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Events are subject to change. Confirm event details with the location/host.
Art
Ongoing: Art Exhibition - Art in Village Buildings
Dates: November 2025 – March, 2026
Times: During business hours
Location: Village Hall and Founders Park, 87000 and 86800 Overseas Hwy
Morada Way Art Walk
Date: Thursday, 1/15/2026
Time: 6:00 PM-9:00 PM
Location: Morada Way
The Morada Way Art Walk is MWACD’s landmark, monthly event. On the Third Thursday of each month, Keys-inspired fine artists, vendors, residents, and visitors congregate on Morada Way in Islamorada to celebrate Art & Culture in the stunning Florida Keys. Originating in 2011, this event allows emerging artists, musicians, chefs, and local retailers to showcase their creativity.
FEATURED: The Connections Project: A Mosaic of the Keys 2026 - Pop Up
Date: Wednesday, 1/14/2026
Time: 5:00 PM-7:00 PM
Location: Kona Kai Resort, Key Largo
The Connections Project: A Mosaic of the Keys 2026 spotlights visual and performing artists throughout the County at 10 annual "pop-up" events! Almost 150 unique canvases created by Keys artists will be on display and local musician Leah Sutter will perform. Art lovers may select a canvas of their choice for a donation of $100 and take it home that evening, all proceeds support grants for artists living and working in the Florida Keys. The Connections Project will also pop up at Art Under the Oaks on Saturday.
Art Under the Oaks
Date: Saturday, 01/17/2026
Time: 9:00 AM-4:00 PM
Location: San Pedro Catholic Parish
A festival of fine art and original crafts. Free Admission. Onsite parking $5 donation. Additional parking at Plantation Key Elementary School.
Classes and Workshops
Painting the Keys: Paint a Coconut Class
Date: 1/13/2026
Time: 4:00 PM-7:00 PM
Location: Robbies of Islamorada
Cost: $35 per person or $100 for a group of four, all supplies are included. Join us from 4-7 PM at Robbie's of Islamorada (MM77.5) for our Paint a Coconut with a Local class. Just show up and join in! Choose from a variety of fun designs and create your down island keepsake. Food and drinks from The Hungry Tarpon Restaurant are available for purchase.
Open Studio: Painting Workshop with Robin
Date: 1/14/2026
Time: 11:00 AM-1:00 PM
Location: Banyan Tree
Cost: $50 per person includes instruction and materials. Canvas size upgrade available at additional cost.
Beginners welcome! Every student will work on a different project. Choose from Watercolor, Acrylic or Mixed Media. Bring your own drinks/snacks. Please call (305-664-3433) or email (Robin@banyantreeboutique.com) to reserve your space.
Introduction to Watercolors with Monica Bankowski - Clouds over Water: Beginner Basics
Date: 1/15/2026
Time: 9:30 AM-12:30 PM
Location: Our Place in Paradise
Cost: $90 per class includes paper, paint, & brushes to use $70 per class when participant brings their own supplies.
For beginner watercolor painters, learn about paint, paper, and brushes while learning color mixing and techniques. Class work is from reference and direct observation. Minimum 3 Students - Maximum 8 Students.
Open Studio: Painting Workshop with Robin
Date: 1/15/2026
Time: offered twice! 11:00AM – 1:00PM and 5:30 PM – 7:30 PM
Location: Banyan Tree
Cost: $50 per person includes instruction and materials. Canvas size upgrade available at additional cost.
Beginners welcome! Every student will work on a different project. Choose from Watercolor, Acrylic or Mixed Media. Bring your own drinks/snacks. Please call (305-664-3433) or email (Robin@banyantreeboutique.com) to reserve your space.
Intermediate Watercolors with Monica Bankowski - Blue Sky with Palms: Graded Washes and More
Date: 1/15/2026
Time: 1:00 PM-4:00 PM
Location: Our Place in Paradise
Cost: $90 per class includes paper, paint, & brushes to use $70 per class when participant brings their own supplies.
For painters with watercolor experience, sharpen your painting techniques while you advance your color mixing skills. Class work is from direct observation and reference Minimum 3 Students - Maximum 8 Students
Dance
Square Dance: Baygrass Bluegrass Festival
Date: Saturday, 1/17/2026
Time: 6:30 PM-8:30 PM
Location: Blue Marlin Courtyard Stage at Morada Way Arts and Cultural District
Lecture & Museums
Greetings from the Past: Vintage Postcards from the Florida Keys with Cori Convertito, PhD
Date: Wednesday, 1/14/2026
Time: 6:00 PM-8:00 PM
Location: Florida Keys History & Discovery Center
Cost: Tickets $10, Free for Members.
