How to spend 3 Days on Anna Maria Island, Florida
There is something magical about Anna Maria Island located about an hour south of Tampa, Florida on the Gulf of Mexico. This charming island is a favorite of many for its “Old Florida” style. With powdery white sand beaches and turquoise blue water, it is one of the most beautiful destinations in Florida. So, come along with us for a visit and find out how we spent 3 days on Anna Maria Island, Florida. Take your time, I’ll wait. Cause we are on Island Time.
Anna Maria Island is divided into three cities: Bradenton Beach, Holmes Beach, and the City of Anna Maria from south to north and strung along seven miles of the Gulf of Mexico. Mix in a few seaside shops, old Florida Mom & Pop motels, delicious restaurants, and scenic fishing piers with water so clear it was all I could do to keep myself from diving in.
Rent a Bike or a Golf Cart at Beach Bums
Riding a bike or a golf cart is the best option for getting around the island. Many of the main attractions on the island have bike racks, including most of the beaches. A lot of the beaches have bike trails, too. There are several companies on the island where you can rent bicycles but my favorite is Beach Bums. You can make arrangements for your bikes to be dropped off and picked up from your rental home too, which is pretty convenient!
Another option if you are lazy like me, is to rent a golf cart. We packed up a small cooler with water and snacks and we motored our way around the island. You are allowed to drive the cart on any street where the speed limit is 35 or under. You have to follow the same rules as if you were driving your vehicle. So, grab your sunscreen, a hat, and your sunglasses, and start touring the island.
Anna Maria Island Trolley
If you prefer someone else to do the driving, a free trolley will take you up and down the island. The Anna Maria Island trolley runs daily from 6 a.m. to 10:30 p.m. and offers both air-conditioned and open-air seating. You can hop on at any stop on the island where the trolley picks up about every 20 minutes. It makes a continuous loop from the Anna Maria City Pier, on the north end, to Coquina Beach on the south end.
Anna Maria Island today is divided into the three cities of Bradenton Beach on the south end, Holmes Beach in the middle, and Anna Maria in the north. On our first day, we will start on the South Island.
Day One – Bradenton Beach & South Island
Spend the Morning at Coquina Beach
You can find Coquina Beach located at the south end of Anna Maria Island in Bradenton Beach. It has the longest stretch of silky, white sand on the island which feels so good on your bare feet.
There is plenty of free parking along with other amenities like lifeguards, changing huts, restrooms, a playground for the kids, picnic tables, and a concession stand that serves ice cream.
If you want to escape the sun for a while, there are picnic tables under the tall Australian pine trees where you can enjoy some shade. A nice paved path along Gulf Drive is perfect for biking or walking to your perfect spot on the beach.
2650 Gulf Dr, Bradenton Beach
Lunch at StarFish Restaurant in Cortez
For lunch, we decided to take a trip across the bridge to the historic fishing village of Cortez. This is one of the few places in coastal Florida that looks exactly like it did 40 or 50 years ago. Cortez is one of Florida’s last commercial fishing communities. It was a no-brainer that an authentic fishing village in Florida would be the best place to get fresh local seafood.
We settled on the Star Fish Company which is right on the waterfront. Seafood lovers stand in line and order from a CASH-only window. Entrees are served in cardboard boxes and diners sit on the deck at a picnic table to enjoy a colorful view of the fishing boats, and pelicans looking for a tender morsel. I ordered the Fried Shrimp & Oyster Combination, Cheese Grits, & Coleslaw. John had the pressed Cuban and Jeff scarfed down a delicious Crab Cake Sandwich. Simple food in a casual setting.
Address: 12306 46th Ave W, Cortez, FL 34215
Bridge Street Pier
After a delicious seafood lunch, we took a walk down the historic Bridge Street and the Bridge Street Pier in Bradenton Beach. This a beautiful pier, with an entrance that features a clock tower as the central focus.
