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Festive Florida Holiday Events on the Gulf Coast • McCool Travel

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Festive Florida Holiday Events on the Gulf Coast • McCool Travel

Favorite Florida holiday events include festive boat parades, Christmas lights, Santa visits, and fun ways to kick off the new year. Dream of a white Christmas with your bare feet in the luscious soft sugar sand of the Florida Gulf Coast.

Santa’s cheeks may be red from too much sunshine from his rounds of golf but at Christmas Eve midnight look up in the sky to see his sleigh pulled by eight magic manatees. Or maybe gators. Or perhaps flamingoes. Not sure which Florida Gulf Coast magical animals Santa will recruit this year. Let me know what you see.

Florida Holiday Events on the Gulf Coast: Seasonal Festivals in Southwest Florida

tropical Christmas decorations: Florida edition
Festive Florida Holiday Events, pictured here is Naples, Florida

The holiday period typically starts after Thanksgiving and ends by mid-January, including Christmas and New Year’s Eve

Florida Gulf Coast Holiday Festivals

This collection of Florida holiday events extends from Key West in the south, through Naples, Ft Myers, and Sarasota, finally up to Tampa and St Pete. These popular Florida Gulf Coast holiday activities feature fun tropical Christmas decorations like palm trees decorated with Christmas lights, holiday boat parades, and quirky New Year’s Eve events.

tropical Christmas decorations: Florida edition
have a beachy Christmas along the Florida Gulf Coast

Florida Keys Holiday Events 2023 Dates

Did you know that Jimmy Buffett was born on Christmas Day? R.I.P. Jimmy!

Most Key West visitors probably do not know that but the holiday vibe in the Florida Keys is festive with a tropical flair.

Schooner Wharf Bar Lighted Boat Parade, Key West, December 9, 2023

Calling themselves the “last little piece of Old Key West,” Schooner Wharf Bar hosts an Old Florida traditional Christmas boat parade.

Key Largo Boat Parade, Key Largo, December 9, 2023

Light up your festive floating vessel for a chance at $2,500 in prizes, including the $500 grand prize.

Key West New Year’s Eve, December 31, 2023

Sushi and the Red High Heel Drop at midnight is the most famous new year’s eve event in Key West, broadcast on CNN each year. But there are several other Key West new year’s eve celebrations to ring in the new year. Look for the lowering of the pirate wench, the conch shell drop, and much more. One year, I had a late dinner at a Key West restaurant and it was mayhem approaching midnight.

>>> Plan your Florida Keys visit with our Key West Tips guide.

Marco Island and Naples Holiday Events

Naples, Marco Island, and Everglades comprise the Paradise Coast. Christmas in paradise sounds nice, right?

Night Lights in the Garden, Naples Botanical Garden, November 24, 2023 – January 7, 2024 (closed December 24, 25, 31)

Stroll pathways adorned with millions of lights while listening to live holiday music and savoring festive beverages.

Annual Christmas Walk and Tree Lighting, December 8-9. 2023

The main street in Naples Florida closes for this two day spectacular holiday event—featuring a living nativity, cooking demos, al fresco dining, and a skating rink.

Christmas Boat Parade on Naples Bay, December 9, 2023

Join a boat and be in the parade or watch the festive flotilla from a cozy spot on land (our choice would be the rail at Pinchers Tin City with two dozen stone crabs).

Annual Christmas on Third, Naples, November 25 – December 25, 2023

Head over to the other Naples main street for a month-long celebration.

New Year’s Eve Fireworks at Naples Pier, December 31

Christmas Island Style events in Marco Island include

  • Canine Pet Parade, December 5, 2023
  • Street Parade, December 9, 2023
  • Boat Parade on December 16, 2023
  • Cookies and milk with Santa and Mrs Claus, December 16, 2023

>>> Try our favorite Naples FL restaurants: Places to Eat in Naples, Florida

Fort Myers Events

If I were Santa, find me on Dec 26 relaxing somewhere on the 2.5 miles of brilliant beach of South Seas Resort on Captiva Island. To get there from the Florida mainland, drive through Fort Myers and Sanibel.

key lime pie at Fish-Tale in Fort Myers Beach
make time for a slice of key lime pie at Fish-Tale in Fort Myers Beach

Festival of Trees, Davis Art Center, Fort Myers, November 30 – December 3, 2023

View Christmas trees decorated by local businesses and organizations, while supporting local charities.

Holiday Nights at Edison and Ford Winter Estates, November 24 – December 31, 2023

Santa’s Dolphin and Wildlife Cruise, December 24, 2023

Santa is hiding on an island and this cruise will try to find him and save Christmas!

>>> Plan your Ft Myers visit with our Fort Myers Beach guide.

Punta Gorda Holiday Events

Translated from Spanish, Punta Gorda means “fat point.” Something Santa and I have in common. 

A fresh caught feast at Peace River Seafood in Punta Gorda FL
fresh Florida Gulf Coast seafood at Peace River Seafood in Punta Gorda

Festival of Lights, Fishermen’s Village, November 19 – December 31, 2023

The Fishermen’s Village comes alive with over 1 million Christmas lights along with live music, Christmas decorations, and so much more. Also enjoy the Lighted Canal Cruises and the New Year’s Eve Celebration.

