Cool Things to Do in Anna Maria Island Florida • McCool Travel

Superlatives are not my thing. McCool Travel articles are not full of “best” or “must see” or “worst” attributes. Well, at least I hope so. I better double check.

Anna Maria Island beach, though, is MY favorite beach. That is a subjective designation and I hope your beach is different. Certainly, Anna Maria Island beach may not be my favorite beach forever or even at the end of this year.

I was fortunate for the opportunity to return to my current favorite beach when Bradenton Gulf Islands recently hosted me (and other travel writers) for a Guy’s Getaway weekend, to discover and explore things to do in Anna Maria Island and share my findings with the McCool Travel network.

Please enjoy this McCool Travel look at some cool things to do in Anna Maria Island. Please consider this a starter list as you explore and find your own cool things to do in Anna Maria Island. When you do, please leave a comment below.

Getting to Anna Maria Island

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

Anna Maria Island Activities

beach sunsets

Sunsets are not the only reason to visit Anna Maria Island but they may be the reason you stay.

Anna Maria Island has the sugar white sand found all along Florida’s gulf coast. The sand is cool even on those scorching hot days. So nice!

Anna Maria Island morning beach walks

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.


Flying above the water with TOP GUN Flyboards was one of the coolest activities I have done. EVER! Since there are no known videos of me flyboarding, I included this photo. No, this is not me, silly, because I flew much higher. Ha.


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.

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

Anna Maria Island Events

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

Where to Eat in Anna Maria Island (and Drink)

Beach Bistro

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 Novey style (named for owner Sean Murphy’s home of Nova Scotia).

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.

Ginny’s and Jane E’s Bakery

This trip resulted in my second time visiting the eclectic, quirky, and whatever other oddball term I can conjure for Ginny’s and Jane E’s Bakery Cafe.

You most definitely must (there is that “rarely” used word again) order a righteous cinnamon roll at Ginny’s and Jane E’s Bakery. Looking at the breakfast menu I found a Cuban Egg breakfast sandwich. Muy Bueno!

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, pretty 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?

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.

The Doctor’s Office

Experience an extensive menu of house blended or custom craft cocktails at Doctor’s Office. I went 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.

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: skip the omelet.

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 is available at the nearby Publix, along with fish fillets from our fishing trip.

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.

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.

Our Island Real Estate contact even brought donuts to the house one morning to thank us for staying there. Of course, no guarantee the same will happen when you rent a house but even without doughnuts the house is spectacular.

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:

Bradenton Area CVB: website | Facebook | Instagram | Twitter

Sun, Sand, and Fishing on a Guys Weekend in Bradenton Florida

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




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Charles McCool

Charles McCool

I help people #Travel #Happy and save companies tons of money. Find me at & on unpaved roads.

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