Dive into Islamorada’s Exciting Winter Events: Art, Music, and Community Fun!

Hello, Islamorada friends and visitors! As we embrace the delightful Florida winter, our vibrant community is buzzing with some fantastic events you won’t want to miss. Whether you’re a seasonal visitor, a luxury buyer, a fishing enthusiast, or simply in love with the island lifestyle, there’s something for everyone in our little slice of paradise.

Art Under the Oaks: A Celebration of Creativity

Kicking off our winter festivities is the 40th Annual “Art Under the Oaks” festival, happening on Saturday, January 13, 2024. Join us from 9 a.m. to 4 p.m. at the picturesque San Pedro Church Gardens. This festival is a treasure trove of fine art and original crafts—a perfect opportunity to find that unique piece you’ve been looking for! Indulge in a variety of refreshments from specialty and international food booths, and don’t miss the home-baked goodies at our bake sale. With live entertainment and raffles, the event promises a day full of joy and artistic discovery. And the best part? Admission is absolutely free!

Event Details:

  • Location: San Pedro Church Gardens, MM 89.5, US 1
  • Dates: Saturday, January 13, 2024
  • Time: 9:00 AM – 4:00 PM
  • Admission: FREE

Beats on the Bay: A Night of Bluegrass and Stars

The following day, January 14th, we continue the celebration with the “Beats on the Bay” music series. The Baygrass Bluegrass Finale Concert is set to serenade you at the Islamorada Founders Park Amphitheater. It’s a night under the stars with soulful music, delicious food trucks, and a selection of beer and wine. Entry is free, but there’s a $10 parking fee. Remember to bring your own seating, and note that no outside food or coolers are allowed.

Event Details:

  • Location: Founders Park Amphitheater, 87000 Overseas Highway Islamorada, FL 33036, US
  • Dates: Sunday, January 14, 2024
  • Admission: FREE
  • Parking: $10

Monthly On-Going Events

1. Thirsty Thursdays

Mark your calendars for Thirsty Thursday on January 18th! This time, we’re hosting a Karaoke night from 6-8 pm. Get ready to belt out your favorite tunes, enjoy cocktails, and snack on tasty treats. It’s a perfect evening to mingle with locals and fellow visitors, showcasing your vocal talents (or just enjoying others’ performances!).

2. Morada Way Arts & Cultural District Art Walk

Another ongoing highlight is our Morada Way Arts & Cultural District Art Walk. This vibrant 2-day event, starting on January 18th, showcases the incredible work of local artists. It’s an artistic journey accompanied by food, drinks, and live music. Be sure to visit the Taylor Hale Studio & Gallery, Morada Way Clay, Jessica Ann’s locations, and the Limelight Studio + Gallery.


3. Giving Back to the Community

In Islamorada, we believe in giving back to our beautiful environment. With every sale made in our community, we commit to planting one tree. It’s our way of ensuring that the natural beauty of our island paradise continues to thrive for generations to come.


Whether you’re looking for a winter home, contemplating a vacation spot, or just here to enjoy the island vibe, Islamorada’s array of events and community spirit are sure to make your stay memorable. So, come join us in celebrating art, music, and the joy of community this winter—we can’t wait to share it with you!