Top Sarasota Trolley Tours

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.

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.

Join us on Tuesdays January-April for our NEW Venice, FL Tours! Experience a full day of fun on our 10 AM Venice City Sightseeing Tour or our 1 PM Circus Secrets of Venice tour. Discover the history, landmarks, neighborhoods, natural beauty, and things to do in Venice, FL on the Venice City Sightseeing Tour! Offered in partnership with Venice Florida Tours guides. Tours depart from the Venice Area Chamber of Commerce – 597 S Tamiami Trail, Venice, FL 34285. ALL guests must be ages 10+. Every guest must have a paid ticket in order to board. Tour ticket includes FREE Parking!

This interactive highly entertaining tour is the perfect way to celebrate date night, girls night out, birthdays, 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.

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.

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.

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.

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.

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.

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.

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.