Bright and “belighted” subtropical holidays in the Florida Keys and Key West are filled with warmth, inspiring good cheer throughout the 125-mile-long island chain. 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.
Select Keys holiday events in Key West and the Lower Keys are outlined below, while additional events can be found at fla-keys.com/calendar.
Dec. 3, Dec. 17, Dec. 31
- Artisan Market. Key West. 10 a.m. to 2 p.m. at Indigenous Park at Higgs Beach, 1801 White St.
Friday, Nov. 24
- Black Friday Shopping Extravaganza. Key West. Key West Artisan Market, Truman Waterfront Farmers Market, 10 a.m. to 6 p.m.
Saturday, Nov. 25
- Lower Keys’ Island Art Festival. Big Pine Key. Enjoy live music and food throughout the event, slated for 9 a.m. to 3 p.m. on the Chamber of Commerce grounds, mile marker 31 oceanside. Visit lowerkeyschamber.com or call 305-872-2411.
Friday, Dec. 1
- Wesley House Family Services Holiday Village and BeLighted Bike Ride. Key West. The family-friendly Holiday Village is set for 4-8 p.m. with community vendor booths, holiday-themed inflatable obstacle courses for kids, rides, food trucks, a “best bike” contest and photos with Santa. Visit wesleyhouse.org/events/belighted2023 or call 305-809-5000.
- Islamorada Chamber of Commerce’s annual Holiday Fest from 4-10 p.m. at Founders Park, Islamorada. Enjoy a 30-foot snow mountain, pictures with Santa, a holiday bazaar and a Christmas tree that spreads the cheer. The parade kicks off at 7:30 p.m. Visit islamoradachamber.com/holiday-fest/ to learn more.
Saturday, Dec. 2
- Key West Hometown Holiday Parade. Key West. The parade kicks off at Bayview Park’s White Street and Truman Avenue location at 7 p.m.
Thursday, Dec. 7
- I Love Stock Island’s Taste of Stock Island Trolley Tour with a Holiday Twist. Stock Island. Board a trolley for an early-evening culinary tour of favorite Stock Island restaurants. Visit ilovestockisland.org.
Dec. 8 and 15
- Holiday Historic Inn Tours. Key West. Friday evenings of 6-8 p.m. tours offer a glimpse at lavish decorations and unique architecture.
Dec. 8-12 and 15-23
- Conch Tour Train’s Holiday Sights & Festive Nights Tours. Key West. Tours depart from Key West High School, 2100 Flagler Ave., at 6:30, 7, 7:30, 8 and 8:30 p.m. Visit conchtourtrain.com or call 305-707-5775 or 305-296-6688.
Dec. 8-23
- Old Town Trolley’s Holiday Sights & Festive Nights Tours. Key West. Trolleys showcase Key West’s best-decorated neighborhoods, buildings and homes. Tours depart each evening from Mallory Square at 6:30, 7, 8 and 8:30 p.m.
Friday, Dec. 8
- Key West Art & Historical Society Holiday Concert & Bazaar. Key West. Takes place on the porch and walkway of the Custom House Museum at 281 Front St. from 5-9 p.m.
- Stock Island Lighted Boat Parade. Visit keywestrotary.com.
Saturday, Dec. 9
- Schooner Wharf Bar Lighted Boat Parade. Visit schoonerwharf.com.
- Pet Pictures with the Key West Grinch. Key West. Hard Rock Café, 313 Duval St., noon to 3 p.m. $20 donation supports the senior dog sanctuary River’s Wish. Contact jeanne@riverswishinc.org for information.
- Key Largo Boat Parade on Blackwater Sound. The parade begins at 7:30 p.m. Viewing spots include Jimmy Johnson’s Big Chill, Sundowners, Caribbean Club and Reefhouse. This year’s parade theme is “Christmas Around the World.” Sign your boat up for free. Cash prizes are available. Visit keylargoboatparade.com to learn more.
Sunday, Dec. 10
- Christmas on the Sheriff’s Animal Farm. Stock Island. 5501 College Road, 1 to 3 p.m.
- Eaton Street Christmas Stroll. Key West. Wander the blocks between Whitehead and Simonton between 3:30 and 7 p.m., stopping at venues like St. Paul’s Episcopal Church at 401 Duval St. for a traditional Christmas concert, and Tropic Cinema at 416 Eaton St. for some classic cartoons. The Studios of Key West hosts an open house at 533 Eaton St. during the event. Visit tskw.org.
Tuesday, Dec. 12
- Pet photos with the Grinch. Big Pine Key. 5-7 p.m. at 30085 Overseas Hwy. Visit fkspca.org or call 305-743-4800.
Dec. 15-30
- Key West Waterfront Winter Wonderland. Key West. A family-friendly holiday experience including light displays, an ice-skating rink, games, rides, attractions, music and more. Visit thekeywestamp.com/events.
Dec. 29-30
- Home Tours ‘Holiday Style.’ Key West. The Old Island Restoration Foundation’s Key West Home Tours are among America’s longest-running home tours. Visit oirf.org for tickets or call 305-294-9501.
Sunday, Dec. 31New Year’s Eve ‘Drops’ in Key West. Ring in 2024 with a “conch shell drop” at Sloppy Joe’s Bar, 201 Duval St.; a super-sized red high-heel shoe carrying a drag queen at the Bourbon St. Pub/New Orleans House complex, 724 Duval St.; the lowering of a pirate wench 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 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.
