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.

While the sun-soaked shores of Siesta Key draw in visitors, don’t forget that Sarasota’s city streets are just as warm and welcoming. Discover this city’s many art galleries, boutique shops, and cozy restaurants while you play this app-based scavenger hunt. Roam around the city in search of items, complete challenges, and answer trivia questions to earn points. Each player has a unique role, so everyone can complete their own interactive challenges.

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.

On this self-guided bicycle tour, you’ll discover how an unlikely cast of characters – from a Fig Newton millionaire, to platform divers who dodged sharks – transformed a barrier island into a beloved community. You’ll encounter the island’s famous “mosquito jail” – a 1927 lockup with barred windows but no glass, where biting insects proved more effective than bars at deterring crime. You’ll pedal past the Roser Memorial Church, built by Charles Roser, who created the Fig Newton cookie and the process to make it then sold his creation Nabisco for a million dollars in 1890 Along the way, you’ll learn about the making of Hollywood’s 1948 film On an Island With You, and explore Bean Point where the island’s first homesteader settled in 1892. You’ll also ride past sites devastated by 2024’s hurricanes and discover how this community of 1,000 residents rallied to rebuild.

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.

Guided walking tour of Sarasota's downtown food scene. Learn about the history of downtown Sarasota from a local guide. Sample enough local delights that you won't need that dinner reservation! See a different side of Sarasota as you traverse the streets and make new friends along the way.

Discover the charming allure of St. Armands Circle, once owned by circus magnate John Ringling, on this engaging afternoon tour. Delight in a unique blend of shopping and tasting experiences as you browse stylish boutiques while sampling gourmet tea and olive oil. Enjoy a Mediterranean-inspired sampler plate paired with a glass of bubbles, and explore a luxury art and gift boutique with another glass in hand. Conclude your day with a personal shopping experience or visit the enchanting St. Armands Magical Garden, topped off with a sweet treat to savor the day. - Explore locally-owned shops and boutiques on historic St. Armands Circle - Enjoy a Mediterranean-inspired tasting platter and bubbly - Participate in tea and olive oil sampling for a culinary experience - End with a visit to the St. Armands Magical Garden or personal shopping time

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.

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.

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.

Craft a personalized itinerary or rely on the expertise of your captain to showcase the best of Sarasota and its surroundings. Destinations may include iconic landmarks, secluded islands, and popular waterfront attractions. Heading North you can visit Egmont Key or Passage Key in Tampa Bay or heading South there is Venice Island, Stump Pass or Boca Grande.

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.

What makes this sunset cruise truly unique is the unparalleled combination of natural beauty and effortless relaxation, offering more than just a view, but an immersive experience. As the sun dips below the horizon, you're not simply watching a sunset; you're enveloped in the tranquil waters of the Gulf and Sarasota Bay, witnessing the dynamic interplay of vibrant colors reflecting off the water against the breathtaking backdrop of the Sarasota skyline and nearby keys. Beyond the stunning visuals, our comfortable boat, with its ample seating, provides a truly laid-back and intimate environment, perfect for unwinding whether you’re seeking a romantic escape or quality time with loved ones. Adding to this special journey is the potential for magical encounters with playful dolphins in their natural habitat, turning a beautiful evening into an unforgettable moment of wonder.

What makes this Sarasota Restaurant/Pub Dock Hop truly unique is its seamless blend of culinary exploration and scenic cruising directly along the intracoastal waterways. Unlike traditional dining experiences, you'll embark on a delectable journey by boat, effortlessly hopping between a diverse array of waterfront restaurants, casual beachside eateries, upscale establishments, and vibrant tiki bars – all accessible directly from the water. The breathtaking cruise itself becomes an integral part of the adventure, offering stunning views of the Sarasota coastline, nearby islands, and the chance to witness a spectacular sunset as you navigate between stops. Adding to its distinctiveness, the tour is entirely customizable, allowing your group to tailor the duration and number of stops to your preferences, ensuring a perfectly paced and personalized libation and culinary exploration.