Fun Things to Do on Anna Maria Island in January and February

There’s always plenty of fun in the sun on Anna Maria Island every month of the year. Once the holiday season winds down, tranquility returns to the island, making the early months a perfect time to visit without crowds and to stay in our Anna Maria Vacation Rentals.

With plenty of upscale vacation rentals and beachfront attractions, Anna Maria Island won’t disappoint. Check out the Anna Maria Island events in January and February listed below to find some unique, community-oriented things to do while on vacation here.

people at dinner drinking wine

A Chamber Sunrise Breakfast

Location: 4000 Gulf Dr., Holmes Beach, FL

If you’re keen to start the New Year off on the right foot, try getting acquainted with local politics on AMI. The Anna Maria Island Beach Café is hosting a scenic beachside sunrise breakfast for both long-time residents and newcomers.

Those visiting the island can get acquainted with the AMI Chamber as they start the year fresh. It is also a great way for guests to parse the area and the community while considering a long-term residence and getting involved.

For current members, it is a great opportunity to reconnect with the community and throw in your hat to help organize one of the Anna Maria Island events in 2018.

The breakfast takes place on January 10 from 7:45 a.m. to about 9 a.m. The cost is $16 for non-members and $8 for members. Call the Chamber at 941-778-1541 or email for more information.

Rusty Crickett’s Wine Down Wednesdays

Location: 615 15th St. W., Bradenton, FL

Have you ever clamored for a glass of wine to help usher in the second half of the week? Rusty Crickett’s in nearby Bradenton is now making those mid-week slump dreams come true. Get to know locals at Wine Down Wednesdays – even if you’re on vacation.

Rusty Crickett’s Coastal City Cottage hosts this fantastic get-together for the local community every Wednesday from 5 to 7 p.m. Visitors cannot only drink great wine at discounted prices but can also win great prizes provided by businesses in the local community.

The event takes place every Wednesday evening starting January 3rd and will continue into the spring. Contact 941-745-3131 for more details. Ask for your new favorite wine and one of the Anna Maria Island restaurants.

Plan Your Trip

Just because it’s winter doesn’t mean that the fun slows down on Anna Maria Island. Check out our available rentals for this time of year now!

AMI Privateers’ Thieves Market

Location: 2650 Gulf Drive, Bradenton Beach, FL (Coquina Beach Park)

Yoho, yoho, a pirate’s life for me!

The Thieves Market, a collection of pirate-themed pop-up shops on the beach, will have you singing this song into the evening. The market is filled with extravagant pirate attire, recovered treasures, and low-cost novelty items. Definitely add this unique event to your list of things to do and places to shop on AMI.

The Thieves Market will be a great day of fun for the whole family, as kids enjoy pirate-themed activities amidst hundreds of vendors selling local treasures.

Visitors can find hand-crafted jewelry, sharks’ teeth, local produce, fishing equipment, and many pirate trinkets that will turn the whole family into sea dogs for the day – all in support of the local community.

This event is run by the AMI Privateers to raise funds for Anna Maria Island children’s programs. Admission is free for this annual event. The Privateers’ Thieves Market takes place Saturday, January 13, from 8 a.m. to 3 p.m. on Coquina Beach.

The Seahorses Art Show

Location: Bridge Street, Bradenton Beach, FL

Bridge Street is a top Anna Maria Island historical area and hub for dining, shopping, and island events such as performing arts. It is lined with many attractions and restaurants, including both newer and long-established options. Starting January 26 at noon, The Seahorses Art Show will join the fun.

Wind your way along the aisles of acclaimed marine-inspired art. View and purchase prints, abstract paintings, human-sized canvases covered in majestic beach views, and glass art of all shapes and sizes. An online silent auction begins January 26, but you can buy any of the pieces featured until February 25.

If you’ve ever thought about a stay – long or short – on Anna Maria Island this winter, the start of the year is a great time to enjoy the island free of the larger spring and summer crowds.

Contact us at 941-782-8152 for details on our available vacation rentals on Anna Maria Island. Stay at one of our comfortable rentals while you explore the community here on Florida’s beautiful southwest coast.