• Key West BrewFest

    Because the last 9 Key West BrewFest events have been so much fun and an amazing success for the local charities, the committee is teaming up to bring it to you again! Join the Southernmost Beach Resort and Key West Sunrise Rotary over Labor Day weekend to celebrate BEER! Happening from...

  • Southernmost Marathon & Half

      Imagine running through the southernmost island in the United States while enjoying a break from the ordinary. The Southernmost Marathon & Half/Key West Running Festival promises just that – 26.2, 13.1, 6.2, or 3.1 miles of ocean and gulf views, as well as iconic Key West landmarks. The...

  • Fantasy Fest

    2019 celebrates 40 Years of Fantasy Fest! Fantasy Fest is an annual, adult-themed, 10-day party in paradise. Founded in 1979 by a small group of Key West locals, the party was created to bring visitors to the island in what was a typically quiet, but beautiful time of year....

  • The Smart Ride

    Have you ever wanted to ride your bicycle for a great cause? You can – all while cruising down A1A with the Atlantic and Gulf of Mexico on either side of you, the wind blowing through your hair, and the sun shining on your face. Join other bikers on a 2 day, 165...

  • Key West Literary Seminar

    Join writers and readers from around the world January 10th – 18th, 2019 to enjoy a packed four day seminar in our ocean side city.  Listen to discussions between writers, learn from authors during lecture series, and partake in writing workshops. 2019 brings the 37th Literary Seminar to Key West....

  • Key West Half Marathon

      Participate in the Key West Half Marathon in Key West, Florida! Race through Key West’s historic Old Town and waterfront areas January 20, 2019, during the annual Key West Half Marathon and 5K run. Special rates are available for Key West Half Marathon and 5K runners at our resort....

  • Key West Events

    Key West is home to many unique events from art and film festivals to gourmet food and wine tastings. Explore the islands culture during Ernest Hemingway Days, find a treasure over Mel Fisher Days, and feel the rush from Key West Super Boat International Races. Key West Calendar of...

  • Key West Food and Wine Festival

    Join fellow food and wine lovers for the 9th annual Key West Food and Wine Festival taking place January 24 – 28, 2018. Events take place all over the tiny island taking you from the Atlantic to the Gulf. Take part in dinners, neighborhood strolls, chef cook-offs, and seminars. Eat,...

  • Key West Songwriters Festival

    The festival revolves around five days and nights where live music bliss introduces crowds to the faces, voices and stories behind the songs. Southernmost Beach Resort plays host to 4 days of live musical performances. Here’s why you should Key West Songwriters Festival attend the Thursday, May 10th @...

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