Punta Gorda Boat Parade, December 23, 2023

Also called “Saturday Night Before Christmas Eve Boat Parade” so that you can always remember the date. Four mile lighted boat parade with no commercial or political entries. YES!

Christmas Light Canal Cruises, December 1 – 30, 2023

View Christmas decorations on Homes, boats, Seawalls, and docks from a Punta Gorda canal cruise.

>>> Plan your Punta Gorda visit with our guide to Things to Do in Punta Gorda.

Sarasota Holiday Events

Do the Siesta Key Drum Circle participants wear Santa hats in December? If you visit Sarasota County around Christmas, skip on over there and let me know.

Holiday Tour of Lights trolley tour, Sarasota, December 2 – 29, 2023

Ride an open air trolley through Sarasota’s best and brightest neighborhoods.

Lights in Bloom at Selby Gardens, Sarasota, December 8, 2023 – January 3, 2024

Visit Santa’s Workshop and Toyland overlooking Sarasota Bay and topical holiday decorations.

>>> Plan your Sarasota visit with our guide to Things to Do in Sarasota.

Anna Maria Island and Bradenton Holiday Events

Bradenton and the Gulf Islands (Anna Maria Island and Longboat Key) are in Manatee County and my Christmas wish is have eight sea cows pull my kayak and lead me from Palma Sola Bay to Beer Can Island while I sip egg nog. With rum of course!

tropical Christmas decorations: Florida edition
tropical Christmas in Anna Maria Island Florida

Hunsader Farms County Christmas, Bradenton, 2023 dates not yet announced

Enjoy a country Christmas with over 300,000 Christmas lights, campfires, petting zoo, hayrides, train rides, and Christmas movies, music, and treats.

Holiday Lights in the Gardens, Florida Botanical Gardens, 2023 dates not yet announced

Experience 1 million twinkling holiday lights, along with laser displays, model trains, and much more festive holiday Florida Gulf Coast funness.

Manatee River Holiday Boat Parade, December 9, 2023

Christmas on Bridge Street, Anna Maria Island, no 2023 event scheduled

>>> Plan your visit with our Things To Do in Anna Maria Island guide.

Tampa Holiday Events

Santa might visit Tampa Bay. Their pro sports teams are super hot, the Tampa food scene is amazing, and Gasparilla is only a month after Christmas.

Winter Village at Curtis Hixon Park, November 17, 2023 – January 1, 2024

Visit Tampa’s only outdoor ice skating rink, buy holiday gifts from local artisans, ride the Curtis Hixon Park choo choo through the Winter Village Tampa.

Tampa Bay’s Festival of Lights & Santa’s Village, Nov 23 – December 31, 2023

Two-mile drive-thru continuous light experience followed by visit to Santa’s Village. At Hillsborough County Fairgrounds.

Tampa Holiday Lighted Boat Parade, December 23, 2023

Find a spot along The Tampa Riverwalk for the popular and fun lighted boat parade, featuring small and large boat parades. Check the website for best places to see both. We love Water Works Park to see the magnificent oak trees decorated with lights.

>>> Plan your Tampa visit with our guide to Ways to See Tampa.

St Pete Clearwater Holiday Events

Holiday colors when you visit St Pete Clearwater might include the red sunsets over their amazing US Gulf Coast beaches and the lush green at area parks like Clam Bayou in Gulfport.

Chihuly display at Morean Arts Center in St Petersburg FL
Chihuly display at Morean Arts Center in St Petersburg FL

Epiphany Celebration, Tarpon Springs, January 6, 2024

USA’s largest Epiphany Day celebration (January 6) is celebrated by this predominate Greek Orthodox Church community. The highlight for most attendees of the Tarpon Springs Epiphany is the bishop tossing a cross into the water and the scrum dive to retrieve it.

>>> Plan your St Pete visit with our guide: St Pete FL Art Museums

Daily Florida Gulf Coast Events and Festivals

The following fun and quirky events occur every single night along the Florida Gulf Coast. Attend as much as possible.

Nightly Siesta Key Sunset Celebration and Drum Circle

Celebrate another glorious US Gulf Coast day with some music, dancing, and fun. Arrive about an hour before sunset and let your ears guide you to one of the most interesting daily spectacles you will find anywhere in the world. On our last visit, hundreds of people gathered around the Siesta Key drum circle, complete with dancers, drummers, funness for all types and ages, and, yes, a little funky odor.

Siesta Key FL sunset drum circle
Siesta Key FL sunset drum circle

Key West Sunset Celebration

Mallory Square is the scene of a vibrant nightly festival, hosting visitors from around the world who come to witness and participate in the magicians, jugglers, clowns, psychics, local musicians, artists, and food vendors that combine for an incredible cultural experience.

sunset from Key West, Florida
Catch the magnificent Key West sunset. Every night!

If you are Festivus fan, see our article Festivus: Airing of (Travel) Grievances

Obviously there are hundreds of other Florida Holiday events and festivals so leave a comment with your favorites so that everyone else will know. For events throughout he year along the entire Gulf Coast (from Key West to South Padre, Texas), see US Gulf Coast events.

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