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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

Schooner Wharf Bar “Rigging” in the New Year 2022!

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

\ Join your friends and make new ones at the Schooner Wharf Bar New Year’s Eve Celebration. The popular waterfront watering hole once again will [...]

Schooner Wharf Bar & Galley St. Patrick’s Day Celebration

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

Extend your Irish Heritage and celebrate St. Paddy’s Day at Schooner Wharf! The Schooner galley will be cooking up their popular annual beer steeped corned [...]

Free

Reef Relief’s 2nd Annual Luau Fundraiser

Lagerhead's Beach Bar 0 Simonton St, Key West, FL, United States

Come celebrate Earth Day, enjoy a family-friendly night of live music, games, and silent auction, along with tropical food and drink specials! WHEN: Friday, April [...]

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

Reef Relief Winter Party Fundraiser

Hyatt Centric Key West 601 Front Street, Key West, FL, United States

HYATT CENTRIC KEY WEST RINGS IN THE HOLIDAY SEASON WITH WINTER BEACH PARTY BENEFITTING REEF RELIEF 100% of the proceeds from the event’s raffle will [...]

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

The Harbor Walk of Lights 2023

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

The “Harbor Walk of Lights” stretches along the seawall past Greene, William and Margaret Streets to the Key West Ferry Terminal. A nautical theme honors the [...]

Pet Pictures with Santa 2023!

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

Photo: Rob O'Neal Friday, December 1 – FREE to attend 6:00pm – 8:00pm 2023 Pet Pictures with Santa™ – Hosted by The All [...]

Schooner Wharf Bar 2023 Tree Trimming Party and Toy Drive

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

Sunday, December 3 – FREE to Attend Schooner Wharf Bar 2023 Tree Trimming Party and Toy Drive Starting at 6:00PM LOCATION: Schooner Wharf Bar and Galley [...]

Old Town Trolley Holiday Lights & Sights Tours 2023

201 Front Street, Key West, Florida 33040

Old Town Trolley Holiday Lights & Sights Tours December 8-23, 2023 | Multiple nightly tours convey caroling passengers through streets and neighborhoods to revel in [...]

Schooner Appledore 2023 Lighted Boat Parade Party

Saturday, Dec. 9 Schooner Appledore Lighted Boat Parade Party 7:30pm – 9:30pm Be a participant in the 2023 The Lighted Parade aboard the Schooner Appledore [...]

Conch Republic Seafood Company’s 2023 Holiday Classic Car Show

Conch Republic Seafood Company parking lot – Greene & Elizabeth St. 631 Greene Street, Key West, FL, United States

Sunday, December 17 – FREE The Florida Keys Southernmost Car Club presents  cele FREE • 11:00am – 3:00pm LOCATION: Conch Republic Seafood Company – on the [...]

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