Clearwater Jazz Holiday anchors one of the busiest live music weekends of the fall, running all three days at Coachman Park with a headliner list that includes Arturo Sandoval, Sheila E. & The E-Train, Larkin Poe, Big Sam’s Funky Nation, Dumpstaphunk Plays Sly, and The Wood Brothers. Grab a blanket, claim a spot on the grass, and settle in.
Beyond Clearwater, the weekend spreads across the coast. Rumours of Fleetwood Mac plays Van Wezel on Saturday and Ruth Eckerd Hall on Sunday. Free Fallin: The Tom Petty Concert Experience hits Bonita Springs on Sunday, and The Concert: A Tribute to ABBA closes things out at Van Wezel that same night. One note for planners: The Living Tombstone’s Friday show at The RITZ Ybor in Tampa was already sold out as of October 13, so skip that drive unless you have a ticket.
The rest of the schedule runs from Tampa through Bradenton, Cortez, Sarasota, Venice/Nokomis, North Port–Wellen Park, and down to Bonita Springs and Naples, with blues, reggae, dueling pianos, and waterfront sets filling in the gaps. Listings were checked October 13, and venues advise confirming lineups, times, admissions, and weather plans before traveling. So which night are you claiming, Friday, Saturday, or Sunday?
