The Hidden Charm of Anna Maria Island, Florida

A vacation in Anna Maria Island (AMI) is about as laid-back and relaxed as they come. While there are certainly large and beautiful vacation homes, there is nothing pretentious or flashy about this place. You can wake up and bike to the beach, kayak through a variety of waterways, shop in mom-and-pop stores on Pine Avenue, and then, at the end of the day, walk into a restaurant without makeup or a reservation. It is the kind of place where you settle in with a book and lose track of time, where the only thing on the schedule is the gorgeous sunset.

Many of our vacations are adventure-filled or driven by sightseeing. This one was not and every day we found ourselves saying, “When we come back…” We all agreed, without even needing to discuss it, that this would not be our last visit. The trip described below was just four days in December 2025 with our nine- and twelve-year-old.

Practical Takeaways

Anna Maria Island is on Florida’s Gulf Coast, near Sarasota and Tampa. If you’re seeking a winter getaway where you plan to swim in the ocean and enjoy hot weather well into the night, this is not the place. During our trip, daytime temperatures hovered around 75 degrees, with evenings dipping to 55–60 degrees. There was zero humidity, and we thought the weather was absolutely perfect, but it is considered “off-season,” which also makes it more affordable.
We flew into Tampa, which is roughly an hour north of Anna Maria Island. Sarasota’s airport is much closer, but it offers fewer flight options. We rented a car to get from Tampa to the island and used it a few times during the trip, though once there we mostly relied on walking, bikes, and a rented golf cart.
Anna Maria Island is about 7 miles long from north to south and roughly ½ mile wide at its widest point. We stayed in the Bean Point area at the northern tip of the island. Bean Point is full of beautiful homes, stunning beaches (both Gulf and bay), and locally owned shops and restaurants along Pine Avenue. As you travel farther south, the island becomes more commercial, with more hotels and shopping centers. If you’re looking for something quiet and quaint, Bean Point is the place to be. For more activity, head south.

Accommodations

One of the things we loved most about Anna Maria Island was the variety of vacation homes available for rent. As we biked around, we oohed and aahed over many of them and also appreciated how large, multi-story homes sit right next to small bungalows. We stayed in a one-story bungalow on Gladiolus Street, and it was perfect for our needs.

The location allowed us to walk to the beach in under five minutes, bike to Pine Avenue for ice cream, and relax on lounge chairs with coffee and a book in the afternoons. While small, the house had everything a family of four needed. We passed by the Anna Maria Island Resort, which piqued my interest, but if we return, I’d still choose a rental home for the convenience of having a kitchen and the comfort of a living room for movie nights.

Anna Maria Island Activities

The Beach:
As mentioned, December in Anna Maria Island isn’t typical Florida beach weather. That didn’t stop us from setting up chairs to read and toss a football on the sand. My husband and kids didn’t seem to mind the cool water temperatures, though they were among the few brave enough to venture in. Bean Point Beach is stunning, with white sand and clear blue water, and the sunsets in the evening are phenomenal.

We didn’t venture to the bay-side beaches or Holmes Beach – we thought Bean Point is as good as it gets.

Rentals:
One of the best things about AMI is how flat the roads are, making them perfect for biking and golf carts. There are very few cars, which makes it easy and safe for kids to ride. One of the best decisions we made before the trip was calling Beach Bums and having bikes delivered to our rental home before we arrived. Having bikes for the entire stay allowed us to hop on whenever we felt like it. I can’t recommend this enough if you rent a house here.

Within a few hours of arriving, our kids were begging us to rent a golf cart. On day two, we gave in and rented one for 24 hours from Beach Bums. Our only regret was not doing it sooner. Zipping to dinner and ice cream with the breeze blowing and kids giggling in the back was pure joy. Before the trip, I thought renting a car, bikes, and a golf cart seemed excessive but next time, we’ll rent all three for the entire stay. It’s part of what makes AMI fun.

