Breaking Travel News

What’s on this season in the Florida Keys & Key West

What’s on this season in the Florida Keys & Key West

With warm, sunny weather and plenty of tropical pre-holiday cheer, now’s a great time to visit the Florida Keys and Key West. From Key Largo to Key West, the 2023 holiday season features spirited events such as lighted boat parades, only-in-the Keys frivolity, sparkling waterfront celebrations and other island festivities. 
Here’s what visitors to the island chain can expect in the run-up to Christmas and New Year.

Lower Keys’ Island Art Festival, 25 November, Big Pine Key

Sleigh rides and snowball fights aren’t on the menu of holiday amusements in the subtropical Lower Florida Keys, but visitors don’t need them to celebrate the season at the Lower Keys’ Island Art Festival. The open-air event is set to take place on Saturday, 25 November, in the shaded grounds of the Lower Keys Chamber of Commerce Visitor Center on Big Pine Key.

The good-spirited gathering provides an opportunity for visitors and locals to mingle, enjoy the balmy Keys climate and kick off the holidays in authentic island style. Scheduled highlights include as many as 50 booths featuring original art, crafts and other items by regional artists and artisans. Other festival attractions include exhibits by not-for-profit groups and live music by local bands and entertainers. Food and beverages from on-site vendors will be available to add to the seasonal cheer.

Islamorada Holiday Fest, 1 December, Islamorada


Islamorada’s 19th annual Holiday Fest is set for 4-10 p.m. on Friday, 1 December, on the Great Lawn inside Founders Park, Islamorada. Highlights include a 30-tonne snow mountain and the celebration’s centrepiece, a 35-foot-tall holiday tree with “magical” snow blowing through its branches. The annual holiday parade, themed “Happy Holidays and Best Fishes!” is scheduled at 7:30 p.m. featuring decorated floats, including one carrying Santa himself. Other attractions include musical and dance performances on an outdoor stage throughout the event. There will also be a holiday gift bazaar including crafts created by local artisans. Entry is free.

Mote Marine’s Ocean Fest, 3 December, Key West

Ocean aficionados and eco-travellers can celebrate the unique marine environment of the Florida Keys, including the continental United States’ only coral barrier reef, during Mote Marine Laboratory’s 2023 Ocean Fest. 

Set for Sunday, 3 December, at Key West’s Truman Waterfront Park, the family-friendly festival is designed to entertain and educate while raising awareness about the Keys’ marine ecosystems and the need to preserve them. Attendees can explore conservation and environmental exhibits, encounter live animals, view and purchase the creations of local marine artists and craftspeople, rock to the sounds of live music and enjoy experiential activities for all ages. Scientists from Mote and other conservation and environmental organisations are to be on hand to provide insights into their work and explain how individuals can play a role in ocean preservation. 

Taste of Stock Island Trolley Tour with a Holiday Twist, 7 December, Stock Island

Board a trolley for an early-evening culinary tour of favourite Stock Island restaurants curated by I Love Stock Island. Highlights include a small plate and beverage pairing at each stop as well as insights from the chef, owner, sommelier and/or brewmaster.

Key West Triathlon, 10 December, Key West

Athletes seeking a warm-weather event to test their physical and mental stamina can compete in the annual Key West Triathlon set for Sunday, 10 December, near the entrance to the continental United States’ southernmost island of Key West. Produced by Integrity Multisport and presented by Mack Cycle, the racing challenge includes swimming in Gulf of Mexico waters, biking a portion of the scenic Florida Keys Overseas Highway and running along a water’s-edge course. Competitors can choose the event’s international-distance triathlon; long or short sprint-distance triathlon; duathlon or aquabike competitions. 

Conch Tour Train’s Holiday Sights & Festive Nights Tours, 8-12 and 15-23 December, Key West

Tours onboard the Conch Tour Train depart from Key West High School on Flagler Avenue at 6:30, 7, 7:30, 8 and 8:30 p.m. The one-hour tour takes riders past the island’s most elaborately decorated houses, buildings and neighbourhoods, complete with holiday carolling. 

Or hop aboard the Old Town Trolley’s Holiday Sights & Festive Nights Tours (8-23 December). The popular green and orange trolleys, festively adorned with holiday lights, will showcase Key West’s best-decorated neighbourhoods, buildings and homes on fun-filled 60-minute excursions. Tours depart each evening from Mallory Square at 6:30, 7, 8 and 8:30 p.m.

Lighted Boat Parades, 8, 9, 10, 16 December, Stock Island, Key Largo, Key West, Key Colony Beach, Little Torch Key

Lighted and festively decorated boats are to cruise waters surrounding the Florida Keys:

Holiday Lighted Boat Parade on Stock Island, 8 December
Key Largo Boat Parade on Blackwater Sound, 9 December
Schooner Wharf Bar Lighted Boat Parade around the Key West Historic Seaport, 9 December
Key Colony Beach Christmas Boat Parade, 10 December
Kiki’s Sandbar Lighted Boat Parade on Little Torch Key, 16 December
Key West Waterfront Winter Wonderland, 15-30 December, Key West

The Coffee Butler Amphitheater at Truman Waterfront Park becomes the Key West Waterfront Winter Wonderland for a family-friendly holiday experience including stunning light displays, an ice-skating rink, games, rides, attractions, music and more. Visitors can also look forward to a variety of food options and wares by local artisans.

New Year’s Eve “Drops” in Key West, 31 December, Key West

Ring in 2024 with a “conch shell drop” at Sloppy Joe’s Bar on Duval St.; the descent of a super-sized red high-heel shoe carrying a drag queen at the Bourbon St. Pub/New Orleans House complex on Duval St.; the lowering of a pirate wench at midnight from atop a tall ship’s mast at the Schooner Wharf Bar on William St.; and a huge replica of a Key lime pie wedge splashing down into a larger-than-life margarita glass at Ocean Key Resort & Spa on Duval St. Revellers can also witness the “flight” of a uniformed “stewardess” in a section of a replica aircraft and enjoy a ticketed Gatsby-style party at First Flight Island Restaurant & Brewery on Whitehead St., known as the birthplace of Pan American Airways.

For more information on the Florida Keys & Key West, visit