Top Sarasota Historical Tours

Discover the best of Sarasota, Florida as you embark on a sightseeing tour of the city. Climb aboard your air-conditioned vehicle and see several points of interest including the Ringling Museum and College, Selby Library, and the Sarasota Opera House. While you ride, learn about the vibrant history and culture of the city from your guide.

The Greatest Show on Wheels! Our tour guide, circus historian Bob Collins, has loads of great stories about how the Big Top helped to shape Sarasota's quirky arts and culture scene. Tours with fewer than 10 guests will travel in our air-conditioned 9-passenger van.

Cover more ground than walking tours while exploring much of central Sarasota on this 3-hour Segway tour. After meeting on the Boulevard of the Arts, follow your guide from historic downtown to the bayfront and eventually through St. Armand’s Circle and Lido Beach. Check out panoramic views of the city and bay from Island Park before heading back to the departure point.

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.

Our tours are unique because our guides love what they do, to share the beauty and highlights of Sarasota. They've lived in the area since they were born, or enough years to be considered a native. You'll have fun on this tour. Our guides are selected not just for their knowledge, but their personality. You'll find this private tour to be a great opportunity to learn, enjoy and maybe even make a new friend. We welcome you to join us and find out for yourself!

Increase your chances of spotting manatees and dolphins during an eco-friendly kayak tour of the Lido Key in Sarasota. Ideal for lovers of nature and wildlife, this experience lets you escape the crowds on land and is suitable for both beginner and advanced paddlers. Plus, traveling in a non-motorized vessel means you’re less likely to scare away animals.

Immerse yourself in Sarasota's coastal mangrove forests, look out for dolphins and manatees, and practice your kayaking or stand-up paddleboarding skills on this immersive, small-group tour. After departing from Ted Sperling Nature Park, you'll paddle out on Sarasota Bay and can practice with your equipment. Then, head into the mangrove tunnels for your best chance to see local marine life.

Enjoy one of Florida's best beaches at sunset on an electric bike tour. With 5-level pedal assist and an on-demand throttle, the electric bike allows you to put in as much or as little effort as you want as you ride along Siesta Key. All experience levels are welcome. Booking in advance ensures you won't miss out on this small-group tour.

Discover the delectable highlights of Sarasota's thriving dining scene on this small-group, dinnertime tasting tour. Meet your guide in central Sarasota, and come with an appetite: you'll visit up to five local restaurants, and will enjoy enough samples to add up to a generous meal (alcoholic drinks additional expense). As you go, soak up the convivial atmosphere, and learn more about Sarasota's unique culture and culinary offerings.

Discover the best that Sarasota has to offer and see the city at its most photogenic on this sunset tour. Explore historic downtown neighborhoods and see top points of interest including the Ringling Museum, Selby Library and Gardens, and the Sarasota Opera House. End your tour by watching a beautiful sunset on Sarasota Bay and a better understanding of the coastal city.

All tours are private, and we offer many options to customize each experience. This tour can be combined with a sunset cruise. Extended hours may be available if arranged in advance.

Tour guide Seamus (aka Steve McAllister) will regale you with Irish jokes, songs, and stories, along with the history of Sarasota's Irish pubs, and lead a sing-along at an Irish Pub. Tours with fewer than 10 guests will travel in our air-conditioned 9-passenger van.

Actress and tour guide Kathryn Chesley specializes in donning period costumes and portraying Sarasota's most influential women -- Mable Ringling, Rose Wilson, 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.

Hop onboard our fun-filled Sarasota trivia tour, with local performer and guide Steve McAllister. Show off your love of Sarasota trivia, win bar and restaurant gift certificates during trivia games and sing along to your favorite Florida-inspired songs during the 90-minute air-conditioned tour. Enjoy a stop at the Bahi Hut, the oldest tiki bar in Sarasota, for samples of their world-famous Polynesian cocktails that are sure to spice up your night. Includes free beer or wine at the Trolley Cottage Tiki Bar before boarding.