Kayaking:
There are many kayaking options in and around AMI. We chose a two-hour guided kayak tour in clear-bottom boats at Robinson Preserve, hoping to see manatees. Unfortunately, we didn’t see any, and the clear-bottom boats felt a bit gimmicky. That said, it was still a fun (and challenging) experience. We enjoyed the guide’s knowledge of local birds and the break at the observation tower. Next time, we’d opt for a shorter, self-guided paddle.

After kayaking, we visited The Nest at Robinson Preserve, a netted play area suspended in the trees. It’s a unique experience geared toward kids ages 4–10. We were pretty exhausted after kayaking, but it would be a great activity earlier in the day.

Shopping:
Pine Avenue is full of charming local shops and great restaurants. You can easily spend an afternoon popping in and out of stores. A few favorites included Pineapple Marketplace, which sells crafts and goods from over 30 local vendors. They also have a hair-styling station where my daughter got fairy hair. We also loved browsing The Shiny Fish Emporium. If we had stayed longer, we would have tried our hand at sand dollar painting that they offer. We saw kids, parents, and grandparents doing this together at tables in front of the shop.

Anna Maria Island Farmer’s Market:
I love a good farmer’s market, and the AMI market is especially unique because it’s right on the beach. We drove twenty minutes to the southern tip of the island to Coquina Beach for this. The setting was beautiful. While my daughter and I shopped, my son and husband tossed a football on the sand. The highlight was a Cuban sandwich from a stand that was also offering over 30 varieties of guacamole and dips. The market is only held on certain days and is seasonal, so check the schedule before heading to Coquina Beach.

Manatee Viewing Platform:
Since we didn’t see any manatees on AMI, we stopped at the Manatee Viewing Center on our way to Tampa Airport. This is a reliable spot to see manatees, which are drawn to the warm water from the nearby power plant. The center is free to visit, though it can get crowded. After the quiet calm of AMI, the crowds felt a bit jarring, but seeing these enormous, gentle creatures up close made it worthwhile.

We paired the visit with lunch at Circles Waterfront Restaurant in Apollo Beach. Circles offered great views of Tampa Bay and even a hammock to relax in before heading to the airport.

Dining

Hometown Desserts: The Key Lime Pie Cake and Orange Dreamsicle Cake are worth hopping on a plane and returning to AMI for. On your first day, you may want to stop here and buy a whole cake. Then, you can enjoy it throughout the entire trip.

Donut Experiment: This is a fun place to visit. You fill out a form with your custom donut toppings, hand it over, and watch your donut come together.

Pizza Social: The pizza here is great, and it’s as laid-back and casual as they come. There are only four tables inside, so if you can’t snag one – and the weather is chilly – be prepared to take your pizza to go.

Ginny and Jane: This is a great spot for brunch. We enjoyed the avocado toast and the strawberry & goat cheese toast. The gift shop is quirky and fun, too.

Sandbar: The Sandbar was the only place we visited that required a reservation. It’s right on the beach, so your kids can run around while you sip a delicious piña colada. The main event here is the sunset. Before making your reservation, look up the sunset time and book for about 20 minutes earlier so you can settle in and enjoy the show.

Grub Tropical BBQ: This is a casual BBQ spot with good food and an easy walk-in setup for dining in or taking out. We recommend the coconut creamed corn, and we also enjoyed the banana bread that comes with every meal.

North Shore Café: We stopped by here for a late-morning smoothie. You could easily spend some time in their outdoor area with a book.

Helpful Hints

The Anna Maria Island General Store on Pine Avenue carries many everyday items you may need for your stay, including milk, cereal, slices of Hometown Bakery cake, and beer and wine. It does not carry fruit, vegetables, or meat. If you plan on cooking more than the basics, consider stopping at a supermarket on your way into town.
If you’re visiting in the “off-season,” bring a sweater and pants for the evenings. It gets chillier than you might expect for Florida.
With more time, we would have considered booking a dolphin boat ride and/or a fishing excursion.
For another Florida vacation idea, check out my post on Marathon, FL.