Top 10 Likely to Sell Out 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.
Come experience Anna Maria Islands best year round boat tour with Gulf Islands Adventures! With 7+ years in business you are sure to enjoy 2+ hours on the water with our guided Craigcat boat tour. Drive your on Craigcat while following a guide, feeling like a kid the entire trip!
Known For: Sarasota Seasonal, Sarasota Likely to Sell Out, Sarasota Likely To Sell Out, Sarasota Private and Luxury, Sarasota Adventure Tours, Sarasota Water Tours, Sarasota Small Group.
Duration: Around 2 hours.

Destination: Sarasota.
If you've ever wanted to witness the wonder of manatees in their natural habitat, our Manatee Discovery Tour is the perfect choice for you. What sets our activity apart is the opportunity to embark on a kayaking journey specifically designed to encounter these magnificent creatures. Led by our experienced naturalists, our small group guided tours last for 1.5 hours and take place in the AMI/Bradenton area, where manatees are commonly spotted. As you explore the serene waters, keep your eyes peeled for not only manatees, but also dolphins, ospreys, and other local wildlife that may make an appearance. It's an extraordinary experience, so come join us and create memories that will last a lifetime.
Known For: Sarasota Top Product, Sarasota Kayaking Tours, Sarasota Nature and Wildlife Tours, Sarasota On the Water, Sarasota New Product, Sarasota Excellent Quality, Sarasota Best Conversion, Sarasota Likely to Sell Out, Sarasota Wildlife Watching, Sarasota Likely To Sell Out.
Duration: Around 2 hours.

Destination: Sarasota.
The 2 seater CraigCat Catamarans! It’s a unique watercraft that is in a class of its own with its Compact Boats. It’s the world’s finest and only compact power catamaran of its kind on the market. The ergonomic, side-by-side seating and dual-action controls provide an incredible, one of a kind experience you can only get with a CraigCat. When it comes to a sporty runabout vessel, no one does fun like CraigCat.
Known For: Sarasota Extreme Sports, Sarasota Water Tours, Sarasota Likely To Sell Out, Sarasota Top Product, Sarasota Likely to Sell Out, Sarasota New Product, Sarasota Audio Guides, Sarasota Catamaran Cruises , Sarasota Adventure Tours, Sarasota Small Group, Sarasota Excellent Quality.
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.
Step aboard the trolley for a thrilling and historical musical journey through Sarasota’s eerie past with Lady Melody & Mystery Spirits! Hear stories about famous murders, visit spirited buildings, and explore unsolved crimes during this 75-minute, air-conditioned nighttime tour. Haunted Sarasota Tour runs nightly in October. Prizes for best costumes, so come dressed to kill! This is not a scary or paranormal tour. It is a fun, historical ghost tour of haunted buildings in Sarasota! Tour includes complimentary beer or wine for guests 21+ at the Trolley Cottage Tiki Bar before boarding. ALL guests must be 12+. Every guest must have a paid ticket in order to board. FREE Parking! PLEASE NOTE: Video, audio and film recording of any performance by patrons is strictly prohibited.
Known For: Sarasota Private and Luxury, Sarasota Music Tours, Sarasota Likely To Sell Out, Sarasota Ghost Tours, Sarasota Art Tours, Sarasota Trolley Tours , Sarasota Likely to Sell Out, Sarasota Excellent Quality.
Duration: Around 1 hour and a half.

Destination: Sarasota.
The 2nd Annual Art Crawl Trolley tour runs Jan 10, Feb 14, Mar 14, & Apr 11, 2025. Book your boarding time (every 15 min) on one of 3 trolleys that visit 6 art district locations on a 45-min tour route in downtown Sarasota. Arts districts include: Main St. N. Palm, S. Palm, Burns Ct., Towles Ct. & Limelight District. Visit 20+ galleries & studios. This tour includes hop-on/hop-off transportation to all art gallery hub stops. $5 from each ticket will be donated to The Arts & Cultural Alliance of Sarasota County. No guide will offer any tour content but staff & volunteers will direct you to all galleries & tell you about each district. Three trolleys run in rotation every 15 min from 4 PM – 8 PM. If you are unable to catch one of the trolleys back before 7:45 PM, you are welcome to take an Uber or walk back to the Trolley Cottage. Before you board, browse our Trolley Cottage Gift Shop & enjoy complimentary beer/wine. ALL guests must be 21+.
Known For: Sarasota Private and Luxury, Sarasota Street Art Tour, Sarasota Likely To Sell Out, Sarasota Art Tours, Sarasota Trolley Tours , Sarasota Likely to Sell Out, Sarasota Excellent Quality.

Destination: Sarasota.
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!
Known For: Sarasota Cultural Tours, Sarasota Likely to Sell Out, Sarasota Food & Drink, Sarasota Likely To Sell Out, Sarasota Historical Tours, Sarasota Beer & Brewery Tours, Sarasota Trolley Tours .
Duration: Around 2 hours.

Destination: Sarasota.
⭐ Top-Rated Vacation Photoshoots 2025 We’re not just photographers, we’re storytellers capturing your holiday exactly as it feels. With over six years of experience photographing travellers around the world, our small team specialises in authentic, natural photography that truly reflects your trip. In Anna Maria Island, we combine creativity with local knowledge to show you hidden gems, secret angles, and the best light. You’ll not only get beautiful, professional photos but also insider tips to make the most of your time here. We’re proud to be recognised among the top-rated photography tours of 2025, trusted by travellers worldwide for our relaxed style and stunning results.
Known For: Sarasota Photo Shoots, Sarasota Honeymoon Packages, Sarasota Zombie, Sarasota Likely To Sell Out, Sarasota Photography Tours, Sarasota Likely to Sell Out.
Duration: Around 1 hour.