Naples Season Is Here: 11 Events That Make Winter Here So Special

Season is the reason so many of my buyers fall for Naples in the first place. Naples season runs from about November to April, and the calendar fills fast: garden lights and a downtown parade in December, art fairs, the boat show and the wine festival in January, golf and more art in February, and a St. Patrick’s parade on Fifth Avenue South in March. Here are 11 events worth planning your winter around, with the dates that are already set.

Dates change, so check each event’s own site before you book anything. Where a date isn’t announced yet, I’ve only listed the month.

November and December

1. Night Lights at Naples Botanical Garden

The Garden glows with lights from November 27, 2026 to January 3, 2027, closed December 24, 25 and 31. Tickets are sold by date, so book early. Details on the Naples Botanical Garden site.

2. Art in the Park

Naples Art fills Cambier Park downtown with artists on Saturday, November 28, 2026, and again on February 6 and April 10, 2027. It’s an easy morning with coffee from Fifth Avenue South.

3. The City of Naples Christmas Parade

The parade comes through downtown on Tuesday, December 8, 2026, starting at 6:30 pm. Come early for a spot along the route, and check the City of Naples parade page for the map.

4. Holiday nights on Fifth Avenue South

Fifth Avenue South decorates for the holidays and usually hosts its Christmas Walk in early December. The 2026 dates weren’t posted yet when I wrote this, so watch the Fifth Avenue South events calendar.

5. A night at Artis Naples

Season is when Artis Naples, home of the Naples Philharmonic, has its fullest schedule of concerts and shows. Many seasonal residents buy a few nights early so they have plans waiting when they arrive.

January

6. The Naples New Year’s Art Fair

Start the year in Cambier Park on January 2 and 3, 2027, from 10 am to 5 pm.

7. The Naples Boat Show

The boat show takes over Sugden Regional Park in late January. If a boat is part of your Naples plan, this is a good place to start. It’s also why I tell buyers to ask about boat and RV storage early; my post on boat and RV storage in Naples explains the options.

8. The Naples Winter Wine Festival

The festival returns January 29 to 31, 2027, at The Ritz-Carlton Naples, Tiburón. It’s a charity event, and the money raised supports children’s programs in Collier County.

February and March

9. The Naples National Art Fair

One of the biggest weekends of the year in Cambier Park, held in February. Naples Art posts the exact days on its site.

10. The Chubb Classic

PGA TOUR Champions golfers play at Tiburón in February. If you love golf, my post on choosing a private golf club in Naples is a good next read.

11. The St. Patrick’s Day Parade

Fifth Avenue South turns green for a Saturday parade in March. Get there early for a spot near the shops and restaurants.

Making the most of season

• Book early: popular tickets, restaurant tables and tee times go fast from January to March.
• Stay close to what you’ll use: a home near your events, your club and the beach saves you a lot of season traffic.
• Think lock and leave: if you’ll head north in spring, a home you can close up easily makes the off-season simple.

Featured home: 3059 Horizon Ln #1602

If you want to be here for season and travel the rest of the year, my listing at 3059 Horizon Ln #1602 in gated Bridgewater Bay, North Naples, is easy to enjoy and easy to leave. Offered at $459,900:

• A second-floor end residence with lake views from a private screened lanai
• Three bedrooms and two and a half baths, about 1,849 square feet, with vaulted ceilings and tile flooring
• New Trane air conditioning in 2025, plus fresh paint and a new washer and dryer in 2024
• A one-car attached garage, and a community clubhouse, pools, fitness center, tennis, pickleball, bocce and fenced boat and RV storage

See the photos and details on the 3059 Horizon Ln #1602 listing page, or call me for a private showing.

How I help

Many of my buyers are seasonal residents, and I help them find a place that fits how they really live here: close to the events and clubs they love, simple to leave in the spring. Read my take on first-floor condos in Naples, my Naples luxury homes guide, or the Florida tax benefits if you’re thinking about making Naples home. In English and Spanish, since 2013.

When is season in Naples?
Season runs from about November to April, with the busiest months from January through March, when most seasonal residents are in town.

What are the biggest events of Naples season?
Some of the best known are Night Lights at Naples Botanical Garden, the City of Naples Christmas Parade, the Naples Winter Wine Festival, the Naples National Art Fair, the Chubb Classic and the St. Patrick’s Day Parade.

Is a condo a good choice for seasonal living in Naples?
For many seasonal buyers, yes. A condo in a gated community with shared amenities is easier to close up when you leave in spring. Check the community’s rules on rentals and pets before you buy.

When should I buy if I want to be here for season?
Start looking in late summer or early fall if you can. That gives you time to close, furnish and settle in before the busy months begin.

Ready for season? Search every home for sale in Naples, or call or text me at (239) 289-0749. Se habla español.