Oct1–31
All month • Siesta Key
Scarecrow Stroll
Local businesses display handmade scarecrows throughout the island. Walk the route during regular business hours and vote for your favorite online.
2026 things to do on Siesta Key
Siesta Key
events.
From Sunday drum circles and Village music to world-class sand sculpture—find Siesta Key events and a free local ride there and back.
Save the date
Next on
the Key.
These are the next major Siesta Key events currently listed by the Siesta Key Chamber. Pick the event, check the official details, then call us for an easy ride.
Oct30
4–6pm • Siesta Key businesses
Safe Treats
A family-friendly afternoon of trick-or-treating at participating island businesses. No family registration is required.
Nov13–16
Siesta Beach • Ticketed area
Crystal Classic
Four days of world-class sand sculpture, live entertainment and a vendor village. Saturday’s ticketed sculpture area stays open until 9pm.
Nov28
Santa 3–5pm • Parade 5:30pm
Holiday Parade
Visit Santa at the Chamber’s Visitor Center, then watch the annual parade make its way into Siesta Key Village.
Dec12
8–9am • Siesta Beach
Sandy Claws Run
The 50th annual beach run includes a chip-timed 5K and a relaxed one-mile fun run on Siesta’s hard-packed sand.
Checked Sep. 15, 2026: Dates and hours can change. Use each official event link before leaving, then read our latest beach report for same-day weather and Gulf conditions.
The island’s weekly rhythm
Same time.
Great tradition.
SunSunset
Siesta Beach
Sunday
Drum Circle
Hundreds gather with drums, instruments and dance. Arrive 30–60 minutes before sunset for a good spot. Free to attend and free to join.
Siesta Key’s most iconic traditionSun8am–1pm
Siesta Key Village
Farmers
Market
Fresh local produce, baked goods, honey, handmade crafts and live music along Ocean Boulevard. Runs year-round, rain or shine.
The perfect start before the beachThu–SunEvenings
Village bars
Live Music
Nights
SKOB, Daiquiri Deck, Gilligan’s and Beach Club keep the Village active with bands, DJs and dancing throughout the weekend.
Most locations have no coverDailySunset
Crescent Beach
Point of
Rocks
A quieter local favorite for sunset photos, with a rocky shoreline and excellent daytime snorkeling. Bring a towel and stay for the color.
Less crowded than the main beachA year on the Key
Plan by
the season.
Peak season
Art festivals, boat shows, the Sarasota Film Festival and a Village buzzing every night. Book dinner early.
Spring into summer
Spring break winds down, turtle nesting begins in May and Memorial Day launches the summer season.
Local summer
Warm Gulf water, afternoon storms, quieter crowds and spectacular July 4 fireworks over Sarasota Bay.
Perfect weather
Shoulder season begins, Halloween arrives in the Village and restaurants roll out seasonal specials.
Crystal Classic
World-class sculptors turn Siesta’s quartz sand into massive works of art. Tens of thousands attend.
Holiday season
Village decorations, special dinner menus and New Year’s Eve celebrations welcome the returning snowbirds.
Need a ride to the event?
Your ride
there and back.
Don’t stress about parking or driving. We’ll get you there and bring you back—air conditioned, comfortable and hassle-free.
Call 941-600-8380 →Free local rides • Tips appreciated • Available daily