A vacation on Anna Maria Island is destined to be one that you will never forget as you lounge on white sand beaches, frolic in turquoise waters, and relax in comfort and luxury in our Anna Maria Life Vacation Rentals sanctuaries. You probably already have most minutes of your vacation planned out, penciling in shopping sprees, devouring fresh caught grouper sandwiches, and sipping frothy margaritas on the balcony of your island retreat as the sun sets over the water. But although our island is a small one, one that is only recently recuperating from last year’s big storms, we know there is so much more you can do during your stay, including this list of five unexpected things to do on Anna Maria Island that will enhance your vacation experience!

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Go to Jail, 402 Pine Avenue

Wait, are we suggesting that you commit a crime and get locked up for it during your vacation on Anna Maria Island? Of course, we aren’t! AMI doesn’t even have a functioning jail, and the island went through enough in those storms we just talked about, but the Old City Jail, or the remnants of the Old City Jail, is a fascinating spot to visit. There is no roof, no doors, not even bars left in the windows of this building that was constructed in 1927, meant to house unruly inhabitants who probably had a bit too much to drink. There is, however, a great amount of charm, providing an ideal backdrop to any selfies you may want to take and when you post the pic of your stint in jail on Anna Maria Island, it will definitely be something your friends and family back home will think is unexpected!

Anna Maria Island Clear Kayak Tours, 752 Manatee Avenue in Holmes Beach

Kayaking is a popular island activity, and it isn’t the activity that will surprise you as much as the kayak you will be using during your adventures. The clear kayaks utilized by AMI Clear Kayak Tours offer a new dimension to your paddling fun, allowing you to not just enjoy the sun, the sky, and any dolphins that might be frolicking near you, but giving you the opportunity to see all the creatures that inhabit the water, swimming under your feet. Also offering LED lit glass bottom kayak tours, tours that take you through the mangroves, and maybe our favorite, manatee tours, your water adventures will be unlike any other you have ever experienced.
kayaking

Sip and Savor at Fiorelli Wines, 4250 County Road 675 in Bradenton

The towns that surround Anna Maria Island offer their own set of unexpected adventures and in Bradenton, visitors can visit the only vineyard in this part of Florida, Fiorelli Wines. Closed on Mondays and Tuesdays, their wine tastings cost $12 per person for flights of six, or for another $5, guests can sample all the wines they have available. On weekends they provide live music to go along with the tastings and also offer the occasional yoga class and on the 28th of June guests can attend their Red, White, and Blueberry Celebration, that offering food trucks, live music, drink specials, kids’ activities, and an end of the night fireworks show that will have you saying all the oohs and ahhs. Admission is free, but parking costs $10 and it will cost for food and drinks.

Painting Sand Dollars at the Shiny Fish Emporium, 306 Pine Avenue on Anna Maria Island

Shopping is, of course, a traditional vacation experience, but shopping at the Shiny Fish Emporium is anything but usual, offering an interesting selection of souvenirs, French toys, and artwork. Your favorite part of visiting Shiny Fish, it offers the chance to paint sand dollars to take home for the most unexpected souvenir you have ever found. It costs just $15 for this cool souvenir and your kids will be so proud of their art masterpiece, making it worth every penny. Also known for its Swarovski crystal earbuds, you should plan on spending more than a few minutes in this shop and may want to make it your last shop of the day so you can carry all your goodies back to your Anna Maria Life Vacation Rentals Florida sanctuary and not have to carry heavy bags around the streets of the island.

Puttering Around at Home with Anna Maria Life Vacation Rentals

Every property we provide for our guests is different from the others, offering amenities that are expected (swimming pools, hot tubs, and state of the art televisions) as well as unexpected ones like the putting greens that can be found in the backyards of some of our popular Anna Maria island rentals! Also offering waterfront retreats, laundry rooms, coffee bars, and deep tubs, and private patios, every minute of your stay with us will be your favorite. Reserve the one that speaks to your soul today!