In Key West, there’s always something worth celebrating. Legendary festivals spill onto Duval Street, live music fills the island, and food, art, culture, and a few wonderfully Key West traditions give every season its own reason to visit.
From five historic inns in the heart of Old Town, experience the events that bring the island to life, then come home to a stay with a story of its own.
Buy One, Get One Margaritas & Mojitos
🌴 Bungalow Bar at Winslow’s Bungalows
🌴 Isabel’s at Lighthouse Hotel
Complimentary Pour of Roseblood Rosé.
🌴 Ella's Cottages
Complimentary house made Sangria.
🌴Ridley House
Drink Specials from 4pm - 6pm.
🌴 Isabel's at Lighthouse Hotel
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.
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.
🌴Bungalow Bar at Winslow's Bungalows
Half off wines from 6pm to close.
🌴Winslow's Bungalows
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.
Enjoy $10 Classic Cocktails.
🌴 Bungalow Bar at 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.
Buy One, Get One Margaritas & Mojitos
🌴 Bungalow Bar at Winslow’s Bungalows
🌴 Isabel’s at Lighthouse Hotel
Complimentary Pour of Roseblood Rosé.
🌴 Ella's Cottages
Complimentary house made Sangria.
🌴Ridley House
Drink Specials from 4pm - 6pm.
🌴 Isabel's at Lighthouse Hotel
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.
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.
🌴Bungalow Bar at Winslow's Bungalows
Half off wines from 6pm to close.
🌴Winslow's Bungalows
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.
Enjoy $10 Classic Cocktails.
🌴 Bungalow Bar at 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.
| 16:00 | Sunset Celebration at Mallory Square |
| 15:00 | Paradise, Poured |
| 13:00 | Truman Waterfront Park Thursday Market |
| 11:00 | Throwback Thursday |
| 10:00 | The Studios of Key West |
| 15:00 | Cypress Sangria |
| 16:00 | Bungalow Bar's Daily Happy Hour |
| 16:00 | Live Music from Jamie Sellers |
| 16:00 | Live Music with Sam Carlson |
| 16:00 | Happy Hour at Isabel's |
| 16:00 | Sunset Celebration at Mallory Square |
| 15:00 | Paradise, Poured |
| 10:00 | The Studios of Key West |
| 00:00 | Flocktail Friday |
| 15:00 | Cypress Sangria |
| 16:00 | Bungalow Bar's Daily Happy Hour |
| 16:00 | Live Music from Aaron Luka |
| 16:00 | Live Music from Wavy Davy |
| 16:00 | Happy Hour at Isabel's |
| 16:00 | Sunset Celebration at Mallory Square |
| 15:00 | Paradise, Poured |
| 10:00 | The Studios of Key West |
| 09:00 | Live Music from Toko Irie |
| 09:00 | Live Music from Wichita Jack |
| 14:00 | Live Music from Nina Newton |
| 15:00 | Cypress Sangria |
| 16:00 | Bungalow Bar's Daily Happy Hour |
| 16:00 | Happy Hour at Isabel's |
| 16:00 | Sunset Celebration at Mallory Square |
| 15:00 | Paradise, Poured |
| 10:00 | The Studios of Key West |
| 12:00 | oktoBREWfest Pool Party |
| 15:00 | Cypress Sangria |
| 16:00 | Bungalow Bar's Daily Happy Hour |
| 16:00 | Happy Hour at Isabel's |
| 16:00 | Sunset Celebration at Mallory Square |
| 15:00 | Paradise, Poured |
| 14:00 | Rum, Lime, and Sunshine |
| 15:00 | Cypress Sangria |
| 16:00 | Bungalow Bar's Daily Happy Hour |
| 16:00 | Happy Hour at Isabel's |
| 16:00 | Sunset Celebration at Mallory Square |
| 15:00 | Paradise, Poured |
| 11:00 | From Sunrise to Sunset |
| 10:00 | The Studios of Key West |
| 15:00 | Cypress Sangria |
| 16:00 | Bungalow Bar's Daily Happy Hour |
| 16:00 | Happy Hour at Isabel's |
| 16:00 | Wine Down Wednesday |
| 16:00 | Sunset Celebration at Mallory Square |
| 15:00 | Paradise, Poured |
| 10:00 | The Studios of Key West |
| 15:00 | Cypress Sangria |
| 16:00 | Bungalow Bar's Daily Happy Hour |
| 16:00 | Live Music from Sam Carlson |
