Beautiful sunny day in Anna Maria Island, Florida.

We all have our favorite places we like to hang out.  How these places become our favorite is based, I believe, on some emotional tie to the place.  It’s a place that you’ve had fun at with your friends and family, so much that you bring visitors to that place hoping that they will create that same emotional bond that you have. Or it’s the place that they have made you feel welcome and part of the group. In this blog I was trying to think of my top 5 places, and I found it incredibly hard to choose.  So rather than choosing 5 places I thought I would write about the three distinct shopping districts on Anna Maria Island.

I’ll start with Pine Avenue and Anna Maria – The street is lined with these super cute cottages and has a variety of shops.  Pine Avenue is old Florida at its best.  There really isn’t anything you can’t find there if you take the time to look.  From great beach gifts, to great dress shops, to some great eats.  My favorite thing is to just stroll the street and see what I can find…I of course, must stop for a maple syrup donut with bacon crumbles on top from The Donut Experiment.  Here’s a confession, I grew up in Western New York State and I do not like maple syrup.  I’m sure that I have failed my home state and all of New England but, there it is.  Having said that, this donut is pure pleasure from the first to the last bite.  Another great spot for divine eatables is the Waffle Press.  The toppings are enough to start a drool but, then when you pair it with a hot freshly made waffle that are light and fluffy…WOW!    The Waffle Press is in Pineapple Marketplace, which is 30 different little stores in one building.  Howluckyami is “lucky” enough to be a part of this fabulous Marketplace.  Sticking with the eats there are three other places that I truly enjoy.  I love the fresh crab salad at The Waterfront paired with a glass of Albarino, any fish prepared at The Rod-n- Reel, and some amazing sushi from Ocean Star.  Coming soon or coming back depending how you choose to look at it is the Anna Maria City Pier.  The old pier was a great place to sit and watch the world go by, so I’m sure the new one will be just as wonderful.  Another great thing in Anna Maria is the local theater.  This amateur troop puts on some very good performances.  Two other points of interest are the old jail and the Anna Maria Island Historical Society.  The old jail offers a fun photo op and the historical society has great photos of what was on Anna Maria.

One of Anna Maria Islands most spectacular sites is on the north end.  Bean Point gives the island it’s drumstick shape as it wanders off into the Gulf of Mexico and Tampa Bay.  Here’s an interesting tidbit about our little splash of paradise.  Anna Maria Island is the oldest barrier island in Florida.  It formed about 3000 year ago with the completion of the island’s iconic shape in the 1880’s.  Bean Point is the oldest part of the island.

Moving down Gulf Drive from Pine Avenue is another collection of shops and restaurants from the Egret Stores, Harry’s Grill, to the famous Ginny and Jane E’s.  Locals and Visitor’s flock to one of the north end’s favorite hangouts.  The busiest time of the day is breakfast time and lunch, as it has a deli style restaurant in the back but, it’s full of a huge collection of eclectic stuff.  You could go in there every morning and never see the same cool stuff twice.

From Gulf drive moving down Palm Drive is mostly residential but, on Palm Drive is what the locals affectionately call the “skateboard church”.  It’s really the Gloria Dei Lutheran Church.  The architecture makes it one of the island’s landmarks…when giving directions it’s either after or before the “skateboard church.”

The next hamlet on Anna Maria Island is Holmes Beach.  Holmes Beach is what most of us consider the shopping district of the island.  It has the most stores per capita which include the basics like the two hardware stores, pharmacies and the Publix.  I know this is crazy but, I love going to the hardware stores. They both have an amazing group of people that work there, and someone always knows what I want and how to fix it.  I do try not to walk in and ask stupid questions but, someone always know that when I ask for a “hooby” (made up word that to me describes a lot of things that I don’t know the name of) that does such and such they know exactly what I am talking about.  At the True Value one of the guys even asks me when I go in, “What “hoobies” are you looking for today?”

Some other favorite haunts in Holmes Beach are Eliza Ann’s Coastal Kitchen at The Waterline and Hurricane Hanks.  Both places are great whether you go with a group or on occasion just for a girl to go have a drink on her own.  The food is very good too!  Another cool spot for a cocktail is the Doctor’s Office, aptly named as it used to be the actual Doctor’s Office…their Bourbon, Scotch, and Vodka choices are divine.  They have wine and beer too but, I’m a bourbon girl and they have some of my favorites. One of the most amazing things I have ever put in my mouth is an appetizer here, the potato nachos! OMG! 

My favorite lunch spots, if you are a working person, are Scott’s Deli and The Feast.  Scott’s has a hot sandwich called the Coquina….so yummy!  The Feast makes great burgers and salads.  The Blue Burger with caramelized onions and their Beet Salad with house made dressing is just great. 