The Florida Keys History and Discovery Center presents the 2025-2026 Lecture Season, sponsored by Islander Resort. Doors open at 5pm. Cash bar and light appetizers. Registration requested.
Music
Monday 1/12
The Carousers
Time: 5:00 PM-9:00 PM
Location: Lorelei Cabana Bar
Florida Keys Concert Association 2026 Season Preview Party
Time: 5:00 PM-7:00 PM
Location: Florida Keys History & Discovery Center
Discover the Music, Meet the Community
– Learn about the world-class artists performing in the Keys this winter
– Enjoy video and audio highlights of the music they’ll bring to life.
– Connect with fellow music lovers in a relaxed social setting.
Cost: Free Admission
Drinks: Cash Bar Available
Don’t miss this chance to preview one of the best cultural traditions in the Keys — and to be part of a vibrant community that’s been celebrating great music for over half a century!
Registration requested at link above.
Circus Mutt
Time: 6:00 PM-9:00 PM
Location: Florida Keys Brewing Company
Ryan Kozel
Time: 6:30 PM-9:30 PM
Location: Hog Heaven
Tuesday 1/13
Leah Sutter
Time: 5:00 PM-9:00 PM
Location: Lorelei Cabana Bar
John Ciulla
Time: 6:00 PM-9:00 PM
Location: Florida Keys Brewing Company
Wednesday 1/14
Webb & Davidson
Time: 5:00 PM-9:00 PM
Location: Lorelei Cabana Bar
Micah
Time: 6:00 PM-9:00 PM
Location: Florida Keys Brewing Company
Thursday 1/15
Paul Family
Time: 12:00 PM-4:00 PM
Location: Islamorada Fish Company
Jimi Dred
Time: 5:00 PM-9:00 PM
Location: Islamorada Fish Company
Webb & Davidson
Time: 5:00 PM-9:00 PM
Location: Lorelei Cabana Bar
Lee Hagan
Time: 7:00 PM-10:00 PM
Location: Hog Heaven
Friday 1/16
Paul Family
Time: 12:00 PM-4:00 PM
Location: Islamorada Fish Company
Dennis Holmes
Time: 5:00 PM-9:00 PM
Location: Islamorada Fish Company
Ericson Holt
Time: 5:00 PM-8:00 PM
Location: Florida Keys Brewing Company
Uncle Rico
Time: 5:00 PM-9:00 PM
Location: Lorelei Cabana Bar
FEATURED: Songs from the Road Band: Beats on the Bay - Baygrass Bluegrass Festival Kickoff!
Time: 6:30 PM-9:30 PM
Location: Founders Park Amphitheater
Southern Stampede
Time: 7:30 PM-11:30 PM
Location: Hog Heaven
Saturday 1/17
Paul Family
Time: 12:00 PM-4:00 PM
Location: Islamorada Fish Company
FEATURED: Silas Powell Family Band Duo: Baygrass Bluegrass Festival
Time: 1:00 PM-4:00 PM
Location: Florida Keys Brewing Company
Kate Engelmeyer
Time: 2:00 PM-5:00 PM
Location: Islamorada Brewing Co
Brothers of Others
Time: 5:00 PM-9:00 PM
Location: Lorelei Cabana Bar
FEATURED: Uproot Hootenanny: Baygrass Bluegrass Festival
Time: 6:00 PM-9:00 PM
Location: Florida Keys Brewing Company
Ego Freek
Time: 7:30 PM-11:30 PM
Location: Hog Heaven
Sunday 1/18
Austin Vahan
Time: 1:00 PM-5:00 PM
Location: Islamorada Fish Company
FEATURED: Nick and Kris: Baygrass Bluegrass Festival
Time: 1:00 PM-4:00 PM
Location: Florida Keys Brewing Company
Ryan Kozel
Time: 2:00 PM-5:00 PM
Location: Islamorada Brewing Co
Dennis Holmes
Time: 5:00 PM-9:00 PM
Location: Islamorada Fish Company
Webb & Davidson
Time: 5:00 PM-9:00 PM
Location: Lorelei Cabana Bar
John Ciulla
Time: 6:00 PM-9:00 PM
Location: Hog Heaven
FEATURED: Grass is Dead: Baygrass Bluegrass Festival
Time: 6:00 PM-9:00 PM
Location: Florida Keys Brewing Company
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