Music and Gatherings Along the Water

Events & Live Entertainment in Waretown for waterfront nights with live music and seasonal marina gatherings

Live music and seasonal waterfront events turn standard restaurant visits into social gatherings where live entertainment anchors the evening beyond the meal itself. Caribbean Pete's schedules live music throughout the season. The entertainment calendar also includes community-focused events like the June 21 Dog Show benefiting All Fur One animal rescue, blending local engagement with the vacation-style atmosphere that defines the marina location.


The waterfront setting amplifies live entertainment, as outdoor acoustics carry music across the bay and seating arrangements allow groups to watch performances while maintaining table conversations. BYOB policies integrate with event nights, where guests bring bottles suited for extended stays and the restaurant handles food service paced around performance timing.


Check the live entertainment schedule online before planning your visit to align your arrival with specific performances or seasonal events along the Waretown waterfront.

Musician singing and playing guitar at Caribbean Pete’s Island Grill
Caribbean Pete’s logo with palm trees, waves, an anchor, and “Key West Outpost” banner
Caribbean Pete’s June live music lineup poster for Key West Outpost, with dates, bands, and times.
Colorful poster for Caribbean Pete's fashion dog show with a dressed-up poodle and event details; June 21, 12 PM.
Tequila tasting and cigars event poster with man in hat, burning cigar, and three tequila bottles