Key West Events

May
26
Sat
2018
Key West Theater presents: Howie Mandell (2 Shows!)
May 26 all-day
Key West Theater presents: Howie Mandell (2 Shows!)

Howie Mandel has remained a constant force in show business for over 30 years. Mandel is executive producer of many shows through his production company ALEVY PRODUCTIONS, which has produced the series Take It All and Howie Do It for NBC, Deal With It for TBS and Mobbed for FOX, among others. He currently serves as a judge on NBC’s hit summer talent competition series, America’s Got Talent, now in its 11th season with this being Mandel’s seventh season on the series. Shows at 6:30 p.m. & 9:30 p.m.

Jun
1
Fri
2018
Original Big Pine & Lower Keys Dolphin Tournament
Jun 1 – Jun 3 all-day
Original Big Pine & Lower Keys Dolphin Tournament

The Lower Keys Chamber of Commerce presents its 25th annual event, where anglers contend for more than $35,000 in cash prizes and awards. A special cash prize of $20,000 is awarded for the largest dolphin over 50 pounds. Additional prizes await winners in the open, ladies and youth divisions.

Jun
9
Sat
2018
Sixth Annual VFW Fishing Tournament
Jun 9 all-day

Sponsored by the Southernmost VFW Post 3911, this family oriented inshore and offshore tournament offers cash prizes for dolphin, wahoo, tuna, snapper and grouper, along with prizes for heaviest fish by a lady angler, heaviest fish by a juvenile angler, pee-wee, senior angler and active service member. The heaviest Dolphin: 1st-$3000.00; 2nd-$1000.00; and 3rd $500.00. Weigh-in at Murray Marine. All proceeds benefit VFW Relief Fund for Monroe County veterans, and local charities.

Jul
4
Wed
2018
Rotary Club of Key West Annual Fireworks Show
Jul 4 all-day

Since 1976, the Rotary Club of Key West has presented the island’s annual fireworks show. Staged from the Edward B. Knight Pier (formerly called White Street Pier) overlooking the Atlantic Ocean where White Street meets Atlantic Avenue, fireworks are to begin at 9 p.m. Attendees can purchase food, drinks, burgers and hot dogs to benefit the Rotary Club’s scholarship funds at a booth across from the pier on Atlantic Avenue.

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.

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
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.

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