Nov 04, 2018 - Nov 11, 2018

High-speed offshore powerboats race in Key West Harbor and surrounding waters to continue Key West’s longstanding tradition in this annual challenge, known internationally as the Indianapolis 500 of powerboat racing. A portion of the 6.5-mile course runs through Key West Harbor, meaning smooth water where racers can achieve speeds above 140 mph and provide fans breathtaking displays of skill and power.

Contact: 305-296-6166


Mar 31, 2016

When two frustrated London housewives decide to rent a villa in Italy for a holiday away from their bleak marriages, they recruit two very different English women to share the cost and the experience. There, among the wisteria blossoms and Mediterranean sunshine, all four bloom again—rediscovering themselves in ways that they could never have expected. Tickets available online.

Contact: 305-294-5015 (Box Office)

Jul 23, 2016

This is the original and oldest ongoing 5K Run in Key West and takes place as part of the the annual Hemingway Days Festival. The race course is a scenic flat course that runs past Key West’s most famous landmarks including the Ernest Hemingway Home, the iconic Southernmost Point and the famous Green Parrot Bar. Visit website for more details.

Contact: Barb Wright at 305-240-0727


Oct 19, 2018 - Oct 21, 2018

This exuberant street party showcases island arts and crafts, music and food in the heart of Key West’s historic Bahama Village neighborhood. The festival’s main entertainment stage is located at the corner of Petronia and Fort Street and features nonstop musical entertainment ranging from gospel to reggae. This family friendly street party continues on Saturday! Noon to midnight; FREE.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.

Oct 19, 2018 - Friday

It’s one final caucus with the candidates for King & Queen of Fantasy Fest! This fabulous 2-hour stage show includes entertainment by local celebrities and the candidates themselves hosted by Bria Ansara and produced by Erin McKenna! General admission is a suggested $10 donation at the door; VIP reserved seating for $95 includes a 3-course plated dinner (with a cash bar). For tickets go to or call 305-296-6196. This is a benefit for AIDS Help, Inc. Casa Marina, A Waldorf Astoria Resort, 1500 Reynolds St.; 6 - 10 PM.

Oct 21, 2018 - Sunday

Rise from the dead and join your newly awakened zombies as they gather at Zombieland in Fort East Martello at 2 PM to get their blood flowing, bodies painted, and mid-afternoon snack from 2-6 PM. Hop on your bike and join the thousands of costumed zombies at 6 PM when the zombie invasion heads down US1 to Duval Street for the Zombiefest in Downtown Key West. Register now at Zombie Bike Ride

Oct 22, 2018 - Monday

Be super, be evil, be AWESOME and get your run on! Dress up as your favorite Superhero or Super Villain and run, walk or fly to the finish line. The first 400 to register get a puzzle piece finisher medal! Only offered this year. Race starts and finishes near the beach at the Southernmost Beach Resort parking lot on South Street, and runs through historic Old Town Key West. Free beer and snacks after the race. Be part of the Fantasy Fest family friendly FUN! For registration and information: Theme

Oct 26, 2018 - Friday

Thousands of masked and costumed partiers are to unleash their intergalactic alter egos during the free-spirited Fantasy Fest Masquerade March, a lively walking parade through Key West’s historic Old Town. The masquerade march typically attracts spirited bands and merrymakers wearing everything from feathered masks and finery to offbeat costumes inspired by the festival theme. Free to enter and watch, the 2018 promenade is to start at 5 p.m. at the Key West Cemetery’s Frances Street entrance. Participants are to proceed along two routes, stopping for libations at bed-and-breakfast inns along the way. The fun doesn’t end just because the marching does! The Old Town Masquerade March Madness continues at 7:30 p.m.on Friday, October 27th as the Green Parrot Masquerade March After-Party keeps the ball rolling as The Green Parrot Ukulele Association Band marches down Southard Street and onto The Green Parrot stage.

Oct 27, 2018 - Saturday

Join 70,000 exuberant partygoers as this year’s Fantasy Fest parade rolls down Duval Street. Featuring glittering floats, spectacular costumes, and dazzling dancing groups, it doesn’t get any wilder than this! Parade steps off at 7 PM;

Oct 28, 2018 - Sunday

A family event featuring food, rides, games, arts and crafts and a costume contest for children located at Bayview Park. Truman Ave. and Eisenhower Dr.; Noon to 5 PM; 305-292-8912.