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5 Can't-Miss Winter Events in Naples, Florida

January 22, 2024

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Are you looking for fun ways to enjoy the winter months in Naples, Florida? You're sure to find something for everyone with events such as the Winter Wine Festival, Cars on 5th Concours, and the Chubb Classic. These events not only offer entertainment but also embody the spirit of Naples, making it a must-visit winter destination. Here are five can't miss winter events in Naples, Florida.


Related Blog: Discover the Charm of Naples, Florida: A Hidden Gem to Call Home

1. Naples Winter Wine Festival

The Winter Wine Festival held annually in Naples, Florida is one of the world’s most prestigious charity wine auctions. Guests will enjoy world-class food and wine inside private homes while bidding on travel and wine experiences. The event will be held at The Ritz-Carlton Naples, Tiburón from January 26th - 28th.

All sales benefit The Naples Children & Education Foundation who work hard to improve the education, emotional, and health outcomes of underprivileged and at-risk children. 

2. Cars on 5th Concours

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Are you a car enthusiast? Then you’ll want to mark your calendars for the 20th Annual Cars on 5th Concours held on Saturday, February 3rd in Naples, Florida. Organized by the Naples Chapter of the Ferrari Club of America, this event will feature over 650 amazing cars on display including more than 150 Ferraris and other exotic, vintage cars and more this year! The event will be raising important funds for St. Matthew’s House, which helps people suffering from homelessness, hunger, addiction, and poverty issues in Southwest Florida. 

General admission is $35 and VIP tickets are $125. VIP tickets include access to the VIP Scuderia area containing the highest value exotic cars at Cars on 5th Concours, two drink tickets (beer and wine available), food by Delicious by Design Catering, and private restroom facilities, as well as general admission to the main Cars on 5th Concours show.

If you're looking for something fun to do in Naples this winter, then Cars on 5th is an automotive experience you won't want to miss!

3. Naples Seafood and Music Festival

If you're looking for a unique winter experience, head to the 3rd Annual Naples Seafood and Music Festival! This event brings together the best of Naples' seafood, live music, and entertainment for a weekend full of fun. Select from delectable foods cooked on site incorporating the freshest ingredients by local restaurants and food purveyors. A variety of seafood entrees and vegetarian dishes will be available, along with a diversity of side dishes, desserts, and alcoholic and non-alcoholic drinks.

The festival takes place on ​​March 15th - 17th. Festivities begin Friday evening from 4pm-10pm and continue Saturday 11am-10pm and Sunday 11am-6pm. General admission is FREE!

4. 2024 Chubb Classic

The Chubb Classic, a revered fixture on the PGA TOUR Champions circuit, returns to Naples, gracing the lush fairways of Tiburón Golf Club's Black Course from February 15th - 18th. As the longest-standing PGA TOUR Champions event in one metropolitan area, this tournament showcases golfing legends vying for glory. With diverse ticket options, the Chubb Classic invites enthusiasts to immerse in the thrill of the game, complemented by exclusive corporate engagements and volunteering avenues. 

5. Naples St. Patrick's Day Parade 

Naples beckons with its vibrant St. Patrick's Day Parade, set to paint the town green on March 16, 2024. This festive event, orchestrated by The Naples St. Patrick’s Foundation Inc., begins with a flag-raising ceremony at 9:30 a.m. in Crayton Cove, followed by the parade at 11 a.m. As a cherished community tradition, it offers a lively celebration of Irish culture, featuring an array of floats, marching bands, and the spirited involvement of local organizations. A day of joyous revelry, it's a must-attend for both locals and visitors.


At Moorings Park Communities, we strive to ensure our residents experience the best of what Naples has to offer. From our luxurious residences and world-class healthcare services to our award-winning dining options and vibrant social events, Moorings Park Communities is the premier place to live in Naples. Schedule your tour today and see why we are the top choice in luxury retirement living.

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