Anna Maria Winter Art & Craft Show: A Premier Island Event January 17–18 in Holmes Beach

Anna Maria Winter Art & Craft Show: A Premier Island Event January 17–18 in Holmes Beach

Each January, art lovers, craft aficionados, locals, and visitors alike flock to Anna Maria Island for one of the most anticipated cultural events of the winter season — the Anna Maria Winter Art & Craft Show. Scheduled for January 17–18 at City Field in Holmes Beach, this vibrant two‑day show celebrates creativity, coastal charm, and community spirit against the backdrop of Gulf breezes and island sunshine.

The Heart and Soul of Anna Maria Island’s Winter Art Scene

Now in its annual tradition, the Anna Maria Winter Art & Craft Show brings together an exceptional variety of artists and makers from across the region to showcase their work in every imaginable medium — from fine art and photography to ceramics, jewelry, mixed media, and handcrafted goods.

This free‑admission outdoor show runs from 10:00 AM to 5:00 PM each day and is known for its high‑quality, jury‑selected vendors who represent a wide range of artistic disciplines. Whether you’re looking for an original painting, artisan jewelry, a unique gift, or simply seeking inspiration in an idyllic setting, the show delivers an engaging and leisurely experience for families, collectors, and casual attendees alike.

In addition to the art and craft booths, visitors can enjoy live music, food vendors, and plenty of opportunities to meet the creators behind the work. These elements combine to make the event more than a market — it’s a community celebration of creativity and connection.

An Extensive History: From Humble Beginnings to Island Tradition

The Anna Maria Winter Art & Craft Show has evolved into one of the island’s signature winter events over the past several years. Originally organized to give local makers and artists a venue to showcase their work during the quieter winter months, it has grown in both size and reputation thanks to passionate organizers and enthusiastic community support. Early editions featured local talents and a modest number of booths; each successive year has seen more artists from around Florida and beyond applying to participate.

By embracing a jury‑selection process, the show has maintained a high standard of quality and artistic diversity. Vendors are carefully chosen to ensure that attendees experience original, handcrafted work rather than mass‑produced goods, giving the event a creative integrity that draws repeat visitors annually.

The show’s placement at City Field in Holmes Beach places it at the heart of the island’s cultural life. Holmes Beach itself was incorporated in 1950 and has been a popular destination for beachgoers and visitors ever since.

In recent years, organizers expanded entertainment offerings to include live music performances that enhance the festive and social atmosphere. From acoustic sets to lively bands, the backdrop of music complements the visual art, making the event as much about social engagement as artistic discovery.

Over time, the festival’s success has inspired collaboration with other local events and initiatives — strengthening Anna Maria Island’s reputation as a cultural destination in the Gulf Coast region. For more about the broader arts scene on the island, you can explore resources like the Anna Maria Island Chamber of Commerce or check local event calendars on Sarasota Events Calendar.

Art to Eat By: What You’ll Find at the Show

The Anna Maria Winter Art & Craft Show is known for its welcoming environment and diverse range of artistic categories:

• Fine Art & Painting – Original works in watercolor, oil, acrylics, and more.
• Jewelry & Wearables – Handmade necklaces, bracelets, and wearable art.
• Ceramics & Pottery – Functional and decorative pieces.
• Photography & Mixed Media – Captivating images and innovative compositions.
• Textiles & Accessories – Scarves, bags, hats, and crafted textiles.
• Sculpture & Woodwork – Hand‑carved and sculptural pieces that highlight craftsmanship.

Alongside the art, the event spotlights live music, typically with a lineup of local performers whose sounds range from soothing acoustic to more upbeat island rhythms — adding a lively backdrop as you stroll the booths. Food vendors and casual snacks also create an energizing environment for families and friends to enjoy throughout the weekend.

Perfect Pairings: Start at 5350 The Pourhouse and Stay All Day

If you’re planning to make a day of the Winter Art & Craft Show, be sure to start your morning at 5350 The Pourhouse, the perfect opening stop just minutes from City Field. This local favorite offers exceptional morning coffee, freshly baked pastries, and a welcoming atmosphere where you can fuel up before exploring the art show.

The aromatic smell of freshly brewed coffee and house‑made pastries — from flaky croissants to sweet scones — makes 5350 The Pourhouse an ideal first stop to settle into island time and prepare for a day of discovery. Come in early, grab a latte or cappuccino, and enjoy the relaxed vibe before the show’s crowds arrive.

As the day unfolds and the sun warms the island, 5350 The Pourhouse continues to be a great place to take a break. Its spacious seating and refreshing beverage options — from cold brews to craft mocktails — provide a perfect midday reprieve. You can swap stories with friends about your favorite finds, cool off from the Florida sun, or just enjoy a refreshing pause before heading back to the art.

Later in the afternoon or evening, when the Winter Art & Craft Show winds down, there’s no better place for dinner and drinks than 5350 The Pourhouse. With a menu full of creative bites and craft drink options, it’s the perfect way to cap off an inspiring day. That evening meal — whether a shareable small plate or a full entrée — is a great way to continue the conversations sparked by island art and creativity.

Make a Weekend of It

The Anna Maria Winter Art & Craft Show is more than an event — it’s a celebration of artistic talent and community, a place to uncover treasures, meet creators, and enjoy island life at its best. With free parking, waterfront views, and an easygoing timetable, it fits seamlessly into any winter getaway or local tradition.

Whether you’re shopping for unique gifts, seeking inspiration, or simply enjoying the atmosphere with friends and family, the weekend offers a memorable blend of art, music, and island charm. And with 5350 The Pourhouse just around the corner, you’ll have everything you need to start strong, stay refreshed, and finish full after a perfect day on Anna Maria Island.