Key West Events

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Original Big Pine & Lower Keys Dolphin Tournament
Original Big Pine & Lower Keys Dolphin Tournament @ Big Pine & the Lower Keys
Jun 3 all-day
The Lower Keys Chamber of Commerce presents its 23rd 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[...]
Skippers Dolphin Tournament
Skippers Dolphin Tournament @ Key Largo
Jun 3 all-day
This tournament is headquartered at Skippers Dockside Restaurant (former location of Coconuts), behind the Holiday Inn. A kickoff and final registration party is planned Friday, 6/3; fishing days are 6/4 & 5; cash prizes over[...]
4
Florida Keys Guitar Festival
Florida Keys Guitar Festival @ The Florida Keys
Jun 4 all-day
Throughout the Florida Keys. The Florida Keys Guitar Festival presents eight virtuoso classical and jazz concerts in Marathon (6/4 & 5), Key Largo (7/2) and Key West (Aug. 5-7). The inaugural festival is to feature[...]
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Key West Pride
Key West Pride @ Key West
Jun 8 all-day
Key West shows its Pride every day, and this is your chance to be a part of the celebration! The five-day schedule includes daytime pool and beach parties, late-night drag shows, on-the-water adventures ranging from[...]
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10
Fourth Annual Ladies Dolphin Tournament
Fourth Annual Ladies Dolphin Tournament @ Islamorada
Jun 10 all-day
Hosted by the Florida Keys Elks Lodge, this event welcomes female angler teams to compete for the highest aggregate weight of three dolphin fish. Cash and prizes are awarded to first- through third-place finishers, and[...]
Third Annual Mystery Writers Key West Fest
Third Annual Mystery Writers Key West Fest @ Key West
Jun 10 all-day
Renowned mystery writers and acclaimed storytellers are to infiltrate the island where Hemingway and Tennessee Williams found their inspiration. Open to authors, aspiring authors and non-writing mystery-buffs alike, MWKWF/2016 welcomes keynote speaker, New York Times[...]
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Guy Harvey Outpost Inaugural Blazing Mako Tournament & Festival
Guy Harvey Outpost Inaugural Blazing Mako Tournament & Festival @ Islamorada
Jun 16 all-day
The event is to include a not-for-profit fishing tournament; innovative art exhibits featuring recycled materials, conservation organization displays and local vendors, all showcased in a 100 tent “Conchservation” Village to highlight ‘trash-to-treasure’ art exhibits and[...]
Key West West Africana Festival
Key West West Africana Festival @ Key West
Jun 16 all-day
Explore music, art, and Key West’s Afro-Caribbean culture during a three-day destination retreat focusing on thought, culture and wellness. The festival is to integrate music, art and cultural tourism, exploring Afro-Caribbean culture in Key West.[...]
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Gold Cup Tarpon Tournament
Gold Cup Tarpon Tournament @ Islamorada
Jun 20 all-day
With founders including baseball great and avid fly fisherman Ted Williams, this challenge appeals to “tarpon addicts,” and both experienced and novice anglers can compete. The event is limited to 25 anglers and proceeds are[...]
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6th Annual Univ. of Miami Sports Hall of Fame Celebrity Dolphin Tournament
6th Annual Univ. of Miami Sports Hall of Fame Celebrity Dolphin Tournament @ Islamorada
Jun 24 all-day
Anglers can fish with some favorite former Miami Hurricanes All-Stars in the one-day tournament that features cash prizes for the heaviest dolphin. Other attractions include a charity auction and more., Contact: Judy Layne 305-598-2525, Email:[...]
Marathon Super Boat Grand Prix
Marathon Super Boat Grand Prix @ Marathon
Jun 24 all-day
Offshore powerboat racing events are held along a course parallel to the Marathon shoreline near the world-famous Seven Mile Bridge. Enjoy free admission to view the boats and meet drivers and crews at the Race[...]
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Key West events are so much fun! There's always something going on in the Southernmost party city! So you're wondering what Key West things to do. Find what concert, musician, local bands and so much more on our Key West events party guide calendar.  Our Party in Key West destination guide will make your visit to Key West the best ever!

