Key West Events

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First Fridays on Fleming
First Fridays on Fleming
Jan 1 all-day
First Day on Fleming – Key West boutique owners in “The Fabulous 500 Block of Fleming Street” have kicked off a monthly First Fridays on Fleming 6-9 p.m. block party to encourage local buying. First …

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New Year’s Eve Dockside Bash on Schooner America 2.0 9:30 pm
New Year’s Eve Dockside Bash on Schooner America 2.0
Dec 31 2019 @ 9:30 pm – Jan 1 2020 @ 12:30 am
Enjoy a front-row seat for the famous “Lowering of the Wench” at Schooner Wharf Bar! This special adults-only event features complimentary beer, wine, champagne, well drinks, soda, and water and delicious hot and cold hors …

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New Year’s Eve Pirate Wench Drop At Schooner Wharf Bar 10:00 pm
New Year’s Eve Pirate Wench Drop At Schooner Wharf Bar
Dec 31 2019 @ 10:00 pm – Jan 1 2020 @ 1:00 am
Ring in the new year pirate style! For piratical partiers, a New Year’s Eve salute to Key West’s rowdy seafaring roots is scheduled at the island’s Historic Seaport. At midnight, a winsome pirate wench is …

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New Year’s Eve Shoe Drop Celebration 10:00 pm
New Year’s Eve Shoe Drop Celebration
Dec 31 2019 @ 10:00 pm – Jan 1 2020 @ 1:00 am
New Year’s Eve Shoe Drop Celebration in the Southernmost City celebrates with a descending 6-foot red high heel shoe carrying drag queen Sushi at the Bourbon Street Pub/New Orleans House complex, 724 Duval St. Seconds …

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New Year’s Eve: Conch Shell Drop at Sloppy Joe’s 10:00 pm
New Year’s Eve: Conch Shell Drop at Sloppy Joe’s @ NEW YEAR'S EVE: CONCH SHELL DROP AT SLOPPY JOE'S
Dec 31 2019 @ 10:00 pm – Jan 1 2020 @ 1:00 am
Enjoy the New Year’s Eve Conch Shell Drop at Sloppy Joes and party it up right! The arrival of of the New Year is to be heralded on the island’s Duval Street with the “drop” …

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First Fridays on Fleming
First Fridays on Fleming
Jan 3 all-day
First Day on Fleming – Key West boutique owners in “The Fabulous 500 Block of Fleming Street” have kicked off a monthly First Fridays on Fleming 6-9 p.m. block party to encourage local buying. First …

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Mile Zero Fights to Continue Rich Key West Tradition Jan. 18 9:20 am
Mile Zero Fights to Continue Rich Key West Tradition Jan. 18
Jan 6 @ 9:20 am – 10:20 am
The Key West boxing tradition that dates back to Ernest Hemingway is to be celebrated Saturday, Jan. 18, when aficionados can watch 11 fights in an open-air waterfront setting at the island’s East Quay Wall …

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Florida Keys Cuda Bowl to Pit Anglers Against Barracuda Jan. 30 – Feb. 1 12:01 pm
Florida Keys Cuda Bowl to Pit Anglers Against Barracuda Jan. 30 – Feb. 1
Jan 7 @ 12:01 pm – 1:01 pm
While Super Bowl teams make last-minute preparations for the big game, anglers can tangle with a different kind of big game in the Florida Keys: the toothy barracuda, prey for competitors in the 2020 Cuda …

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Mile 0 Fest Brings ‘Red Dirt’ and Americana Stars to Subtropical Key West 12:30 pm
Mile 0 Fest Brings ‘Red Dirt’ and Americana Stars to Subtropical Key West
Jan 7 @ 12:30 pm – 1:30 pm
Fans of Americana and “Red Dirt” music can enjoy performances by the genres’ leading acts in a subtropical setting Tuesday through Saturday, Jan. 28 through Feb. 1, at Key West’s third annual Mile 0 Fest.N
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Elizabeth Bishop Birthday Celebration to Open Poet’s Key West Home 11:06 am
Elizabeth Bishop Birthday Celebration to Open Poet’s Key West Home
Jan 8 @ 11:06 am – 12:06 pm
Readers and literary fans can honor the life and work of renowned American poet Elizabeth Bishop — and participate in the first public viewing of her Key West home — during the inaugural Elizabeth Bishop …

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Key West Literary Seminar
Key West Literary Seminar @ Key West Literary Seminar
Jan 9 – Jan 12 all-day
Key West Literary Seminar @ Key West Literary Seminar | Key West | Florida | United States
Each year, the Key West Literary Seminar explores a particular literary theme. In 2020, for the first time, we’ll look at writing about sports. For “Reading Between the Lines: Sports and Literature” (January 9-12, 2020), …

