Perfect 3 Day Itinerary for Anna Maria Island, Florida

February 2025

I have had a visit to Anna Maria Island on my mind for awhile ever since I learned about it from none other than an Orlando theme park vlogger, TimTracker. They featured their vacations there on their YouTube channel and it really looked like a wonderful place to visit and relax. It is super family friendly with an old Florida charm and award winning white sanded beaches touching clear blue water – I knew this would be a great long weekend destination.

Anna Maria Island is a barrier island off of Florida’s Gulf Coast and has three towns to explore in its seven miles – Anna Maria at the north, Holmes Beach in the middle, and Bradenton Beach at the south. There is tons to do on this small island with the entire west coast covered in perfect beaches and picture perfect sunsets every night. While cars are permitted, the island is also known for non-car alternatives for getting around including golf carts and bikes as well as a free public trolley. And you won’t find high rise condos, fast-food restaurants, or chain shopping here – it is truly a local vibe with old Florida charm.

Know before you go

While golf carts and bikes are certainly an ideal way to see Anna Maria Island, you will likely want a car to get to the island though it is definitely not a requirement. We rented a car to get to and from the airport as well as getting around the island. If you need to fly as we did, nearby airports include Tampa and Sarasota – Tampa being the bigger airport with more frequent flights but an hour away and Sarasota being quite close to Anna Maria Island but is a smaller airport with less flight traffic.

Peak season tends to follow the school schedule with spring into summer being very popular and more expensive. However, Anna Maria Island is a great all year round. We traveled in February over President’s Day Weekend and did not find it crowded and the weather was perfect. Be mindful of hurricane season which runs late summer through the end of the fall – you may find cheaper rates but make sure to have refundable or cancel-able plans.

Where to stay?

Anna Maria Island has three towns – Anna Maria at the north, Holmes Beach in the middle, and Bradenton Beach at the south. We actually ended up staying off the island itself in Bradenton. Bradenton is just five minutes from Anna Maria Island as it had a significant discount in price per night. Since we had a car to get around the area, staying five minutes away from the island in exchange for more affordable accommodations made sense to us. We loved our Airbnb both for the location and comforts it provided. We even had access to a full complement of beach essentials – chairs, umbrella, blankets, and more – so we could enjoy a beach day easily. That being said, if you want to stay on Anna Maria Island proper and have the full experience renting the golf cart and bikes, I would stay north of Holmes Beach to make your base for the trip.

What is there to do?

Go to the Beach

There are so many beaches to explore along the 7 miles of Anna Maria Island. Our personal favorite was Anna Maria Beach but you can also visit spots like Bean Point Beach, Holmes Beach, Bradenton Beach, Manatee Beach, among many more. You can rent beach gear, bring or purchase your own, or stay in an accommodation that provides it as well. We sat near My Beach Concierge tents which is a fantastic idea for anyone that does not want to bother with hauling beach accessories, getting up early to get a spot during peak season, or any other reason. They have several packages you can choose from but I had not seen this concept before and thought it was very neat.

Sunsets

Do not miss sunsets on Anna Maria Island – though they will be hard to miss since the island is so small, it is easy to catch a glimpse from practically anywhere. I love the opportunity to see a sunset on the east coast. Grab a blanket and relax on the beach while the sun disappears into the ocean.

Get on the Water

There are so many opportunities to get on the water! You can go fishing, book a sightseeing boat cruise for dolphin watching or sunset, rent kayaks to explore the mangroves to search for manatees, you can even ride horses through the ocean. There are so many ways to spend a few hours and enjoy the brilliant ocean water and perhaps even spot some wildlife.

Spot some Wildlife

Speaking of wildlife, one of the aspects that attracted us to this area was the opportunity for bird watching and wildlife. The Bradenton area is home to a wide variety of wildlife – from sea turtles to manatees, bald eagles and alligators. Depending on what you want to see will drive which activity you should choose. Kayaking and boat tours are great for manatees and dolphins where as hiking the numerous nature preserves will give you a great opportunity to bird watch. We opted for the bird watching Robinson Preserve but there are a number of wildlife preserves you can choose from for your trip.

Stroller Pine and Bridge Streets

There are plenty of boutique shops, storefronts, cafes, and more to explore throughout the island, particularly on Pine Street (Anna Maria) and Bridge Street (Bradenton Beach). There are also numerous piers around the entire island that is great for sightseeing and grabbing a bite to eat or your beverage of choice. Since parking on the island is tough, sometimes driving from point to point is not ideal. This is where renting a golf cart or bike either for the day or the length of your trip comes in handy when you are just cruising the island and seeing what catches your eye. There is a free public trolley you can take advantage of as well.

Where to eat?

The food scene on Anna Maria Island is fantastic so make sure to save enough stomach space to try as much as you can! From donuts and ice cream, to fresh seafood and fine dining – you can find anything you are craving here. And the best part, you will not any fast-food restaurants or chains here – everything is local! Here are a few of the places I had marked to visit and I know there are plenty more to enjoy as well.

Anna Maria	Holmes Beach	Bradenton Beach
Ginny’s & Jane E’s Cafe and Gift Store The Donut Experiment Dips Ice Cream at Anna Maria General Store North Shore Cafe The Porch Restaurant Sandbar Seafood + Spirits Two Scoops Ice Cream Pizza Social	Anna Maria Island Coffee Shack Ugly Grouper Blueberries Cafe The Doctor’s Office Beach Bistro Island Fresh Market The Cheesecake Cutie & Cafe Graze Street	Pane e Amore Italian Cafe Island Scoops Back Alley Treasures Bamboo Island Bar

Itinerary

This itinerary makes for a great long weekend – the power of a three day weekend is strong and just by using one PTO day! Mix and match the days to make the trip that works for you.

Here is how to experience the best of the Anna Maria Island in three days!

Day	Time	Activity
Day 0	Evening	Arrive to Anna Maria Island
Day 1	Day	Beach Day
	Evening	Explore Bradenton Beach and Bridge Street
Day 2	Day	Wildlife Preserve or Water Activity
	Evening	Explore Anna Maria and Pine Street
Day 3	Day	Explore Holmes Beach
	Evening	Depart

Perfect 3 Day Itinerary for Anna Maria Island, Florida

Know before you go

Where to stay?