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Annual Events in Key West

January 2017

12th Annual Florida Keys Seafood Festival

Saturday, January 14 - Sunday, January 15, 2017

Come out and enjoy this seafood lover's event. Fresh, locally caught seafood will be served. Additional entertainment includes live music, marine displays, a kids zone, arts & crafts vendors, and more.

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Quantum Key West Yachting Race Week

Sunday, January 15 - Friday, January 20, 2017

The only annual race week in North America. This year marks the 30th anniversary and includes 150 sailboats.

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Key West Food & Wine Festival 2017

Wednesday, January 25 - Sunday, January 29, 2017

Eat. Taste. Learn. Flip flops required.

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February 2017

Sloppy Joe's 13th Annual Put-In-Bay Music Festival

Thursday, February 9 - Sunday, February 11, 2017

Three days of fun and music with various musicians including the famous Pat Daly from Put-In-Bay, Ohio! If you're from the North, you probably know about Put In Bay, and Pat! 

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The Old Island Days Art Festival

Saturday, February 25 - Sunday, February 26, 2017

This year marks the 52nd year for this event. A two-day fine art festival, it features over 100 artists practicing in various mediums. Set amongst beautiful and historical Key West attractions such as the Audubon House and the Mel Fisher Museum, visitors can stroll through three blocks of beautiful art. If you're an art enthusiast, you won't want to miss this.

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March 2017

39th Annual St. Patrick's Day Bar Stroll

Saturday, March 18, 2017

Whether or not you're Irish, St. Patrick's Day is always a fun time! This is a highly anticipated event and sure to be a great time.

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April 2017

22nd Annual Taste of Key West

Monday, April 24, 2017

Located on the Truman Waterfront Pier, this event is a mecca for Key West's finest foods. Some 50 restaurants participate in this culinary event where visitors can sample from a horseshoe of savory edibles, including appetizers, main course bites, and desserts; all along the waterfront.

May 2017

22nd Annual Key West Songwriter's Festival

Wednesday, May 10 - Sunday, May 14, 2017

The largest festival of its kind in the world, this annual showcase of musical talent features America's foremost performing songwriter's across multiple stages set in intimate, audience friendly island settings.

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June 2017

Mystery Fest Key West 2017

Friday, June 16 - Sunday, June 18, 2017

The 4th annual Mystery Fest Key West is for the mystery reading / writing enthusiast. From South Florida's favorite storytellers to writers of international renown, this is a meet and greet where authors can catch up with old friends and readers can chat with their favorite mystery writers, collect signed books, and more!

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Photo Gallery

Tour our beautiful Key West hotel through photos in our gallery. View our lush grounds and gardens, cozy rooms, property map, and tranquil pools.

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Wedding Gallery

You’ve always pictured your perfect wedding day. View the photos in our Wedding Gallery to see what your destination wedding can be like at Westwinds Inn.

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Calendar of Events

There’s always something going on in Key West, from food and literary festivals to fishing and sailing tournaments. View our Events Calendar for the latest happenings.

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