The lighting of the Key West Historic Seaport ‘Harbor Walk of Lights’ on Thanksgiving eve, Wednesday, Nov. 22, marks the official kick-off of the 2023 Key West Holiday Fest. (Photo: Carol Tedesco/KeyWestHolidayFest.com)
As they do everything, Key West treats the holidays a little differently. That's why as a Florida resident, you need to experience Key West around the holidays at least once. While we're on the topic of holidays, St. Augustine has a pretty amazing display as well. But let's discuss the goings on on the island this season at Key West Holiday Fest.
Key West Holiday Fest begins on Thanksgiving Eve and lasts through New Years.
If you're planning a trip before the end of 2023, here's some of the events you can expect to see.
Wednesday, Nov. 22, pre-sunset: People of all ages gather at Greene Street Plaza where it meets Lazy Way Lane for the exciting countdown and 6:00pm official lighting of the Key West Harbor Walk of Lights at the Historic Seaport.
Wednesday, Nov. 22, through New Year’s Eve, Key West Harbor Walk of Lights at the Historic Seaport: Revel in a wonderland of light-bedecked palm trees, Christmas trees, ships, shops, restaurants and watering holes, dazzlingly decorated for the holiday season from Lazy Way Lane at the Green Street Plaza to the Ferry Terminal at Grinnell Street.
Friday, Nov. 24, 10:00am-6:00pm: Black Friday Holiday Shopping Extravaganza at the Truman Waterfront mole by the USCGC Ingham Maritime Museum. Fine arts and crafts, jewelry, apparel, produce, delicious foods and more abound at this open-air bazaar.
Monday, Nov. 27, 5:30pm, City of Key West Tree Lighting Ceremony at Bayview Park, 1320 Truman Ave.
Friday, Dec. 1, 6:00-8:00pm, Pet Pictures with Santa: Pack up Fifi and Fido and delight in Pet Pictures with Santa at the Christmas tree at the foot of William Street at the Key West Bight Marina. Proceeds benefit the Boys & Girls Club of the Keys.
Friday, Dec. 1, 4:00-8:00pm, Wesley House Family Services Holiday Village and BeLighted Bike Ride at Coffee Butler Amphitheater: Celebrate the holidays with a family friendly party with Santa Claus, music, crafts, food trucks, goodies, games, and rides for the kids, and a festive illuminated pedaling party through the streets of Key West, which will depart the Amphitheater at 8:00pm and conclude with a “Best Bike” contest. Admission fee includes Holiday Village and Bike Ride, and benefits Wesley House Family Services.
Saturday, Dec. 2, 6:00-9:00pm, Key West Hometown Holiday Parade:
Spectators line the streets for the homegrown parade which kicks off at Bayview Park and travels along Truman Ave and Duval Streets with festooned floats and marching groups consisting of adults, children, and elves, along with assorted hoofed and whiskered friends.
Sunday, Dec. 3, 4:30-6:30pm, Santa, Sweets, and Holiday Tree Lighting at the Key West Woman’s Club: Celebrate the season with the Key West Woman’s Club and Mayor Teri Johnston at the beautiful historic Hellings Curry Museum at 319 Duval St. Guests can enjoy appetizers, deserts, Amsterdam eggnog and holiday music performed by the Bahama Village Children’s Choir and the Key West Community Orchestra. Donations of unwrapped, new clothing items for students K-12 appreciated.
Sunday, Dec. 3, 7:00pm, “Messiah” concert at Key West United Methodist Church, 600 Eaton Street.
Dec. 8-12, 15-23, Conch Tour Train Holiday Sights and Festive Nights Tours: Multiple nightly tours depart from Key West High School and convey caroling passengers through streets and neighborhoods to revel in the magically illuminated city of Key West. One of the best ways to experience Key West Holiday Fest,
Dec. 8-23, Old Town Trolley Holiday Lights & Sights Tours: Multiple nightly tours begin at Mallory Square and convey caroling passengers through magically decorated streets and neighborhoods.
Friday, Dec. 8, Holiday Historic Inn Tours – Night 1, 6:00pm-8:00pm:
Explore four beautifully decorated locations and their unique architecture and history while enjoying light sweet and savory holiday treats and libation samplings: the Key West Butterfly Conservatory, Wicker Guesthouse, The Mermaid and the Alligator, and the Marquesa Hotel. Tickets can be purchased by calling 305-296-4959 or at KeysTix.com.
