In Southwest Florida, the winter season arrives with a unique blend of charm, warmth, and festivity that sets it apart from the frostier regions of the country. While snowflakes may be a rarity in this corner of the Sunshine State, the spirit of the holiday season shines as brightly as the tropical sun. As the year draws to a close and the temperatures remain mild, the region comes alive with a host of delightful winter holiday events that are sure to captivate visitors and locals alike.
From the picturesque coastal cities of Naples and Fort Myers to the quaint communities nestled among the lush, subtropical landscapes, Southwest Florida has carved out its own distinctive way of celebrating the most wonderful time of the year. This region's winter holiday events offer a unique blend of tradition, culture, and entertainment against the backdrop of palm trees swaying gently in the breeze and the sparkling waters of the Gulf of Mexico.
In this article, we invite you to embark on a journey through the enchanting world of winter holiday events in Southwest Florida. Whether you're a snowbird seeking a warmer holiday escape or a local resident looking to savor the season's magic close to home, we have a treasure trove of festivities to share with you. From boat parades along picturesque canals to festive holiday markets and spectacular light displays, Southwest Florida's winter events are a testament to the region's vibrant spirit and commitment to celebrating the holidays in style.
Join us as we dive into the heart of Southwest Florida's winter wonderland, where you'll discover the sun-drenched, festive experiences that make this part of the state truly unique during the holiday season. So, grab your sunscreen and flip-flops, and let's embark on a journey through the warmth and wonder of winter holiday events in Southwest Florida!

Wed - 1

The Naples Players - Miss Bennet: Christmas at Pemberley
Through Nov. 19
McSpadden Hall
United Church of Christ
5200 Crayton Road, Naples
(239) 263-7990

Fri -10

Elf the Musical
Through Dec. 25
Broadway Palm Theatre
1380 Colonial Blvd., Fort Myers
(239) 278-4422

Thu - 16

Gulfshore Playhouse presents The Winter Wonderettes
Through Dec. 17
The Norris Center
755 8th Ave. s., Naples
(239) 261-7529

Fri - 24

Annual Holiday Nights
through Dec. 31
Edison and Ford Winter Estates
2350 McGregor Blvd., Fort Myers
Opening Celebration 5:30 - 9 pm
(239) 334-7419

Tue - 21

Holly Daze Art Sale
Cape Coral Art Center
4533 Coronado Pkwy, Cape Coral
9 am - 4 pm
(239) 574-0802

Wed - 22

A Merry Little Murder
Through Dec. 24
Murder Mystery Dinner Train
Seminole Gulf Railway
2805 Colonial Blvd, Fort Myers
(239) 275-8487

Tue - 28

Ho! Ho! Ho! The Christmas Show
Through Dec. 24
Players Circle Theater
13211 McGregor Blvd., Fort Myers
(239) 800-3292
Florida Repertory Theatre presents A Sherlock Carol
Through Dec. 17
Historic Arcade Theatre
Bay Street, Downtown Fort Myers
(239) 332-4488

Wed - 29

Festival of Trees Preview Party
Sidney and Berne Davis Art Center
2301 First St., Fort Myers
6-8 pm
(239) 333-1933
Snowbird Follies
Through Dec. 23
Music & Arts Community Center
13411 Shire Lane, Fort Myers
(239) 277-1700
Tree Lighting Ceremony & Holiday Cirque Experience
Mercato
9110 Strada Place, Naples
5 - 830 pm
(239) 254-1080
Lee Greenwood: A Tennessee Christmas in Concert with special guest Ben Allen
Caloosa Sound Amphitheater
2101 Edwards Drive, Fort Myers
Gates open at 6 pm, show at 7 pm
Festival of Trees
Through Dec. 3
Sidney and Berne Davis Art Center
2301 First St., Fort Myers
(239) 333-1933
Holiday Tree & Menorah Lighting
Cape Coral City Hall
1015 Cultural Park Blvd., Cape Coral
6 pm
Joyful! Joyful!
Through Dec. 30
Westcoast Black Theatre Troupe
1012 N Orange Ave, Sarasota
(941) 366-1505
Thr Christmas Express
Through Dec. 17
Lemon Bay Playhouse
96 W Dearborn St, Englewood
(941) 475-6756

Thu - 30

A Tuna Christmas
Through Dec. 17
The Players Centre
The Crossings at Siesta Key
3501 S Tamiami Tr, #1130, Sarasota
(941) 365-2494
Holidays with Heather Ivy
Bonita Performing Arts Center
10150 Bonita Beach Rd, Bonita Springs
7:30 pm
(239) 495-8989