Key West Events

 

Jun
16
Thu
2016
Guy Harvey Outpost Inaugural Blazing Mako Tournament & Festival @ Islamorada
Jun 16 all-day

The event is to include a not-for-profit fishing tournament; innovative art exhibits featuring recycled materials, conservation organization displays and local vendors, all showcased in a 100 tent “Conchservation” Village to highlight ‘trash-to-treasure’ art exhibits and conservation efforts in the Florida Keys; a trivia event; beach and water sport competitions; a Rum Village and Kids Pier Fishing Tournament; fishing seminars and the traditional burning sculpture bonfire, a 15-foot mako shark design, beachside. The event will also aid in raising funds for marine sciences scholarships., Contact: John Bell 954-684-5155, Email: [email protected], Islamorada /6/16/2016, Morada Way Arts & Cultural District presents: Third Thursday Art Walk, Showcasing the fine arts, music and culinary nuances of the Purple Isles, the Morada Way Arts & Cultural District features national and local artisans who are showcased in galleries at Morada Way between mile marker 81 and 82 – formerly named Industrial Road – as well as “culinary art” and live music from 6-9 p.m. Free admission. Art Walk is held the third Thursday of each month., Key West /6/18/2016, Key West Island Swim: FKCC Swim Around Key West, The officially sanctioned event is a 12.5-mile swim clockwise around the island of Key West that is open to all age groups. Individual swimmers and relay teams can compete. The route takes swimmers through the waters of the Atlantic Ocean and Gulf of Mexico, ending where they began at Higgs Beach., Contact: Lori Bosco 305-809-3562, Email: [email protected]; [email protected]

Key West West Africana Festival @ Key West
Jun 16 all-day

Explore music, art, and Key West’s Afro-Caribbean culture during a three-day destination retreat focusing on thought, culture and wellness. The festival is to integrate music, art and cultural tourism, exploring Afro-Caribbean culture in Key West. Join scholars as they discuss their research and wellness experts present their practice areas., Contact: Chris Norwood, Email: [email protected]

Jun
20
Mon
2016
Gold Cup Tarpon Tournament @ Islamorada
Jun 20 all-day

With founders including baseball great and avid fly fisherman Ted Williams, this challenge appeals to “tarpon addicts,” and both experienced and novice anglers can compete. The event is limited to 25 anglers and proceeds are to benefit the Florida Keys’ fishing industry’s Guides Trust Foundation., Email: [email protected]

Jun
24
Fri
2016
6th Annual Univ. of Miami Sports Hall of Fame Celebrity Dolphin Tournament @ Islamorada
Jun 24 all-day

Anglers can fish with some favorite former Miami Hurricanes All-Stars in the one-day tournament that features cash prizes for the heaviest dolphin. Other attractions include a charity auction and more., Contact: Judy Layne 305-598-2525, Email: [email protected]; [email protected]

Marathon Super Boat Grand Prix @ Marathon
Jun 24 all-day

Offshore powerboat racing events are held along a course parallel to the Marathon shoreline near the world-famous Seven Mile Bridge. Enjoy free admission to view the boats and meet drivers and crews at the Race Village dry pits and wet pits., Contact: John Carbonell 305-296-6166

Jul
2
Sat
2016
Fourth Annual Key Lime Festival @ Key West
Jul 2 all-day

A wacky talent show, pie-eating and cooking contests and other tasty temptations await Key West visitors during the fourth annual Key Lime Festival. A Key Lime martini Sip and Stroll, and Key lime rum sampling and distillery tour are among events to kickoff the weekend-long event., Key West /7/04/2016, 32nd Annual Hospice of the Florida Keys & Visiting Nurse Association Picnic, Benefits Hospice of the Florida Keys and the Visiting Nurse Association takes place at the luxurious Casa Marina Resort & Beach Club, A Waldorf Astoria Collection, located at 1500 Reynolds St. overlooking the Atlantic Ocean. The celebration is scheduled to start at 5 p.m. with fireworks starting at 9 p.m., courtesy of the Key West Rotary Club. Live music, a silent auction and lots of children’s games round out the fun-filled family festivities., Contact: Casa Marina 305-294-8812, Key Largo /7/04/2016, Fireworks Show on Blackwater Sound, Blackwater Sound provides the perfect nighttime mirrorlike surface to make the annual fireworks display seem like a 3-D viewing experience designed to dazzle. The show is to take place on the bayfront in Key Largo at 10 p.m., 7/4. The best seating can be found at Jimmy Johnson’s Big Chill, Sundowners and Senior Frijoles restaurants, Caribbean Club and Marriott Key Largo Bay Resort, all located around mile marker (MM) 104 bayside. Reservations are suggested because seating is limited; contact restaurants directly., Marathon /7/04/2016, Marathon Beach Party & Fireworks Show, For one of the Keys’ largest and longest fireworks displays, families gather for a full day of activities in Marathon for a patriotic parade that begins around 10:30 a.m. and proceeds from Marathon High School on Sombrero Beach Road (MM 50 oceanside) to free-admission Sombrero Beach, where a daylong celebration features food, drink, kids’ crafts and entertainment, capped off after dark with fireworks. Marathon is known as the Boating Destination of the Keys, and hundreds of boaters line up in front of the beach for a preferred view of the festivities., Contact: 305-743-5417, Email: [email protected]

