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Live Music from Hub Chason

Join us at Winslow’s Bungalows 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.

Whether you’re stopping in for a bite, enjoying a cocktail, or gathering with friends, settle in and enjoy live music at one of Key West Historic Inns’ favorite neighborhood destinations.

Location

Winslow’s Bungalows

Date

September 11, 2026

Time

4:00 PM to 6:00 PM

More Events You May Like

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Sep10

Throwback Thursday

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.

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  • Winslow’s Bungalows
  • 11:00 AM to 8:00 PM
Sep10

Live Music from Wavy Davy

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.

  • Learn More
  • Winslow’s Bungalows
  • 4:00 PM to 6:00 PM
bartender at winslows bungalow
Sep10

Bungalow Bar’s Daily Happy Hour

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.

  • Learn More
  • Winslow’s Bungalows
  • 4:00 PM to 6:00 PM
Drums
Sep12

Live Music from Toko Irie

Start your Saturday with the sounds of reggae as Toko Irie performs live at The Bungalow Bar. Known for his smooth rhythms and uplifting island sound, Toko Irie brings an authentic reggae performance to the heart of Old Town, creating the perfect backdrop for a leisurely morning.

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  • Winslow’s Bungalows
  • 9:00 AM to 11:00 AM

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