Every event here was checked on the organizer's own site. Tap one to open it.
58 events
Pickle food festival with craft marketplace. Rain or shine.
Wine and blues night on Main Street.
Juried fine art around the Circle, free admission.
Tastings from local chefs plus wine, beer and spirits. Free parking.
Indoor jazz weekend on three stages — John Pizzarelli Trio and Anat Cohen headline. Ticketed.
Outdoor shopping and craft show on the harbor.
Dog-friendly festival for Golden Retriever Rescue of SWFL: dock diving, 100+ vendors, live music.
80+ plant vendors, food trucks and live music. Bring a cart or wagon.
Sixth year: food trucks, craft beer garden, live music and kids' activities.
Holiday lights in the garden. Closed Dec 24, 25 and 31.
Poker run.
SKY Adventures festival with entertainment, vendors, food and a kids zone. Tethered balloon rides are $35 per person, limited and weather dependent (organizer ticket page). Admission price not confirmed — check tickets. Parking is paid. Weather may change balloon timing; rides are not free flights.
6pm. Lit boats from Mandalay Channel around Island Estates, past Coachman Park and Sand Key Bridge to the Beach Marina. Free to watch; free to enter your boat.
6pm. Theme: Stars, Stripes & Santa Lights. Rain date Dec 13. Date from the organizer's event post.
Poker run.
Free family NYE party with rides and games; fireworks finale at 9pm.
Poker run.
Free admission, downtown Main Street.
Three-day waterfront chalk-art festival — 40+ artists, live music Sat & Sun, food trucks, kids zone. Free.
Sailboat racing.
Poker run.
Parking is limited — carpool or rideshare.
10am–5pm both days, free admission.
39th annual — 200+ artists on Main Street, 10am–5pm, free admission.
Poker run — Cass Cay is the waterfront restaurant at Burnt Store Marina.
Free blues and seafood festival. 2027 dates not posted yet — check the city site before going.
IndyCar plus NASCAR Trucks on Saturday.
Free. 250+ artists. Sat 9–6, Sun 10–5.
Sailboat racing.
Poker run.
Sailboat racing.
Multi-day invitational run to the Keys.
17 days — 1,000-ton walk-through sand sculpture exhibit, 8 nights of free beach concerts, fireworks on select Saturdays. Shephard's is the official after-party. Exhibit $16 + tax.
World championship sailboat racing on Tampa Bay.
Free. 250+ juried artists. Sat 9–6, Sun 10–5.
Beach raft-up party off Pine Island.
Ten days of independent film, 200+ films, parties and filmmaker talks.
Big spring sailing regatta on Tampa Bay.
Poker run.
Contemporary art from Tampa Bay and Sarasota artists across several museums.
Round-the-world race stop listed on the yacht club's schedule.
15th annual catch-and-release tarpon tournament benefiting the refuge.
Dragon boat racing — free to watch from shore.
Invitational fly-fishing tournament, dates from the organizer's future calendar.
Save-the-date from the resort.
Two weeks of classical concerts by rising young musicians and faculty.
12pm–2pm. Live music in the garden, included with admission.
8am–2pm. Tropical fruit tastings and plant sale.
6:30pm. Tickets through Live Nation.
Fireworks cruise listed with the Charlotte County Chamber — book ahead.
5pm–10pm. Free; paid BOOM Zone tickets on sale May 2027. Cape Coral Parkway Bridge closes.
9am–5pm. Pine Island's tropical fruit fair — mango contests, growers, live music, art & craft vendors. $5 donation at the gate.
Race World Offshore powerboat racing. Date from the organizer's 2027 schedule.
Race World Offshore powerboat nationals — 200+ mph boats, free beach viewing. Date from the organizer's 2027 schedule.
APBA offshore powerboat racing. Date from the series schedule.
Coffee roasters and local artists. Exact venue on the ticket page.
Tides & fishing, day by day
Live from NOAA and local captains and shops — these change daily, so they have their own pages.