Top Sarasota Historical Tours

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 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.

Hop aboard Discover Sarasota Tours’ air-conditioned Dolly the Trolley for our Sunset Cabaret music and craft beer tour with local tour guide, actor, songwriter and raconteur Steve McAllister. This engaging tour kicks off with free wine/beer in the Trolley Cottage Tiki Bar, and then heads on a two-hour adventure. The tour includes stops at Lido Beach timed for the amazing view of the setting sun over the gulf and at Sun King Brewery in the Limelight District for craft beer samples and a mini-tour. Enjoy entertaining tales about Sarasota’s colorful history, seasoned with cabaret-style songs, jokes, city history and trivia along the way. This tour is fun for visitors or locals alike! You’re sure to learn something about Sarasota, even if you’ve lived here all your life. Complimentary beer or wine for guests 21+ at the Trolley Cottage Tiki Bar before boarding! Tour ticket includes FREE Parking!

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.

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!

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.

Let’s Roam is the #1 app-led scavenger hunt company. Walk to all the best landmarks and hidden gems, answering trivia questions and solving challenges. Work with your team or compete against them, as you learn new facts and create memorable experiences. Let’s Roam Scavenger Hunts are great as an everyday activity, or for bachelorette parties, birthday parties, corporate team building events and more! Each player chooses an interactive role, with challenges varying by person.

Join us on a spooky and fascinating journey through this city’s haunted history! You'll visit historic sites like the Palmetto Historical Park, the Great Chime Bell, the Riverside Bed & Breakfast, and the J.A. Lamb House. Along the way, you'll learn about the legends and folklore of the area and use equipment like spirit boxes to detect paranormal activity. Led by an experienced and passionate guide, the tour takes you through the city's dark history and shares stories of ghosts, spirits, and other supernatural beings that still roam the streets. Who knows? You might even meet Pistol Pete! What's Included: A brief history of the city Ghost hunting equipment Instructions on how to find ghosts What's Not Included: Bottled water Gratuities are not required but always appreciated Important You must be able to walk 1-2 miles at a leisurely pace to participate. All ages.