Key West Events Calendar
Good times and good vibes are always on deck. Check out our activities and the local music scene at Ocean Key Resort and Sunset Pier.
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Jul25
Island Experiences
Hemingway Days
Fans of Ernest Hemingway’s literary greatness and vigorous life – including scores of bearded Hemingw...
Date: July 23 - 27, 2026Time: Varies by eventLocation: Key West (Sloppy Joe's Bar, 201 Duval St., and other venues)
Jul25
Island Experiences
Sunset Sails
There is nothing quite like a Key West sunset, and the second-best place to view one (after the Sunset Pier...
Date: May 9, 2026 - July 31, 2026Time: Saturday's, Varies (sunset)Location: Off-Site (Key West waters)
Jul25
Music
Live at Sunset Pier - Meghan Barter
Join us at the Sunset Pier for live music over the water as you enjoy tropical libations and delicious bite...
Date: Saturdays | July 4, 2026 - July 25, 2026Time: 1:00 pm - 4:00 pmLocation: Sunset Pier
Jul25
Music
Live at Sunset Pier - Sunset Blues & Andy Westcott
Join us at the Sunset Pier for waterfront live music, breathtaking sunset views and delicious cocktails and...
Date: Saturdays | July 4, 2026 - July 25, 2026Time: 7:00 pm - 9:00 pmLocation: Sunset Pier
Jul26
Island Experiences
World Class Fishing
The Florida Keys are known for amazing fishing. From the flats and shallows, sight fishing for permit, tarp...
Date: May 10, 2026 - July 31, 2026Time: Sunday's, Varies by charterLocation: Off-Site (Florida Keys waters)
Jul26
Food & Drink
Sunday Brunch
Come experience one of the Island’s best waterfront brunches featuring unlimited traditional Florida ...
Date: May 17, 2026 - July 31, 2026Time: 11:45 am – 12:45 pmLocation: Hot Tin Roof