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Rams Head Promotions Presents Grace Potter
Rams Head Promotions Presents Grace Potter @ Rams Head Promotions Presents Grace Potter
Jan 12 all-day
Rams Head Promotions Presents Grace Potter – An acclaimed songwriter and electrifying performer, Potter has commanded stages around the world. Sunset Green Event Lawn is a multipurpose event space located between 24 North Hotel and …

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Rams Head Promotions Presents Sinbad at Key West Theater 9:00 pm
Rams Head Promotions Presents Sinbad at Key West Theater @ Rams Head Promotions Presents Sinbad at Key West Theater
Jan 14 @ 9:00 pm – 11:00 pm
Rams Head Promotions Presents Sinbad at Key West Theater Actor and comedian Sinbad has had audiences laughing for over three decades. His storytelling style of comedy is profound without being profane. Sinbad has recently appeared …

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Annual Key West Half Marathon & 5K Run
Annual Key West Half Marathon & 5K Run
Jan 15 – Jan 20 all-day
Annual Key West Half Marathon & 5K Run Recognized by Runners World magazine as one of the 10 great half-marathons of the winter season, the race follows a 13.1-mile course that includes Old Town Key …

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Enter by Super Bowl Sunday to Win a ‘Florida Keys Superfan’ Coral Reef Restoration Eco-Adventure 10:39 am
Enter by Super Bowl Sunday to Win a ‘Florida Keys Superfan’ Coral Reef Restoration Eco-Adventure
Jan 15 @ 10:39 am – 11:39 am
For travelers seeking “voluntourism” opportunities to help sustain the continental United States’ only living coral barrier reef, the “Florida Keys Superfan” eco-adventure giveaway offers an enticing prize.N
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Key West Kingfish Mayhem Fishing Tournament
Key West Kingfish Mayhem Fishing Tournament
Jan 16 – Jan 19 all-day
Big fish, big money! Come fish for some of the largest kingfish in Florida Keys waters in this new tournament. Fishing headquartered at Stock Island Marina. First prize could earn $15,000 cash, based on a …

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New Video Explores Key West’s LGBTQ Heritage and Appeal 11:12 am
New Video Explores Key West’s LGBTQ Heritage and Appeal
Jan 17 @ 11:12 am – 12:12 pm
The Monroe County Tourist Development Council, the destination-marketing organization for the Florida Keys & Key West, recently debuted a video exploring Key West’s heritage as a pioneering LGBTQ destination and its contemporary attractions for some …

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Florida Keys Seafood Festival
Florida Keys Seafood Festival @ Florida Keys Seafood Festival
Jan 18 – Jan 19 all-day
Florida Keys Seafood Festival A family-friendly event with local fresh Keys seafood, drinks, marine-related crafts, youth activities, and live music. $5 admission per person; hours open from 11 a.m. – 8 p.m. on Saturday; 11 …

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Key West House & Garden Tours
Key West House & Garden Tours
Jan 18 all-day
Key West House & Garden Tours
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 …

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Conch Revival Picnic
Conch Revival Picnic
Jan 21 all-day
Conch Revival Picnic The Key West Art & Historical Society, Great Events Catering, and Isle Cook Key West team up to present the fourth annual Conch Revival Picnic, an informal Conch heritage dinner prepared by …

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Lower Keys’ Clear Night Skies to Draw Astronomers to Winter Star Party 9:36 am
Lower Keys’ Clear Night Skies to Draw Astronomers to Winter Star Party
Jan 21 @ 9:36 am – 10:36 am
Amateur and professional astronomers can experience unparalleled viewing of southern constellations, comets and stars in the Lower Florida Keys during the 36th annual Winter Star Party.N
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‘Connections Project’ Links Artists and Art Lovers Throughout Florida Keys 10:44 am
‘Connections Project’ Links Artists and Art Lovers Throughout Florida Keys
Jan 22 @ 10:44 am – 11:44 am
Fans of visual art can find it in galleries, exhibitions and pocket parks throughout the Florida Keys island chain — but only in the Connections Project mural can they view the work of more than …

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Fish From Key Largo in Jimmy Johnson Billfish Championship for Nearly $2 Million Dollar Purse 12:55 pm
Fish From Key Largo in Jimmy Johnson Billfish Championship for Nearly $2 Million Dollar Purse
Jan 22 @ 12:55 pm – 1:55 pm
Some of sportfishing’s most-proficient billfish anglers along with notable National Football League players and celebrities are expected to join two-time Super Bowl-winning coach and Pro Football Hall of Fame inductee Jimmy Johnson during his namesake …

