November Events Across Southwest Florida

Southwest Florida comes alive this time of year with food festivals, holiday celebrations, waterfront traditions, and community favorites. Whether you want a fun night out, a family friendly activity, or a coastal experience you can only find here, this week brings something for everyone. Here are ten events across Charlotte, Lee, and Collier counties to help you enjoy the season.

Grand Illumination 2025

When: November 22, 2025 | 3 PM to 7 PM
Where: The Village Shops on Venetian Bay, Naples
What: Watch Naples tallest Christmas tree light up over the water with more than 100,000 sparkling lights. Enjoy photos with Santa, Dickens carolers, festive characters, boutique shopping, and a magical snowfall at 6 PM.
More Info →

Holiday Vendor & Craft Fair

When: November 29, 2025 | 10 AM to 3 PM
Where: Englewood Elks Club, 401 N Indiana Ave, Englewood
What: Outdoor craft fair open to the public featuring local artisans, vendors, and food trucks for a small-business-style shopping experience.When: September 5, 2025 | 5 PM – 9 PM
More Info →

Another Elf’n Pub Crawl

When: November 29, 2025 | 7 PM to 11 PM
Where: South Cape, Cape Coral
What: Festive onesies encouraged. Hopping through South Cape bars with seasonal cocktail samples, appetizers, limo-bus drop-offs, a passport contest, photo-booth fun.
More Info →

Mistletoe Market

When: November 22, 2025 | 9 AM to 2 PM
Where: New Hope Church, 431 Nicholas Pkwy E, Cape Coral
What: Vendor market filled with unique gifts from local artists and small businesses, plus food trucks and raffle baskets. Entry $5 cash — supports local missions.When: November 22, 2025 | 9 AM to 2 PM
More Info →

Fort Myers Turkey Trot 5K

When: November 27, 2025 | 7 AM (5K Run/Walk)
Where: 2350 McGregor Blvd, Fort Myers (start & finish at Edison & Ford Winter Estates)
What: A local Thanksgiving-morning tradition: 5K run/walk, family friendly, thousands of participants, beautiful historic course.
More Info →

Marco Island Blessing of the Fleet & Seafood Celebration

When: November 29, 2025 | 10 AM to 4 PM
Where: Rose Marina, Marco Island
What: Local fishing fleet receives a traditional blessing, with fresh-seafood vendors, live music, maritime displays and waterfront fun.
More Info →

Venice Holiday Parade

When: November 29, 2025 | 7 PM
Where: Downtown Venice
What: Community parade with floats, marching bands, performers and lively local participation — a fun night out with family and friends.
More Info →

Autumn Garden Festival at Edison & Ford Winter Estates

When: November 22–23, 2025 | 9 AM to 4 PM
Where: Edison & Ford Winter Estates, 2350 McGregor Blvd, Fort Myers
What: Explore fall themed garden displays, enjoy live music, browse art and plant vendors, and stroll through the historic waterfront grounds for a relaxing seasonal outing.
More Info →

Sarasota Medieval Fair

When: November 22–23, 2025
Where: Woods of Mallaranny, near Venice
What: VStep back in time with live jousting, medieval reenactments, artisan markets, food, musicians and performers at one of the most popular themed festivals in the region.
More Info →

Thanksgiving Eve Celebration featuring Rock Republic

When: November 26, 2025 | 3 PM to 9 PM
Where: Fort Myers Brewing Company, 12811 Commerce Lakes Drive, Fort Myers
What: Celebrate the start of the holiday weekend with live music by Rock Republic, DJ sets, food trucks, craft brews and a lively community atmosphere.
More Info →

21st Annual Turkey Drop (Food Drive)

When: November 22, 2025
Where: St. Matthew’s House at First Naples Church, with additional sites across SWFL
What: Join volunteers giving back by helping pack and distribute thousands of Thanksgiving meals to families in need throughout Southwest Florida.
More Info →

There is no better time to explore all that Southwest Florida has to offer. Mark your calendars, share these events with friends and family, and support the local businesses and organizations that make our community special. If you need recommendations, real estate guidance, or things to do in your area, reach out to our team anytime. We are here to help you enjoy the best of SWFL.