16 Cool Things to Do in Anna Maria Island Florida

The most cool, happy, and fun things to do in Anna Maria Island include savoring world class sunsets, enjoying the cleanest and whitest beach sand in the world, eating amazing grouper tacos with your toes in said sand, and flying above water. What? Yes, flying!

Anna Maria Island Florida is my favorite beach. There I said it. I got that out of the way.

Superlatives are typically not my thing. McCool Travel articles are not full of “best” or “must see” or “worst” attributes. Well, at least I hope not. I better double check. Let me know if you see any and I will buy you a margarita, probably at an Anna Maria Island bar, such as The Doctor’s Office (see below).

gorgeous clean white sand of Anna Maria Island beach
the gorgeous beach is one of the best things to see in Anna Maria Island FL

16 Cool Things To Do in Anna Maria Island Florida

Anna Maria Island beach IS, though, my favorite beach. Favorite or best beach is a subjective designation but I really hope your favorite beach is different than mine. Certainly, Anna Maria Island beach may not be my favorite beach forever or even at the end of this year.

This article is based on experiences from several Anna Maria Island trips including one when Bradenton Gulf Islands hosted me (and other travel writers) for a Guy’s Getaway weekend.

Getting to Anna Maria Island FL

Anna Maria Island is about a 25 minute drive from Sarasota airport (SRQ) and 75 minutes from Tampa airport (TPA). If more convenient, make the two hour drive from Orlando airport. Check smaller airlines for nonstop flights into SRQ—like Allegiant (from Cincinnati, Indianapolis, and Pittsburgh) and Elite Airways (from Portland Maine, White Plains New York, and Pittsburgh). Here is a convenient and useful resource list of nonstop destinations from SRQ airport.


Anna Maria Island Activities

fun beach sign in Anna Maria Island
cool beach signs are among the cool things to see in Anna Maria Island Florida

1. Anna Maria Island Beach sunsets

The remarkable US Gulf Coast sunsets are one of the best nature spots in Florida for photos.

Anna Maria Island has that lovely soft sugar white sand found all along Florida’s gulf coast. The sand is cool even on those scorching hot days. So nice! Recommended places to view the glorious US Gulf Coast sunsets include near 64th Street (near Beach Bistro), Manatee Public Beach (directly across from the main bridge entrance to Anna Maria Island), but really any beach will do.

Head to Bean Point, at the top of Anna Maria Island (north end) for wider beaches, sand dunes, but also breezier winds and multi-directional currents (careful when swimming). In addition to unobstructed sunset views over the Gulf of Mexico, you can see Edgmont Key straight north and the magnificent Sunshine Skyway Bridge to the northeast.

McCool Travel tip: Turn left (south) when driving onto Anna Maria Island from the Manatee Avenue bridge and in less than one mile find a parking spot steps from the sand of Coquina Beach. Besides Coastal Mississippi, this is one of the most convenient and FREE places to visit the beach along the entire US Gulf Coast.

2. Morning Beach Walks on Anna Maria Island

While sunsets are for socializing with rum drinks—oohing and aahing at the vibrant sky show—beach mornings are for early day activity. Daybreak is a nice time to say hello to temporary neighbors and commiserate about the people “back home” suffering through another harsh winter.

Good morning from Holmes Beach on Anna Maria Island. Yassssssssss! Visit Bradenton Gulf IslandsIsland Real Estate – Anna Maria Island

Posted by Charles McCool on Friday, December 1, 2017


My new office. Anyone fancy a meeting?

Posted by Charles McCool on Sunday, December 3, 2017

3. Flyboarding

Flying above the water was one of the coolest activities I have done. EVER! I felt like James Bond and Travis Pastrana at the same time. Visit TOP GUN Flyboards to learn about the most fun you can have with your clothes on.

