Florida Keys Holidays to Sizzle with Sparkle and Warmth

Sunny, breezy subtropical holidays in the Florida Keys & Key West are filled with warmth and good cheer throughout the 125-mile-long island chain. The 2022 Key West holiday season features spirited events such as lighted boat parades, historic inn tours, only-in-the Keys frivolity, sparkling waterfront celebrations and other island festivities.

Select Keys holiday events are outlined below, while additional Key West events can be found at keywesttourist.com/festivals-events/.

Nov. 20, Dec. 4, Dec. 18, Jan. 1: Artisan Market. Key West. A “shop local” holiday tradition, the open-air bazaar is from 10 a.m. to 2 p.m. at Indigenous Park at Higgs Beach, 100 Atlantic Blvd. Each event is given a theme and all feature Keys artists, authors, chef-made cuisine, craftspeople, performers, live music and adult beverages. Admission is free. Visit facebook.com/KeyWestArtisanMarket.

Nov. 23: Lighting of the Harbor Walk of Lights. Key West. The Harbor Walk of Lights at the Key West Historic Seaport stretches along the harbor past Greene, William and Margaret streets to the Key West Ferry Terminal. Activities include lighting of a 20-foot-tall Fishing Buoy tree, a 16-foot Nautical Christmas tree and a Key West Lobster Trap tree. Music is to begin at 5 p.m. with the lights coming on at 6 p.m. Visit keywestchristmas.org.

Nov. 23 – Dec. 31: Key West Holiday Fest. Key West. A merry range of celebrations during the island city’s busy holiday season includes lighting of the Harbor Walk of Lights, Holiday Historic Inn Tours and a lighted boat parade with festively decorated vessels and good cheer. Visit keywestholidayfest.com

Nov. 25: Black Friday Shopping Extravaganza, Truman Waterfront Park. Key West. Join the Key West Artisan Market, the Truman Waterfront Farmers Market and Shop Mom and Pop Key West members from 10 a.m. to 6 p.m. Meet Keys artists, crafters and makers offering one-of-a-kind-gifts, unique handmade items, art and delicious culinary delights and beverages, in a waterfront setting with views unlike those at any indoor mainland mall. Visit facebook.com/events/745018340100819/.

Dec. 2: Wesley House Family Services Holiday Village and BeLighted Bike Ride. Key West. The annual family-friendly Holiday Village is hosted 4-8 p.m. with community vendor booths, food trucks, a best bike contest at 7 p.m. and photos with Santa. The festive bike ride, featuring a parade of bicycles decorated with holiday lights, leaves from the Coffee Butler Amphitheater at Truman Waterfront Park at 8 p.m. Admission is $15 for adults, $10 for children and free for kids age 4 and younger. To enter the best bike contest, there’s a $30 donation, which includes a stocked swag gift bag. Visit WesleyHouse.org/BeLighted2022.

Dec. 3: Key West City Hometown Holiday Parade. Key West. Local holiday spirit abounds in this eagerly awaited 7 p.m. parade that features marching bands, school groups, creatively styled floats and community participation. The parade kicks off at Bayview Park’s White Street and Truman Avenue location. Seeing Santa is a highlight for kids.

Dec. 4: Eaton Street Christmas Stroll. Key West. Arts, theatrical and cultural venues and churches unite for this annual community Christmas stroll, slated to begin at 4 p.m. at St. Paul’s Episcopal Church, 401 Duval St., with secular and religious music. The venues of Old Stone First United Methodist Church, Tropic Cinema, Studios of Key West, Williams Hall and SALT Gallery each host a holiday offering. Admission is free, but reserved tickets are recommended for guaranteed seating. Visit tropiccinema.com/event/2022-eaton-street-christmas-stroll/.

Dec. 4: Pet Pictures with Santa. Key West. Pets and their humans can meet Santa for pics and treats for all at the 16-foot-tall Nautical Christmas tree on the Harbor Walk of Lights at William Street. Photos with Santa are priced at $20 each (cash only) and benefit Boys and Girls Club of the Florida Keys. The event is hosted by the All Animal Clinic with photos by photographer Mary Martin.

Dec. 7-11: Nutcracker Key West. Key West. Eighty Florida Keys children and adults appear with 18 professional dancers from the New York Dance Project in a stunning Keys-themed adaptation of the classic holiday ballet. The performance depicts the island’s colorful history, vibrant coral reef environment, a breathtaking Sea Star Fairy and even free-roaming local roosters. Six performances are scheduled, with tickets priced from $25 to $45 per person, at Tennessee Williams Theatre, 5901 College Road. Visit nutcrackerkeywest.com.

Dec. 8-23: Old Town Trolley's Holiday Sights & Festive Nights Tours. Key West. The popular green and orange trolleys, festively adorned with holiday lights, showcase Key West's best-decorated neighborhoods, 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. Visit trolleytours.com/key-west/christmas-holiday-tours.