Fish From Key Largo in Jimmy Johnson Billfish Championship for Nearly $2 Million Dollar Purse Read More »

Steal The Sky Band at Sloppy Joe’s Bar 10:00 pm
Steal The Sky Band at Sloppy Joe’s Bar
Jan 22 @ 10:00 pm – 10:00 pm
Steal The Sky Band at Sloppy Joe’s Bar On stage 10:00pm to 2:00am. Click for more information. Rock, pop, dance band playing Rihanna to Zeppelin. From Philadelphia, PA
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Steal The Sky Band at Sloppy Joe’s Bar 10:00 pm
Steal The Sky Band at Sloppy Joe’s Bar
Jan 23 @ 10:00 pm – 10:00 pm
Steal The Sky Band at Sloppy Joe’s Bar On stage 10:00pm to 2:00am. Click for more information. Rock, pop, dance band playing Rihanna to Zeppelin. From Philadelphia, PA
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The Art of Chocolate 9:56 am
The Art of Chocolate
Jan 24 @ 9:56 am – 10:56 am
Visitors to Key Largo are discovering that chocolate isn’t just a delicious treat found in pastries, cookies and more. They’re learning that creating chocolate confections is truly an art form, thanks to the passion and …

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Stroll, Sip and Savor the Artistry of the Keys 10:00 am
Stroll, Sip and Savor the Artistry of the Keys
Jan 24 @ 10:00 am – 11:00 am
Artists are drawn to the Florida Keys because of the island chain’s deeply-hued, richly colorful natural scenery and an intensively creative spirit that infuses its culture.N
Tune In to the Florida Keys’ Live Music this Season 10:03 am
Tune In to the Florida Keys’ Live Music this Season
Jan 24 @ 10:03 am – 11:03 am
Live musical performances, concerts and music festivals provide Florida Keys visitors a well-rounded winter 2020 roster of arts and cultural events.N
Key West International Airport Upgrades Facilities, Gets More Flights 3:04 pm
Key West International Airport Upgrades Facilities, Gets More Flights
Jan 24 @ 3:04 pm – 4:04 pm
Key West International Airport, serving visitors traveling into the Florida Keys from 13 U.S. cities, is implementing $28 million in upgrades and adding more departure seats.N
Steal The Sky Band at Sloppy Joe’s Bar 10:00 pm
Steal The Sky Band at Sloppy Joe’s Bar
Jan 24 @ 10:00 pm – 10:00 pm
Steal The Sky Band at Sloppy Joe’s Bar On stage 10:00pm to 2:00am. Click for more information. Rock, pop, dance band playing Rihanna to Zeppelin. From Philadelphia, PA
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Key West Craft Show
Key West Craft Show @ Key West Craft Show
Jan 25 – Jan 26 all-day
Key West Craft Show The Key West Craft Show is a two day juried outdoor craft festival. This nationally recognized Craft Show brings over 100 fine and skilled craft artists to this beautiful historic area …

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Steal The Sky Band at Sloppy Joe’s Bar 10:00 pm
Steal The Sky Band at Sloppy Joe’s Bar
Jan 25 @ 10:00 pm – 10:00 pm
Steal The Sky Band at Sloppy Joe’s Bar On stage 10:00pm to 2:00am. Click for more information. Rock, pop, dance band playing Rihanna to Zeppelin. From Philadelphia, PA
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Key West Food & Wine Festival
Key West Food & Wine Festival
Jan 26 – Feb 2 all-day
Key West Food & Wine Festival @ Key West | Florida | United States
Key West Food & Wine Festival is an event where all of the top chefs and restaurants in Key West Top chefs a display culinary creativity and the Keys’ indigenous cuisine in a flavorful schedule …

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Key West Master Chefs Classic – Annual Key West Event
Key West Master Chefs Classic – Annual Key West Event @ Key West Master Chefs Classic
Jan 26 all-day
Local restaurants vie for top honors in appetizer, entrée and dessert categories. Attendees sample the culinary treats while judges pick the winners. The show is held from 4-7 p.m. at the Margaritaville Resort & Marina …

