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September 2025 Events on the Paradise Coast

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The start of fall has nearly arrived, which means you've got tons of great events to look forward to in Paradise Coast communities. This time of year offers an excellent mix of outdoor events, fun festivals, family-friendly activities, and live performances, so family members of all ages can get in on the fun. Our real estate agents have more on upcoming September events that you can enjoy in Paradise Coast communities.

  • Bark on the Ark – 1200 5th Ave. S., Naples, FL 34102
    With beautiful weather and September sunshine, this is the perfect time for a visit to Keewaydin Island with your four-legged friend. Bark on the Ark is a special boat trip from Pure Florida for people and pups, offered on the second Saturday of every month. Take a cruise to Keewaydin Island, with plenty of time to explore and play on the beach. Reserve your tickets online for the next Bark on the Ark, which takes place on September 13, 2025.

  • Princess Tea Party – 550 Port O'Call Way, Naples, FL 34102
    The Princess Tea Party is a special, kid-friendly cruise on the Naples Princess, where they can meet their favorite movie princesses, including Cinderella, Belle, and Tiana. The cruise includes musical performances, storytime, princess training, and even a walk down the red carpet, complete with a photo op. Enjoy a fairytale day on September 13, 2025, and give your kids an experience they won't soon forget.

  • Morning Art Breaks at Amy Art Gallery – 950 1st Ave. N., Naples, FL 34102
    We've mentioned the popular Morning Art Breaks at Amy Art Gallery series earlier in the summer, and September is the last chance to experience it for this year. On September 20, 2025, visit the gallery for Behind the Scenes at Amy Art Gallery, a tour of artist Amy Moglia Heuerman's works, which delves deep into her creative processes. The tour is hosted by Amy Art Gallery Director Dr. Leslie Vega and features refreshments from the excellent Bakery at Grappino.

  • Baile y Comida: Taste and Move to History – 451 Connecticut St., Fort Myers Beach, FL 33931
    In honor of Latinx Heritage Month, the Mound House Museum will be hosting its special Baile y Comida: Taste and Move to History event on September 13, 2025. Learn about local history, savor a delicious Latin American meal, and hit the dance floor for an invigorating group dance lesson. Tickets can be reserved online, with discounts available for Mound House Museum members.

  • A Day In Hollywood, A Night on Broadway: A Musical Revue – 13211 McGregor Blvd., Fort Myers, FL 33919
    Whether you're enjoying a film on the big screen or a musical on the Broadway stage, song is such an essential part of the experience. A Day In Hollywood, A Night on Broadway: A Musical Revue takes you on a journey through some of the biggest blockbuster songs from film and stage, with all-stars from the Players Circle Theater as your guides. Take in one of their evening shows from September 18-20, 2025, or spend your afternoon with a special matinee performance on September 21, 2025.

  • Island Hopper Songwriter Fest – Fort Myers, FL
    The annual Island Hopper Songwriter Fest is a must-see for music lovers, with performances in Downtown Fort Myers, Fort Myers Beach, Captiva Island, and Cape Coral from September 19-28, 2025. There will be more than 60 free performances spread across those dates, as well as ticketed events featuring top artists from the BMI record label. Performances here come from a wide range of genres, and the artists tell the stories behind their most popular songs throughout the performances.

Searching for Naples luxury homes for sale this fall? Our local team is here to help with all of your real estate needs. Contact us to buy and sell homes in your favorite Paradise Coast communities.

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