From an international sand sculpting competition to powerboat races and world-class sidewalk chalk art festival, visitors to Sarasota can enjoy an array of fall activities
SARASOTA, Fla. This fall brings beautiful weather and an assortment of fun activities and new experiences to Sarasota County. Travelers to the region can now stay in the new St. Regis Longboat Key Resort, celebrate seasonal festivals and enjoy annual favorites such as the Sarasota Chalk Festival and the milestone 40th Annual Sarasota Powerboat Grand Prix.
St. Regis Longboat Key Now Open
Nestled along the sugar-white sands of a Sarasota barrier island, The St. Regis Longboat Key Resort pairs oceanside luxury with an unprecedented level of bespoke hospitality. Now open, Longboat Key will mark the only St. Regis launching in the U.S. this year and the largest development on the island in over 50 years. The resort offers guests a world-class beachside sanctuary spanning across 18 acres complete with 800 feet of private beach, multiple pools and cabanas, a 20,000 square foot oceanfront St. Regis Spa, winding waterway and a one-of-a-kind saltwater lagoon wildlife experience with stingrays and more. The resort is conveniently located near Sarasota Bradenton International Airport and the vibrant St. Armands Circle.
The Florida Highwaymen: Interstate Connections at Marie Selby Botanical Gardens
The Florida Highwaymen: Interstate Connections features beautiful landscapes of the Sunshine State produced by the Highwaymen, a group of African American painters active in Fort Pierce on Florida’s east coast beginning in the mid-1950s. The exhibition celebrates the achievements of these talented artists, while also making connections between their remarkable story and the experience of the African American community in Sarasota in the middle decades of the 20th century. Now-September 15
Endless Summer Menu at EVOQ Sarasota
From the minds of chefs Craig McAvoy and Daniel Revander, EVOQ Sarasota, located at The Westin Sarasota, is offering an Endless Summer menu. For $40 per person, guests will be able to select one appetizer, main course and dessert from a highly curated menu. For $52, guests will be able to enjoy a selected three oz. wine pairing with each dish. These dishes celebrate the spirit of Sarasota and ensure the summer season never truly ends. Now-September 30
40th Annual Sarasota Powerboat Grand Prix
The 40th Annual Sarasota Powerboat Grand Prix begins with a Pit Party in the Van Wezel parking lot, featuring live music, food and plenty of powerboats that will be on display for the general public to enjoy. The weekend will continue when race fans enjoy powerboat races off Lido Beach. Sarasota is the second-longest running US powerboat race, with varying degrees of right turns and a leftward dogleg on the backward stretch. September 13-15
2nd Annual St. Armands Circle Craft Festival
For two days, festival goers to the 2nd Annual St. Armands Circle Craft Festivalwill enjoy works from the state’s best talent of crafters along with the newest names on the contemporary craft scene. September 21-22
Sharktoberfest
Raise a glass with Mote Marine Laboratory & Aquarium during Sharktoberfest, a craft beer festival in the aquarium after hours. The event will feature local and regional breweries that will provide samples of their staple selections alongside unique, seasonal brews. Each guest will receive a commemorative tasting glass for sampling. Sharktoberfest guests will enjoy Mote Aquarium with live entertainment, food stations, merchandise vendors and special experiences provided by Mote’s Education department. October 5
Discover Sarasota’s Haunted Sarasota Tour
Step aboard Discover Sarasota’s Haunted Sarasota trolley tour for a thrilling and historical musical journey through Sarasota’s eerie past with Lady Melody and Mystery Spirits. Hear stories about famous murders, visit spirited buildings and explore unsolved crimes during this adults-only, 75-minute nighttime tour. October 11-18; 20-25; 27-31
Benderson Chase
Benderson Chase is one of the largest fall rowing regattas in the state, attracting hundreds of spectators and bringing together over 1,100 athletes to battle for gold and glory. As the athletes battle for glory, Regatta Island will transform into a vibrant hub of festivities, where you can indulge in a delightful array of culinary delights, explore the bustling vendor village and engage in a variety of games and activities. October 11-13
Discover Sarasota’s The Boomobile
Hop on board Discover Sarasota’s The Boomobile for a fun, family-friendly Halloween part on the trolley. This 45-minute magical tour is led by WitchyPoo, who goes on a delightfully musical hunt for her dear missing Pumpkin all around downtown Sarasota’s historic landmarks. Don’t forget to come dressed up for a chance to win a prize. October 11-12; 18-19; 24-27; 29
Sarasota Water Lantern Festival
The Sarasota Water Lantern Festival is an incredible experience where friends and family will create a magical memory together. This unforgettable evening is filled with food trucks, fun music, activities and thousands of lanterns lighting up the night. October 19
Sarasota Art and Dance Night
Experience glamour and artistry at the Sarasota Art and Dance Night Gala at the Art Ovation Hotel in Downtown Sarasota. The star-studded evening will be graced by reigning Latin Rising Star National Dance Champions Ron Garber and Klaudia Petriti. Additional entertainment will feature professional guest dancers along with singers and entertainment from the Sarasota Opera. In addition, this will be a fully immersive experience for guests including an exclusively curated display of fine art, a premier silent auction, 50/50 raffle, and luxury retail showcases. November 2
International Sarasota Chalk Festival
The International Sarasota Chalk Festival will once again turn the pavement in downtown Sarasota into a “Museum in Motion” as artists create masterpieces and 3D illusions using chalk as their medium and the road surface as their canvas. New this year will be Flower Tapestries, a centuries old art form involving large canvases of flowers, sand and other natural elements. November 8-10
Siesta Key Crystal Classic Sand Sculpture Competition
The 14th annual Siesta Key Crystal Classic returns to Siesta Key. This four-day festival features 24 master sand sculptors competing for prizes in solo and duo categories. Their masterpieces transform Siesta Beach into an outdoor art gallery. The festival also features live music along with a variety of 80-plus shopping, food and drink vendors. November 15-18
Holiday Themed Circus Performance – “A Brave New Wonderland” presented by Nik Wallenda and the Circus Arts Conservatory
Join Nik Wallenda and the Circus Arts Conservatory for an extraordinary holiday spectacle, “A Brave New Wonderland,” under the Circus Arts Conservatory’s holiday-themed Big Top at UTC. “A Brave New Wonderland” will take audiences on a heartwarming and visually stunning journey that brings together the enchantment of the winter holidays and their unique traditions. Tickets go on sale October 1 and performances begin November 18, running through January 5.
Whether it’s a hotel, resort, condo, vacation home, or RV park, Sarasota County provides a variety of accommodation options to suit any travel preference. Visitors can book their getaway at www.visitsarasota.com and check out even more to do on the destination’s events calendar.
About Sarasota County
Situated on Florida’s Gulf Coast, Sarasota County welcomes more than 3 million visitors annually. Within its 725 square miles, the county serves up a diverse menu of cultural and recreational activities and attractions, including award-winning dining, world-class fine arts and performing arts, professional and amateur sports, and the area’s circus heritage. Vacationers can enjoy city life in downtown Sarasota, revisit old Florida in Englewood and Venice, enjoy some of the best beaches in the U.S. on Siesta Key and Longboat Key, or play in North Port’s many parks and waterways. Sarasota County is perhaps best known for its 35 miles of pristine coastline in addition to 6 barrier islands, delivering options for beach getaways that are unrivaled almost anywhere else in the U.S., including Siesta Beach, named the No. 1 beach in Florida, the No. 2 beach in the U.S. and No. 9 in the world in TripAdvisor’s 2024 Travelers’ Choice Awards. To learn more, visit www.visitsarasota.com. Connect via Facebook, YouTube, and Instagram.
