SARASOTA FESTIVALS

Sarasota’s festivals and special destination events draw tens of thousands to world-class entertainment. Interested in the best sand sculpting in the world? What about the best street chalk art that’s absolutely gallery quality? Oh, I know: you’re interested in the huge powerboats racing across the Gulf, 1000s of motorcyclists descending on Sarasota, arts & craft festivals, or the Medieval Fair. Yep, Sarasota offers it.

CHALK FESTIVAL

VENICE

Can you imagine museum quality art using chalk and a traditional black asphalt road? What Sarasota artist Denise Kowal envisioned and launched in 2007 has grown into the most attended International Chalk Festival in the world, attracting 250 artists and 200,000 visitors in 2017 while impacting Sarasota’s local economy by $6-10 million. Paying homage to Sarasota’s circus heritage in 2012 at the annual chalkfest in Burns Court presented stunning street art, live music performances throughout the ten days, street performances including a jaw-dropping high-pole balancing act by Sarasota’s Nik Wallenda and his equally talented wife, Erendira. Though ChalkFest has outgrown Sarasota’s Burns Court, relocating to Venice, it continues to wow audiences with museum-quality street chalk art, attracting more artists, more musicians, more entertainers, more food & drink, and create good family fun.

CRYSTAL CLASSIC INTERNATIONAL SAND SCULPTING FESTIVAL

SIESTA KEY

In 2010, a few artists gathered at Siesta Beach on a November day for what has transformed into an annual destination event attracting thousands of visitors. The good & great have introduced the unfortuante as well. In the early years, teams of two artists created their 10-foot-plus sand masterpieces on the beach with visitors able to admire their talents. With each passing year, event organizers erected fences, taller and further way. Vendors’ tents have enclosed the art venue, admission has increased each year, and a more commercialized atmosphere overtakes the festival. It was bound to happen. To truly appreciate these amazing sand masterpieces, created by talented artists, consider checking in each day. Please don’t just marvel at the finished sculptures. See the masterpiece emerge from a pile of sand, formed level-by-level by the artists themselves who aren’t prima donnas. They arrive to a large pile of sand. What transforms from that pile of sand is 100% their vision, hard work, and God’s blessings for good weather.

GRAND PRIX POWERBOAT FESTIVAL

LIDO KEY

Since 1984, the Annual Grand Prix Powerboat Festival each July attractsa thousands of race fans to the shores of Lido Beach on Lido Key. The Festival attracts the top international racers who race the biggest & loudest powerboats. For 8-10 days, the Festival includes charity golf and fishing tournaments, “Meet & Greet” with the race teams, block party with top local bands,  car & motorcycle show, & July 4th fireworks over Sarasota Bay. Notably, the Grand Prix Powerboat Festival has remained free to the public while all proceeds benefit  the event organizer, Suncoast Charities for Children & its inimitable Director, Luci Nicandri. For all the best reasons, you’ll want to experience this Festival. It’s fun and for the best cause in the world, benefitting children, families, and a struggling support system that appreciates your support and generosity.

MEDIEVAL FAIR

SARASOTA

Who knew that tucked away in the Ringling Woods behind the Sarasota Fairgrounds you’d discover an historical journey back in time to the Middle Ages, comprising kings and queens, knights in shining armor, wizards, jousting, human combat chess matches, rides and games, turkey legs and hearty ales from the English pubs. Enjoy Celtic music and the artisan marketplace with over 100 shops, food and snack booths, Washing Well Wenches, Wheel of Death, the Carillon Stage & the amazing “Cast in Bronze,” and full-armored full-contact jousting tournaments The Medieval Fair appeals to the entire family.  The added & unexpected bonus is the visitors who arrive in period costumes, who interact with the volunteer cast members, and who extend the wonders of the Medieval Fair experience.

SIESTA FIESTA ART FESTIVAL

SIESTA KEY

The Siesta Fiesta Art Show combines with other weekly art shows to attract the best local and out-of-state artists each winter & spring. Some shows feature fine arts. Other shows feature crafts. One artist takes fallen palm tree seed pods to create stunning art that looks like sailboats. Below, you’ll see examples. My guess is that you’ll agree those art pieces would look awesome on your wall.

THUNDER BY THE BAY

SARASOTA

Since 1997, Thunder by the Bay has been an annual party for motorcycle enthusiasts from around the country. Despite muted “thunder” and no “by the Bay” any longer, event organizer Suncoast Charities for Children continues to wow loyal attendees with great live entertainment, a safe, enjoyable venue at its new home at the Sarasota Fairgrounds. This destination event is not a “Hell’s Angels” biker weekend. It’s doctors, lawyers, accountants, teachers, welders, developers, electricians, and people from all walks of life who justify $40,000 for a motorbike. It’s commaderie. It’s motorcyle vendors presenting new accessories.

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MORE TO EXPLORE

BEACHES

BEST OF SARASOTA

7 DAYS TRIP

THINGS TO DO

WATER FUN

CASUAL DINING

EVENTS & FESTIVALS

LIFESTYLE GEAR

TIKI BARS

ROAD TRIPS

FESTIVALS

PLACES TO SEE

14 local beaches you must experience

Sarasota Lifestyle’s Mike Payne shares
top picks

Experience the “best of” the Sarasota area

All ages will love this “to-do” list

Sarasota’s best water fun hotspots

Best casual dining around Sarasota

You’ll bookmark this growing events
calendar

Secret to good beach vibes in frozen
tundra

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BEST one-tank Florida road trips

You MUST experience these festivals

Discover Sarasota’s off-the-beaten path

MORE TO EXPLORE

BEACHES

BEST OF SARASOTA

7 DAYS TRIP

THINGS TO DO

WATER FUN

CASUAL DINING

EVENTS & FESTIVALS

LIFESTYLE GEAR

TIKI BARS

ROAD TRIPS

FESTIVALS

PLACES TO SEE

14 local beaches you must
experience

Sarasota Lifestyle’s Mike Payne
shares top picks

Experience the “best of” the
Sarasota area

All ages will love this “to-do”
list

Sarasota’s best water fun
hotspots

Best casual dining around
Sarasota

You’ll bookmark this growing
events calendar

Secret to good beach vibes in
frozen tundra

8 local bucket list tiki “bars”

BEST one-tank Florida road
trips

You MUST experience these
festivals

Discover Sarasota’s off-the-
beaten path