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Steal The Sky Band at Sloppy Joe’s Bar 10:00 pm
Steal The Sky Band at Sloppy Joe’s Bar
Jan 26 @ 10:00 pm – 10:00 pm
Steal The Sky Band at Sloppy Joe’s Bar On stage 10:00pm to 2:00am. Click for more information. Rock, pop, dance band playing Rihanna to Zeppelin. From Philadelphia, PA
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Community Theater Performances Enliven Florida Keys Stages 12:13 pm
Community Theater Performances Enliven Florida Keys Stages
Jan 27 @ 12:13 pm – 1:13 pm
A first-rate performing arts community in the Florida Keys & Key West offers audiences seasonal musicals, comedies and award-winning performances. A selection of early 2020 highlights is outlined here.N
Springtime Family Fun Planned March 28-29 at Island Fest in Islamorada 12:26 pm
Springtime Family Fun Planned March 28-29 at Island Fest in Islamorada
Jan 27 @ 12:26 pm – 1:26 pm
For visitors to and residents of Islamorada, springtime means heading outdoors to enjoy balmy subtropical weather and the 29th annual Florida Keys Island Fest, scheduled Saturday and Sunday, March 28-29.N
Meetings in the Florida Keys are Unconventionally Unforgettable 12:47 pm
Meetings in the Florida Keys are Unconventionally Unforgettable
Jan 27 @ 12:47 pm – 1:47 pm
Though they might have a subtropical island atmosphere, the Florida Keys & Key West off the southern tip of the Florida mainland are easily accessible for meetings and groups.N
Steal The Sky Band at Sloppy Joe’s Bar 10:00 pm
Steal The Sky Band at Sloppy Joe’s Bar
Jan 27 @ 10:00 pm – 10:00 pm
Steal The Sky Band at Sloppy Joe’s Bar On stage 10:00pm to 2:00am. Click for more information. Rock, pop, dance band playing Rihanna to Zeppelin. From Philadelphia, PA
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Mile 0 Fest Key West
Mile 0 Fest Key West @ Mile 0 Fest Key West
Jan 28 – Feb 1 all-day
Mile 0 Fest Key West @ Mile 0 Fest Key West | Key West | Florida | United States
Mile 0 Fest Key West is a “must see” music festival in the burgeoning Red Dirt & Americana music scene. Take in big shows at Truman Waterfront Park Amphitheatre, a state-of-the-art facility located blocks off …

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GardenFest to Spotlight Key West Tropical Forest & Botanical Garden Feb. 15-16 11:01 am
GardenFest to Spotlight Key West Tropical Forest & Botanical Garden Feb. 15-16
Jan 28 @ 11:01 am – 12:01 pm
Nature enthusiasts can discover a rare and protected Florida Keys habitat Saturday and Sunday, Feb. 15-16, during the 17th annual GardenFest Key West: The Green Market Place 2020 at the historic Key West Tropical Forest …

GardenFest to Spotlight Key West Tropical Forest & Botanical Garden Feb. 15-16 Read More »

Steal The Sky Band at Sloppy Joe’s Bar 10:00 pm
Steal The Sky Band at Sloppy Joe’s Bar
Jan 28 @ 10:00 pm – 10:00 pm
Steal The Sky Band at Sloppy Joe’s Bar On stage 10:00pm to 2:00am. Click for more information. Rock, pop, dance band playing Rihanna to Zeppelin. From Philadelphia, PA
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Cuda Bowl – Key West Fishing Tournament
Cuda Bowl – Key West Fishing Tournament @ Hurricane Hole Marina
Jan 31 – Feb 1 all-day
Cudu Bowl is an annual Key West fishing tournament. Shallow water flats anglers and guides are invited to hook-up and fight their barracuda rivals. Event is to be headquartered at Hurricane Hole Marina, Stock Island. …

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Exclusive Tours to Showcase Key West’s Private Gardens Feb. 28-29 11:40 am
Exclusive Tours to Showcase Key West’s Private Gardens Feb. 28-29
Jan 31 @ 11:40 am – 12:40 pm
Nature lovers can tour the lush and lovely gardens surrounding four private Key West homes Friday and Saturday, Feb. 28-29, during the once-a-year tours presented by the Key West Garden Club.N
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Annual Key West Half Marathon & 5K Run
Annual Key West Half Marathon & 5K Run
Jan 15 all-day
Annual Key West Half Marathon & 5K Run Recognized by Runners World magazine as one of the 10 great half-marathons of the winter season, the race follows a 13.1-mile course that includes Old Town Key …

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10:39 am Enter by Super Bowl Sunday to Win a ‘Florida Keys Superfan’ Coral Reef Restoration Eco-Adventure
Enter by Super Bowl Sunday to Win a ‘Florida Keys Superfan’ Coral Reef Restoration Eco-Adventure
Jan 15 @ 10:39 am – 11:39 am
For travelers seeking “voluntourism” opportunities to help sustain the continental United States’ only living coral barrier reef, the “Florida Keys Superfan” eco-adventure giveaway offers an enticing prize.N