Jul
8
Fri
2016
Islamorada Summer Classic @ Islamorada
Jul 8 all-day

A family-formatted boat tournament series is to feature nine target backcountry and oceanside species. Trophies are awarded to the top boats in weight and release categories, as well as private vessel and charter divisions., Contact: Dianne Harbaugh 305-522-4868 , Email: [email protected], Big Pine & the Lower Keys /7/09/2016, 32nd Annual Underwater Music Festival, The nationally-acclaimed submerged songfest is held at Looe Key Reef in the Florida Keys National Marine Sanctuary. The marine musical event is set 10 a.m. to 2 p.m. and staged by Keys radio station US1 Radio 104.1 FM. The music is broadcast underwater via Lubell Laboratory speakers suspended beneath boats positioned above the reef. All participants are encouraged to come in costume!, Contact: 305-872-2411 , Email: [email protected]

Jul
11
Mon
2016
Del Brown Permit Tournament @ Key West
Jul 11 all-day

Anglers fly-fish on the flats in a challenge that honors the late angling pioneer Del Brown, who caught and released more than 500 permit off the Keys. Professionals and guides are allowed to compete as well., Contact: Loren Rea 305-360-6969, Email: [email protected]

Jul
20
Wed
2016
Bacardi Oakheart Key West Marlin Tournament @ Key West
Jul 20 all-day

Anglers ply the waters once fished by novelist Ernest Hemingway, vying for $50,000 in guaranteed cash prizes. Held in conjunction with Key West’s annual Hemingway Days festival, the event awards $25,000 to the first-place team. Teams can enter one fun fish (dolphin, tuna, wahoo or released sailfish) per day to add to their point total., Contact: Tim Greene 305-304-0317, Email: [email protected], Islamorada /7/21/2016, Morada Way Arts & Cultural District presents: Third Thursday Art Walk, Showcasing the fine arts, music and culinary nuances of the Purple Isles, the Morada Way Arts & Cultural District features national and local artisans who are showcased in galleries at Morada Way between mile marker 81 and 82 – formerly named Industrial Road – as well as “culinary art” and live music from 6-9 p.m. Free admission. Art Walk is held the third Thursday of each month., Key West /7/21/2016, Key West Theater presents: Leon Russell, Leon Russell is a music legend and perhaps the most accomplished and versatile musician in the history of rock ‘n roll. Leon has played on pop, rock, blues, country, bluegrass, standards, gospel, and surf records. As a session musician, arranger, producer, singer, songwriter, pianist, guitarist, record company owner, bandleader, and touring musician, he has collaborated with hundreds of artists from Joe Cocker, Frank Sinatra, Eric Clapton, Bob Dylan and scores more., Contact: 305-985-0433, Email: [email protected], Key West /7/23/2016, Hemingway 5K Sunset Run & Paddleboard Race, 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, Email: [email protected]

Hemingway Days @ Key West
Jul 20 all-day

The 36th annual celebration of the legendary author’s work and lifestyle features literary readings, Running of the Bulls, short story competition, fishing tournament, Sloppy Joe’s Look-Alike Contest and a birthday “party” commemorating Ernest’s 7/21st birthday., Contact: (305) 296-2388 (Look-Alike); 797-0579 (literary)

Aug
11
Thu
2016
Tropical Heat @ Key West
Aug 11 all-day

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., Contact: 305-294-4603, Key Largo /8/20/2016, Anything that Floats Race, Grab your oars and anything that floats and enjoy this family-fun event – an on-the-water race of vessels crafted from items around the house – on Blackwater Sound, mile marker 104 bayside. Waterfront bars and restaurants offer excellent viewing areas for observing the race and enjoying a Keys sunset, with live music and more fun to follow., Contact: 305-451-4502, Email: [email protected]

