The Sweetest Tour of Anna Maria Island
Ice cream, candy, chocolate & a little vacation competition
Your next island tradition might start with a single scoop.
Beach days have a way of ending with one important question: What sounds good for dessert? On Anna Maria Island, the answer can take you from an ice cream counter in Anna Maria to chocolate on Pine Avenue, then south to a sweet finish on Bridge Street.
Make it a choose-your-own dessert tour. Pick a stop near the day's plans, save another for tomorrow, and let everyone nominate a favorite. These eight spots are all on the island, across Anna Maria, Holmes Beach, and Bradenton Beach. No mainland detours required.
Anna Maria: Scoops, sweets & Pine Avenue discoveries
Start at the north end, where a dessert stop fits naturally into a little island exploring.
Two Scoops Ice Cream
101 S. Bay Blvd., Anna Maria
Serving island visitors since 2007, Two Scoops has a flavor board that makes choosing part of the fun. Names like Gator Tracks and Trashcan invite a second look. Will you stick with your usual, or let the name choose for you?
Dips Ice Cream
503 Pine Ave., Anna Maria
Stop on Pine Avenue for ice cream and a little candy-shop nostalgia. This is a good place to make room for an old favorite, whether that means a familiar scoop or a sweet you remember from childhood.
Chocolate Emporium
216C Pine Ave., Anna Maria
Give the cone a break and browse handcrafted chocolates and house-made saltwater taffy. The shop's key lime pie truffle adds a Florida-inspired contender to your dessert shortlist. A few treats to share can turn into tomorrow's taste test.
Flip Flop Shop & Candy Stop
315 Pine Ave., Anna Maria
Keep the Pine Avenue wander going with a candy stop and a browse for island souvenirs. Let everyone choose one small treat for later. It is an easy way to bring a little vacation fun back to the house.
Holmes Beach: A scoop now, a treat for later
Holy Cow Ice Cream & Other Cool Stuff
3234 E. Bay Dr., Holmes Beach
Sundaes, milkshakes, or a classic scoop? Holy Cow advertises 36 flavors, with dairy-free, vegan, and sugar-free options among its offerings. Ask the team about the day's choices and any dietary needs before ordering.
Small Town Creamery
5404 Marina Dr., Holmes Beach
Ice cream, homemade fudge, and candy give this stop plenty of possibilities. Choose something cool for now or a little fudge to enjoy later. Your family may need separate awards for best scoop and best take-home treat.
Bradenton Beach: A sweet finish on Bridge Street
Gelato-Go Anna Maria Island
119 Bridge St., Unit 150, Bradenton Beach
Change up the tour with Italian-style gelato. Pick a flavor that catches your eye, then enjoy a relaxed stroll along Bridge Street. It is a simple addition to an afternoon out or an after-dinner wander.
The Fudge Factory
117 Bridge St., Bradenton Beach
Next door, fresh fudge, handcrafted chocolates, nostalgic candy, and ice cream keep the choices coming. Will your final vote go to a scoop, a chocolate, or a piece of fudge? There is no rule against a tie.
Save a little room for a new tradition
A beach day, an evening stroll, and a stop for something sweet can become the part of a vacation everyone remembers. Pick your first stop, follow your curiosity, and leave room for a return visit.
Explore more island experiences and plan your next getaway with AM Island Properties.
A curated island-only tour, not an exhaustive directory. Menus and hours can change; check the shop before heading out. Dietary options do not guarantee an allergen-free environment.