Dec 08, 2018 - Dec 16, 2018

Nucracker Key West is dazzling and unique with her tiny chickens, humorous roosters, lively shrimp, and brilliant jewels of the Atocha. A sumptuous, artful theatrical experience wrapped as a perfect holiday gift for the Southernmost City – Key West’s very own NUTCRACKER!

Tennessee Williams Theatre, 5901 College Rd.

Dec 09, 2018 - Dec 17, 2018

Holiday Historic Inn Tours

Enjoy an enchanted evening to include trolley transportation between several participating inns, each decorated for the holidays. Treats and libations are offered at each inn. Event-goers also can provide their own transportation or bicycle to the inns. Contact the Lodging Association of the Florida Keys and Key West to purchase tickets. December 9 & 16, 2016 at 6:00 PM
Contact: 305-296-4959

Dec 31, 2018 - Monday

The Southernmost City celebrates with a descending 6-foot red high heel shoe carrying drag queen Sushi at the Bourbon Street Pub/New Orleans House complex, 724 Duval St. Seconds before midnight. The high heel bearing and lavishly gowned Sushi is to be lowered from the second-story balcony of the complex toward the cheering crowds below.

Contact: 305-293-9600


Jan 19, 2019 - Jan 21, 2019

The Seafood Festival celebrates our community by bringing families and friends together in a joyful and fun environment to sample the local catch. This family-friendly event was created to showcase local seafood and the Keys’ commercial fishing industry by providing the freshest seafood available. Each year our fishermen and women are proud to offer the community a variety of seafood at reasonable prices along with celebrity chef demonstrations, hands-on eco activities, a boat show and live entertainment all day long.

May 08, 2019 - May 13, 2019


200 Performers, 50 Shows 5 Nights. This annual showcase of musical magic features America’s foremost songwriters. The largest festival of it’s kind in the world entertaining locals and visitors alike. Concerts are staged in intimate, audience-friendly and island settings, introducing audiences to the faces, voices and and stories behind the songs.