Visiting Key West this December? Here is a look at the month’s top events. 

Key West Lighted Bike Ride

Dec. 4 at 7pm
Bayview Park
This family-friendly holiday event is for a good cause. Partake in the festive bike ride by bringing an unwrapped toy or monetary donation which will be gifted to struggling, working families in the community. Decorate your bike and head to Bayview Park for pictures with Santa before the ride begins.

Coast is Clear Music & Arts Festival

Dec. 5-7
Bahama Village in Old Town
The third annual Coast is Clear Music & Arts Festival features local art events and live music from performers like Tim Reynolds and Rayland Baxter. The event is hosted by Coast Projects, the Key West Art & Historical Society, the Green Parrot Bar and Blue Heaven Restaurant.

TriKW Sprint & Olympic Triathlon

Dec. 7
Higgs Beach, S. Roosevelt Boulevard & Smathers Beach
Watch as some of the best triathletes swim the Atlantic, cycle the U.S. 1 and finish with a sprint along Smathers Beach. See details.

Hometown Holiday Parade

Dec. 7 at 7pm
Starts at Bayview Park
For a small-town local feel, the hometown holiday parade features local high school bands and floats on Dec. 7 at 7 pm. The parade starts at Bayview Park and continues down Duval Street to Eaton Street.

12th Annual Rudolph Red Nose 5k Run

Dec. 14 at 8am
Southernmost Beach Café, 1405 Duval St.
Put on a red nose and join in the annual Rudolph Red Nose Run in Key West. The run helps to benefit A Positive Step Monroe County, a non-profit organization that serves Monroe County’s highest risk kids and their families. Sign up today!

Schooner Wharf’s 29th Annual Key West Lighted Boat Parade

Dec. 14 at 8pm
Schooner Wharf Bar
Head to the water and see boats decked out like a Christmas Fantasy Fest float! This competitive Christmas boat parade has over $20,000 in prizes, awarded by the judges at Schooner Wharf Bar. Arrive to the Key West Bight early to take in holiday music, shopping and dinner. More info here.

Holiday Concert & Bazaar at Custom House Museum

Dec. 18 at 5pm
Custom House Museum, 281 Front St.
This gathering at the Custom House Museum is not to be missed. Finish your last-minute holiday shopping at this outdoor bazaar while enjoying live entertainment, food, drink, and free entrance to the Custom House Museum. Vendors will set up outside the Custom House.

The Play That Goes Wrong

Dec. 19-20 at 8pm
Tennessee Williams Theater, 5901 College Rd.
This Olivier Award-winning comedy is a hilarious hybrid of Monty Python and Sherlock Holmes. Welcome to opening night of The Murder at Haversham Manor where things are quickly going from bad to utterly disastrous. With an unconscious leading lady, a corpse that can’t play dead, and actors who trip over everything (including their lines). Buy tickets.

Blackberry Smoke

Dec. 28 at 4pm
Key West Amphitheater, Truman Waterfront at 21 Quay Rd.
Southern rock fans will be thrilled to see an evening of performances from Blackwater Smoke, Georgia Satellites and Bishop Gun, featuring a blend of rock and roll, soul and blues. Tickets available online.

Key West Dachshund Walk

Dec. 31 at noon
Fleming Street, between Whitehead and Duval streets
Described as a “wiener wonderland,” watch as up to 200 mostly-costumed dachshunds strut along Fleming Street between Whitehead and Duval streets. It’s an annual tradition that is bound to put everyone in a good mood. See the event page for more.

New Year’s Eve Shoe Drop Celebration

Dec. 31 at midnight
Bourbon Street Pub at 724 Duval St.
What’s New Year’s Eve in Key West without a drag queen descending to Duval Street in a giant, red high heel? Watch this annual tradition with the lovely Sushi seconds before midnight at the Bourbon Street Pub on Duval Street.

New Year’s Eve: Conch Shell Drop at Sloppy Joe’s

Dec. 31 at midnight
Sloppy Joe’s Bar, 201 Duval
A shoe isn’t the only thing that drops at midnight. In true Conch Republic style, Sloppy Joe’s Bar will drop an oversized, man-made conch shell. Thousands gather on Duval for the annual event, which is a memorable way to ring in the new year.

New Year’s Eve: Pirate Wench Drop at Schooner Wharf

Dec. 31 at midnight
Schooner Wharf Bar, 202 William St.
Watch as the pirate wench begins her annual descent down the mast of a ship as cannons go off in celebration of the new year at Schooner Wharf. Live music, dancing and other festivities are planned for the evening.

If you’re thinking about a visit to Key West, don’t delay! It’s always summer in the Conch Republic.

The Gates Hotel is a Condé Nast award-winning hotel located in New Town, which offers free hourly shuttle service to Old Town. Exciting onsite amenities – like a food truck, cigar lounge, and a spectacular swimming pool – puts The Gates in its own special category. Check out our special offers online.