Naples, Florida, is a coastal gem that turns into a tropical winter wonderland during the holidays. Experience holiday spirit without the snow as the town comes alive with festive decorations, light displays, and cheerful celebrations. This enchanting atmosphere is sure to fill your heart with joy. Here is our guide to the activities and experiences you can enjoy when vacationing in Naples, FL throughout December.
Third Street South’s Celebration of Lights
Don’t miss the Third Street South’s Celebration of Lights, a unique event where snow falls in balmy Naples. Experience the magic of snowflakes gently descending during this spectacular celebration. Discover why this event is a holiday must-visit.

The Annual Christmas Boat Parade
Naples Bay hosts an annual lighted nighttime boat parade that’s a true Florida holiday tradition. Watch as boats adorned with twinkling lights create a mesmerizing spectacle on the water. Find out where to catch the best views of this dazzling parade.
Festive Decorations and Enchanting Nights at Naples Botanical Garden
Explore how Naples decks the halls with festive lights and decorations, including attractions like the Naples Botanical Garden and Palm Cottage. Discover the historical significance of these beautifully adorned locations. Also, make sure to experience the magic of Johnsonville Night Lights in the Garden at Naples Botanical Garden. Marvel at the illuminated garden on select December nights and enjoy the beauty of this unique holiday event.

Unforgettable Holiday Experiences at Ritz-Carlton, Naples
The Ritz-Carlton, Naples, offers magical holiday experiences for guests of all ages. Dive into the world of a life-size Gingerbread House and enjoy Teddy Bear Teas with Santa Claus. Learn how this luxurious resort adds a touch of holiday magic to your stay.
Cultural Delights at Theatre Zone
Indulge in the holiday spirit with Theatre Zone’s seasonal performances. Experience the joy of Broadway classics and “lost treasures of Broadway” during your Naples visit. Find out why tickets sell out quickly.
Unique Shopping at Village Shops on Venetian Bay
Experience the Christmas Extravaganza at Village Shops on Venetian Bay, featuring Dickens carolers, Santa Claus, and snow. Explore upscale shopping, dining, and unique gift stores. Learn why this district is a shopper’s paradise during the holidays.

Christmas Fest on 5th Avenue South
Celebrate the holidays at Christmas Fest on 5th Avenue South. Enjoy a tree lighting ceremony, live Nativity scene, and engaging kids’ activities. Learn why this event is a Naples holiday tradition.
Snowfall at Third Street South
Get ready for a snowy surprise during the Third Tree Lighting & Snow Celebration. Discover the enchantment of snowfall during this festive celebration in Naples.

Experience the Holidays in Naples, FL While Staying at Winterwind: A Water Lover’s Dream
Winterwind – A Water Lover’s Dream is an exclusive waterfront vacation home that defines luxury living. Our remarkable retreat is your gateway to unforgettable holiday memories in Naples, Florida.
At Winterwind, we’ve carefully curated an array of amenities to make your holiday stay truly exceptional. Step onto the spacious open-air lanais and bask in the warmth of the December Florida sun. Imagine celebrating the season around a lavish 26′ x 15′ heated swimming pool, where every splash is filled with joy. Challenge your loved ones to a friendly round of mini-golf on our private course, adding an extra layer of fun to your holiday.
As the sun sets, gather around the fully-equipped grilling station to savor delicious meals with your family and friends. But that’s not all – our luxury home offers something that sets it apart from the rest: direct Gulf access with a brand new state-of-the-art dock.
For boating enthusiasts seeking the perfect vacation rental, Winterwind is a dream come true. Our dock features a hydraulic boat lift that accommodates vessels up to 36 feet or two jet-skis. Picture yourself gliding through the serene Gulf waters, exploring hidden coves, and making memories that will last a lifetime.

The Perfect Holiday Retreat in Naples, FL
Whether you’re captivated by the stunning interiors, the lavish outdoor spaces, or the convenience of Gulf access, Winterwind is the perfect place to celebrate the holidays. Embrace the coastal charm of Naples while enjoying the luxury and comfort of your private retreat.
Naples, Florida, shines even brighter during the holidays, and Winterwind is your luxurious home base for experiencing it all. Create cherished memories in this exquisite waterfront enclave, where every amenity and comfort has been thoughtfully provided. Don’t miss the opportunity to make this holiday season truly special.