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Top Winter Events of Anna Maria Island

With the holiday season winding down and temperatures dropping, now is a great time to stay at one of our luxury rentals on Anna Maria Island.

Winter on Anna Maria Island is a great time for dry weather and day after day of comfortable sunshine. While you’ll probably be spending a lot of your vacation relaxing in the sun, you may want to check out some of the island’s many community events.

Below is a list of some of the best winter activities on the island – add a few to your list of things to do for days when you need a break from the beach.

Holmes Beach Art District Art Walk

Location: Holmes Beach Art District, Holmes Beach, FL

Creativity lines the streets of Holmes Beach once a month this winter with Anna Maria Island’s annual ArtWalks.

Participating businesses around the Gulf Drive and Holmes Boulevard area, known as the Holmes Beach Art District, will feature local art from the island and surrounding area on the second Friday of each month from January 12 to April 13 from 5:30 to 7:30 p.m.

Check out everything from acrylic and mixed-media representations of the sea, local pottery and glass, and stunning landscape and wildlife photography from a number of local gulf coast artists.

Participating businesses include: Waterline Marina Resort & Beach Club (5325 Marina Dr.), Restless Natives (5416 Marina Dr.), Artists’ Guild of Anna Maria Island (5414 Marina Dr.), The Anna Maria Island Art League (5312 Holmes Blvd.), Island Gallery West (5368 Marina Dr.), and SteamDesigns (5343 Gulf Dr. #660).

Enjoy complimentary refreshments and music as you browse the local works of art in downtown Holmes Beach.

anna maria winter events

Bradenton Area River Regatta

Location: Green Bridge, Palmetto, FL

For a day of sport, water, food, and fun, head to the annual Regatta on the Manatee River.

On February 3, boats will take to the water and spectators can watch the excitement from the Bradenton and Palmetto riverbeds and the Green Bridge. The event is free of charge, and features Formula 2 boat racing, among other races.

Live music will be played throughout the day on stages in both Bradenton and Palmetto. Some of the acts include Three Dog Night lead singer Chuck Negron, Let’s Groove Tonight (an Earth, Wind & Fire cover band), and Adam D. Tucker, a Las Vegas country star who covers country star Tim McGraw.

For the first time this year, Wheel of Lights, a giant Ferris wheel offering incredible views of the river and neighboring cities, will be available during the day and into the evening. A stunt dog show, a number of kids’ activity zones, and a 5K run are among other activities available to spectators.

Food stalls and trucks will be serving up hot food and cold drinks all day long to keep visitor fed and quenched. The event runs from 8 a.m. to 10 p.m., with fireworks over the river capping off the day’s events at 6:45 p.m.

anna maria jass festival

15th Annual Anna Maria Jazz Festival

Location: 100 Spring Ave., Anna Maria Island, FL

What better way to spend an afternoon on Anna Maria Island than on the beach with a cocktail in hand listening to jazz?

The Anna Maria Jazz Festival is an annual event that draws in crowds of both residents and visitors. Musicians include the Gulf Drive Band and Koko Ray Hansen, who will be playing jazz tunes from the last 70 years at the Sandbar Restaurant Pavilion right on the beach.

The event takes place Feb. 6 from 3 to 5 p.m. Proceeds of the benefit concert go to the Anna Maria Island Concert Chorus. Tickets are $10 in advance and $15 at the door.

anna maria music festival

Music in the Park

Location: Mosaic Amphitheatre, Riverwalk, Bradenton, FL

For other kinds of music, head to the Bradenton Riverwalk any Friday between March 9 and April 27 for a free concert series.

Perfect for a family activity or a date night with your significant other, pack picnic blankets and baskets, snacks and drinks to enjoy while you listen to the music.

Craft beer and snacks will be available for sale, and proceeds will go to Realize Bradenton, a local community development non-profit.

To kick off the concert series, Renesito will take to the stage with dance-worthy Cuba, jazz, and Rumba music. This stands as one of the best music related Anna Maria island events.

This concert series is pet-friendly, so guests are welcome to bring their furry friends along for the event – on a leash, of course.

The musicians grace the stage of the Bradenton Riverwalk Mosaic Amphitheatre from 6 to 8 p.m. Fridays – a great way to kick off the weekend.

Give us a call at 941-778-4178 to find the perfect place to stay at one of our many standard or luxury vacation rentals on Anna Maria Island while you enjoy these fun winter events!


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