• Key West BrewFest

    Because the last 7 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...

  • Wine Dine Key West

    Key West’s second annual restaurant month is happening September 15 – October 15, 2017. Enjoy discounts on 2-course lunches and 3-course dinner all over the island as well as right at our very own Southernmost Beach Café.   Food isn’t the only thing you will get a discount on. Many...

  • 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

    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. Fantasy Fest has grown every year since...

  • 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 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. 2018 brings the 36th Literary Seminar to Key West. Check back soon for the...

  • 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 14, 2018, 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 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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