Sep
1
Thu
2016
Seventh Annual Key West Brewfest @ Key West
Sep 1 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., Contact: 800-354-4455, Email: [email protected]

Sep
2
Fri
2016
Heroes Salute Tribute Weekend @ Marathon
Sep 2 all-day

Each fall, Hawks Cay Resort on Duck Key hosts an annual Heroes Salute program to honor military, fire and rescue, law enforcement and medical personnel; a special Labor Day Weekend event is planned to include an All-American barbecue, heroes tribute, country music concert and fireworks show., Contact: 1-877-484-9342, Email: [email protected]

Sep
8
Thu
2016
Womenfest Key West @ Key West
Sep 8 all-day

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., Contact: 305-294-4603

Sep
9
Fri
2016
Robert James Sales S.L.A.M. Celebrity Tournament @ Key West
Sep 9 all-day

In the first of three tournaments in the annual Redbone Celebrity Tournament Series, also called The Trilogy, anglers target tarpon, permit and bonefish to achieve the coveted “flats grand slam.” The event raises funds for the fight against cystic fibrosis., Contact: Susan Ellis 305-664-2002, Email: [email protected], Key Largo /9/10/2016, Lionfish Derby for Divers, Teams of up to four divers compete for cash and prizes. Derby divers who successfully remove invasive lionfish from sanctuary waters can win for most, largest and smallest lionfish. The Upper Keys derby is held at John Pennekamp Coral Reef State Park. Visit REEF website to register; teams of up to four people can join. Divers can participate in a derby from their own private vessel or join a professional dive operator’s charter., Contact: REEF 305-852-0030, Email: [email protected]

Sep
15
Thu
2016
44th Annual Phil Peterson’s Key West Poker Run @ The Florida Keys
Sep 15 all-day

It’s an All-American event as motorcycle enthusiasts from around the U.S. travel the Keys’ scenic Overseas Highway – designated Florida’s only All-American Road – from mainland Florida to Key West to raise money for charity. Winner takes all, and can win a new Harley-Davidson Motorcycle or cash. Stops are arranged throughout the Keys with a final celebration in Key West. Keys-wide events are planned., Contact: Drew Peterson 305-235-4023, Email: [email protected]

Sep
16
Fri
2016
17th Annual Herman Lucerne Memorial Backcountry Fishing Championship. @ Islamorada
Sep 16 all-day

Named after the man known affectionately as “Mr. Everglades,” the event is headquartered at the Islander Resort, A Guy Harvey Outpost. Anglers are challenged to target fish in multiple species only in the boundaries of Everglades National Park, fishing areas that Lucerne favored., Email: [email protected], Islamorada /9/17/2016, Fourth Annual Islamorada Swim for Alligator Lighthouse, In the event’s fourth year, swimmers participate in a 9-mile roundtrip race from Islamorada to the Alligator Lighthouse and back. Proceeds benefit the Friends of the Pool in Islamorada, helping provide scholarship opportunities to those in need, and preserve treasured historic lighthouses on Florida’s coastal waterways., Contact: Rob Dixon 305-664-7149, Email: [email protected]

Sep
23
Fri
2016
Take Stock in Children Backcountry Challenge @ Key Largo
Sep 23 all-day

This 17th annual tournament offers anglers the opportunity to win coveted trophies for trout, snook and redfish. A popular Sunday evening dinner and auction showcase is open to the public. Proceeds support local vocational scholarships for all ages, and Take Stock in Children scholarships for financially challenged Upper Keys students., Email: [email protected]

Sep
24
Sat
2016
Conch Scramble “On the Water” Golf Tournament @ Islamorada
Sep 24 all-day

Join an on-the-water wacky weekend charity golf tournament that brings together four-person teams to enjoy a game of nine holes by boat, to “drive” biodegradable golf balls toward floating greens – without any sand traps. A live or silent auction as well as a 50/50 cash raffle also are planned. Proceeds benefit local Keys charities., Email: [email protected]

Marathon International Bonefish Tournament @ Marathon
Sep 24 all-day

This challenge recognizes individual and team champions scoring the largest bonefish and permit, and the top anglers in fly and grand slam divisions (for the top spin or fly angler who releases the largest bonefish, permit and tarpon “slam”). The event is one of the few tournaments where anglers can fish without a professional guide., Contact: Barb 305-304-8682, Email: [email protected]