Top 10 Trolley Tours in Sarasota

Destination: Sarasota.
Actress and tour guide Kathryn Chesley specializes in donning period costumes and portraying Sarasota's most influential women -- Mable Ringling, Marie Selby, and Bertha Palmer -- and telling the story of the Sarasota and how each of these women and their unique contributions helped to make the city what it is today. The past comes to life in an informative and entertaining way on this historical 90-minute city trolley tour led by costumed guide, Kathryn Chesley, as she plays the parts of Mable Ringling (wife of John Ringling), Marie Selby (wife of William Selby and Philanthropist), or Bertha Palmer (Rancher and Developer) on alternating tours. Find out what Sarasota was like 100 years ago through the eyes of each of these impactful women during the time they lived here. See the historical places in Sarasota and learn about its key development. Each week’s air-conditioned tour features a different leading lady founder and focuses on her unique contributions to Sarasota.
Known For: Sarasota Cultural Tours, Sarasota Private and Luxury, Sarasota Likely To Sell Out, Sarasota Likely to Sell Out, Sarasota Trolley Tours , Sarasota Historical Tours.
Duration: Around 1 hour and a half.

Destination: Sarasota.
Discover Circus City USA’s secret places and charming stories on this unforgettable tour! It is a tour of the circus history in Sarasota and provides a wonderful historical perspective of the impact the circus has had in our area. Stop by circus landmarks with your engaging tour guide, Bob Collins (former marketing executive for Ringling Bros. and Barnum & Bailey Circus), who tells stories about the colorful cast of circus characters, showmen, and performers who called Sarasota home. Meander through historic neighborhoods such as Indian Beach, Payne Park, and Downtown’s Main Street to learn about the rich history of Ringling Bros. and Barnum & Bailey, which moved its Winter Quarters to Sarasota in 1927. Explore several remaining sites intimately involved in Sarasota’s circus history including John Ringling’s private rail car “Jomar,” the Little People’s Houses and many more circus “secrets” hidden in plain sight! This 90-minute tour is a fun-filled adventure in Circus City USA!
Known For: Sarasota Private and Luxury, Sarasota Excellent Quality, Sarasota Trolley Tours , Sarasota Historical Tours, Sarasota Cultural Tours.
Duration: Around 1 hour and a half.

Destination: Sarasota.
Get in touch with Sarasota’s metaphysical community on this interesting 90 minute “energy” tour. Learn why Sarasota is considered a psychic and spiritual energy center, sometimes called “Sedona by the Sea”. Join psychic and tarot reader, Deni Dreazen on a metaphysical exploration trolley tour of Sarasota. Visit Pixie Dust Gift Shop, experience a sound healing at the Crocker Memorial Church with sound healer, Kaylene McCaw, and then walk the labyrinth. Along the way, experience mini tarot and spirit gallery readings. Explore the tools psychics and mediums use and hear about the history of the tarot. You can also book a 15-minute personal tarot reading at the cottage after the tour. Each 15-minute reading is $30. Only 4 readings are available per tour, so book early! Just select Adult + Tarot Reading on the booking form when you reserve your tour. Ages 18+. Limited to 20 guests. Tour ticket includes FREE Parking! Includes complimentary orange or pineapple mimosas before the tour.
Known For: Sarasota Trolley Tours , Sarasota Private and Luxury, Sarasota Excellent Quality, Sarasota Cultural Tours.
Duration: Around 2 hours.

Destination: Sarasota.
Sarasota is home to an amazing architectural legacy. On this 105-minute air-conditioned tour, guests will visit some outstanding examples of architecture and design, with tours featuring three of the city’s most distinctive styles: Art Deco, Mediterranean Revival, and Mid-Century Modern (featuring the "Sarasota School" of architecture, a regional adaptation of 20th-century International Style modernism that flourished in Florida from the 1940s to the 1960s.) These tours sell out weekly so book early!
Known For: Sarasota Likely to Sell Out, Sarasota Likely To Sell Out, Sarasota Private and Luxury, Sarasota Historical Tours, Sarasota Excellent Quality, Sarasota Architecture Tours, Sarasota Trolley Tours .
Duration: Around 1 hour and a half.

