Captivating Key West Events

Key West Rum Fest celebrates the island's enduring connection to rum, a tradition shaped by its maritime roots and Caribbean influence. Throughout the festival, handcrafted cocktails, live music, local art, and island-wide gatherings come together to capture the vibrant spirit of Key West.

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.

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.

Enjoy Tito's drink specials all day at The Bungalow Bar, located at Winslow's Bungalows. From your first afternoon cocktail to an evening nightcap, discover refreshing Tito's favorites served throughout the day in the heart of Old Town.

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.

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.

Kick off your Friday with live music from Aaron Luka at Isabel's Lighthouse. Blending acoustic favorites with an easygoing island style, Aaron's performances set the tone for a relaxed afternoon in the heart of Old Town.

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.

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.

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.