New year, same island. Kick off the season with outdoor festivals and jam packed foodie events ranging from the Key West Food & Wine Festival to races on land and sea. Don’t miss the hottest events happening in Key West this January.

1. Key West Food & Wine Festival

Photo // foodandtravelmagazine.com

Get ready to wine and dine during the 14th Annual Key West Food & Wine Festival, with over 30 events “including waterfront tastings, winemaker/chef collaborations, and local events that present an authentic taste of Key West.” We’re looking forward to having Conch Fritters paired with Rosé. From Jan 21st – 26th

2. Mile Zero Fest

3. Attend a Literary Seminar

Source // kwls.org

Once a year writers and readers congregate in the warm weather for the literary seminar, a 4-day event with “presentations by some of the best writers of our time.” The 2025 theme is “Family” which as we all know can be a loaded word. There’s the family we are born into, the one we choose for ourselves and quite possibly the one we run far away from. The writers will help us untangle the often complicated ties that bind, and how they shape our world.   (Jan 9-12)    Registration is now open

4. Quantum Race

Photo // quantumsails.com

Stand along the harbor and watch a fleet of more than 100 racing boats compete for the tittle of the Quantum Key West Race. It’s truly a sight to see.

5. Southernmost Food Tour

Photo// Shayla Dawn Photography

Discover the local side of Key West on our signature food tasting & cultural walking tour. With a progressive lunch, you’ll experience regional, local dishes and the history behind them. Why have lunch at one place when you can dine at six?

6. House Tours

Photo // rentkeywest.com

Do you daydream about living in Key West? Check out the house tours, presented by the Old Island Restoration Foundation, and walk through five houses and gardens in old town Key West. Creative restorations, renovations, and unique interiors will have your imagination running wild.

7. Half Marathon

Photo // historichideaways.com

Burn off all that food on a half marathon! The 25th annual scenic 13.1 mile competition is a favorite bucket list race for runners around the world.  If you’re not feeling like a marathoner, there’s also a 5k.   Jan 18th & 19th

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