Captivating Key West Events

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.

Ease into the island’s rhythm with live jazz and folk music woven into your stay. Sip tropical cocktails and enjoy local musicians next to the pool in true Key West style.

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.

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.

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 America while soaking up a lively arts-festival atmosphere.

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

Join us for an extended daily local favorite with half off select libations from 4 – 6 PM.

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

Join us for an extended daily local favorite with half off select libations from 4 – 6 PM.

Ease into the island’s rhythm with live music woven into your stay. Sip tropical cocktails and enjoy local musicians next to the pool in true Key West style.

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.

Ease into the island’s rhythm with live music woven into your stay. Sip tropical cocktails and enjoy local musicians next to the pool in true Key West style.