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Annual Events in Key West

Key West Artisan Market

A vibrant venue to facilitate the exchange of unique merchandise and creativity! Learn More

Key West Concert Series

Rams Head Promotions provides top tier entertainment in Key West, Florida for the Key West Theater, Sunset Green Event Lawn and the Key West Amphitheater at Truman Waterfront, as well as other nationally recognized venues. Learn More

Conch Republic Independence Celebration

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January 2019

14th Annual FL Keys Seafood Festival

January 19-20, 2019

This two-day celebration of the bounty of the sea takes place at Bayview Park. This family-friendly event features the freshest local catches, seafood for purchase, celebrity chef demonstrations, hands-on eco activities, boats on display, and live entertainment.

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21st Annual Key West Half Marathon & 5K

January 20, 2019 - 7:00 AM

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Key West Food & Wine Festival 

January 23-27, 2019

Wine and food themed events showcasing a diverse range of wines and inventive cuisine. Over 30 unique events including waterfront tastings, winemaker/chef collaborations, and local funky events indicative of this small, vibrant island.

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34th Annual Key West Craft Show

January 26-27, 2019

This two-day outdoor craft festival brings over 100 finely skilled artists together. Visitors can expect to see beautiful displays of pottery, fabric, glass, wood, jewelry, and other handmade wares. 

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February 2019

Sloppy Joe's 15th Annual Put-In-Bay Festival

February 6-9, 2019

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Garden Fest 

February 16-17, 2019

A fair of nature, arts, crafts, food, and entertainment for the whole family. Set amongst the beautiful Key West Tropical Forest & Botanical Garden, this family-friendly event is free and a lot of fun.

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The Old Island Days Art Festival

February 23-24, 2019

This fine art show, now in its 53rd year, will feature photography, paintings from watercolor to oil and acrylic, decorative sculpture, and other fine arts from the selected artists. 

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March 2019

52nd Annual Conch Blowing Contest

March 2, 2019

An island tradition for over 50 years, this unique contest celebrates the historic importance of conch in the Keys and features contestants in several age categories attempting to make "music" with fluted conch shells.

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2019 Southernmost Air Spectacular

March 30-31,2019

This family-friendly free event will have the most seasoned aeronautical enthusiasts brimming with excitement. Spectators can expect to enjoy spectacular flying, static displays, a Kid's Zone, souvenirs, and concessions. Come out and see your military in action!

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April 2019

Rams Head Productions Presents: The Beach Boys

April 4, 2019

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28th Annual Florida Keys Island Fest

April 6-7, 2019

Music, art, food, and fun complement this annual art show with nearly 100 artists and crafters. Visitors will enjoy live music and a "taste of the islands" food  competition. Admission is free and the festival hours are 10:00 AM - 5:00 PM at Founder's Park. On-site parking is available for a donation of $5. 

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37th Annual Conch Republic Independence Celebration

April 19-28, 2019

Enjoy activities such as a lighthearted sea battle featuring tall ships at this 10-day birthday celebration for the Conch Republic. 

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May 2019

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June 2019

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July 2019

Seventh Annual Key Lime Festival

July 4-7, 2019

A wacky talent show, pie-eating and cooking contests, and other tasty temptations await visitors to this annual event. Visit this event and see why Key West is the key lime capital of the world!

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Hemingway Days

July 16-23, 2019

The 39th annual celebration of the legendary author's work and lifestyle features literary readings, the Running of the Bulls, a short-story competition, fishing tournament, 5K Run, paddle board race, and of course Sloppy Joe's famous look-a-like contest. 

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August 2019

22nd Annual Key West Lobsterfest

August 8-11, 2019

Marking the official opening of lobster season, this is a big party on Duval. Event features street fairs, live music, arts & crafts. Street fair with free live concert on Saturday and so much more!

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9th Annual Key West Brewfest

2019 Dates to be determined 

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September 2019

9th Annual Key West Brewfest

Dates to be determined

This popular event features more than 150 varieties of beer, including many award-winning micro brews. Event includes seminars, tastings, pool parties, and meals. The big event is the Signature Tasting on Saturday, September 2nd at South Beach. Cost is $75 a person for that event and advance tickets are required. 

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October 2019

37th Annual Goombay Fest 2019

Check back for dates

This street party brings out all the locals to Bahama Village and features street fair cuisine (conch ceviche made fresh is popular), vendors selling a variety of wares, and live music at the bottom of Petronia. This is a free, family-friendly event and runs from Noon until Midnight. 

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Fantasy Fest 2019

October 18-27, 2019

This outrageous 10-day costuming and masking celebration features flamboyant masquerade competitions including one for pets, a headdress ball, exuberant promenades, street fairs and a grand parade that stars marching groups, island-style bands and lavish floats.

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November 2019

38th Annual Key West World Championship Races

November 3-10, 2019

Super Boat International returns with teams from all around the world who compete April through October in the National Series Points races and conclude in November for the famous Key West World Championships. High-speed offshore powerboats race in Key West Harbor and surrounding waters to continue Key West's longstanding tradition in this annual challenge, known internationally as the Indianapolis 500 of powerboat racing. A portion of the 6.5-mile course runs through Key West Harbor, meaning smooth water where racers can achieve speeds above 140 mph and provide fans breathtaking displays of skill and power.

December 2019

It's still too early! Check back for details

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Pool and garden at our key west bed and breakfast

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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Activities & 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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