Past Events

Home/Events/

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 [...]

2023 Key West City “Hometown Holiday Parade”

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

2023 Key West City “Hometown Holiday Parade” SATURDAY, DECEMBER 2, 2023 - FREE! Starts at 7:00pm LOCATION: Parade starts on Truman Ave. (at White St.) then [...]

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 [...]

18th Annual Florida Keys Seafood Festival

Bring the whole family for the freshest seafood caught, cleaned, prepared and served by local fishermen, along with live music both days, plus a kids [...]

26th Annual Key West Marathon and Runfest

26th Annual Key West Marathon and Runfest January 14th - Half Marathon starts at 6:30am and the 5K starts at 7:00am. Key West Half Marathon [...]

Schooner Wharf Knot & Shot Competition

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

2024 Schooner Wharf Knot & Shot Competition Key West wouldn't be Key West without sailors and Schooner Wharf Bar, and sailors wouldn't be sailors without [...]

39th Annual Schooner Wharf Wreckers Cup Race 2024

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

39th Annual Schooner Wharf Bar Wreckers Cup Race Series 2024 No protests, no pageantry, just race with us - or against us! Wrecker's Race 2024 [...]

2024 Annual Schooner Wharf Wreckers Cup Race – Second Race

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

Annual Schooner Wharf Bar Wrecker’s Cup Race Series 2024 February 25 No protests, no pageantry, just race with us - or against us! Wrecker's Race [...]

24th Annual Schooner Wharf Open Air Art & Music Affair

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

Call To Artists! The 24th Annual Schooner Wharf Open Air Art & Music Affair is scheduled for Saturday, March 2nd, 2024. Open to artists of [...]

Key West Pride 2024

Celebrate PRIDE on a tropical island that is legendary for its laid-back style and its open and accepting atmosphere. Whether you’re looking to party with [...]

Hemingway 5K Sunset Run & Paddleboard Race

Runners, walkvers and paddleboard enthusiasts can test their skills and celebrate Ernest Hemingway’s sporting lifestyle Saturday, July 20th during the Hemingway 5k Sunset Run and [...]