The discovery of Anna Maria Island, Florida began like this: typing “best quaint Florida beach towns” into the search engine. Like what often happens when you discover something new, it begins popping up everywhere in daily life – people I follow on Instagram were visiting, coworkers were talking about this place, and I’d see random strangers at the grocery store wearing Anna Maria t-shirts. Our family has visited Fort Myers Beach, Florida several times over the years and I knew we wanted something with a similar island vibe, but new to us. Last year, together with our families, Katie and I had booked a really cool house on Anna Maria Island for our kids’ Spring Break but had to cancel due to the pandemic, so I was still itching to visit.
Anna Maria Island is located on the gulf side of Florida, anchored by St. Petersburg, Bradenton and Sarasota. The 7-mile long island itself is actually made up of several towns but collectively called “Anna Maria Island” – Bradenton Beach to the south, then Holmes Beach, then Anna Maria at the most northern point. (More on these different locations later!) From my understanding, Anna Maria Island was much more “Old Florida” than it is now with the newer construction homes but it still keeps the charm without the major high-rise condos and chain restaurants.
Traveling to and around on Anna Maria Island
We had some prior flight credits to use from last year’s cancelled trip, so we booked flights from the Milwaukee airport (MKE) to Tampa International Airport (TPA). Overall, the airport and flight felt relatively safe with many social-distancing precautions in place and mask requirements.
Arriving at the Tampa Airport, we had a car rental booked through Costco Travel (always our go-to car rental!) using Alamo. I had booked this rental car reservation several months in advance and I’m very glad I did – the costs skyrocketed the closer the trip got and eventually all vehicles were sold out. We had a Dodge Durango SUV, which was probably bigger than we needed but was nice for hauling our luggage, plus groceries, and occasionally our beach wagon and chairs to and from the beach. The Tampa airport was about an hour drive to Anna Maria Island, but definitely longer during peak times of day with beach traffic. (*Note, there is also a tollway on the main route with a cost of $1.50 per car)
Other options for flying include the smaller Sarasota (about 30 minute drive) or Clearwater airports and I’ve even heard people fly into Fort Myers or Orlando and make the 2-hour drive if flights were cheap. Many companies offer shuttle service from the airport to the surrounding towns if you didn’t want to rent a vehicle. Once on Anna Maria Island, there are several transportation options:
Bike and Golf Cart Rentals
Several local rental companies offer bike and golf cart rentals for cruising around the island. There were also little go-kart looking 2-seater cars called Scootcoupes that my kids wanted to ride in so bad 🙂
City Bus via Manatee County Area Transit (MCAT)
We didn’t use the city bus at all, but the website has all the info with routes and schedules
MCAT Anna Maria Island Trolley
This free trolley runs up and down the island seven days a week, with the times varying depending on season. We used this several times and found the trolley to run about every 20 minutes. I downloaded an app on my phone called “MyStop” that was very helpful in showing us the real-time trolley location and finding the stops to get on and off.
Another free option (just tip the driver!) is the Monkey Bus on AMI, a 16-passenger shuttle bus that runs until from 12noon to 3am, and just requires a phone call for pickup!
Where to stay on Anna Maria Island?
As mentioned earlier, the island is made up of three towns. I read a lot of travel forums prior to booking the trip to determine which area would be best for our family and most people said to “pick the rental home you like, not the location on the island because it’s all good”. I do agree with this to some extent, but our family preferred certain areas over others. Even though the next section will make Anna Maria Island sound big, it’s really not – just trying to break down the fuzzy lines that divide each town.
Bradenton Beach, southern end of the island
We found the Bradenton Beach area to be busier – a fun place to hang out for a day or evening but not our preferred place to stay. (Also, during the time we visited, masks weren’t required in this town so we didn’t stick around long but that’s just our personal preference). This area had a good stretch of beach, as does anywhere on the island. Bridge Street was a fun area with a lot of restaurants, live music and the historic City Pier.
Anna Maria, northern end of the island
The northern-most town on the island is Anna Maria – this was our favorite town and would choose lodging here if we go again. We personally loved the dining and shops on Pine Avenue, the restaurant options around the shore, and was a bit more small-town quaint feeling. The island narrows in width here too, so getting around is easier. The biggest downside: parking is really hard to come by mid-day so we’d try to get out early and park if we were planning to spend the day in Anna Maria.
