Anna Maria Island, Florida

Traveling during Covid has provided a lot of challenges. My husband and I have for the most part, hunkered down at home (in addition to quite a few road trips to see my family in Iowa!). But as Fall started to set in, we realized that it was going to be a long winter of working from home in our NYC apartment. So, we started dreaming about warmer destinations. After multiple 17 hour drives to Iowa, we figured what’s a few more hours to get us safely to Florida? Of course I would have much preferred to fly, but with Covid numbers rising and being pregnant, that option wasn’t in the cards for us.

My husband took the initiative and did all of the research for this trip. At the time, I was in my first trimester and feeling miserable pretty much 24/7. He started looking up houses on the West Coast of Florida (as my parents decided to join us and the west coast was a more convenient meeting point!). He somehow narrowed in on Anna Maria Island, and quite honestly, booked it without knowing much about it.

Fast forward to today, and after spending a full month in Anna Maria Island, I can easily say that it exceeded all of our expectations, and we can’t wait to come back someday! Here are my recommendations on how to get there, where to stay and eat, and what to do (spoiler: it includes a lot of beach walks and hanging out!)

GETTING THERE

Likely, you will fly into Clearwater, Tampa, or St. Petersburg to get to Anna Maria Island. All of which are within 1 hour. If you’re crazy like us and decide to drive, it’s long but doable at 18 hours from NYC, and 22 hours from Iowa.

STAY

There are a few very small hotels on the island (Bali Hai looked cute!), but I would highly recommend renting a house. There are a ton of local rental companies (AMI Locals and Anna Maria Accommodations) and a majority of the houses on the island are for rent at some point during the year. We found a great house to rent from Anna Maria Accommodations (exact house here), and it ended up exceeding all of our expectations. We stayed just north of Pine Avenue (where there are a ton of cute shops, restaurants, and a weekly farmers market), and our house was only 2 blocks from the beach. This area is really pretty with tons of beautiful houses on canals right near the beach.

Anna Maria Island is divided into three different “towns”, you have Bradenton Beach, Holmes Beach, & Anna Maria. While Bradenton and Holmes seem to have a lot more condos and hotels, we preferred that Anna Maria was mostly just houses, which made for a much quieter vibe.

EAT

We were trying to be as covid safe as possible, so we only went out to dinner one time (which I’ll talk more about below!) but, that didn’t stop us from trying all of the local cuisine! We ordered take out from all of the popular spots in Anna Maria and enjoyed every single one of them. Our favorites included…

The Sandbar: We especially loved the Grouper Tacos! If you are comfortable going out to eat, this is definitely your spot. With seating right on the beach (perfect for sunset!) it was always packed with people enjoying fresh food and delicious drinks.

Harry’s Grill: Amazing burgers — no fuss. Skinny’s Place also came highly recommended but we never made it there.

The Waterfront: Great place for takeout. We loved the frutti di mare, salmon, and the chicken sand which.

Pizza Social: We picked up salad and pizza here a few times to take to the beach for sunset. Really enjoyed the California Salad and Hawaiian Pizza

The Donut Experiment: This place is hopping! Thankfully it was only a 2 minute walk from our house, so we would go very early in the morning before it got too crowded (go before 9AM to beat the lines!). With homemade made to order donuts, and an assortment of frostings and toppings, you can’t go wrong. We loved the classic vanilla with sprinkles and cinnamon sugar.

It wouldn’t be vacation without ice cream. We tried both Dips and Two Scoops, and all agreed that Dips was better (but hey, all ice cream is delicious if you ask me!)

North Shore Cafe: Great Coffee, Acai Bowls, and healthy-ish Sandwiches. They also have an amazing outdoor area to eat.

Beach Bistro: We saved our one experience dining out for Beach Bistro. It’s an award winning restaurant right on the beach, with sunsets overlooking the Gulf. Right now, they are doing 5-course tasting menus, with vibrant and classic dishes. It was an absolutely wonderful experience and I’m so glad we decided to book it. We felt completely comfortable as tables were very far apart from other guests.

Other spot around town: Poppo’s Taqueria, Ginny’s and Jane E’s, Beach House Restaurant, Anna Maria Oyster Bar on the Pier, The Waffle Press, & Ugly Grouper

DO

Shop on Pine Street — So many cute little stores to explore on this street. We especially loved… key lime pie from Hometown Desserts, the ridiculous assortment of meats, cheeses and wine at Anna Marie Olive Oil Outpost (seriously, we LOVED this place!), Painting Sand dollars at The Shiny Fish Emporium, buying baby clothes at Decor de France, and Anna Maria Island tourist-y tees from Two Sides of Nature.

There’s a pretty nice Farmer’s Market every Tuesday from 8AM - 2PM

Go for a lovely walk on the beach. We did this daily, with walks around the island as well as the beach, always finding new access points to enter. It was so much fun exploring.

Rod & Reel Pier (for food, drinks, and/or fishing!)

Rent the cutest beach setup from Beach Suites for a low key day at the beach

Rent a Golf Cart or Bike around the entire island, exploring all of the adorable streets and beach access points.

Kayaking or Paddle Boarding with Happy Paddler or AMI Paddleboard Rentals. 

Eat fresh seafood from Star Fish Company at the Cortez Historic Fishing Village

If you end up with a cloudy or rainy day, just know that the weather can change in about 2 seconds. However, on one particular day, we did enjoy an afternoon at the Hyde Park Village shopping center.

We didn’t make it to Longboat Key, but I heard it’s a beautiful place to explore. A friend also recommended St. Armands Circle in Sarasota for a day trip as well as St. Pete Beach.

Nearby destinations: Sarasota, 16 miles, Siesta Key, 19 miles, Cape Coral, 80 miles, Bay Lake, 92 mile, Orlando, 108 Miles, & Miami, 196 Miles