Painting Paradise: A Guided Plein Air Experience
Session One: Shrimp Boat Sound

Painting Paradise: A Guided Plein Air Experience

Slow down, step outside, and see Key West through a different lens.

As part of Just a Few Friends, we’re offering intimate guided plein air sessions at iconic island locations that played a role in the creative life and inspiration behind Key West’s music, storytelling, and laid-back way of being. Whether you’re an experienced artist or simply enjoy sketching, this relaxed outdoor experience invites you to capture the architecture, light, and atmosphere that define the island—your way.

Each two-hour session includes a brief introduction to the site, light guidance from a local instructor on composition and capturing Key West’s distinctive light, and plenty of time to create your own interpretation. There are no rules on what to paint—just the freedom to follow what inspires you.

Session Details

Each session is $25 and includes paper and a board for painting on. Participants may bring their own materials or add on a basic watercolor kit. Artists are welcome to work in any medium, including watercolor, acrylic, oil, colored pencil, ink, or mixed media.

Session One: Shrimp Boat Sound

Friday, September 4, 2026 · 8:00–10:00 AM

Paint at the historic studio that played an important role in shaping the island’s musical legacy. You might focus on the building itself, the quiet charm of Lazy Way, or any detail along the historic waterfront. Morning light and architectural lines create the perfect setting for a focused study in color and shadow.

Session Two: Louie’s Backyard

Saturday, September 5, 2026 · 9:00–11:00 AM

Set along the water just steps from where Jimmy once lived, Louie’s Backyard was quite literally part of his backyard—and a place he spent time enjoying the very lifestyle this festival celebrates. From the house and iconic bar to Dog Beach or the sweeping ocean views, there’s no shortage of inspiration—just choose your perspective and make it your own.

Guests may register for one session or both. Space is limited to 20 participants per session to maintain a relaxed and personal experience.

Participants are invited to display their finished work during the “Painting Paradise” pop-up exhibit at Party in the Park.

Artists may choose to:

Retrieve their artwork at the end of Party in the Park

Donate their piece to be sold or auctioned, with proceeds benefiting festival charities

A Judge’s Choice and People’s Choice will be awarded from submitted works. Winners will receive a ribbon, $50 cash prize, and badges to next year’s festival.

Sponsored by Keys Framing & Art Supplies