Kay Smith has been a working artist for over five decades. In her studio, she produced a mixed-media piece called “Echoes Through the Archipelago,” a 43-by-58-inch meditation on Grand Cayman’s Mt. Trashmore landfill, social media, and the gap between curated island life and environmental reality. She describes her own work as “environmental, emotive and emotional.”
“Painting is more than a job; it’s an obsession.” — Kay Smith
For travelers who have seen the usual beach imagery, meeting the actual artists behind Cayman’s visual culture offers a far more complex and rewarding picture. This guide introduces the painters, sculptors, and mixed-media artists shaping the islands’ creative identity right now.
Cayman’s art scene is small but remarkably deep, ranging from self-taught visionaries like Gladwyn K. “Miss Lassie” Bush to a new generation of formally trained artists exhibiting at the National Gallery. The infrastructure—Cayman Art Week, the National Gallery’s biennials, and community spaces like the Dart Community Gallery—is growing fast, making it an exciting time to engage with local art.
Here is a quick reference to some of the key figures shaping the conversation right now.
| Artist | Medium | Key Theme | Generation |
|---|---|---|---|
| Kay Smith | Mixed Media / Collage | Environment, Social Media, Loss | Established (52 yrs full-time) |
| Zuri Hannah Whittaker | Painting | Memory, Elders, Cultural Legacy | Emerging (Teens) |
| Jessica Dawson | Painting (Gouache) | Island Life as Confinement, Belonging vs. Isolation | Emerging |
| Krisi Ilizabeth Smith | Painting | Scrutiny, Visibility, Peer Pressure | Emerging |
| Randy Chollette | Painting / Drumming | Intuitive, Self-Taught, Cultural Roots | Mid-Career |
These artists represent just a slice of the creative energy on display across the three islands.
Emerging Voices: The Next Wave at the National Gallery
In mid-2026, the National Gallery’s Dart Community Gallery hosted “Next Wave,” an exhibition featuring over twenty young artists, most still in their teens. The show was described as a collective act of emotional honesty. Zuri Hannah Whittaker’s “Woven Voices Strengthen Our Legacy” depicts an elderly Caymanian man playing guitar on a beach for a young girl. His body fades at the edges, the shoreline visible through him, holding joy and loss in the same frame.
Jessica Dawson’s “Submerged” uses layered gouache waves to create a barrier that is both beautiful and suffocating. White fluttering shapes resemble butterflies but behave as persistent, inescapable obstacles. Dawson visualizes a contradiction specific to island life: simultaneous belonging and confinement. Krisi Ilizabeth Smith’s “Eyes Off Me” places a young woman’s face at the center of a ring of disembodied eyes arranged like clock points, capturing the tension between wanting to be seen and fearing constant scrutiny.
What’s still being debated in Cayman’s art scene is how much these emerging voices will challenge or integrate with the island’s more established, commercially oriented art market. The “Next Wave” exhibition suggests a generation less interested in idyllic scenes and more willing to engage with psychological and environmental complexity.
Environmental Conscience: Kay Smith’s “Echoes Through the Archipelago”
Kay Smith’s career spans a period of dramatic change in the Cayman Islands. She attended art school at fifteen, worked in graphic design, and has been a full-time artist for fifty-two years. Her recent work, “Echoes Through the Archipelago,” directly confronts the island’s most visible environmental problem: the Mt. Trashmore landfill.
It’s easy to assume Caymanian art is limited to beach scenes and palm trees. Smith’s work, along with the “Next Wave” exhibition, shows a vibrant critical practice engaging with waste, tourism, social media, and cultural loss. The scene is far more layered than souvenir art suggests.
The piece combines collaged photographs and resin to lampoon modern social media culture. A woman in a stylish gas mask stands on a dock, viewing the Cayman Islands through her phone, while the world around her shows broken cars and junk. A dome encapsulates the past—important for the present but highlighting the need to address modern society’s issues. Smith donated the piece to Compass Media, declining a private buyer because she wanted it displayed for a broader audience.
Building a Market: Cayman Art Week and the National Gallery
Cayman Art Week 2026, running from 26–31 May across all three islands, marked six years since Natalie Urquhart founded the festival. Urquhart, who also serves as National Gallery director, aimed to support artists with a platform promoting local talent and generating sales. The festival featured free exhibitions, artist talks, studio tours, and hop-on hop-off bus services in Grand Cayman and Cayman Brac.
Parliamentary secretary for culture and heritage Julie Hunter spoke at the official launch. Artist Randy Chollette, a George Town–born intuitive, self-taught artist who won ‘Best in Show’ at Blue early in his career, performed drumming at the event. His work was concurrently on display at the National Gallery.
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If you’re visiting Grand Cayman, check the National Gallery’s exhibition schedule ahead of time. Entry is often free for the permanent collection, and the gallery shop carries works by local artists—a far better souvenir than mass-produced T-shirts. For a guided deep dive, consider a cultural tour of Grand Cayman that includes artist studio visits and gallery stops. Cayman Art Week usually falls in late May.
