hear stories and commentary about the city’s performing past and its quirky art and culture scene, including tales of showmen and performers of the circus.

Join a tarot reader to explore a side of Sarasota most tourists don’t get to see. From a sound bath at the Crocker Memorial Church with a sound healer to shopping at the Pixie Dust Metaphysical Boutique, your guide will take you through the city on a comfortable trolley, giving a mini tarot and spirit gallery readings on the way.

Let your local guide, who’s also an actor and songwriter, show you around Sarasota on this cabaret-style tour of the city. Start with free wine or beer in the Trolley Cottage Tiki Bar before setting off in an air-conditioned trolley, with stops at Lido Beach in time for sunset, and Sun King Brewery for some craft beer tasting and a tour.

Hop onboard the air-conditioned trolley with Owner Tammy for a fun trip with singing and wine trivia to visit your own Fiorelli Vineyards for wine tasting, live music, lunch and a tour. Learn about the wine made at Fiorelli, sample 6 of their local wines and add on a lunch option (Caprese Salad, Italian Panini or Charcuterie Board) to eat while you enjoy the music in the gardens. Shop in the gift shop and bring home your favorite wine. Enjoy singing along to wine-inspired songs on the way down and back.

Learn all about Sarasota’s most famous women, including Rose Wilson, Bertha Palmer, and more, on this entertaining group tour, where the guides dress up in period costumes. Easily find your guide and group, then get settled into your air-conditioned vehicle. All the logistics are taken care of, so you just need to show up ready to learn about some influential Sarasota women in a fun way.