Friday, Dec. 8, 5:00-9:00pm, 6th Annual Holiday Concert & Bazaar at the Key West Museum of Art & History at the Custom House: This festive free party features some of Key West’s finest artisans, musicians and choirs, along with a spectacular holiday light show. 281 Front Street.
Saturday, Dec. 9, noon-3:00pm: Pet Pictures with The Grinch at the Hard Rock Cafe: Bring your critters for pet pictures with The Grinch. Proceeds benefit River’s Wish, Inc., a 501(c)(3) non-profit senior dog sanctuary.
Saturday, Dec. 9, 10:00am-2:00pm (9:00am check-in), 10th Annual Parade of Paws & Holiday Bazaar at Higgs Beach / Higgs Dog Park: Benefits the Florida Keys SPCA. Costumes encouraged!
Saturday, Dec. 9, 8:00pm, Schooner Wharf Annual Key West Lighted Boat Parade:
A glittering parade of illuminated watercraft. Arrive at the Key West Bight Marina at the Historic Seaport early in order to stroll through the magical Key West Harbor Walk of Lights. Definitely a highlight of Key West Holiday Fest.
Sunday, Dec. 10, 10:00am-3:00pm, Key West Artisan Market’s Holiday Shindig on the Beach: Shop for holiday treasures from local artisans while enjoying live music, tasty treats, fun drinks, activities for the kids – including a ‘snowman’ building contest and even a visit from old St. Nick. Southernmost Beach Resort, 1317 Duval St.
Sunday, Dec. 10, 1:00-3:00pm: Monroe County Sheriff’s Office Christmas on the Farm. The Monroe County Sheriff’s Office invites everyone to come meet the animals during its annual Christmas on the Farm event. 5501 College Road, Stock Island. Donations welcomed!
Sunday, Dec. 10, 5:00pm: City of Key West Menorah Lighting Ceremony
Friday, Dec. 15, Holiday Historic Inn Tours – Night 2, 6:00-8:00pm: Explore four beautifully decorated locations and their unique architecture and history while enjoying light sweet and savory holiday treats and libation samplings: the Hemingway Social Club at Papa’s Pilar Distillery, Island City House, The Conch House Heritage Inn, and the Lighthouse Hotel. Tickets can be purchased by calling 305-296-4959 or at KeysTix.com.
Friday, Dec. 15 and Saturday, Dec. 16, 8:00pm: Key West Burlesque presents “A Stripmas Carol: Holiday Show Spectacular”, a cheeky burlesque take on the holiday classic for adult audiences. Key West Theater, 512 Eaton St.
Friday, Dec. 15 through Saturday, Dec. 30, Key West Waterfront Winter Wonderland: The Coffee Butler Amphitheater at Truman Waterfront Park will welcome revelers of all ages to a holiday wonderland with beautiful lighting displays, an ice skating rink, rides, attractions, music and more.
Saturday, Dec. 16, 7:00am check-in, 8:00am start time, 14th A Positive Step 5K Rudolph Red Nose Run: Don your festive holiday jammies and join in the 15th A Positive Step 5K Rudolph Red Nose Run, starting and ending at the Southernmost Beach Café, 1405 Duval Street. Runners and walkers of all ages and abilities are welcome to participate; first 100 registrants receive a free t-shirt.
Saturday, Dec. 16, 8:00pm, Fiesta de Navidad Tropical:
Featuring grooves such as salsa, bachata, and cha cha cha, this high energy live performance event presented by the Key West-based Pasión Project studio features World Salsa Champion dancers Carine & Rafael and Mambo royalty Eddie Torres, Jr. with his partner Princess. With live music by Caribe and friends, get ready to move, shake and celebrate all night long, and maybe even dance onstage with the band! Tennessee Williams Theatre.
Sunday, Dec. 17, 11am-3:00pm, Holiday Classic Car Show: See classic cars from a variety of eras at the official show of the Florida Keys Southernmost Car Club, and choose a People’s Choice winner with your votes. Located at the Conch Republic Seafood Company parking lot at the corner of Greene and Elizabeth Streets. Attendees are asked to bring an unwrapped toy for the Monroe County Domestic Abuse Shelter.