Holmes Beach, middle part of the island
The town between Anna Maria and Bradenton is Holmes Beach, which is where our rental home was located. Overall, a great option too, we just found that we were often heading north to Anna Maria for dining, shopping and the beach. It’s also wider here, so had some busy roads to cross when walking to the beach. However, there are still some great restaurant options and shops.
OUR RENTAL HOME IN HOLMES BEACH
While looking for lodging, there were several things that surprised me – how expensive lodging was (at least during this peak season), that most rental homes are managed by real estate companies (and don’t always show up on the usual rental home site), the limited number of resorts and hotels, and how many private homes had pools.
We were fine staying in a small resort for this trip since it was just my husband and our two kids and knew we wouldn’t spend much time inside, but happened to find the week we needed available in a private home at a relatively inexpensive price, at least by AMI standards.
Here’s the link to the home we rented: Heliconia House in Holmes Beach
Overall, the home was perfect for our needs. We loved having our own private, heated pool and it had all the amenities we needed for the beach like wagon, chairs, cooler, etc. It was about a 10-minute walk to the beach but did have to cross busy Gulf Drive. The neighborhood had a great park with a ton of amenities too. Our kids shared a queen bed but they were so wiped by the end of the day that they didn’t even fight about it 🙂
Family-Friendly Things to Do in Anna Maria Island
This was a family vacation over peak season of Spring Break during a pandemic, so things were slightly limited due to these factors. But here’s a few of the things we enjoyed:
INDOOR / OUTDOOR ACTIVITIES
Cannot say enough about the beach – it’s where we spent our time every single day, even on the cool and cloudy days. We are just a family that loves the beach, even if we spent a day there in winter jackets! The white sand beach stretches the entire island along the Gulf side so there are no bad locations. There are a few public beaches with bathroom facilities and concessions, like Coquina Public Beach and Manatee Public Beach, but the entire island is fair game for beautiful scenery. We preferred the northern end on Anna Maria, since it was walkable to shops and restaurants (and bathroom breaks!). Every morning in the Holmes Beach section, there were people fishing along the shore, which was fun for the kids to watch.
Note: alcohol is not allowed on any of the beaches, but if you’re discreet and not causing trouble, it won’t be a problem (wink wink!)
Bean Point is a quiet sandy area at the northern tip of AMI. There aren’t any bathrooms or anything “to do” here but it was a pretty area and a great change of scenery to watch the sunset.
There was a park near our rental home in Holmes Beach that had a fenced-in dog park, courts for pickleball, tennis, basketball and shuffleboard, along with a nice playground. While we prefer the Gulf side, the bay side of AMI had a nice park called Bayfront Park.
Sarasota Jungle Gardens
This was a fun activity for our family, as our daughter’s 8th birthday fell on our vacation week. A coworker had recommended Sarasota Jungle Gardens to me and it ended up being even cooler than we’d thought. We purchased tickets online ahead of time for a slight discount and made sure to get there when they opened (it was super busy by the time we were leaving around 1pm!). There were a variety of scheduled animal shows, some encounters that could be purchased for a small additional cost like holding a baby gator, birds, etc. and plenty of area to walk around and look at the different tropical animals.
Make your own jewelry at Anna Maria Rocks
My daughter would say this was her favorite activity of our trip. She’d seen a sign to “make your own shark tooth necklace” early in our trip and it was on her must-do list. The two women working the shop that day were SO sweet and helpful. My daughter picked our her own pendant (a shark tooth) and chose the cord and beads, while the staff helped her string them on and finish it off, all while talking to her about the kind of shark her tooth pendant had come from. Highly recommend!
Paint a sand dollar at Shiny Fish Emporium
We didn’t do this but looked like a fun rainy-day activity. This was a cute shop with all kinds of gifts and goodies that had several tables set up for painting sand dollars.
Anna Maria Island has shops scattered about the island, from knick-knacks to women’s boutiques and specialty gift shops. My favorite shops were along Pine Avenue for unique gifts but Holmes Beach had a few good ones too.
Other recommended activities that we didn’t do:
Several people recommended Mixon Fruit Farms to me, but we didn’t get a chance to get there. Additionally, Mote Marine Aquarium was high on the recommended list. Several towns had local Farmer’s Markets, always good to add to the list to get some fresh local fruits and veggies.
