Winter Festivals and Events Happening Throughout Southwest Florida


During the winter months Southwest Florida becomes a vacation destination for travelers from all around the world.

Whether you’re coming to enjoy the spring-like weather, the tropical beaches and golf courses, or simply to enjoy a weekend in paradise – there are plenty of reasons to come to the Sunshine State.

Due to the fact Southwest Florida’s population skyrockets in the winter months, many local businesses and nonprofits have scheduled their winter activities, events, and festivals during that time.

If you are planning a winter vacation or looking to make weekend plans, here are some of the most popular winter events happening throughout Southwest Florida.

Naples Winter Wine Festival | February 3rd – 5th

Photo: Naples Winter Wine Festival

One of the most popular festivals in Southwest Florida is the Naples Winter Wine Festival. This world-class event takes place on Friday, February 3rd and goes until Sunday, February 5th.

The Naples Winter Wine Festival has been ranked among the Top 10 Arts and Entertainment Events for Wealthy Americans by the Luxury Institute for its exclusive guest list, quality and prestige.

Foodies, wine connoisseurs, and visitors alike will enjoy more than 20 of the world’s most prominent wineries, hundreds of fabulous auction lots, celebrity chef-created meals and live entertainment.

All proceeds for the event benefit the Naples Children & Education Foundation, whose vision is to make a profound and sustaining difference in the quality of children’s lives. Since its inception in 2001, the Naples Winter Wine Festival has raised nearly $244 million for children in need.

For more information on the Naples Winter Wine Festival, visit https://www.napleswinefestival.com/

Naples Outdoor Art Festival | Monthly, Starting in December

Photo: Michael Caronchi | Naples Art

Throughout the winter, Naples Art Institute and Art in the Park host multiple outdoor art festivals in some of the area’s most prestigious locations. The monthly exhibitions will take place at Mercato, on 5th Avenue South, and in Cambier Park from December to April.

These outdoor art festivals connect local artists with buyers and judges as approximately 40 professional artists from all over the state showcase their work with mediums including ceramics, glass, printmaking, jewelry, metals, mixed media, painting, sculpture and more.

The events will have live music, breathtaking works of art, and a festive atmosphere as the locations are minutes from award-winning restaurants and designer shopping.

Learn more at, https://www.naplesart.org/outdoor-art-fairs

Swamp Cabbage | February 25th and 26th

Photo: Pete Cross | Swamp Cabbage Festival

The Swamp Cabbage Festival is an annual event located in Labelle, just east of Fort Myers. This family friendly festival will take place on Saturday and Sunday, February 25th & 26th.

Each year, Florida Power and Light puts on the Swamp Cabbage Festival named after the Sabal Palm tree dish, and hosts dozens of food vendors, live entertainment, a family friendly parade, and even “armadillo races.”

The event attracts anywhere between 30,000 to 50,000 people in just two days and is perfect for a fun family weekend. Swamp Cabbage is free to attend, while food, beverages and games are available for purchase.  

For more information visit https://www.labelleswampcabbagefestival.org/

Live the Southwest Florida Lifestyle

Southwest Florida isn’t just a place for a tropical vacation, it’s the ideal place to live – infinitely! If you’re looking to live on the Paradise Coast, explore the residential opportunities at Infinity at The Colony.

Located in the renowned golf course community of The Colony, this 22-story tower will include 96 luxurious residences overlooking the blue waters of Estero Bay, The Gulf of Mexico, and The Colony’s championship golf course.

Infinity is located in the heart of Bonita Springs and is just a short drive away from all of the previously mentioned festivals and events. Infinity is also just minutes from white-sand beaches, boutique and designer shopping and award-winning restaurants.

Infinity’s luxurious high-rise offers breathtaking views and open-concept residences ranging from 2,950 to 3,915 square feet.

Residents will enjoy access to a multi-slip marina and a 34-acre private sugar sand beach just minutes away from their high-rise condominium.

Infinity is also designed with exciting amenities such as resort-style pools, poolside cabanas, a par-3 putting course, guest suites, fitness center, private theater and much more.

If you are interested in Infinity at The Colony, home to its own slate of onsite events, be sure to act fast as the residences are currently approaching 50% sold.

For more information, contact our sales team today at 239-362-9550 or visit InfinityColony.com