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Best Things To Do in January in Key West

Welcome the new year with the best events Key West has to offer, ranging from boat races, food events, tours, half marathons, and more!

1. Key West Food & Wine Festival

Flip Flops Required. Top chefs and restaurateurs display culinary creativity and the Keys’ indigenous cuisine in a flavorful schedule of events for food lovers. Highlights include the lively “Old Town Uncorked,” neighborhood wine strolls, food and wine pairings, intriguing seminars, winemaker dinner series and a grand tasting. Learn more

2. Annual Wrecker’s Cup Race

This fun race series recalls the tradition of the wreckers in the Key West of the 1800’s. Vessels with rich cargoes from Gulf and Caribbean ports often became victims of the unmarked reefs 7 miles off Key West. The first wrecker to reach the site had the responsibility to save the passengers and crew, but they also won the right to salvage the cargoes.

3. Annual Florida Keys Seafood Festival

The 2 day 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 at Bayview Park features local fresh Key’s seafood, drinks, chef demonstrations, marine-related crafts, youth activities, and live local music. Enjoy some local stone crab. Learn more

4. Try a New Restaurant or Bar

Looking to try a new Key West bar or restaurant since your last visit? We’ve got your covered.

5. Key West Half Marathon & 5K

Recognized by Runners World magazine as one of the 10 great half-marathons of the winter season, the race follows a 13.1-mile course that includes Old Town Key West and the scenic waterfront. Learn more

6. Key West Annual Craft Show

The Key West Craft Show, which attracts buyers from locals, cruise boats and tourists, was rated by Sunshine Artists in the top 100 shows, most recently at #45. The 2017 show had attendance estimated over 25,000 visitors. This show is popular with locals and tourists alike and is only one block from the popular Duval Street. Learn more

7. Annual Master Chef’s Classic

Local restaurants vie for top honors in appetizer, entrée and dessert categories. Attendees sample the culinary treats while judges pick the winners. The show is held from 4-7 p.m. at the Margaritaville Resort & Marina pier, 245 Front St. Event proceeds benefit the nonprofit Monroe Association for ReMARCable Citizens. Learn more

8. Annual Key West House & Garden Tours

Tour elegant and unique private homes of Key West, ranging from exquisite restorations to creative renovations, and the interior design that complements each. Proceeds benefit the foundation’s Oldest House Museum, grant and scholarship programs. Learn more

9. Historic Key West Cemetery Stroll

During the stroll, small groups of visitors will be escorted to gravesites where interpreters will tell the stories of the deceased in brief monologues. Among the gravesites to be visited are those of the Los Martires de Cuba, the Figueredo plot, the Benjamin Albury family restoration, the Otto plot, and Piedad Ayala. Learn more

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