Things to Do in Key West During the Winter

Take the Holiday Sights & Festive Nights Tour

For a truly relaxing and festive Key West experience, head over to Mallory Square and board the Old Town Trolley. Sip cider and indulge with holiday cookies as the Holiday Sights & Festive Nights Tour transports you through the city in search of the best holiday light displays. You’ll even be given special holiday lights glasses to ensure you enjoy all the sparkle. This 1-hour tour runs on select days throughout December.

Ride the Historic Conch Tour Train

Another great way to get in the spirit of the season is aboard the historic Conch Tour Train. This special Holiday Lights Tour will journey around the island past some of the most beautiful holiday light displays and elaborately decorated houses. Sing along to carols, enjoy cider and cookies and witness the island as it twinkles and glows.

Key West Ghost Tour

Many find Key West strange during the day; but after the sun goes down, the restless souls of the island’s frightful past begin to stir. You will hear their tales that have been all but forgotten as you travel the narrow, dark streets of Old Town – filled with 19th century wooden houses that hold on to the secrets of their former inhabitants. Stories so tragic, so chilling, you’ll see why Key West is one of the top ten most haunted cities in America.This and more await you on Key West ghost tour.

 Lighted Boat Parade

A beautiful sight to witness is the parade of lighted boats as they cruise along the Key West bight and harbor. It’s a tropical tribute to the season, including boats of all sizes and types, and is popular among locals and visitors. The parade takes place in mid-December.

Key West Holiday Parade

This annual hometown parade is fun for everyone. Marching bands, colorful floats and much more make their way down Truman to Duval. Be sure to catch this spectacle during the first week of December.

Sails to Rails Museum

Embark on a journey through Key West’s maritime past at the captivating Sails to Rails Museum. Discover the remarkable transition from sailboats to steamships and railways that shaped the island’s history. Explore meticulously preserved artifacts and interactive exhibits, including the opportunity to lift a real silver bar and delve into maritime tales. Immerse yourself in the sights and sounds of Key West’s rich heritage with a Fort Jefferson diorama, offering a glimpse into the island’s strategic importance.

Mile 0 Fest

Mile 0 Fest is a new music festival that takes place during winter at the Truman Waterfront Park Amphitheater. If you’re traveling to Key West in February or are considering a winter escape south, this is a “must-see” event, especially for fans of the Red Dirt & Americana scene. The main stages of the festival are located right off of Duval, but throughout the weekend you can catch sporadic acoustic sets at multiple theaters and bars.

Annual Key West House & Gardens Tour

Take a self-guided tour through festively decorated Key West homes and gardens. Presented by the Old Island Restoration Foundation, this annual event takes place on select evenings in December.

Take a Sunset Cruise

The breezes coming off the water are still pleasant during the winter in Key West. Experience the dazzling hues of orange, red and yellow as the sun sets over the water aboard a sunset cruise. One of the most popular cruises on the island, Fury Water Adventure’s Commotion on the Ocean includes live music on deck, so you can dance the night away as you chase down to world famous Key West sunset.

New Year’s Eve Conch Shell Drop

An annual favorite, the Conch Shell Drop is a New Year’s Eve celebration done in Key West style. Thousands of people gather on Duval Street as the giant man-made conch shell is lowered onto the roof of Sloppy Joe’s Bar. Come dance in the street, countdown to midnight and join in the revelry.

New Year’s Eve Shoe Drop Celebration

The New Year’s Eve Shoe Drop is by far one of the most unique events on the island. A 6-foot high, red high heel shoe carrying famed drag queen Sushi makes its descent from the second story of the Bourbon Street Pub New Orleans House on Duval Street. Be a part of this unique celebration along with thousands of other party-goers.

Celebrate the Season with Tinsel & Tunes

Get into the holiday spirit with a live concert at Truman Little White House – brought to you by the American Bombshells. Enjoy a tree-lighting ceremony and an inspiring performance of American classics and holiday favorites. These all-American singing beauties will amaze you with their voices and patriotic spirit.