Captivating Key West Events

The Studios of Key West is a historic Old Town arts center offering sunset rooftop happy hours, rotating art exhibitions, performances, film screenings, workshops, and unique spaces for meetings and events bringing together local and visitors in an inspired island setting.

Kick off your Key West experience with live music during your stay at Winslow’s Bungalows and Lighthouse Hotel, where we spotlight the local talent that brings the island to life. All Key West Historic Inns guests are warmly invited to join us.

Kick back Key West style — where chilled Twisted Tea canned cocktails meet unbeatable island vibes. The perfect afternoon pick-me-up served daily in our Breakfast Room at Ella's Cottages.

Classic, delightful lemonade with a twist! Gather around the retro bar cart in our lobby daily for a crisp lemonade and a floater of locally-made Wreckers Vodka by Key West Trading Co. at The Fitch Lodge.

Join us for a refreshing twist on relaxation with our bottomless build-your-own sangria bar. Bask in the sun, take in the poolside vibes and sip on a chilled libation daily under our gazebo at Ridley House.

A nightly festival and community tradition held right on the waterfront at Mallory Square. Every evening, locals and visitors gather to watch the sun sink into the Gulf of Mexico while soaking up a lively arts-festival atmosphere.

Sip, relax and unwind with drink specials served daily at Bungalow Bar at Winslow's Bungalow's.

Join us for a daily local favorite with half off select libations from 4–5 PM.

Sip, relax and unwind with drink specials served daily at Isabel's at Lighthouse Hotel.

Join us for a daily local favorite with half off select libations from 4–5 PM.

The Key West Artisan Market is held select Sundays from November through April at Higgs Beach, featuring local artisans, fresh food, enjoy live entertainment, and experience rotating weekly themes celebrating island life and local charities.

Key West Farmers Market brings local vendors together every Thursday from 1–6 PM at Truman Waterfront Park, featuring fresh produce, artisan foods, native plants, handmade goods, and local crafts. A perfect way to shop by the sea and experience the island community.

Stroll into Key West’s creative side at Walk on White, a lively monthly art walk in the White Street Gallery District. On the third Thursday of each month galleries stay open late, and artists provide complimentary sips along the way.

Savor a Taste of Key West, a waterfront fundraising event featuring leading local chefs, restaurants, and beverage partners for a night of culinary island magic in the Gulf breeze.