4. Fishing

Egmont Key Adventures is conveniently located across the street from the Waterline Marina in the center of the Anna Maria Island commercial district. Egmont offers offshore, nearshore, and inshore excursions. Captain Harrison took us on a half day adventure and we caught plenty of snook, pesky needlefish, redfish, and a trout or two.

fisherman holding fish in Anna Maria Island
Egmont Key Adventures fishing excursion in Anna Maria Island

McCool Travel tip: arrange for take-out sandwiches, amazing sweet treats, drinks, and sides from Scott’s Deli.

monster sandwich from Scott's Deli in Anna Maria Island
monster sandwich from Scott’s Deli in Anna Maria Island

5. Anna Maria Island Events

We were in town for the Bradenton Blues Festival but there are hundreds of Florida Gulf Coast events year round. For a complete and current list of Anna Maria Island and Bradenton area events, check with Visit Bradenton tourism website.

washboard musician Zydeco at Bradenton Blues festival
Bradenton Blues Festival is one of the most fun events near Anna Maria Island

Where to Eat in Anna Maria Island (and Drink)

things to do in Anna Maria Island. Photo and article by Charles McCool for McCool Travel.

6. Beach Bistro in Holmes Beach

Yes, I expected to eat fresh seafood in Anna Maria Island. No, I did not expect to eat at one of the most highly rated restaurants in the USA. Beach Bistro is one of 11 US restaurants with a 4.9 Zagat rating. Goodness. We started with lobster appetizers in two forms: phenomenal lobstercargots and lobster Novey style (named for owner Sean Murphy’s home of Nova Scotia).

Nova Scotia style lobster appetizer at Beach Bistro
Beach Bistro on Anna Maria Island is one of the best USA restaurants

Expertly prepared entrees and desserts arrived amongst many different exotic and elegant drinks. Beach Bistro also hosts nightly sunset celebrations and has a lively “Old Florida” bar environ.

7. Ginny’s and Jane E’s Bakery

A perfect place for breakfast in Anna Maria Island is Ginny’s and Jane E’s Bakery Cafe. It is quirky, fun, cool, and serves amazing food.

eclectic interior of Ginny's and Jane E's in Anna Maria Island
Ginny’s and Jane E’s in Anna Maria Island

Definitely order a righteous cinnamon roll at Ginny’s and Jane E’s Bakery. My favorite breakfast menu item is the Cuban Egg breakfast sandwich. Que Bueno!

On my third visit to Ginny’s and Jane E’s Bakery, I discovered that they have amazing key lime pie. For only $3 a slice. Thus the next day I made my fourth visit!

8. Sandbar Restaurant

Ironically there are not too many places along the Florida Gulf Coast where you can eat with your toes in the sand. The Sandbar Restaurant on Anna Maria Island is an epic Florida waterfront restaurant and they have one of the most fun gift shops as a bonus!

McCool Travel tip: the grouper fish tacos cost $9 less than the grouper platter and has about the same amount of rice and grouper. Better deal!

fish tacos at a Florida beach restaurant
amazing grouper fish tacos at The Sandbar Restaurant

9. Gulf Drive Cafe and Kokonut Hut Tiki Bar

I absolutely love putting my feet in sand while staring at the water when I eat. Nothing makes me feel more like wasting away, Jimmy Buffett style. So, Gulf Drive Cafe passed that test. Then the food was pretty darn good. Breakfast omelets were huge, quite decent for four hungry guys. The giant thatched roof tiki bar was not open during our breakfast visit but I imagine it draws a super fun crowd later in the day. Something for me to go back and experience. Want to join me?

Oh, and the tropical holiday decorations at Kokonut Hut Tiki Bar are really fun.

tiki hut on beach in Anna Maria Island
Gulf Drive Cafe is one of the most fun Anna Maria Island restaurants

10. Star Fish Company, Cortez Florida

Even at 11am there was an impressive line of local residents ordering food at the hidden gem seafood wholesale market Star Fish Company in the tiny hamlet of Cortez, Florida. The CASH ONLY, no frills “restaurant” is out back, overlooking the absolutely magnificent Sarasota Bay. Worth the wait? This blackened grouper was 1/3 the price of nearby sit down restaurant versions and twice as tasty. One of the most memorable things I ate in 2017.

blackened grouper at Starfish Seafood in Cortez
Star Fish Company in Cortez is one of best places to eat along the Florida Gulf Coast

11. The Doctor’s Office

Experience an extensive menu of house blended or custom craft cocktails at Doctor’s Office. I opted for custom, request something spicy and rummy from the bartendress. Located in a former doctor’s office (duh), when it is at full occupancy, a rope across the entrance says “NO NEW PATIENTS AT THIS TIME. SORRY.” So cool. The Doctor’s Office is owned by Sean Murphy of the above Beach Bistro.