| 16:00 | Happy Hour at Isabel's |
| 16:00 | Sunset Celebration at Mallory Square |
| 15:00 | Paradise, Poured |
| 13:00 | Truman Waterfront Park Thursday Market |
| 11:00 | Throwback Thursday |
| 10:00 | The Studios of Key West |
| 15:00 | Cypress Sangria |
| 16:00 | Bungalow Bar's Daily Happy Hour |
| 16:00 | Live Music from Jamie Sellers |
| 16:00 | Live Music with Sam Carlson |
| 16:00 | Happy Hour at Isabel's |
| 16:00 | Sunset Celebration at Mallory Square |
| 15:00 | Paradise, Poured |
| 10:00 | The Studios of Key West |
| 00:00 | Flocktail Friday |
| 15:00 | Cypress Sangria |
| 16:00 | Bungalow Bar's Daily Happy Hour |
| 16:00 | Live Music from Aaron Luka |
| 16:00 | Live Music from Wavy Davy |
| 16:00 | Happy Hour at Isabel's |
| 16:00 | Sunset Celebration at Mallory Square |
| 15:00 | Paradise, Poured |
| 10:00 | The Studios of Key West |
| 09:00 | Live Music from Toko Irie |
| 14:00 | Live Music with Nina Newton |
| 15:00 | Cypress Sangria |
| 16:00 | Bungalow Bar's Daily Happy Hour |
| 16:00 | Happy Hour at Isabel's |
| 16:00 | Sunset Celebration at Mallory Square |
| 15:00 | Paradise, Poured |
| 10:00 | The Studios of Key West |
| 09:00 | Live Music from Gi & Rolando |
| 15:00 | Cypress Sangria |
| 16:00 | Bungalow Bar's Daily Happy Hour |
| 16:00 | Happy Hour at Isabel's |
| 16:00 | Sunset Celebration at Mallory Square |
| 15:00 | Paradise, Poured |
| 14:00 | Rum, Lime, and Sunshine |
| 15:00 | Cypress Sangria |
| 16:00 | Bungalow Bar's Daily Happy Hour |
| 16:00 | Happy Hour at Isabel's |
| 16:00 | Sunset Celebration at Mallory Square |
| 15:00 | Paradise, Poured |
| 11:00 | From Sunrise to Sunset |
| 10:00 | The Studios of Key West |
| 15:00 | Cypress Sangria |
| 16:00 | Bungalow Bar's Daily Happy Hour |
| 16:00 | Happy Hour at Isabel's |
| 16:00 | Wine Down Wednesday |
| 16:00 | Sunset Celebration at Mallory Square |
| 15:00 | Paradise, Poured |
| 10:00 | The Studios of Key West |
| 15:00 | Cypress Sangria |
| 16:00 | Bungalow Bar's Daily Happy Hour |
| 16:00 | Live Music from Sam Carlson |
| 16:00 | Happy Hour at Isabel's |
| 16:00 | Sunset Celebration at Mallory Square |
| 15:00 | Paradise, Poured |
| 13:00 | Truman Waterfront Park Thursday Market |
| 11:00 | Throwback Thursday |
| 10:00 | The Studios of Key West |
| 15:00 | Cypress Sangria |
| 16:00 | Bungalow Bar's Daily Happy Hour |
| 16:00 | Live Music from Jamie Sellers |
| 16:00 | Live Music with Sam Carlson |
| 16:00 | Happy Hour at Isabel's |
| 16:00 | Live Music from Martin Sedlak |
| 16:00 | Sunset Celebration at Mallory Square |
| 15:00 | Paradise, Poured |
| 10:00 | The Studios of Key West |
| 00:00 | Flocktail Friday |
| 00:00 | Fantasy Fest |
| 15:00 | Cypress Sangria |
| 16:00 | Bungalow Bar's Daily Happy Hour |
| 16:00 | Live Music from Wavy Davy |
| 16:00 | Happy Hour at Isabel's |
| 16:00 | Sunset Celebration at Mallory Square |
| 15:00 | Paradise, Poured |
| 10:00 | The Studios of Key West |
| 09:00 | Live Music from Toko Irie |
| 14:00 | Live Music with Nina Newton |
| 15:00 | Cypress Sangria |
| 16:00 | Bungalow Bar's Daily Happy Hour |
| 16:00 | Happy Hour at Isabel's |
| 16:00 | Sunset Celebration at Mallory Square |
| 15:00 | Paradise, Poured |
| 10:00 | Key West Artisan Market: Fantasy Fest Edition |
| 10:00 | The Studios of Key West |
| 00:00 | Goombay Festival Key West |
| 09:00 | Live Music from Martin Sedlak |
| 15:00 | Cypress Sangria |
| 16:00 | Bungalow Bar's Daily Happy Hour |
| 16:00 | Happy Hour at Isabel's |
| 16:00 | Sunset Celebration at Mallory Square |
| 15:00 | Paradise, Poured |
| 14:00 | Rum, Lime, and Sunshine |
| 15:00 | Cypress Sangria |
| 16:00 | Bungalow Bar's Daily Happy Hour |
| 16:00 | Happy Hour at Isabel's |
