Anna Maria Winter Art & Craft Show: Celebrate Creativity, Music & Food on January 17–18

Every January, the beautiful Gulf Coast of Florida comes alive with art, culture, and community spirit at the Anna Maria Winter Art & Craft Show. Taking place this year on January 17–18 at Holmes Beach City Hall, this two‑day celebration attracts artists, musicians, and visitors from near and far for a weekend that highlights creative expression against the backdrop of sun, sand, and sea. Whether you’re an art lover, a music enthusiast, or someone searching for delicious food and drink, this event offers something special for everyone.

For visitors planning their day around the show, The Waterfront Restaurant is the perfect destination for breakfast, lunch, dinner, or refreshing drinks. Located conveniently near the event, The Waterfront Restaurant provides a relaxing and tasty place to unwind before, during, and after the festival. In this blog post, we’ll explore the history of the Anna Maria Winter Art & Craft Show, what to expect at this year’s event, and why The Waterfront Restaurant should be part of your weekend itinerary.

History of the Anna Maria Winter Art & Craft Show

The Anna Maria Winter Art & Craft Show has a long and beloved history on the island, stretching back more than three decades. For years, this winter tradition has served as a creative outlet for regional artists and craftsmen to showcase their work while providing residents and visitors alike with a chance to experience unique handmade art amid the natural beauty of Anna Maria Island.

Originally started by local art advocates, the show was designed to encourage community engagement during the quieter season months when snowbirds and tourists alike seek meaningful experiences by the water. Over time, the event has grown into one of the most eagerly anticipated cultural celebrations on the island, drawing hundreds of vendors who present a diverse mix of fine art, jewelry, textiles, woodworking, ceramics, photography, and other handcrafted items.

In addition to the spectacular array of art and craft, the show has always emphasized a family‑friendly atmosphere, welcoming art lovers of all ages. Local musicians add to the festive mood with live performances throughout the day, while food vendors help keep energy levels high with delicious bites and refreshing beverages. The event also reflects the island’s strong sense of community, thanks to local sponsors and volunteers who help keep the tradition thriving year after year.

For more information about the official history and schedule of events, check out the City of Holmes Beach official site and the ArtFestival.com guide to local art shows.

What to Expect at the 2026 Anna Maria Winter Art & Craft Show

This year’s show promises to continue the tradition of excellence, featuring an impressive lineup of creative talent and entertainment. Here’s a look at what visitors can expect from the event on January 17–18:

🌟 Stunning Artwork from Regional Artists

One of the highlights of the Anna Maria Winter Art & Craft Show is the variety of artwork exhibited. From vibrant paintings and coastal landscapes to handcrafted jewelry, pottery, and mixed‑media pieces, the show puts artistic talent front and center. Many artists incorporate themes inspired by Florida’s Gulf Coast — think bright colors, beach scenes, nautical motifs, and nature‑inspired creations that echo the beauty of Anna Maria Island itself.

As you stroll through the vendor booths, you’ll find opportunities to meet artists, learn about their creative process, and even commission custom pieces. This makes the show not just a place to buy art, but a chance to connect with the creative community that helps define the island’s cultural flavor.

🎶 Live Music and Entertainment

Live music is a cornerstone of the event experience. Local musicians and performers take the stage periodically throughout the weekend, transforming the art walk into a lively, interactive experience. You might hear acoustic guitar, jazz ensembles, folk musicians, or beach‑style bands — all contributing to a soundtrack that feels as natural as the ocean breeze.

Bring a chair or blanket, relax with friends or family, and enjoy music that ranges from soothing melodies to upbeat rhythms perfect for the festive atmosphere.

🍴 Tasty Food, Snacks & Refreshments

The Art & Craft Show has plenty of food vendors offering a range of options, from quick snacks to more substantial meals that keep you fueled as you explore. Whether you’re craving something savory, sweet, or refreshing, there’s something to satisfy every palate.

But for those who want to elevate their experience with waterfront views and a full menu of delicious fare, The Waterfront Restaurant is the perfect complement to your day.

The Perfect Pairing: Anna Maria Winter Art & Craft Show + The Waterfront Restaurant

The Waterfront Restaurant has long been a favorite spot on Anna Maria Island for locals, seasonal visitors, and festival‑goers alike. Whether you’re starting your day early with breakfast, looking for lunch between browsing booths, need a cool drink after absorbing all that art and music, or planning a memorable dinner to cap off your weekend, The Waterfront Restaurant delivers on every level.

🍳 Start Your Day Right with Breakfast

After arriving at the art show in the morning, kick off your day with a satisfying breakfast at The Waterfront Restaurant. With scenic views overlooking the water, the restaurant’s breakfast offerings help set the tone for a relaxed and delicious day of exploration. From classic favorites to creative morning dishes, the breakfast menu ensures you’re energized and ready to engage with the artists and performers at the show.

🥗 Lunch to Refuel Mid‑Show

By midday at the art fair, you’re bound to work up an appetite. While there are food vendors on site, lunch at The Waterfront Restaurant adds a welcome escape from crowds and offers a sit‑down experience with fresh, flavorful options. Seafood salads, sandwiches, and chef‑inspired dishes provide just the right meal to refuel before heading back to the artwork, live tunes, and artisan booths.

🍹 Refreshing Drinks for Every Mood

Whether it’s a handcrafted cocktail, an ice‑cold beer, or a refreshing mocktail, The Waterfront Restaurant serves drinks that match the laid‑back yet vibrant spirit of the art show weekend. Treat yourself to a signature drink while watching the sunset after a full day at the festival — the perfect pause before dinner or as a way to unwind and reflect on your favorite discoveries from the show.

🍽️ Dinner with Waterfront Views

As the sun dips into the Gulf and the art show winds down for the day, The Waterfront Restaurant transforms into the ultimate dinner destination. With an extensive dinner menu featuring fresh seafood, local favorites, chef specialties, and seasonal offerings, you’ll find dishes that satisfy every craving. From grilled catch‑of‑the‑day entrées to hearty steaks and creative appetizers, dinner here promises both exceptional food and unforgettable views.

Tips for Making the Most of Your Weekend

To ensure a smooth and enjoyable experience at the Anna Maria Winter Art & Craft Show — and a delicious dining experience at The Waterfront Restaurant — here are a few tips:

Arrive early: The show gets busy, especially on Saturdays, so arriving early means better parking options and more time to explore before crowds build.
Dress comfortably: Wear comfortable shoes and bring sunscreen — you’ll be walking and browsing outside for much of the day.
Plan breaks: Schedule time to sit, relax, and enjoy The Waterfront Restaurant’s food and drinks between art tent visits — your feet (and appetite!) will thank you.
Bring cash and cards: While many vendors accept cards, it’s always helpful to have cash on hand for smaller purchases.
Capture memories: Bring a camera or use your phone to document your favorite pieces, the musicians you loved, and special moments shared with friends or family.

Wrap‑Up: A Weekend of Art, Music & Delicious Dining

The Anna Maria Winter Art & Craft Show is more than just an event — it’s a celebration of community, creativity, and culture set against the stunning backdrop of Holmes Beach. With talented artists, live music, and a welcoming atmosphere, the show has something for everyone and continues to be a beloved island tradition each January.

Whether you’re a longtime fan or experiencing the event for the first time, make time during your weekend to savor the art and then indulge in great food and drinks at The Waterfront Restaurant. Its prime location, excellent cuisine, and relaxed waterfront ambiance make it the ideal complement to your festival experience.

Don’t miss this year’s Winter Art & Craft Show on January 17–18 — and be sure to stop by The Waterfront Restaurant before, during, or after the festivities for a memorable island experience!