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Exclusive Events, Lifelong Memories

At Sugarloaf Hotel, its all about creating memorable experiences. Our on-site events are designed to add excitement to your stay. Dive into the lively scene with live music, themed parties, and more. Discover what's happening during your visit and join the festivities for an unforgettable Florida Keys experience.  

From Seafood Festivals to Music Festivals to Pride Celebrations, there are great events and happening to explore around the lower keys.   Explore local events to help you plan your stay.

 Trivia Night at the Pub

Trivia Night at the Pub

Every Thursday, 6 PM - 8 PM

Get ready to put your knowledge to the test! Join us every Thursday at the Pub for Mania Pub Style Trivia from 6pm to 8pm. Think you know everything? Prove it! Win exciting prizes and enjoy a fun-filled evening of brain teasers and camaraderie.

Live Music at the Pub

Live Music at the Pub

Tuesdays and Saturdays

Experience some of the finest singers and songwriters from the Florida Keys. Our pub is open to everyone, and the music plays from 6pm to 9pm (unless otherwise noted through December).

Enjoy live music every Tuesday from 6pm to 9pm and weekends from 6:30pm to 9:30pm (unless otherwise marked). Get ready for a musical journey you won't want to miss!

US Navy Blue Angels

Southernmost Air Spectacular

March 29 - 20, 2025

Naval Air Station Key West air show featuring the U.S. Navy Flight Demonstration Squadron the Blue Angels.

The show will feature the U.S. Navy Flight Demonstration Team, the Blue Angels, in addition to other talented civilian performers. The maneuvers that the Blue Angels perform are the same fundamental maneuvers that are employed in aerial combat.

Don't miss out on this incredible event with your family and friends. Enjoy spectacular flying, static displays, souvenirs, concessions and more.