January & February 2026: Highlights You’ll Love
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1. Naples Boat Show (Jan 22–25)
Set sail on excitement at the biggest boating event in town! Held at Sugden Regional Park and Naples City Dock, this premier show features both on-land and on-water displays. Enjoy a free shuttle, leisurely strolls among boats of every kind, and marine inspiration for all ages.
2. Naples New Year’s Art Fair (Jan 3–4)
Ring in the new year surrounded by creativity downtown. The Naples Art Association presents a bustling outdoor fair along 5th Avenue, showcasing original paintings, sculpture, prints, photography, handcrafted jewelry, and more—ideal for art lovers and early-year explorers.
3. Festival Under the Stars — Opera Series (Jan 24 & Feb Performances)
Experience the dramatic and operatic under the evening sky at the Wang Opera Center. January brings An Evening of Opera kickstarting the Festival Under the Stars. February features diverse performances, including selections from the Luciano Pavarotti Foundation Voice Competition, opera favorites like Elixir of Love, and other acclaimed productions.
4. Art After Hours at The Baker Museum (Jan 28 & Feb 25)
Make Wednesday nights more memorable with Art After Hours. Visit The Baker Museum for free admission, live music, and light bites every last Wednesday of the month—from 6 PM to 9 PM. January 28 and February 25 are perfect evenings to immerse in culture without lifting your wallet.
5. Chocoholics 5K Run/Walk (Feb 1)
Who says fitness can't be sweet? Join Naples’s most indulgent 5K: end your run with chocolate, a custom T-shirt, lively DJ beats, and a chocolate-filled kids’ dash. It’s the sweetest way to start your February—with steps, smiles, and treats.
6. Cars on 5th Concours (Feb 7)
Fuel your automotive passions at 5th Avenue South with over 400 luxury and exotic vehicles—Ferraris, Lamborghinis, Corvettes, and more. General admission is $30 (ages 13+), with VIP access offering elevated perks—perfect for auto aficionados and casual admirers alike.
7. Naples National Art Fair (Feb 20–22)
Art blooms in Cambier Park and along 8th Street South as the Naples National Art Fair returns. Explore an open-air gallery of paintings, sculptures, and handcrafted works by local and national artists—an idyllic outing for sunny winter afternoons.
8. Chubb Classic PGA Tour Champions (February)
Tee off into spring at the Chubb Classic, Naples’s distinguished PGA Tour Champions event, played at Tiburón Golf Club's Black Course. A refined sporting spectacle for golf lovers and newcomers to the fairway alike.
Frequent Favorites Worth Your Time
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Naples Winter Wine Festival continues its tradition of culinary glamour and charitable giving, offering chef-driven dinners and live auctions that benefit local children’s causes.
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Everglades Seafood Festival celebrates local culinary culture with seafood, crafts, and community spirit—typically held early in February.
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Weekly Farmers Markets—including those at Third Street South and Vanderbilt Shoppes—bring fresh produce, artisan eats, and small-town charm to your weekend routine.
Why January & February Are Special in Naples
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Effortless Outdoor Living: Soothing winter warmth invites beach walks, art strolls, and festival fun—without the crowds.
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Culture & Community: From spontaneous art encounters to long-planned galas, everything feels elevated in these sunlit months.
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A Perfect Time to Visit—or Call Home: Whether you're a seasonal guest, a returning traveler, or looking for a life reset, February offers Naples at its most engaging and welcoming.
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