Recurring

Comfortably Rum, Fridays at Amara Cay 6:30-10:00 PM

Amara Cay Pool Side 80001 Overseas Highway,, islamorada

Comfortably Rum, Fridays at Amara Cay 6:30-10:00 PM 3-piece live band outside by the pool, every Friday from 6:30 to 10pm. Oceanside in Islamorada, MM 80. Great food & drinks on the beach! Classic & alternative rock hits. Free and open to the public.

Free
Recurring

Bill Todd Live

Amara Cay Coastal Lounge 80001 Overseas Highway,, islamorada

Bill Todd @Amara Cay every Monday and Friday 7pm to 11pm in the Coastal Lounge, An eclectic mix of Tropical jazzy Originals and selected covers ,Come for the Music, stay for Dinner.

Free
Recurring

Bill Davidson Solo

Marker 88 88000 Overseas Highway, islamorada

Billy was born and raised in Syracuse, NY. He spent the first dozen years of his carreer playing in various bands touring The Northeast before eventually going solo. In 1990 he relocated to Key Largo with his wife of 43 years, and 23 year old daughter. Billy writes and records his original music (think James

Recurring

Micah & the Barstool Sailors

Florida Keys Brewing Company 81611 Old Hwy,, islamorada

It’s fitting that the passionate Florida singer and songwriter Micah Gardner is based near the Keys town of Islamorada, which is Spanish for “Purple Island.” After all, Micah has made the beautiful, exotic, and mysterious islands of the Keys his musical, spiritual, and lifestyle home for years, and through his signature style of songs called

Recurring

David Feder Bohemian Flamenco

Cheeca Lodge 81806 Overseas Highway, Islamorada

Dave Feder Plays instrumental Romantic Fingerstyle Guitar Music with a Latin Flair. David has a magic way of making you feel like an old friend with songs that are original and intimate.  He is a master guitarist who plays his own intricate Flamenco influenced finger-style music with a laid back island feel.” – NPR “You have a treasure

Recurring

Cliff Jazz

Marker 88 88000 Overseas Highway, islamorada

Solo jazz guitar show - from miles Davis and Charlie Parker to Pat metheny and original featuring Cliff and his 7 string ERB

Recurring

Webb & Davidson

Lorelei Restaurant & Cabana Bar Mile Marker 82, Bayside, islamorada

Billy was born and raised in Syracuse, NY. He spent the first dozen years of his carreer playing in various bands touring The Northeast before eventually going solo. In 1990 he relocated to Key Largo with his wife of 43 years, and 23 year old daughter. Billy writes and records his original music (think James

Recurring

Dave Feder Bohemian Flamenco Live

Marker 88 88000 Overseas Highway, islamorada

Dave Feder Plays instrumental Romantic Fingerstyle Guitar Music with a Latin Flair. David has a magic way of making you feel like an old friend with songs that are original and intimate.  He is a master guitarist who plays his own intricate Flamenco influenced finger-style music with a laid back island feel.” – NPR “You have a treasure

Recurring

Dennis Holmes at The Lorelei

Lorelei Restaurant & Cabana Bar Mile Marker 82, Bayside, islamorada

Acoustic guitar/vocals performing classic rock songs at Lorelei Sunset Cabana Bar

Free
Recurring

Webb & Davidson

Lorelei Restaurant & Cabana Bar Mile Marker 82, Bayside, islamorada

Billy was born and raised in Syracuse, NY. He spent the first dozen years of his carreer playing in various bands touring The Northeast before eventually going solo. In 1990 he relocated to Key Largo with his wife of 43 years, and 23 year old daughter. Billy writes and records his original music (think James