Southwest Florida sings in the new year. In Naples, Rookery Bay National Estuarine Research Reserve hosts its annual Festival of Birds with new sunrise walks and sunset kayak trips. In Fort Myers, artist Sun Smith-Forêt presents her expansive textural works to the region for the first time. And in Punta Gorda, the inaugural Boots & Roots Festival launches, with music from Ben Allen Band and country artist Easton Corbin. Don’t miss these January happenings.
Jan. 3 and 4
Naples New Year’s Art Fair at Cambier Park
Naples Art Institute carries its 46-year relationship with Cambier Park forward with the 30th anniversary of this outdoor art festival. The institute hand-selects 250 local, national and international artists to showcase their work. The scenic, walkable setting draws thousands of art lovers every year to browse work in mediums like acrylic, photography and leather, reinforcing the event as a cornerstone of the local cultural community. Learn more
Jan. 3 and 4
The Kickoff Classic at the USOP National Pickleball Center, Naples
Pickleball enthusiasts take to the court, joining some 800 players and 1,500 spectators for the third annual Kickoff Classic. Across the two-day tournament, 78 open-to-all brackets—men’s and women’s doubles, mixed doubles and wheelchair divisions—set the stage for play. A special MONEYBALL division pits 16 doubles teams against one another to claim cash prizes: $2,000 for gold and $1,000 for silver. Visitors find a yacht display from Naples Marina, cars from Mercedes-Benz of Naples and Mercedes-Benz of Bonita Springs, and a 35-vendor market. Learn more
Jan. 5 — 30
Hunt Slonem at Harmon-Meek Gallery, Naples
The Naples gallery has represented the internationally renowned neo-expressionist for longer than any other gallery in the world. This month, Harmon-Meek draws on its 30-year partnership with Hunt Slonem for a solo exhibition of his latest works, hand-picking favorites from among his whimsical, bunny-focused paintings. Learn more
Jan. 9
The Spinners at Hard Rock Casino, Immokalee
The Spinners, a pop, R&B and soul music group formed in 1954 (then called The Domingoes), performs decade-spanning hits at the Seminole Center. The ensemble has earned six Grammy nominations, created 18 platinum and gold albums, and sold millions of records. Though none of the original members remain, classic lineup collaborators Bobbie Smith and Henry Fambrough kept their promise to sustain the band, recruiting musicians for a fresh group and continuing the legacy. Learn more
Jan. 9 and 10
SWFL Wood Art Exposition and Competition at Charlotte Harbor Event and Conference Center, Punta Gorda
For 40 years, specialty carvers, woodturners and furniture makers have gathered to compete in four proficiency categories. A representation of the region’s creative craftsmanship scene, participants present an array of bespoke carved products: One of last year’s winners was a luxury box made of ebony, coquille d’oeuf—an eggshell-like wood finishing—and Japanese urushi lacquer. For the first time, the expo offers cash prizes for Best of Show, President’s and People’s Choice awards. Learn more
Jan. 10 — Ongoing
There & Here: New Perspectives of the Permanent Collection at Artis—Naples, The Baker Museum
In the works for more than a year, There & Here goes beyond the typical exhibition. The show celebrates Artis—Naples, The Baker Museum’s 25th anniversary with panel discussions and pinnacle pieces of the institution’s permanent collection. A committee of community advisers—curators Tara Backhouse and Tayina Deravile, Miccosukee Business Council secretary William ‘Popeye’ Osceola, and author Annabelle Tometich—organized and executed this exhibit, which highlights migration, ancestry and identity. Learn more
Jan. 10 and 11
Bonita Springs National Art Festival with Arts Bonita, Riverside Park
A regional hub for artists and collectors, this fine art festival returns with revamped operations. This year, Arts Bonita’s new festival director, Richard Sullivan, offers his expertise in art curation, festival direction and nonprofit leadership—expanding artist stations for better art visibility and redesigning the festival layout to cover only one side of the street (Goodbye, crosswalk hazards!). Learn more
Jan. 11
Jay Leno at Artis—Naples
The professional stand-up comedian and former host of The Tonight Show returns to Naples for one night only; his last local appearance was headlining the 2025 Cars on 5th Automotive Experience. Known for his sharp, observational humor, the comic shares his take on current topics and Hollywood experiences in the limelight. This show is part of his ongoing comedy tour, which includes at least 100 performances annually. Learn more
Jan. 13 — 18
SOME LIKE IT HOT at Barbara B. Mann Performing Arts Center Hall, Fort Myers
Broadway makes its way to our slice of Florida with the national tour of this Tony- and Grammy Award-winning musical comedy. Set against the backdrop of Chicago’s Prohibition Era and featuring Roaring Twenties-inspired costumes and props, the production follows two musicians who are chased out of the city and across the country by mob gangsters. Learn more
Jan. 15 — 19
Festival of Birds at Rookery Bay National Estuarine Research Reserve, Naples