The National Gallery’s artist collection reveals the scene’s depth: from Gladwyn K. “Miss Lassie” Bush, a fourth-generation Caymanian who began painting at 62 following a visionary experience, to Jawara Alleyne, a Caymanian artist and fashion designer exploring cultural identity from a Caribbean perspective. The collection spans generations, mediums, and relationships to the islands—born here, moved here, returning home.
Crafting Identity: Traditional Thatching Meets Contemporary Critique
Cayman’s visual culture isn’t confined to gallery walls. The National Gallery’s list of artists includes multiple generations of thatchers—Marlena Anglin, Carmen Conolly, Annalee Ebanks, and Elizabeth “Lizzie” Powell—who learned from parents and grandparents. Deal Ebanks works with traditional Caymanian materials, producing gigs (traditional boats), calavans, singing kites, wauri boards, and walking sticks.
This table sketches the contrast between the island’s traditional crafts and its contemporary fine art scene.
| Aspect | Traditional Crafts | Contemporary Fine Art |
|---|---|---|
| Practitioners | Marlena Anglin, Deal Ebanks, Rose May Ebanks | Kay Smith, Randy Chollette, Zuri Whittaker |
| Materials | Thatch, silver thatch palm, local wood, Caymanite | Mixed media, gouache, digital collage, resin |
| Transmission | Family-based, intergenerational (mother to daughter) | Formal education (BA, MFA) or self-taught intuitive practice |
| Themes | Domestic utility, cultural continuity, natural materials | Environmental critique, identity, psychological interiority |
| Audience | Local households, heritage collectors | National Gallery biennials, international art market |
The relationship between these two streams isn’t adversarial. Many contemporary artists, like Zuri Whittaker, explicitly reference traditional thatch patterns in their work, weaving the older craft into new visual language. The ongoing question is whether the institutional support (National Gallery, Cayman Art Week) adequately reaches both communities, or if the contemporary scene receives a disproportionate share of funding and attention.
- Cayman’s art scene is generatively diverse, spanning self-taught visionaries, family-based craftspeople, and formally trained contemporary artists.
- Environmental and social critique is a central thread in current Caymanian art, not a niche concern.
- Institutional infrastructure (National Gallery, Cayman Art Week) is growing, creating new opportunities for artists and audiences alike.
Questions Readers Ask
Where can I see contemporary Caymanian art in person?
The National Gallery of the Cayman Islands in George Town is the primary venue. Its permanent collection and rotating exhibitions (like “Next Wave”) offer the deepest view. During Cayman Art Week (late May), dozens of pop-up exhibitions and studio tours open across all three islands.
Can I buy art directly from local artists?
Yes. The National Gallery shop sells works by local artists. Cayman Art Week is explicitly designed to facilitate sales directly from artists. Some artists, like Randy Chollette, also sell through their own studios or at events like the launch at the National Gallery.
Is Caymanian art just about beaches and palm trees?
Not at all. While idyllic landscape painting exists, the most talked-about recent work—Kay Smith’s “Echoes Through the Archipelago,” Jessica Dawson’s “Submerged”—engages directly with environmental destruction, social media, and psychological complexity. The scene is far more diverse than souvenir art suggests.
How has the National Gallery shaped the art scene?
The National Gallery acts as curator, archivist, and market-builder. Its biennial exhibitions (“Conversations with the Past in the Present Tense,” “Archipelago”) set the thematic agenda. Its artist collection documents decades of practice. Its director, Natalie Urquhart, also founded Cayman Art Week, creating a coordinated ecosystem for the arts.
What Cayman’s Art Scene Reveals About the Islands
The most striking feature of Cayman’s current art moment is its willingness to hold complexity. These artists are not making brochures. They are making work that asks hard questions about memory, environment, visibility, and belonging—questions that resonate far beyond the islands’ shores. For the visitor willing to look, the art offers a genuine encounter with the place behind the postcard. To explore more of the islands’ creative traditions, have a look at our guide to traditional arts, crafts, and artisan workshops.
Sources and further reading
Cayman Compass. “The National Gallery’s Next Wave: Emerging Voices in Cayman Art.” 2026. 🔗
Cayman Compass. “Artist Kay Smith Donates Work That Highlights Environmental and Social Issues.” 2026. 🔗
Cayman Independent. “Cayman Art Week Showcases Islands’ Vibrant Creative Sector.” 2026. 🔗
National Gallery of the Cayman Islands. “Artists Collection.” 🔗
Related reading on IslandHopperGuides
Crafting Cayman: Exploring Traditional Arts, Crafts and Artisan Workshops — A deeper look into the thatching, boat-building, and craft traditions that ground Cayman’s contemporary art scene.
Local Music Scene: Exploring the Rhythms and Roots of Caymanian Music — The sonic side of Cayman’s creative culture, from drumming to contemporary fusion.
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