Welcome to this month's edition of the Southwest Florida Insider — A sampling of fun things to do and see around our beaches. Please enjoy this snapshot of happenings throughout the month. If you have an event(s) you would like to see us share next month, please let me know.
MARK YOUR CALENDAR
June 14 | Flag Day
June 15 | Father's Day
June 20 | Summer Solstice
STOMP
Experience the global sensation STOMP—an electrifying, one-of-a-kind performance where eight dynamic artists transform everyday objects into rhythmic, high-energy music. Celebrated worldwide for 30 years, STOMP delivers a pulse-pounding blend of humor, creativity, and percussion that captivates audiences of all ages.
Pole Vault in the Plaza
Mercato proudly presents its fourth annual Pole Vaulting Competition, showcasing athletes of all ages—from kids to seniors. Enjoy thrilling feats, outdoor games, concessions, and more at this fun-filled community event!
Evening on Fifth Ave
Live music fills the sidewalks of 5th Avenue South with performances along the avenue, complemented by dining, shopping, and more vibrant experiences.
Summer Wine & Cocktail Series: Spain
Join Campiello’s 2nd annual Summer Wine & Cocktail Series in the ClubRoom for a global culinary adventure. Kicking off June 12 at 6PM with the bold flavors of Spain, guests will wine, dine, and explore world cuisines. Space is limited—reserve now for this unforgettable international tasting experience!
Captivaville
Experience the 7th annual Captivaville Songwriters Weekend at 'Tween Waters Island Resort & Spa! Discover Captiva Island's grandest music festival showcasing talented local singer-songwriters. Enjoy 72 hours of sun, fun, incredible live music, and the summer's most sensational party. Don't miss this remarkable event.
FC Naples vs. Chattanooga
Get ready for an electrifying match as FC Naples takes on Chattanooga on Friday, June 14! Cheer on your hometown team in this exciting showdown filled with high energy, fierce competition, and unforgettable moments. Don’t miss your chance to be part of the action—grab your tickets now!
Luke Bryan @ Jet Blue Park
Live Nation and the Boston Red Sox present Luke Bryan at JetBlue Park’s inaugural concert on Saturday, June 14, 2025. Joining him are special guests Conner Smith, Ashland Craft, Adrien Nunez, and DJ Rock for an unforgettable night of live music.
The Great Canore Races of Naples
After a four-year break, the 45th Annual Great Canoe Races return June 14 at Baker Park, hosted by the Young Professionals of Naples. This lively event features canoe races, a vendor fair, live entertainment, a beer garden, and a special first responders’ heat—celebrating tradition with exciting new twists.
Cars & Coffee: Father's Day Edition
Come celebrate Father's Day at the exhilarating Cars and Coffee event in Mercato Mall. Witness a dazzling array of unique cars while enjoying a cup of coffee. As a special tribute to all dads, each will receive one complimentary beverage and join in for early brunch at The Pub beginning at 9:00 a.m. Don't miss this exciting gathering!
Cars on 1st
The Inaugural Cars On 1st is more than a car show—it’s a community movement supporting youth mentorship and small businesses across Southwest Florida. Admission is free, but voluntary donations are encouraged to help drive meaningful change.
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Amy Nease
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