There are a couple of local burger joints that are just a great place to hang, have a cold one and people watch. Duffy’s and Skinny’s are classic local bars/burger joints where everyone is welcome and “they know your name.” The big question for some is where is the best pizza place on the island?  My goal isn’t to try and answer this question as everyone has their own tastes but, as a New Yorker the Island Grill makes a fabulous thin crust pizza and The Feast has a hearty vegetarian pizza which I of course add sausage to.  For you Chicagoans deep dish pizza is not available on the island, although it’s not Lou Malnati’s, Fratello’s is pretty good.

Holmes Beach also features a lot of boutique stores.  Some of the best local art on Anna Maria Island can be found in the various plaza’s centered in Holmes Beach.  Howluckyami’s main store is in The Island Plaza.  We share a store front with Restless Natives which features AMI’s well known artist, Robert Johnson.  One of my favorite dress shops also is in the Island Plaza, Irene’s has a large selection of casual and dress wear, something for every event on the island and beyond.  For men and women there is Mister Roberts clothing store, which features resort or casual wear, very nice stuff. 

The Most popular beach is Manatee Beach which is in the middle of the two main shopping plazas.  This is a favorite of the locals that live in Bradenton as there’s good parking, a bar that serves food, and bathrooms!

Heading south towards Bradenton Beach is another of my favorite places, the Smoke House.  The pulled pork sandwich is a southern marvel and the Brisket Burger is just awesome…ask for lots of napkins! The best thing I have ever had from there was an appetizer that they served at a Chamber Event.  It was a stuffed jalapeno with crunchy peanut butter wrapped in bacon and then smoked.  Simply put you cannot eat just one.  I’m telling you this because they cater too.

Bradenton Beach is locally known as the party center of Anna Maria Island with several fun beachy bars.  The great part is you can take the trolley or the Monkey Bus to get there.  This is advisable for a couple of reasons:  Parking is a huge problem and by busing it you don’t have to worry about over imbibing.  The trolley does stop at 10 but, the Monkey Bus goes till much later. There are some good eateries in Bradenton Beach: The Wicked Cantina has good Tex-mex and from scratch margaritas; The Beach House has a beautiful bar outside.  They have modernized the Florida Beach bar with style.  The menu has a great variety and one of my favorites.  It is an appetizer that I can eat as a meal… Grilled Brussel sprouts with a glaze drizzled on top, served in a small cast iron skillet.  Sunday Bloody-Mary’s completes the meal, as they come with a ton of vegetables; Bridge Street Bistro and Island Time (although it appears that these are two separate places they are owned by the same people). Bridge Street Bistro is fine dining and Island Time is a fun place to go on the weekends to listen to music while having a bite to eat;  The Blue Marlin has an amazing menu and a really good wine list with Blues playing on the weekends; The Bridge Tender Inn is just fun!  With good sandwiches and a super fun staff to hang out with.  The Anna Maria Oyster Bar is not just for Oyster’s they have a good menu too.  Don’t worry if you want to stay out and play for a while as the Drift Inn and the Sports Bar will be happy to keep serving. 

I don’t want you to think that Bradenton Beach is all for the party crowd as they do have several cute boutiques.  Historic Bridge Street has been changing and growing in the past few years but, keeping it the same loveable fun street that the locals and visitors a like have come to expect.  At the end of Bridge Street is the Clock Tower and the Pier which is fun to stroll or fish off.

At the top of Bridge Street is the Anna Maria Island Moose Club.  It touts one of the largest memberships in all Moosedom.  After the renovation it’s a nice place to whittle the way the hours whether upstairs on the open patio or downstairs undercover.  Drinks are reasonable and they have a small but, good menu.  Unfortunately, you must be a member but, anyone can sponsor you as a new member.  Guys must sponsor guys and the girls the girls…

Some other fun things to do while here when you’re not eating or beaching it…The island has many Captain’s that would love to take you out fishing in the bay or out in the Gulf of Mexico.  If you want to see Anna Maria from up high, try parasailing. 

The AMI Dragonboat Team offer a fun day out showing visitors and locals how to paddle these amazingly beautiful boats.  Be careful though you will get hooked and should you want to join the team, just ask?  Look for our team in 2020 in Benderson Park out by the University Town Mall for the World Dragonboat races.  howluckyami is a proud Sponsor of this fun competitive group of people.

If you want to slow down a bit and go your own way, there are several places that you can rent a kayak or paddleboard from.  It’s a great way to tour our intercoastal water ways and mangroves.  You might even get lucky to see one of Florida’s most beloved animals, the Manatee or Sea Cow!

We also have several preserves that offer a great way to see our intercoastal and mangroves on foot if you are not feeling up to paddling.  A good way to see what we have to offer on Anna Maria is to check out Anna Maria Chamber of Commerce’s website:

The bottom line is there is lots of good eats and a lot of fun places to shop and visit.  We all know… Those of us that live here and those of you that come to visit are coming for the serene beauty of our amazing beaches.  From one end of Anna Maria Island to the other you cannot go wrong with whichever beach you choose to plop your beach towel on… so enjoy it all!