Rookery Bay, an organization dedicated to researching and protecting Southwest Florida’s coastal environment and avian fauna, hosts their annual festival to coincide with the migratory patterns of local wildlife. Around this time of year, sandhill cranes, cedar waxwings and American robins find winter homes in this region. The event features various avian activities and workshops, keynote speaker Paul Gray from Audubon Florida, and field trips to environmental destinations—like kayaking tours through Big Cypress National Preserve and Rookery Bay. Learn more
Jan. 16 and 17
Boots & Roots Festival at Babcock Ranch, Punta Gorda
Babcock Ranch introduces the inaugural Boots & Roots Country Music Festival, a two-day event at Founder’s Square celebrating local and top country artists. Ben Allen Band headlines the festival alongside “All Over the Road” singer Easton Corbin. Beyond the stage, find a line dancing arena, family-friendly zones and country-style cookouts. Partnering with the national nonprofit Save The Music Foundation, the event supports the next generation’s access to music education. Learn more
Jan. 16 — 18
Artful Arrangements: Original Artwork Re-Imagined in Floral Designs at Naples Art District
At this signature annual event, two creative forms merge. Floral artists craft more than 40 flower arrangements that echo paintings from Naples Art District. Paired together for display, the art and arrangements play off each other in a dynamic and playful juxtaposition, where flowers, stems and leaves draw out the hues and forms dreamed up by local artists. Learn more
Jan. 21
Musical Interludes: Ben Rosenblum Jazz at Marco Island Center for the Arts
Award-winning New York City pianist, vocalist, composer and accordionist Ben Rosenblum lands in Marco Island for a world-class jazz performance featuring tunes from the artist’s four self-led albums. The musical multihyphenate has brought his talents to more than 20 genres and 25 countries, captivating audiences large and small—from local stages to Carnegie Hall. Learn more
Jan. 22 — 25
Naples Boat Show at Naples City Dock
A local favorite since 1967, the Naples Boat Show brings local and international brands together to showcase a diverse range of vessels, from flatboats designed for shallow-water fishing to cabin cruisers for deeper-sea exploration. Alongside the boats at this four-day event, guests can expect technologically advanced marine equipment and accessories, insight from boating experts, and nearby dining options like Chez Boet and The Dock at Crayton Cove. Learn more
Jan. 23 — Apr. 17
A Journey to the Oracle, Ebenezer Leyva at BIG ARTS Sanibel Mezzanine Gallery
During gallery director and artist Wilson McCray’s years living in Costa Rica, he shared a studio with an artist whose work he describes simply as “extraordinary.” Now, he’s bringing that experience to Sanibel, with a solo exhibit of works from Cuban artist Ebenezer Leyva Gonzalez. Known for his explorations of perception and connection, the painter, multimedia artist and educator presents a new collection of works rooted in existential questions brought to life in oil and acrylic. Learn more
Jan. 24 and 25
Caloosahatchee Celtic Festival at Caloosa Sound Amphitheater, Fort Myers
Kilts are adorned and Guinness gets poured at the Caloosahatchee Celtic Festival. Attendees celebrate Celtic and Irish traditions with a mix of pop, rock and pipe-based music performances from national and international bands, as well as Gaelic moves from Southwest Florida’s Kellyn Celtic Arts Irish Dancers. Learn more.
Jan. 24 — Mar. 14
Festival Under the Stars at Wang Opera Center and Baker Park, Naples
America’s first outdoor winter opera festival returns bigger than ever for its sixth year. In honor of Opera Naples’ 20th anniversary, the festival stretches a full five weeks—as opposed to the typical three—and marks the event’s return to its original location: Baker Park. The festivities kick off January 24, with An Evening of Opera’s Greatest Hits, a selection of works performed by Opera Naples’ resident artists. Learn more
Jan. 27 — Mar. 1
Circle Forward World Premiere at Gulfshore Playhouse, Naples
Circle Forward, workshopped initially at Gulfshore Playhouse’s New Works Festival in 2023, returns for its world premiere as a fully staged production. A Local Theatre Company award finalist, this dramatic, dark comedy by Deb Hiett centers on a widow traveling the country as a public speaker on grief. Before long, she is faced with the unthinkable: a young stranger claiming to be her husband reincarnated. Learn more
Jan. 27 — Mar. 1
Tuesdays with Morrie at Florida Repertory Theatre, Fort Myers
Based on Mitch Albom’s memoir, Tuesdays with Morrie interweaves themes of friendship, shared wisdom and healing. Directed by Maureen Heffernan—who has led over 20 productions at Florida Repertory Theatre—this drama tells the story of Morrie, who is battling Lou Gehrig’s disease, and his former student Mitch, chronicling their weekly journey to understand life’s meaning. Learn more
Jan. 28 — Apr. 25
Above & Beyond, Artworks by Sun Smith-Forêt at Tribby Arts Center at Shell Point, Fort Myers
Artist Sun Smith-Forêt arrives from St. Louis with a vast portfolio of textural works to display for the first time in Florida. The professional studio artist, teacher and independent curator showcases her 200-foot Riverwork textile, a panoramic project representing themes from the Western frontier to hydroelectric power to literature. While this wall piece wraps around several gallery spaces at Tribby, a collaborative sculpture, 60 basketry works and 36 paintings are also on display. Learn more