Sunday, Dec. 24, Holiday Jazz in the Gardens, 5:00-7:00pm: The Gardens Hotel at 526 Angela street welcomes holiday-goers to festive outdoor jazz in its famous garden, with a full cash bar on site and a 20% Christmas discount on bottled wine and bubbly.
Sunday, Dec. 31: For your midnight toast, chose between an abundance of uniquely Key West New Year’s Eve Celebrations, including the world-famous Red High Heel Drop with Drag Queen Christopher Peterson at the Bourbon St. Pub; the annual “Conch Shell Drop” at Sloppy Joe’s Bar on Duval St.; the “Lowering of the Pirate Wench at Midnight” at Schooner Wharf Bar and Galley at the Historic Seaport, the salty Key Lime Wedge in a Margarita Glass drop and live band at the Ocean Key Resort, and more.
If you're staying in Southwest Florida for the holidays, there's a lot going on here, too.
The year of 2023 is just flying by! Before we know it, it will be the new year! How did we get here so fast?
We're almost half way through November which means Thanksgiving and the mouth watering meal is upon us and it's almost time for Christmas and all the fun holiday cheer that comes along with the season.
I don't know about you, but I am ready to put up the Christmas tree and hang the stocking, wear matching pajamas with my loved ones, watch Christmas movies on repeat and drink hot chocolate (yes, even in Florida).
The weather down here in Southwest Florida is cooling off a bit...just a bit, and getting outside to enjoy the holiday events is so enjoyable.
If you're looking for some fun and exciting holiday festivities, to get your family into the spirit of the holidays this year, look no further. We've put together a list of many of the Southwest Florida holiday events happening over the next several weeks.
Make sure to check back again often for the latest updates as this is an ongoing list. If we missed something, send the event to Diana.Beasley@bbgi.com so we can get it on the list.
Check out these Southwest Florida Holiday Events Happening in 2023:
Fort Myers - Holiday Nights at Edison Ford Winter Estates
Returning for the 48th season, Holiday Nights has been revamped with new light displays and much more.
Holiday Nights runs through December 27th (closed Christmas Eve and Christmas Night). Be sure to check the website to see the nightly schedule.
There will be Santa visits, carolers, science shows and Inside-the-Homes tours on select nights. Lee County residents will receive $5 off admission on Sunday nights.
$20 for adults, $10 for teens (13-19), $2 for children (6-12), and children 5 and under get in free.
Fort Myers - Santa at Bass Pro Shops
Naples - Christmas Walk and Tree Lighting Ceremony
The Fifth Avenue South Business Improvement District (BID) will host the 49th annual “Christmas on Fifth” on Friday, December 2nd from 5 p.m. to 10 p.m. and Saturday, December 3rd from 10 a.m. to 10 p.m. This special festival will combine holiday themed activities along with the ultimate nights of ‘al fresco’ dining on the street.
Fort Myers - Annual Holiday Tree Lighting & Luminary Extravaganza
Mark your calendars for the Annual Bell Tower Tree Lighting, Friday December 1st 6pm-9pm!
Santa Claus will arrive to Bell Tower at 6:30 p.m. in a South Trail Fire Department fire truck at the main entrance near Grimaldi’s and Blue Pointe.
Following his arrival, the festivities will commence in Center Court with a special tree lighting ceremony and a meet-and-greet with Santa Claus, ideal for holiday photo opportunities.
Fort Myers - Holiday Lights at Calusa Nature Center & Planetarium
All December long!
Celebrate the most wonderful time of the year in nature’s wonderland, brimming with holiday cheer! Our 1/3 mile trail will be illuminated with twinkling lights. After walking the trail, cozy up to the fire and enjoy roasting a marshmallow with hot chocolate!
https://www.calusanature.org/holidaylights
Fort Myers - Jingle Jog 5K and Santa Strut Fun Run
Jingle all the way for the most fun, family tradition of the holidays this year and years to come! Join Santa at Lakes Regional Park on December 17, 2023, for a competitive timed 5K run, or a family fun 1 mile Santa Strut, and some traditional Christmas fun!
