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.

Raise a glass to the classics every Thursday at The Bungalow Bar. Enjoy $10 classic cocktails all day, featuring timeless favorites served in the relaxed setting of Winslow's Bungalows.

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.

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 each afternoon at Ella's Cottages for a complimentary glass of Roseblood Rosé, offered daily from 3:00 PM to 4:00 PM.

Gather at Ridley House each afternoon for a complimentary glass of our signature Cypress Sangria, thoughtfully crafted in-house and served daily from 3:00 PM to 4:00 PM.

Join us at Isabel's Lighthouse for live music with Hub Chason. Known for his engaging acoustic performances and wide-ranging repertoire, Hub brings an easygoing island sound that's the perfect complement to an afternoon in Old Town.

Spend the afternoon with live music from Wavy Davy at The Bungalow Bar at Winslow's Bungalows. Find a spot by the pool, enjoy a refreshing drink, and let the laid-back sounds of the island carry you through the day.

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.

Think pink and join us for Flocktail Fridays at Isabel's Lighthouse. Wear your favorite pink attire, tag @KeyWestHistoricInns in your social post, and receive 10% off your bar tab from open to close.