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

January 16, 2023

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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 or the Naples Boat Show. To help you stay engaged this season, we've gathered a list of 5 winter events that you will not want to miss.

Related Blog: A Taste of Florida: A Guide to Seasonal Fruits and Vegetables

1. Naples Boat Show

The Naples Boat Show is an event that celebrates all things marine. The show features various vessels from high-end yachts to recreational fishing boats, paddleboards, and kayaks. This family-friendly event allows boating enthusiasts to check out the latest technology, accessories, electronics, and more. The event will be held January 19th - 22nd from 10 am - 5 pm at Sugden Regional Park and Naples City Dock.

2. 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 online auction begins on Friday, January 27th at 8 am and ends on Tuesday, February 7th at 5 pm. The live auction will be held on Saturday, February 4th from 11 am to 5 pm.

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. This year’s theme “In Perfect Harmony” showcases the curated ensemble of award-winning chefs and world-renowned vintners who come together every year. 

The event will take place at The Ritz-Carlton Golf Resort in North Naples on February 3-5, 2023.

3. Cars on 5th Concours


Are you a car enthusiast? Then you’ll want to mark your calendars for the 19th Annual Cars on 5th Concours held on Saturday, February 4th 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 $30 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!

4. Naples Seafood and Music Festival

If you're looking for a unique winter experience, head to the 2nd 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 ​​February 3rd from 4 pm-10 pm, February 4th from 11 am-10 pm, and February 6th from 11 am-6 pm. General admission is FREE!

5. Naples Craft Beer Festival at Bayfront

The annual Naples Craft Beer Festival at Bayfront is a must-attend event for craft beer lovers. The festival, which takes place on March 4th, showcases a variety of craft beers from local, regional, and international breweries. Attendees can sample over 100 brews, including IPAs, stouts, sours, and more. Plus, the event features live music, food trucks, and beer-related vendors. Whether you're looking to expand your beer knowledge or find new favorites, the Naples Craft Beer Festival has something for everyone.

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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