Labor Day Weekend And What To Do In Key West In September

Key West holds a near endless cache of vacation possibilities for all who venture south for Labor Day Weekend or any time in the month of September. From the many beautiful beaches to famous local watering holes like Sloppy Joe’s, you’ll find a ton of things with a certain Key West touch to explore while in the area. Whether coming alone or in a group of twenty, Key West offers something for everyone. Here are a few September events that may catch your attention and get you packing for an adventure you have been longing for.

Key West Brew Fest. September 2-7

Because the last five  BrewFest’s have been so much fun and such a success, they are bring it back and creating a 6 pack in Key West over the Labor Day weekend, September 2nd – September 7th, 2015.  All proceeds are to benefit the Rotary Club and their charitable efforts.  Events from beer dinners, beer brunches, happy hour parties, pool parties, late-night parties, seminars and the Signature Tasting Festival Event are some of the great activities we have on tap for you! And, try tasting over 150 beers in one weekend! Visit for more information.

Key West Women Fest. September 10-13

Every year just before the summer season winds down, Key West welcomes women from across the globe to an annualwomenfest2014.2 celebration that has become one of the largest gatherings of lesbians and friends in North America—Womenfest!  Each year thousands of women come together over the Labor Day weekend and stay for a wide range of activities and events during four days of revelry and fun. Activities generally include dance parties, poolside gatherings, sailing and snorkeling, live music, comedy performances and more. You can find the schedule of events at www.

Key West Poker Run. September 17-20

An event that started over 40 years ago with 46 riders has grown to become South Florida’s biggest motorcycle party! Known as Phil Peterson’s Poker Run, over 10,000 riders from all over the country enjoy this classic motorcycle ride. Starting in Miami, they rumble their engines all the way to Key West, crossing over the many bridges to our island paradise. The motorcycle riders must make 5 stops and draw a card at each stop. At the end of the ride, the person who draws the best hand wins! Plus, if you draw one of the top 10 hands, you get a chance to play one round of Texas Hold ‘Em at Cowboy Bill’s on Duval Street. In addition to poker game, Key West blocks off 8 blocks of Duval Street where a huge bike show is held in front of Rick’s, Durty Harry’s, and Sloppy Joe’s Bar. Locals, tourists, and bikers enjoy this mini-Mardi Gras with its carnival atmosphere, music, food, and cold beer!