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Pet Pictures with Santa!

Harbor Walk of Lights - 16' Nautical Christmas Tree at the foot of Williams St.

Friday, December 3 - FREE to attend Pet Pictures with Santa TM! Hosted by The All Animal Clinic from 6:00 - 8:00pm LOCATION: At the [...]

City of Key West Hometown Holiday Parade

Truman Ave. (at White St.) - Key West Historic Seaport

Saturday, December 4 - FREE - The City of Key West Hometown Holiday Parade Starts at 7:00pm. LOCATION: Parade starts on Truman Ave. (at White [...]

Hammerhead Surf Shop’s First Annual Holiday Sip and Shop

Hammerhead Surf Shop 201 William Street, Key West, FL, United States

Come out and experience a personal holiday shopping event! We will be debuting apparel just for you, never before seen, with brands like O'Neill, RVCA, [...]

$20

Conch Tour Train Holiday Light Tours

Conch Tour Holiday Tour Dates for 2021: Public tours:   December 12-17, December 20-23 and December 26: 6:30pm & 8:00pm. Private charters are also available. [...]

$26.25

Fury Key West Two-Hour Sunset Sail

6:30 pm – Fury Sunset Sail Join Fury as they put a new twist on the Tea Dance!  This two-hour sunset sail is hosted on one of Fury’s [...]

Blu Q Sunset Sail

6:30 pm – Sunset Sails Open to All Adults (21+) LGBTQ+BYOB! Set sail on the Blu Q Catamaran for a scenic harbor tour and FAB sunset. You [...]

Official Key West Pride 2022 Street Fair

600-900 blocks Duval Street Key West, FL, United States

10 am – 5 pm Official Pride 2022 Street Fair (600 – 900 blocks Duval Street)

Blu Q All Male Sailing Day Trip

11 am – All Male Day Trip aboard the Blu Q! All Male + Clothing Optional 🏳️‍🌈 • Snorkel and relax on a Sandbar (May through October [...]

Blu Q All Male Sailing Day Trip

11 am – All Male Day Trip aboard the Blu Q! All Male + Clothing Optional 🏳️‍🌈 • Snorkel and relax on a Sandbar (May through October [...]

Schooner Wharf’s 2022 Mel Fisher Celebration

Schooner Wharf Bar 202 William St, Key West, FL, United States

Trade treasure tales and priceless memories of Key West’s King – Mel Fisher! Spend a golden evening at Schooner Wharf Bar, where Spanish galleons, treasure [...]

Free

Key West Fantasy Fest 2022

Key West Fantasy Fest is an exciting annual event that takes place in October. Every fall, the streets of Key West come to life for [...]

Reef Relief Under-The-Sea Party

Dante's Key West 955 Caroline Street, Key West, FL, United States

Reef Relief will be hosting an “Under the Sea Party” fundraiser at Dante’s Key West Pool Bar and Restaurant sponsored by Ocean Vodka, on Monday, [...]

Wharfstock at Schooner Wharf Bar – Key West Historic Seaport

Schooner Wharf Bar 202 William St, Key West, FL, United States

  7pm WHARFSTOCK AT THE SCHOONER WHARF BAR - Peace and Love Woodstock-style! Prizes for sexiest Hippie Chick and Grooviest Dude -- judging at 8:30 PM. [...]

31st Annual Schooner Wharf Bar Lighted Boat Parade

Key West Historic Seaport

31st Annual Schooner Wharf Lighted Boat Parade 2022 Mistletoe goes on the mast and running lights will twinkle in the appropriate red and green holiday [...]

Free

Ring in 2023 – New Years Eve Celebration at Schooner Wharf

Schooner Wharf Bar 202 William St, Key West, FL, United States

Celebrate with Schooner Wharf this New Year's Eve for our annual original tradition of The Lowering of the Pirate Wench! Evalena will once again descend [...]

Free

17th Annual Florida Keys Seafood Festival

Bayview Park 1400 Truman Avenue, Key West

17th Annual Florida Keys Seafood Festival - January 14-15, 2023 The 17th Annual Florida Keys Seafood Festival is Saturday, January 14th from 11:00 a.m. to [...]

$10.00