The Doctor's Office, Holmes Beach, Anna Maria Island
the Doctor’s Office is a place to drink in Anna Maria Island

12. Anna Maria Oyster Bar

Located on the Historic Bridge Street Pier, Anna Maria Oyster Bar is another local institution. For no other reason than basking in this glorious setting while your friends back home are shivering in the winter, go to Anna Maria Oyster Bar. While I ordered an omelet, my friends all opted for the Hangover Sandwich. McCool Travel tip: order the Hangover Sandwich. Ha!

waterfront dining in Bradenton Beach
Anna Maria Oyster Bar is a wonderful waterfront Florida restaurant

13. Cookout at the Crib

Preparing our own feast at our vacation house was one of the highlights of our guy’s getaway weekend in Anna Maria Island. Plenty of yummy fresh food and drinks are available at the nearby Publix but the highlight was grilling the fish fillets from our fishing trip.

14. Skinny’s Place

For a quick bite, head to Skinny’s Place, the kitschy, quirky, “Old Florida Original” little burger beach shack, est. 1952, located right across the street from Manatee Public Beach.

15. Florida Craft Breweries Near Anna Maria Island

Two fun local Florida craft breweries within a few miles of Anna Maria Island are 3 Keys and Motorworks. Motorworks Brewing has a huge indoor area and an outside beer garden highlighted by magnificent live oak trees (love them!), music stages, kid and dog friendly space. Try their phenomenal seasonal beers. 3 Keys Brewing is popular for their beer and food. Tuesdays is $5 burger day and their burgers are absolutely delicious. Unfortunately their fish tacos were disappointed but their craft beer is fantastic. And 3 Keys has epic beer flight boards in the shape of the  state of Florida.

beer flight board in the shape of Florida
try delicious Florida craft beer at 3 Keys Brewing

16. Where to Stay in Anna Maria Island Florida

The vacation rental scene dominates lodging on Anna Maria Island. That is a good thing because, as you probably know, I consider vacation rentals a better value than hotels—lower prices, more space, and better amenities. Our vacation rental house was arranged through Island Real Estate. They manage hundreds of homes and the website has convenient search criteria, like gulf front, pet friendly, with pool, and specials.

sweet Anna Maria Island beach houseAnna Maria Island Beaches | Anna Maria Island | Island Real Estate – Anna Maria Island | Visit Bradenton Gulf Islands

Posted by Charles McCool on Saturday, December 2, 2017

Fancy a December morning swim? Yes, please. Good morning from Holmes Beach on Anna Maria Island. Island Real Estate – Anna Maria IslandVisit Bradenton Gulf Islands

Posted by Charles McCool on Saturday, December 2, 2017

Right across the bridge and located on Anna Maria Sound is One Particular Harbour, a Margaritaville residential concept. Also attached to this fun Margaritaville location is a Compass Hotel for short term stays. Fins Up!

Some of the best Anna Maria Island hotels I want to try future #USGulfCoast trips include Waterline Marina Resort, Anna Maria Island Inn, and Bungalow Beach Resort.

Another Anna Maria Island lodging option is a vacation rental, including a condo, apartment, or house. >>> To receive $40 off your first Airbnb rental, use this Airbnb discount code.

McCool Travel bonus: I have not yet been there but on reliable advice I was told to visit Beer Can Island. There, my friend told me, you can swim with dolphins and manatees. Beer Can Island is at the tip of Longboat Key closest to Anna Maria Island, just a 10 minute drive from Manatee Beach. I will check out Beer Can Island on my next trip.

And if you drive to Anna Maria Island from Tampa area, make sure to visit the fishing piers connected to Sunshine Skyway Bridge. It costs $3.20 (per vehicle) to visit either Skyway State Fishing Pier (it is a Florida State Park). BUT (McCool Travel tip) you can visit both fishing piers within one hour, so do it! If you only have time to visit one, go to the north fishing pier (it is longer).

