Key West Paradise

Mar 06 – Feb 5
Market on the Green
Presented by The Keys Collection of resorts, the versatile Sunset Green Event Lawn, located between sister hotels the Gates Key West and 24 North, transforms into a local artisan market the first Saturday of each month, from 10AM to 2PM. ...More

Nov 04 – Jan 31
Arts Council presents 2021 Members Show ‘Dazzling Horizons’
The Opening Reception will be held Nov. 4, from 5:30 – 7:30 pm at the historic Gato Building, 1100 Simonton St. The exhibition will remain on display through January 2022. Dazzling Horizons - a look forward and a look around - the creativity is inspi...More

Nov 24 – Jan 1
Key West 'Bight' Before Christmas
Enjoy a free Keys holiday event to celebrate the spirit of the season. ‘Harbor Walk of Lights’ comes alive each evening at dusk, through New Year’s Eve, and runs along water past Greene St., William St., Margaret St., to the Key West Ferry Terminal....More

Dec 01 – Jan 1
Key West Holiday Fest
A merry range of celebrations during Key West's busy holiday season traditionally includes the Harbor Walk of Lights, Holiday Historic Inn Tours and a lighted boat parade with festively lit vessels and good cheer. Other events include the annual home

Dec 01 – Jul 31
Key West Fishing Tournament
More than 40 species of fish are targeted during the multi-month tournament, with divisions for men, women, junior anglers (ages 10 to 15) and Pee Wees (under 10 years old). The Key West Fishing Tournament strongly encourages the release of game fish...More

Dec 02 – 30
The Studios of Key West presents: Winter Members' Show
The winter members’ exhibition ‘Piece by Piece’ is to be on display in all four galleries: Sanger, XOJ, Zabar Lobby and Zabar Project Galleries. The annual winter members’ show is a celebration and serves as a kick off for TSKW’s season of events. Ga...More

Dec 03 – 5
COAST is CLEAR Music and Arts Festival
Enjoy a weekend in the sun surrounded by close compadres — or simply folks you’ve only just met because of a shared love of music and art. The festival's main event is an all-day concert Saturday. VIP and General Admission tickets still available, at...More

Dec 04
Tri Conch Republic
Athletes will converge on the southernmost island on the United States and enjoy a break from the ordinary. Staged at Higgs Beach, athletes will enjoy a warm Atlantic Ocean swim in full view of spectators.  The bike course is set against along US1 by...More

Dec 04
Key West City Hometown Holiday Parade
Charming holiday spirit abounds in this annual parade in the southernmost city in the continental U.S. Local flavor prevails with marching bands, school groups, motorized and non-motorized floats and lively community participation. The parade kicks o...More

Dec 05
Key West Artisan Market, 'For the Birds' Edition
From 10 a.m. to 2 p.m. in the parking lot at Sonny McCoy Indigenous Park, 1801 White St., across from White Street Pier and the opposite side of the dog parks by the bocce courts. Each Market is themed and pairs with one or more charities to promote ...More

Dec 05
Eaton Street Christmas Stroll
Family Friendly Holiday Event The Stroll begins at 4:00PM at St Paul’s Episcopal Church • 401 Duval St. Keys Choral arts presents a short program of secular & religious music for the season. Continue strolling to: Old Stone First United Methodist...More

Dec 10
Holiday Historic Inn Tours 2021
During this enchanted Friday evening, the annual Holiday Historic Inn Tours offer an opportunity for locals and visitors alike to explore the beautiful architecture and unique history of some of Key West’s most charming inns while making merry with t...More

Dec 10
Fifth Annual Holiday Concert and & Bazaar
Join the Key West Art & Historical Society, from 5-9 p.m., located on the sweeping historic porch and walkway of the Custom House Museum.  The immensely popular celebration is to feature some of the Key West’s finest artisans, musicians and choirs, f...More

Dec 11
Rams Head presents: The Temptations at Coffee Butler Amphitheater
The Temptations, often referred to as “American Music Royalty,” are world-renowned superstars of entertainment, revered for their phenomenal catalog of music, and prolific career. Otis Williams, the sole surviving original Temptation, Ron Tyson, a le...More

Dec 11
Schooner Wharf Bar/Absolut Vodka Lighted Boat Parade
Decorated dinghies, fishing craft and classic tall ships are to light up the Key West Historic Seaport and harbor areas during the 30th annual Schooner Wharf Bar Lighted Boat Parade. Spectators can view the dozens of creatively bedecked vessels from ...More

Dec 11
Eighth Annual Florida Keys SPCA Parade of Paws
Join the Florida Keys SPCA at the Higgs Beach Dog Park from 10 a.m. - 2 p.m. for a family-friendly, fun-filled day of live music, local vendors at the Holiday Bazaar and the crowning of the 2021 Royal Court.  Enjoy pictures with Santa, sloppy kisses ...More