Key West Historic Seaport

37th Annual Key West Fantasy Fest
2016-10-21 - 2016-10-30 | Fantasy Fest, 602 Greene Street, Key West, FL, 33040, United States
This outrageous 10-day costuming and masking celebration features flamboyant masquerade competitions including one for pets, a headdress ball, exuberant promenades, street fairs and a grand parade that stars marching groups, island-style bands and lavish floats. The 2016 festival theme is “Political Voodoo and Ballot-Box Barbarians.”
One Fantasy Fest event taking place at the Historic Seaport is “Dante’s 10th Annual Halos & Horns Pool Party” on October 27, 2016. There will be free body painting, great giveaways, live music, food and drink specials! Head to danteskeywest.com for more details.
Another Fantasy Fest event taking place at the seaport is “Turtle on the Half Shell” at Turtle Kraals. The event is on October 28, 2016 from 2pm-5pm. There will be live music and more than $1,500 in cash and prizes for the best outrageous turtle costume! For more information on this event, check out turtlekraals.com .

Goombay Festival
2016-10-21 - 2016-10-22 | Bahama Village, FL, 33040, United States
Held in Key West’s historic Bahama Village neighborhood, the lively Goombay is known for its island-style food, arts and crafts, nonstop live entertainment and dancing in the streets. Visitors can experience sights, sounds and flavors recalling Key West’s Bahamian heritage.

Key West Halloween Half Marathon & 5k Run
2016-10-16 | Halloween Marathon, 202 William Street, Key West, FL, 33040, United States
The Key West Halloween Half Marathon & 5K offers a scenic running tour of the island as well as an ideal destination for a getaway weekend. Participants can feel good about any partying they do knowing that they have bundled in a run with their fun! We encourage our participants to run in a costume of their choice!

SoMo Marathon & Half Marathon
2016-10-08 | Somo Marathon, 528 Front Street, Key West, FL, 33040, United States
Presented by Pat Croce’s Rum Barrel, this event is one of a kind! Imagine running through the southernmost island in the United States while enjoying a break from the ordinary. The Southernmost Marathon & Half promises just that- 26.2 or 13.1 miles of ocean and gulf views, as well as iconic Key West landmarks.

Womenfest Key West
2016-09-06 - 2016-09-11 | 513 Truman Ave, Key West, FL, 33040, United States
Thousands of singles, couples and groups of women flock to Key West each year for this renowned celebration for lesbians and their friends. Activities generally include dance parties, poolside gatherings, sailing and snorkeling, live music, comedy performances and more.

7th Annual Key West Brewfest
2016-08-31 - 2016-09-05 | 508 South Street, Key West, FL, 33040, United States
More than 150 beers and micro-brews are on tap at this “tasty” annual event that benefits the charitable efforts of the Key West Sunrise Rotary Club of the Conch Republic. 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 offered activities.

Battle of the Bars
2016-08-07 11:00 - 16:00 (America/New_York) | Schooner Wharf Bar, 202 William St, Key West, FL, 33040, United States
Come out for the 23rd anniversary Battle of the Bars event that will benefit Boys and Girls Clubs and Habitat for Humanity of Key West and the Lower Florida Keys. The money raised at Battle of the Bars will help ensure the continuance of both their missions. In the race, team members must mix a perfect margarita, serve it without spilling, tap a keg, sort recyclables, and chug a beer.

Bacardi Oakheart Key West Marlin Tournament
2016-07-20 04:00 - 2016-07-23 13:00
This year’s Key West Marlin Tournament, featuring $50,000 in guaranteed cash prizes is set for July 20. through July 23. 2016, coinciding with the annual Hemingway Days Celebration in Key West, Florida.