Take some time and do some fishing, or just take a leisurely stroll and do some sightseeing admiring the colored buildings against the sapphire blue water. You will want to make plans to stop at the Bridge Street Pier while visiting the island.
Shopping on Bridge Street
Since this is your first day on the island, you are going to want to start shopping for that souvenir to take home. Bridge Street is famous for its souvenir shops, boutiques, bars, restaurants, and the Bradenton Historic Street Pier. I like to snoop around and then decide at the end of my trip what I want to go back for to take home.
Cocktails at Daiquiri Deck
After all that shopping and sunshine, head to The Daquiri Deck to hang out and cool off with a frozen boat drink. 3 pm is the start of happy hour so you will be able to get your frozen concoction for a lower price. Then head to the rooftop for an incredible view. They do have a food menu here as well with seafood, build-your-pizza, sandwiches, and their famous oysters.
Location: 107 Bridge St, Bradenton Beach, FL 34217
Dinner at The Blue Marlin
If you would like to step it up a notch, my brother-in-law highly recommends The Blue Marlin which is just a few doors down on Bridge Street. Decorated with antique fishing memorabilia, this former 1920s fishing cottage serves the freshest local seafood brought in from Cortez just over the bridge. Specialties include shrimp & grits, garlic shrimp, Stone Crab Mac & Cheese, fresh oysters, and daily specials. Enjoy dining outside with live music on the weekends.
Day Two – Middle Island (Holmes Beach)
Breakfast at Anna Maria Beach Cafe
One of my favorite breakfast spots on the island is the Anna Maria Island Beach Café. Not only is it right on the beach but they serve up some of the best pancakes I have had in a while. The added plus is that they will serve you all the pancakes you can eat. When they are not serving breakfast at this beachfront cafe, they offer a tiki bar serving ice-cold beer and drinks.
Beach Time at Manatee Beach
The main public seashore in the town of Holmes Beach is Manatee Beach. It sits right in the middle of Anna Maria Island. Manatee Beach is pristine and offers soft powder white sand and crystal clear waters. If you want to find a parking spot, it’s better to arrive very early. We got here about 9 am and there was quite a bit of parking but the parking lot fills fast, especially on weekends.
4000 State Road 64 and Gulf Drive, Holmes Beach
Lunch at Skinny’s Place
If it is lunchtime, you must be craving a delicious burger and a frosty mug of beer or an ice-cold Coke served in a bottle. Just across the street from the beach you will find Skinny’s Place. This beach shack serves up burgers, hot dogs, and chicken sandwiches all with a side of french fries or onion rings. They have been serving burgers here since 1952 making this burger joint an “Old Florida Original”.
Note: They do not accept credit cards, only cash.
If you want to take some time this afternoon to visit other locations near Anna Maria Island, I have a few suggestions for you. Click the links to learn more.
- Just south at The Ringling Museum in Sarasota, tour the Art & Circus Museums, Ca’ d’ Zan Estate, & Gardens. Ladies & Gentlemen Welcome to the Greatest Show on Earth.
- Get out and enjoy nature at Emerson Point Preserve in Palmetto, Florida.
- Nearby Robinson Preserve consists of mangroves, tidal marshes, and agricultural lands which have been transformed into coastal wetland habitats.
Dinner at The Ugly Grouper
Located in Holmes Beach, The Ugly Grouper restaurant is a great spot to have some fun and grab a bite to eat. They serve up some delicious seafood or burgers for the landlubbers or try their signature Grouper tacos.
All the seats are outside and most are under cover. They have plenty of fans to stay cool in the summer. After dinner stick around and listen to live music played every day. Check out the metal fish that weighs in at over 3,000 pounds made from used cars, motorcycles, license plates, and various other metal objects. I think I finally found my lost mixing bowls.
5704 Marina Drive, Holmes Beach, FL
Day Three – North Island – Anna Maria
Anna Maria City Pier
Today we started the morning by taking a stroll on the Historic Anna Maria City Pier. We made it a priority to walk to the end to grab a cup of coffee from the City Pier Restaurant. Now that I had my morning brew in hand, we could sit and relax on a bench and enjoy the pelicans and people searching for the perfect fishing spot.
