Road trip · Gulf Coast
Gulf Coast events
Festivals, concerts and markets in Boca Grande, Clearwater and Tampa.
20 events
Suncoast Jazz Festival (36th)
Nov 20–22 · Time TBA — check the organizer
Sheraton Sand Key Resort · Clearwater
The Grande Chorus performances
Dec 11 & 12, 2026 · Time TBA — check the organizer
Boca Grande, Boca Grande · Boca Grande
Holiday Lighted Boat Parade (52nd)
Dec 12 · Time TBA — check the organizer
Clearwater Beach Marina (judging area) · Clearwater
Sunset to Sparkle — New Year's Eve on Pier 60
Dec 31 · Time TBA — check the organizer
Pier 60, Clearwater Beach · Clearwater
Back to Boca Bash!
Thu, Jan 7, 2027 · Time TBA — check the organizer
Boca Grande, Boca Grande · Boca Grande
Chalk the Bay Art & Music Festival
Jan 15–17 · Time TBA — check the organizer
Coachman Park, downtown Clearwater · Clearwater
DIYC Commodore's Cup Regatta
Jan 16–17 · Time TBA — check the organizer
Davis Island Yacht Club, Hillsborough Bay · Tampa
Boca Grande Live: Classical Unbuttoned with Julian Gargiulo
Tue, Jan 19, 2027 · Time TBA — check the organizer
Boca Grande, Boca Grande · Boca Grande
Gasparilla Pirate Fest & Parade of Pirates
Jan 30 · Time TBA — check the organizer
Bayshore Blvd & Tampa Riverwalk · Tampa
Florida State Fair
Feb 4–15 · Time TBA — check the organizer
Florida State Fairgrounds, 4800 US-301 N · Tampa
The Grande Chorus performances
Feb 19 & 20, 2027 · Time TBA — check the organizer
Boca Grande, Boca Grande · Boca Grande
Art on Park
Feb 20–21, 2027 · 10:00 am–5:00 pm
Park Ave, downtown, Boca Grande · Boca Grande
Clearwater Sea-Blues Festival
Dates TBC (2026 was Feb 28–Mar 1) · Time TBA — check the organizer
Coachman Park, downtown Clearwater · Clearwater
Gasparilla Festival of the Arts
Mar 6–7 · Time TBA — check the organizer
Julian B. Lane Riverfront Park · Tampa
Pier 60 Sugar Sand Festival
Mar 26 – Apr 11 · Time TBA — check the organizer
Pier 60 · Clearwater
The Grande Chorus performances
Apr 16 & 17, 2027 · Time TBA — check the organizer
Boca Grande, Boca Grande · Boca Grande
Suncoast Race Week
Apr 24–25 · Time TBA — check the organizer
Tampa Bay (DIYC & SPYC) · Tampa
Stick Figure — Enjoy the Ride Tour
Jul 3 · Time TBA — check the organizer
MIDFLORIDA Credit Union Amphitheatre, Tampa · Tampa
Clearwater Beach Offshore Grand Prix
Sep 24–26 · Time TBA — check the organizer
Clearwater Beach (watch from Pier 60 north) · Clearwater
Tampa Bay Coffee & Art Festival (Fall)
Oct 23–24 · Time TBA — check the organizer
North, Tampa · Tampa
Dates checked against organizer pages; confirm before you go. The trip planner reads these same events.