RESTAURANTS AND DINING IN ANNA MARIA ISLAND
Anna Maria Beach Cafe – 4000 Gulf Drive in Holmes Beach
We didn’t eat here but spent several evenings having drinks and ice cream at this spot along Manatee public beachfront. There was live music on the weekends and was the perfect way to end the night and catch a sunset. You can either grab an open table or bring your own chairs and sit within the roped area to have a drink (alcohol is technically not allowed on the beach…)
Website: Anna Maria Island Beach Cafe
Anna Maria Oyster Bar (several locations)
We had lunch at the Sarasota location after visiting the Jungle Garden. A fun thing about this place is that from Sunday-Thursday, the kid’s meals cost one cent per inch of height for your kid. So, our 45″ tall son had a 45-cent meal and our 52″ daughter had a 52-cent meal (just pay for their drinks).
Website: Anna Maria Oyster Bar
The Donut Experiment – 210c Pine Avenue in Anna Maria
A staple for breakfast in Anna Maria, this donut shop will show up on every list of recommended dining in AMI. While we love a good donut, I didn’t have super high expectations of this place… but WAS. I. WRONG.
This shop gets crazy busy with long wait times, so my husband went a few minutes before they opened at 7am and would get in line and bring the donuts home for us.
Website: The Donut Experiment
Ginny and Jane E’s – 9807 Gulf Drive in Anna Maria
We loved this place for breakfast! The pancakes were delicious, as were the breakfast sandwiches and breakfast burritos. We spent a couple mornings grabbing breakfast and coffee here then walking the short two blocks to the beach and eating breakfast on the benches along the ocean.
Website: Ginny and Jane E’s
Pizza Social – 308 Pine Avenue in Anna Maria
We loved this pizza so much, that we ordered it to-go two nights in a row. It is delicious woodfire pizza made with fresh and local ingredients and had a cool atmosphere. Besides the pizza, we loved the garlic parm dough nuggets were that were dripping in garlicky deliciousness. We liked the traditional sausage/pepperoni and the Margherita. So so good…
Website: Pizza Social
Rod and Reel Pier – 875 N Shore Drive in Anna Maria
Another place that will come up on every AMI list is Rod and Reel Pier. Located at the northern end of Anna Maria near Bean Point, this pier has casual bayside dining and drinks. We spent a couple nights having beers on the benches and watching the dolphins and pelicans, then walked over to Bean Point for the sunset. We didn’t eat here but heard the wait times were pretty long, although much shorter for takeout. You can also rent a fishing pole and fish off the pier.
Website: Rod and Reel Pier
The Sandbar – 100 Spring Avenue in Anna Maria
This was hands-down one of my favorite places to eat. The wait times are crazy, so we put our names on the list about 3:45pm and were told it’d be an hour for outdoor dining. They don’t take reservations but there is plenty of space to sit for a drink while you’re waiting (plus, it’s beachfront so who cares!) We ended up with an awesome toes-in-the-sand table along the beachfront. Good tropical cocktails + amazing food (the Shrimp & Gnocchi dish on the dinner menu is now in my top 5 all-time favorite meal list).
Website: The Sandbar Restaurant
Star Fish Company – 12306 46th Avenue in Cortez
This is an ultra-casual dockside restaurant attached to a local fishing company with picnic tables and fresh seafood along the dock. We got box lunches (Justin got the fried grouper sandwich and I got fried gulf shrimp) and cold beers. It’s a cash-only restaurant but there is an ATM inside.
Website: Star Fish Company Dockside Restaurant
Ice Cream Shops + Other Treats
We make a rule on vacation that we must eat ice cream every day, and happy to say we didn’t break the rule once in our seven days 🙂 There are plenty of ice cream and treat shops around the island, but our favorite was Anna Maria Creamery and Bakery because of it’s close location to the beach.
If you haven’t picked up on it by now, we had an amazing week on Anna Maria Island and are already scheming on how soon we can return. Both my husband and I would agree that the beach itself was perfection – the water color, the sand, and the overall vibe of the island was just want we were looking for. The biggest downside to us is the expensive price tag on lodging – it really limits budget-conscious families looking to vacation here. I’d recommend contacting some of the local real estate companies that handle rentals and use their help finding lodging or browsing some of the smaller resorts as well. In my opinion, since we spent such little time inside our rental home, choose based on the location and amenities!
Thanks for a great week Anna Maria… see you again some day!