Dec. 8, 11-13, and 16-23: Conch Tour Train's Holiday Sights & Festive Nights Tours. Key West. Lively Conch Tour Train tours depart from Key West High School, 2100 Flagler Ave., at 6:30, 7, 8 and 8:30 p.m. Included are holiday lights glasses as keepsake items. The tour takes riders past the island's most elaborately decorated houses, buildings and neighborhoods, with holiday caroling. Visit conchtourtrain.com/key-west-holiday-events.html.

Dec. 8: I Love Stock Island’s Taste of Stock Island Trolley Tour, Holiday Edition. Stock Island. Guests are encouraged to wear Hawaiian-style holiday attire to board the Old Town Trolley for an early-evening culinary tour of favorite Stock Island restaurants. Attractions include a small plate and beverage pairing at each stop as well as insights from the chef, owner, sommelier and/or brewmaster. Tickets are required; check-in is dockside along the parking area at the Perry Hotel, 7001 Shrimp Road. For participating restaurants and trolley schedule, visit ilovestockisland.org.

Dec. 9: Key West Art & Historical Society Holiday Bazaar. Key West. The Key West Art & Historical Society hosts its sixth annual concert and holiday shopping event on the sweeping porch and walkway of the historic Custom House Museum at 281 Front St. The 5-9 p.m. free-admission event features a holiday light show produced by Key West High School’s Conch 5 Studios, unique gifts crafted by local artisans, musicians, choirs, food, libations and photos with Santa. Visit kwahs.org/upcoming-event/bazaar.

Dec 9, 10 and 11: Lighted Boat Parades. Stock Island, Key West, Key Largo and Key Colony Beach. Lighted and festively decorated boats are to cruise waters surrounding the Florida Keys. For details about the Holiday Lighted Boat Parade of Stock Island (Dec. 9), visit keywestrotary.com. For the Schooner Wharf Bar/Absolut Vodka Lighted Boat Parade (Dec. 10) around the Key West Historic Seaport and harbor, visit schoonerwharf.com

Dec. 9 and 16: Holiday Historic Inn Tours. Key West. Old Town Key West is filled with unique historic inns, and two Friday evenings of 6-8 p.m. tours offer a chance to glimpse lavish decorations and experience holiday cheer, treats at bed-and-breakfast properties and two popular Key West attractions. Visit keywestholidayfest.com

Dec. 10: Parade of Paws and Holiday Bazaar. Key West. The ninth annual pet parade at Higgs Beach Dog Park at Atlantic Boulevard and White Street supports the Florida Keys SPCA animal care fund. Attractions at the 10 a.m. to 2 p.m. event include photos with Santa, wares by local vendors, entertainment and the popular “Smooch a Pooch” booth. Visit fkspca.org/events-and-news/upcoming-events/.

Dec. 11: Christmas on the Sheriff’s Animal Farm. Stock Island. Children and adults love visiting the unique Monroe County Sheriff’s Office Animal Farm, just northeast of Key West at 5501 College Road. The farm, open 1-3 p.m. on the second and fourth Sundays of each month, is educational for visitors and a haven for feathered, furry and fluffy creatures that are nurtured and cared for by jail inmates. Holiday highlights include photos with Santa.

Dec. 17: Annual 5K Rudolph Red Nose Run. Key West. This spirited early morning run kicks off at 7 a.m. at Southernmost Beach Café, 1405 Duval St. Visit keywestinns.com.

Dec. 28 and 29: Home Tours “Holiday Style.” Key West. The Old Island Restoration Foundation’s Key West Home Tours are among America’s oldest and longest-running, dating from 1960. This 63rd series features self-guided tours of several Key West homes and gardens, each festively dressed. Three additional tour weekends are scheduled in 2023, with dates set for Jan. 13-14, Feb. 17-18 and March 17-18. Visit oirf.org.

Dec. 31: New Year's Eve “Drops” in Key West. Ring in 2023 with a “conch shell drop” at Sloppy Joe's Bar, 201 Duval St.; the 25th anniversary of the descent of a super-sized red high-heel shoe carrying drag queen Sushi at the Bourbon St. Pub/New Orleans House complex, 724 Duval St.; the lowering of a pirate wench at midnight from atop a tall ship’s mast at the Schooner Wharf Bar, 202 William St.; and a huge replica of a Key lime wedge splashing down into a larger-than-life margarita glass, paired with a performance by The Beatle Band, at Ocean Key Resort & Spa, 0 Duval St. Revelers 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, 301 Whitehead St., known as the birthplace of Pan American Airways. In addition, there’s a “tuna drop” at the Smokin’ Tuna Saloon, 4 Charles St. Visit sloppyjoes.combourbonstpub.comschoonerwharf.com, facebook.com/SunsetPierKeyWest/firstflightkw.com and smokintunasaloon.com.

Key West Events Calendar: keywesttourist.com/festivals-events/