Sunshine Skyway Bridge view from the Skyway State Fishing Pier
view of Sunshine Skyway Bridge from the north Skyway State Fishing Pier

Day Trips Near Anna Maria Island FL

Located midway between Tampa and Punta Gorda, Anna Maria Island is a magnificent Southwest Florida Gulf Coast island. Sarasota, Naples, Captiva Island, and Indian Rocks Beach are easy day trips from Anna Maria Island. Plan your Southwest Florida US Gulf Coast getaways with our guides:

What are some of your favorite things to do in Anna Maria Island Florida?

For more information about things to do in Anna Maria Island, visit:

Things to do in Anna Maria Island include world class sunsets, the cleanest and whitest beach sand in the world, and flying above water. What? Yes, flying!

Cool Things To Do in Anna Maria Island Florida was originally published on 28 October 2017.

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40 thoughts on “16 Cool Things to Do in Anna Maria Island Florida”

  1. My wife and I just booked a place on Anna Marie Island for the week of the 4th of July and have one burning question. Where would you recommend for an authentic Cuban?

  2. Your most loved shoreline looks truly cool. A considerable amount of things to keep you occupied from dawn to dusk in Anna Maria Island. Obviously the nightfall looks dazzling and the shoreline perfect for an early morning excursion, tuning in to the music of the ocean and feeling the delicate sand on your feet. Flyboarding resembles an incredible experience choice while the decisions for sustenance and drink look tempting as well.

  3. We can see why you like Anna Maria island so much. It looks like a wonderful place to visit, and the food is quite tempting. Thanks for sharing all of the delicious pictures. It makes us want to plan our own escape.

  4. Beautiful sunset and the food looks really delicious. I wouldn’t mind hanging out there. I have only ever been to Miami. So many places..so little time :-). Perhaps our next trip state side.

  5. I was sold on Anna Maria Island from the get-go, but then you brought up Cuban egg breakfast sandwich. Yes, please!! Seriously, I have spent a good portion of my life along Florida’s Gulf Coast but seem to have missed out on Anna Maria Island. I will have to change that!

  6. I can see why Anna Maria Island is your favourite beach. The beach and the views are beautiful. And the food looks pretty great too. My mouth is watering and I just finished lunch!

  7. Oh man, this place looks awesome. I thought it was down in the Caribbean. I have never heard of this pace, but now we are going to add it to our Florida road trip itinerary next month!!!!

  8. This beach seems so bubbling and full of good things yet remains remote and off the usual touristic track! Never been to Florida, but it looks like a good beginning for falling in love with it!

  9. Such an amazing Island and thanks for your introduction about the Anna Maria island. Glad that you found your very own favorite and it looks like there are a lot of things to see and do there! Would love to join the Bradenton Blues Festival some day, try out the oyster bar, and hang out in the beautiful rental house! @ knycx.journeying

  10. My sister–an Orlando local–rented a beach condo there last summer and raved about it. It was already on my radar, but now, with long days of winter still ahead of me, it’s looking even more enticing (if possible!)

  11. Those lobster dishes look amazing!! I haven’t explored nearly enough of Florida and hope to change that. Anna Maria Island has lots of fun and funky places to see, added to my wish list!

  12. Beautiful photos! Gotta love sunsets along the west coast. Have spent time in Siesta Key and Sarasota and have seen the turn off to St. Armonds and northward, On the list to drive 789 all the way up to there on another visit. Thanks for sharing all the to-do’s!

  13. Your favourite beach looks really cool. Quite a lot of things to keep you busy from sunrise to sunset in Anna Maria Island. Of course the sunset looks gorgeous and the beach ideal for an early morning jaunt, listening to the music of the sea and feeling the soft sand on your feet. Flyboarding looks like a great adventure option while the choices for food and drink look enticing too.

  14. I am currently in Fort Myers Beach and am making note of Anna Maria Island on a future visit. It looks like you found great beaches and I must say a photo of you fly boarding would have been epic! I also see that you enjoy a good doughnut shop, as I do.

  15. Have to agree totally that Anna Maria Island is a gem in many ways. With beaches that rival other top-rated locales but without the crowds, with eclectic shops without the vehicular clog, and food that ranges from fast and easy to full course recasts, this island has it all. The only complaint I have with your article is that more people will discover this idyllic spot.


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