While much of the country bundles up, Florida’s Gulf Coast comes alive with sunshine and celebration. Winter here means festival season — and there’s something happening almost every weekend.
Here’s a snapshot of just some of the Greater Sarasota area's upcoming events to start your Florida Gulf Coast winter season planning.
For the art lovers: Stroll through streets lined with colorful creations at the St. Armands Circle Winter Art Festival & Sidewalk Sale and the Downtown Sarasota Festival of the Arts, where local, regional, and international artists showcase everything from paintings and sculptures to jewelry and photography.
St. Armands Circle Winter Art Festival & Sidewalk Sale
- Saturday & Sunday | January 24-25, 2026 | 10:00am to 5:00pm
- 1 St. Armands Circle in Sarasota, FL | Free Admission
Downtown Sarasota Festival of the Arts
- Saturday & Sunday | February 7-8, 2026 | 10:00 am to 5:00 pm
- 1718 Main Street in Sarasota, FL | Free Admission
For the indie spirits: Discover the unexpected at the Atomic Holiday Bazaar, a lively market full of handmade and offbeat finds from creative makers. Or, explore the Downtown Sarasota Fine Art and Craft Fair for beautiful, one-of-a-kind pieces that make perfect gifts or keepsakes.
- Saturday & Sunday | December 6-7, 2026
4th Annual Downtown Sarasota Fine Art and Craft Fair
- Saturday & Sunday | March 14-15, 2026 | 10:00 am to 5:00 pm
- 1718 Main Street in Sarasota, FL
For the culture seekers: The Winter Opera Festival, hosted by the renowned Sarasota Opera, brings both well-known classics and rarely performed gems to life in a way only Sarasota can through a series of events. Learn more here.
For the thrill seekers:
Rev your engines at
Thunder by the Bay, where motorcycles, live music, and high-energy entertainment fill the Sarasota Fairgrounds.
- Friday - Sunday | February 12-15, 2026 | 3000 Ringling Blvd. , Sarasota, FL
And for a taste of tradition: Don’t miss the Sarasota Highland Games & Celtic Festival, a celebration of athletic competition, bagpipes, and authentic Celtic fare that will make you feel like you’ve traveled straight to Scotland.
- Saturday | January 31, 2026 | Sarasota Fairgrounds
From art walks to bagpipes, Sarasota’s winter festival season is full of warmth, color, and community — proving that in paradise, winter doesn’t mean slowing down.
Source: Visit Sarasota