| 16:00 | Sunset Celebration at Mallory Square |
| 15:00 | Paradise, Poured |
| 12:00 | Greatest Hits Pool Party |
| 11:00 | From Sunrise to Sunset |
| 10:00 | The Studios of Key West |
| 15:00 | Cypress Sangria |
| 16:00 | Bungalow Bar's Daily Happy Hour |
| 16:00 | Happy Hour at Isabel's |
| 16:00 | Wine Down Wednesday |
| 16:00 | Sunset Celebration at Mallory Square |
| 15:00 | Paradise, Poured |
| 10:00 | The Studios of Key West |
| 15:00 | Cypress Sangria |
| 16:00 | Bungalow Bar's Daily Happy Hour |
| 16:00 | Live Music from Sam Carlson |
| 16:00 | Happy Hour at Isabel's |
| 16:00 | Sunset Celebration at Mallory Square |
| 15:00 | Paradise, Poured |
| 13:00 | Truman Waterfront Park Thursday Market |
| 11:00 | Throwback Thursday |
| 10:00 | The Studios of Key West |
| 15:00 | Cypress Sangria |
| 16:00 | Bungalow Bar's Daily Happy Hour |
| 16:00 | Live Music from Jamie Sellers |
| 16:00 | Live Music with Sam Carlson |
| 16:00 | Happy Hour at Isabel's |
| 16:00 | Sunset Celebration at Mallory Square |
| 15:00 | Paradise, Poured |
| 10:00 | The Studios of Key West |
| 00:00 | Flocktail Friday |
| 15:00 | Cypress Sangria |
| 16:00 | Bungalow Bar's Daily Happy Hour |
| 16:00 | Live Music from Aaron Luka |
| 16:00 | Live Music from Wavy Davy |
| 16:00 | Happy Hour at Isabel's |
| 16:00 | Sunset Celebration at Mallory Square |
| 15:00 | Paradise, Poured |
| 10:00 | The Studios of Key West |
| 09:00 | Live Music from Toko Irie |
| 14:00 | Live Music with Nina Newton |
| 15:00 | Cypress Sangria |
| 16:00 | Bungalow Bar's Daily Happy Hour |
| 16:00 | Happy Hour at Isabel's |
| 16:00 | Sunset Celebration at Mallory Square |
| 15:00 | Paradise, Poured |
| 10:00 | The Studios of Key West |
| 09:00 | Live Music from Gi & Rolando |
| 15:00 | Cypress Sangria |
| 16:00 | Bungalow Bar's Daily Happy Hour |
| 16:00 | Happy Hour at Isabel's |
| 16:00 | Sunset Celebration at Mallory Square |
| 15:00 | Paradise, Poured |
| 14:00 | Rum, Lime, and Sunshine |
| 15:00 | Cypress Sangria |
| 16:00 | Bungalow Bar's Daily Happy Hour |
| 16:00 | Happy Hour at Isabel's |
| 16:00 | Sunset Celebration at Mallory Square |
| 15:00 | Paradise, Poured |
| 11:00 | From Sunrise to Sunset |
| 10:00 | The Studios of Key West |
| 15:00 | Cypress Sangria |
| 16:00 | Bungalow Bar's Daily Happy Hour |
| 16:00 | Happy Hour at Isabel's |
| 16:00 | Wine Down Wednesday |
| 16:00 | Sunset Celebration at Mallory Square |
| 15:00 | Paradise, Poured |
| 12:00 | Trop Rock'N Duval - Mick Fury |
| 10:00 | The Studios of Key West |
| 15:00 | Cypress Sangria |
| 16:00 | Bungalow Bar's Daily Happy Hour |
| 16:00 | Happy Hour at Isabel's |
| 16:00 | Sunset Celebration at Mallory Square |
| 15:00 | Paradise, Poured |
| 14:00 | Trop Rock'N Duval -Reggie Starrett |
| 13:00 | Truman Waterfront Park Thursday Market |
| 11:00 | Throwback Thursday |
| 10:00 | The Studios of Key West |
| 15:00 | Cypress Sangria |
| 16:00 | Bungalow Bar's Daily Happy Hour |
| 16:00 | Live Music with Sam Carlson |
| 16:00 | Happy Hour at Isabel's |
| 16:00 | Sunset Celebration at Mallory Square |
| 15:00 | Paradise, Poured |
| 10:00 | The Studios of Key West |
| 00:00 | Flocktail Friday |
| 14:00 | Trop Rock'N Duval - Ricky Lamb |
| 15:00 | Cypress Sangria |
| 16:00 | Bungalow Bar's Daily Happy Hour |
| 16:00 | Happy Hour at Isabel's |
| 16:00 | Trop Rock'N Duval - Dave Freeman & Friends |
| 16:00 | Sunset Celebration at Mallory Square |
| 15:00 | Paradise, Poured |
| 10:00 | The Studios of Key West |
| 09:00 | Live Music from Toko Irie |
| 09:00 | Live Music from Wichita Jack |
| 14:00 | Live Music from Nina Newton |
| 15:00 | Cypress Sangria |
| 16:00 | Bungalow Bar's Daily Happy Hour |
| 16:00 | Happy Hour at Isabel's |