Location: 100 N Bay Blvd, Anna Maria, FL
Breakfast at Ginny and Jane E’s Cafe
How does a giant cinnamon roll sound for breakfast from Ginny and Jane E’s Cafe? If sweet rolls aren’t your thing, they also offer everything from French toast to omelets. Many say this is the best breakfast on the island. To get to the cafe, you have to walk through their store which carries a unique collection of local art and unique finds. There is something different hanging in every nook and corner of the store. You never know what you might find.
9807 Gulf Dr, Anna Maria, FL
The Historical Society Museum
The folks at the Historical Society Museum will be glad to show you around and tell stories like the tale of the Anna Maria City Jail. This tiny, open-air building was built in 1927 because of the tavern-dance hall on the Gulf side of Pine Avenue. Some who frequented the hall would get drunk and cause disturbances. Once the troublemakers spent a night in the facility and were attacked by hundreds of mosquitoes, they usually weren’t too anxious to act up again.
Also in the Historical Park, located next to the museum, is the Belle Haven Historic Cottage. This was one of the original cottages that were built in 1920 on the end of the City Pier. In 1926, it fell into the bay due to diseased pilings. It has been restored and furnished with heirlooms and antiques that give you a glimpse into what early island life was like.
Anna Maria Island Historical Society Museum – 402 Pine Avenue, Anna Maria, FL
Bayfront Park
Bayfront Park is located on the northern tip of Anna Maria Island and offers an impressive view of the Sunshine Skyway Bridge and the Rod and Reel Pier. This park has excellent facilities, and it is an ideal spot for a beach picnic.
The Rod & Reel Pier
The Rod & Reel Pier is a must-visit when you visit Anna Maria Island. The seafood shack that sits at the end of the wooden pier serves up great seafood. Go for the grouper sandwich, and sit out on the pier to enjoy. If you want to hang around for a while (and why wouldn’t you?), bring a fishing pole, for a small fee, and fish right off its dock and walkways.
875 North Shore Drive, Anna Maria,
Shopping on Pine Avenue
If you are looking for something a little nicer than the typical Florida beach souvenirs, head over to the shops on Pine Avenue. You won’t find Macy’s, Target, or Kohl’s here but what you will find are locally-owned businesses like the Pineapple Marketplace, Pink & Navy, Three Island Monkeys, and the Shiny Fish Emporium where you can paint your own sand dollar.
Dinner at The Waterfront
Just across the street from the Anna Maria City Pier sits The Waterfront Restaurant. This is the island’s premier waterfront dining experience, offering New American cuisine and tropical laid-back Old Florida charm the way it used to be. The Waterfront has rotating seasonal menus to ensure you’re getting something fresh and seasonal. The Waterfront Restaurant will “cook your catch” if you went on a fishing trip with Anna Maria Charters which is pretty cool.
111 S Bay Blvd, Anna Maria, FL
Sunset at Bean Point Beach
One of the best places to view the sunset on the island is Bean Point Beach, located on the northern tip of the City of Anna Maria. There are no lifeguards or facilities at this beach and the tides can be strong here so be careful swimming. Sandcastles wait for their fate of a high tide. Fading signs on the shore of a fun day at the beach. This was the perfect way to end our three days on Anna Maria Island.
NOTE: Parking here is difficult to find. You can find beach access at the intersection of Gladiolus Street and North Shore Drive as well as Fern Street and North Shore Drive but be careful parking. This sunset came with a cost of $50 because I didn’t want to park in someone’s grass and had two of my wheels in the street.
Anna Maria Island holds special memories for me as a child. My family would travel to the island for family reunions. My family also owned Anthony’s Restaurant, which was a popular restaurant on the island. We spent the day with our Aunts, Uncles, and Cousins on the beaches enjoying each other’s company. Perhaps this could be a special place for you too as it is for many yearly visitors.