Destination: Sarasota.
Visit the only place in the world that the Amish and Mennonite communities come to vacation en masse and learn about their culture with your tour guide. On this tour, the goal is to create a “bridge of understanding” about these wonderfully unique and close-knit communities. You will learn about the history of their religious beliefs, values, traditions and practices of daily life. Visit Pinecraft, where 500+ Amish and Mennonite families live year-round and where 5,000+ return each season from Ohio, Pennsylvania and Indiana to vacation. Enjoy stops at Alma Sue’s Quilt Shop, The Carlisle Inn and Der Dutchman for shopping and a delicious pie shooter! Gain a new appreciation of the rich culture on this Tripadvisor Certificate of Excellence-rated tour. *During April there may be variations of the tour because typically many of our Amish tourists have returned home, therefore we may visit a local Amish furniture maker to learn about carpentry and its importance to their culture.
Known For: Sarasota Cultural Tours, Sarasota Excellent Quality, Sarasota Trolley Tours , Sarasota Historical Tours, Sarasota Likely to Sell Out, Sarasota Private and Luxury, Sarasota Likely To Sell Out.
Duration: Around 2 hours.

Destination: Sarasota.
Sarasota has an outstanding collection of public art pieces. On this 90-minute tour aboard our enclosed, air-conditioned trolley, visit more than 50 of the city’s public art sculptures, monuments, and murals in charming neighborhoods and downtown Sarasota. Your guide, painter and public art expert Jerome Chesley, helps you see the city through new eyes!
Known For: Sarasota Architecture Tours, Sarasota Trolley Tours , Sarasota Street Art Tour, Sarasota Private and Luxury, Sarasota Art Tours, Sarasota Excellent Quality.
Duration: Around 1 hour and a half.

Destination: Sarasota.
Sarasota's BEST City Sightseeing Tour, a wonderful way to learn where to eat, shop and visit, and about Sarasota's interesting past, whether you are a longtime resident, a newcomer, or a visitor. Guests will travel in our air-conditioned trolley.
Known For: Sarasota Historical Tours, Sarasota Private and Luxury, Sarasota Trolley Tours , Sarasota Cultural Tours, Sarasota Top Product.
Duration: Around 1 hour and a half.

Destination: Sarasota.
Fun, interactive murder mystery theater on the trolley! Someone has murdered the Circus Queen...and suspects abound among the circus folk on board. Everyone seems to have a motive. Wear a circus costume if you wish, find yourself among the suspects, and help our sleuths to solve the mystery! There is no acting. You are only reading lines in a script for speaking parts or wearing a prop for non-speaking roles. In order for the show to work we highly encourage guests to participate- it’s easy and very fun! Our roles are cast in advance, so please contact us Please arrive at least 30 minutes before the tour leaves. 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.
Known For: Sarasota Trolley Tours , Sarasota Private and Luxury, Sarasota Crime Tours, Sarasota Excellent Quality.
Duration: Around 1 hour and a half.
Normal Price: 91.58 USD.
Current Price: 82.42 USD.

Destination: Sarasota.
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.
Known For: Sarasota New Product, Sarasota Art Tours, Sarasota Private and Luxury, Sarasota Hop on Hop Off Buses, Sarasota Music Tours, Sarasota Food & Drink, Sarasota Trolley Tours , Sarasota Wine Tours, Sarasota Wine Tastings, Sarasota Beer & Brewery Tours.
Duration: Around 1 hour and a half.
Normal Price: 79.32 USD.
Current Price: 71.38 USD.

Destination: Sarasota.
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!
Known For: Sarasota Trolley Tours , Sarasota New Product, Sarasota Private and Luxury, Sarasota Cultural Tours, Sarasota Historical Tours.
Duration: Around 1 hour and a half.