Fort Myers - Deck The Halls at Barbara B. Mann PAH
Sunday, December 3rd at 7pm
Celebrate the spirit of the season with Gulf Coast Symphony’s annual holiday tradition! The festive sounds of the season ring through the Barbara B Mann Performing Arts Hall, as the Gulf Coast Symphony presents your most favorite symphonic pops holiday medleys. From Leroy Anderson’s endearing Sleigh Ride, a medley of music from Christmas movie classics, to the Mannheim Steamroller Silent Night, and much, much more! Deck the Halls is your favorite Southwest Florida holiday tradition, perfect for the whole family!
For more details, click here
Fort Myers - Nutcracker! Magic of Christmas Ballet at Barbara B. Mann PAH
Friday, December 29th at 1pm and 5pm
Gather your loved ones for the warm-glow-nostalgia of America’s favorite Christmas celebration. Experience the extraordinary international cast and Ukrainian Principal Artists performing at the peak of classical European Ballet. Be transported by the magic of jaw-dropping acrobatics, larger-than-life puppets and stunning hand-crafted sets and costumes. Don’t miss this chance to experience the wonder of NUTCRACKER!
Fort Myers - Breakfast With Santa at Bell Tower Shops
Join us Saturday November 25th 9am to 11am as Cantina Laredo will be hosting our Annual Breakfast with Santa once again! Proceeds for this event will go to one of our favorite charities, Valerie's House!
Fort Myers - HOWLiday Yappy Hour at Bell Tower Shops
Join us Friday, December 8th for our HOWLiday Yappy Hour featuring pet photos with Santa! A minimum of a $20 donation to Gulf Coast Humane Society for your pet photo with Santa.
Fort Myers - Strolling Santa at Bell Tower Shops
Santa Claus is coming to Bell Tower Shops this holiday season and YOU can snap selfies with the big man himself! Santa's first public appearance will be at our annual Tree Lighting & Luminary Extravaganza but there are many more dates for you to visit him here at Bell Tower throughout the holiday season!
Fort Myers - Holiday Family Fun Night at Bell Tower Shops
Thursday, December 21st from 5-7pm
To provide families a time to bond, have fun doing activities together and get their family rhythm going again.
Marco Island - Christmas Tree Lighting
Saturday, December 2, 2023 - 6:00pm to 9:00pm at Veterans Community Park
Marco Island - Christmas Street Parade
Saturday, December 9th, 2023 6:30pm-8:30pm Free to attend!
*Parade begins at Balfour and San Marco Road and will end at San Marco and Barfield.
San Marco Road is lit up every year for the annual Marco Island Street Parade! The parade will feature floats, marching bands, music, costumes, candy and Santa Claus!
Marco Island - Christmas Boat Parade
Saturday, December 16th at 6pm
Marco Island - Canine Christmas Parade
Tuesday, December 5th, 2023 5:30 pm - 7:30 pm
Watch festive pets in the holiday parade from 5:30 p.m. to 7:30 p.m. at CJ’s on the Bay 740 N. Collier Blvd., Marco Island.
Bonita Springs - Holiday In The Park
The City of Bonita Springs Holiday in the Park event is scheduled for Tuesday, December 5th, 2023, from 4:30 p.m. to 8:30 p.m. The event will include the annual tree lighting, the arrival of Santa Claus, children’s activities, musical performances, as well as food and beverages.
Bonita Springs - Holiday Stroll
Throughout Riverside Park from December 1st, 2023- January 1st, 2024
The park will sparkle with holiday lights and holiday-themed photo opportunities will be available throughout the park for the public to take pictures with. Holiday music will play throughout the park. The music will be scheduled from dusk-9pm nightly unless there is an event scheduled.
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Bonita Springs - Movies in the Park
Friday, December 8th. The aminated holiday movie, A Christmas Carol (2009) [PG], will be shown. Enjoy a magical evening in the park this holiday season with an outdoor movie. The park will be lit up with holiday lights. The movie starts at dusk! The event is free for the community.
Fort Myers - 17th Annual Festival of Trees
The 17th Annual Festival of Trees returns to the Sidney & Berne Davis Art Center! Experience the beautiful trees decorated by local businesses to raise money for Goodwill of Southwest Florida and SBDAC. See these gorgeous creations for just $2 per person, beginning on November 30th!
Naples - Christmas Boat Parade
Saturday, December 9th, 2023
The parade may be viewed from: Naples City Dock (ticketed), Pinchers Tin City, Riverwalk Restaurant, Naples Landing, Kelly’s Fish House, The Boat House on Naples Bay, and Bayview Park.
