Key West Events

Jul
21
Sat
2018
26th Annual Hemingway 5K Sunset Run/Walk & Paddleboard Race
Jul 21 all-day

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.

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Aug
15
Wed
2018
Tropical Heat
Aug 15 – Aug 19 all-day
Tropical Heat

The Key West Business Guild presents this all-male celebration that typically includes pool and dance parties, on-the-water adventures and a fashion show that raises money for a local non-profit organization.

Aug
30
Thu
2018
Ninth Annual Key West Brewfest
Aug 30 – Sep 3 all-day

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.

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Sep
5
Wed
2018
Womenfest 2018
Sep 5 – Sep 9 all-day
Womenfest 2018

Each year thousands of ladies come together over the Labor Day weekend and stay for a wide range of activities and events during four days of revelry and fun. Key West welcomes women from across the globe to an annual celebration that has become one of the largest gatherings of lesbians and friends in North America’s Womenfest.

Oct
5
Fri
2018
SoMo Marathon & Half Marathon
Oct 5 – Oct 7 all-day

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. A full weekend of events including a 10k and 5k are planned.

Oct
19
Fri
2018
39th Annual Key West Fantasy Fest
Oct 19 – Oct 28 all-day

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. 

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Goombay Festival
Oct 19 – Oct 20 all-day

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. FREE event, noon to midnight both days.

Nov
4
Sun
2018
37th Annual Key West World Championship Races
Nov 4 – Nov 11 all-day

Super Boat International returns with teams from all around the world who compete April through October in the National Series Points races and conclude in November for the famous Key West World Championships. 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.

Nov
14
Wed
2018
Key West Film Festival
Nov 14 – Nov 18 all-day

Showcasing films that exhibit excellence in storytelling, the festival’s lineup is to feature screenings and special events hosted at landmark venues throughout Key West, including the San Carlos Institute, Studios of Key West and Key West Theater. The four-day program is to include several films from multiple genres and categories as well as social events with filmmakers, actors and film lovers.

Dec
1
Sat
2018
Key West Triathlon and Expo
Dec 1 all-day
Key West Triathlon and Expo

The Key West Triathlon and Expo expects to host a maximum of 1,000 participants and some of the sport’s best known triathletes; TRIKW allows you to bask in the warm weather and the waters of the Atlantic Ocean while the rest of the country is experiencing winter. Olympic and Sprint distances.

Dec
28
Fri
2018
59th Annual Key West House & Garden Tours
Dec 28 – Dec 29 all-day
59th Annual Key West House & Garden Tours

Presented by the Old Island Restoration Foundation, the annual self-guided tours from 3-7 p.m. each day showcase festively dressed Key West homes and gardens. Tickets are $30 in advance, $35 day-of-tour. Proceeds benefit the foundation’s museum and programs.

Jan
18
Fri
2019
59th Annual Key West House & Garden Tours
Jan 18 – Jan 19 all-day
59th Annual Key West House & Garden Tours

Tour elegant and unique private homes of Key West, ranging from exquisite restorations to creative renovations, and the interior design that complements each. January tours are offered 3 to 7 pm each day. Transportation between homes is available via Conch Train for $40 each, seating is limited. Tickets without transportation are $30 in advance and $35 on tour days. Proceeds benefit the foundation’s Oldest House Museum, grant and scholarship programs.

Feb
15
Fri
2019
59th Annual Key West House & Garden Tours
Feb 15 – Feb 16 all-day
59th Annual Key West House & Garden Tours

Tour elegant and unique private homes of Key West, ranging from exquisite restorations to creative renovations, and the interior design that complements each. January tours are offered 3 to 7 pm each day. Transportation between homes is available via Conch Train for $40 each, seating is limited. Tickets without transportation are $30 in advance and $35 on tour days. Proceeds benefit the foundation’s Oldest House Museum, grant and scholarship programs.

Feb
16
Sat
2019
59th Annual Key West House & Garden Tours
Feb 16 – Feb 17 all-day
59th Annual Key West House & Garden Tours

Tour elegant and unique private homes of Key West, ranging from exquisite restorations to creative renovations, and the interior design that complements each. January tours are offered 3 to 7 pm each day. Transportation between homes is available via Conch Train for $40 each, seating is limited. Tickets without transportation are $30 in advance and $35 on tour days. Proceeds benefit the foundation’s Oldest House Museum, grant and scholarship programs.

Mar
15
Fri
2019
58th Annual Key West House & Garden Tours
Mar 15 – Mar 16 all-day

Tour a series of elegant and unique private homes of Key West, ranging from exquisite restorations to creative renovations, and interior design that complements each. February and March tours are offered 10 am to 4 pm each day. Transportation between homes is not provided. Tickets are $30 in advance and $35 on tour days. Proceeds benefit the foundation’s Oldest House Museum, grant and scholarship programs.

Mar
16
Sat
2019
58th Annual Key West House & Garden Tours
Mar 16 – Mar 17 all-day

Tour a series of elegant and unique private homes of Key West, ranging from exquisite restorations to creative renovations, and interior design that complements each. February and March tours are offered 10 am to 4 pm each day. Transportation between homes is not provided. Tickets are $30 in advance and $35 on tour days. Proceeds benefit the foundation’s Oldest House Museum, grant and scholarship programs.