Places to Eat on Anna Maria Island – Nostalgic Flavors Reinvented

My husband and I used to love traveling, but then we became parents and that all changed. Some kids are great travelers: my sister flew from Key West to Alaska with multiple stopovers with two kids under the age of two and by all accounts it was an amazing trip. 

Just the thought of it makes me break out into hives. Getting our two-year old daughter into a car seat for even the briefest trip can often require hours of negotiation and increasingly esoteric bribes. So when it’s time for a family vacation, we like to stick close to home.

I grew up on Anna Maria Island and still have family there, so it was the perfect place for us to have a quick weekend getaway. We live in nearby Sarasota, less than an hour away, so while we could have just driven down each day we thought we’d save ourselves the hours of car anxiety and rent a place. 

We found a charming rental property (complete with its own private pool) within walking distance of Historic Pine Avenue (The Greenest Little Main Street in America) and prepared ourselves for a blissful car-free weekend. 

Walking Down Historic Pine Avenue with a cranky toddler

 

Our Holidays, it’s all about Food

For us, vacations have always revolved around food. 

We have eaten our way through major culinary destination cities, like New York and Austin and Chicago. So we committed to enjoying the local cuisine as much as possible on our 2-day stay.

Breakfast Treats

We started nice and early on day one with confections from Anna Maria Donuts. We had heard this place was popular, and that was an understatement. 

My husband walked there and arrived promptly at the 7am opening time and discovered people already lining up for these sugary, hand-made breakfast treats. My husband ordered a half dozen of the piping hot donuts that were made right in front of him and got an array of icings and toppings customized to his tastes. 

Our daughter was delighted by a vanilla donut dipped in vanilla icing and topped with crispy Fruit Pebbles, while my husband and I squabbled over a donut dipped in chocolate icing and bedecked with soft marshmallows. 

We devoured the entire box on the front porch as the early morning light began to warm the quiet Island streets. 

Cooler Stock Up

We decided to spend the morning at the beach, so we planned ahead and stopped by the Anna Maria General Store to stock up our cooler. This vibrantly-colored shop is a far cry from your standard convenience store. The shelves are stocked with organic treats as well as the expected snack food, and the deli is full of generously-portioned food. We’ve eaten a lot of Cuban sandwiches in our day and these ranked among our top favorites of all time. We also made a mental note of the surprisingly interesting array of craft beers for later. 

The Waterfront – an Eco Delight

Once we had showered off the beach sand and settled down for a family nap, my aunt came by to babysit for the Munchkin so my husband and I could enjoy a night to ourselves. 

We walked the few short blocks to The Waterfront Restaurant and enjoyed the cool evening breeze at our table on the deck. We were impressed by the selection of sustainable seafood (it seems Anna Maria is earning its eco-friendly bona fides everywhere you look): after splitting the House-Smoked Pacific Salmon Appetizer, I dove enthusiastically into the creamy zesty Shrimp and Grits entrée while my husband devoured fresh and tender grouper tacos. 

Bartender Jeannine at The Waterfront Restaurant

Hand Crafted Cocktail at The Waterfront Restaurant

Ingredients at The Craft Bar @ The Waterfront Restaurant

It was a good thing we had decided to ditch the car for the night: the Waterfront has an impressive and unique craft bar, and we availed ourselves of the opportunity to try unique drinks like Smoked Margaritas and Pineapple Caipirinhas all made with fresh, local ingredients. 

Relish Café, Heart of Anna Maria Historic Green Village

On Day Two, our daughter met the sunrise a little more enthusiastically than we did, so we made sure to find a kid-friendly breakfast spot where she could have a great time while we shook off the lingering aftereffects of the previous night’s tequila. 

Kids Love Eating at Relish Cafe

 

Relish Café fit the bill perfectly. This offbeat eatery nestled in the Anna Maria Historic GreenVillage offers a menu of lightened-up Southern-style comfort food with a twist that was tremendously appetizing to us all. 

Diners on the Deck at Relish Cafe

 

Our daughter enthusiastically selected the French Toast Rosettes topped with syrup, strawberries, and powdered sugar and we were impressed to find such an elegant offering on the kids’ menu for less than six dollars. I’ve never met a breakfast sandwich I didn’t like, so I was intrigued by the Waffle Monte Cristo Sandwich with sweet pineapple jam while my more traditional husband opted for the Biscuits & Gravy Egg Plate. While we waited for our food to arrive we sipped on delicious fresh-brewed coffee and watched our daughter scribble away with great aplomb on the clever chalkboard tabletops. 

Fried Green Tomato BLT from Relish Cafe

Fresh Salad Bar at Relish Cafe

The food was delicious, and when I finished, I even got to do a little shopping: the café is also home to some whimsical vintage items for sale. 

Authentic Mexican Food

Several of our family members had the day free, so we skipped the beach and headed back to our place to try out the pool. 

When my stepdad made an appearance he was loaded down with goodies from Poppo’sTaqueria which serves authentic Mission-style Mexican food made from organically and locally-sourced ingredients. In addition to more expected fare tacos filled with shredded beef or carnitas and topped with pico de gallo, we enjoyed inventive selections like Bison Chili and housemade Pineapple Hot Sauce. I’m originally a Texas gal, so I know my Mexican food, and this was the real deal. 

After a fun day by the pool with family and friends, we reluctantly began to pack up for the trip back home.  But I still had one more trick up my sleeve. 

We Couldn’t Leave without a Burger!

I called ahead to have an order ready, and we made a brief stop on the way out of town at Duffy’s Tavern, home of my favorite burger since childhood. I dashed in and returned to the car with a bag full of perfectly cooked juicy cheeseburgers with just that hint of grease that turns a good burger into a great one. We all three happily snacked on these all the way home and washed them down with the old-fashioned Cokes in a glass bottle that Duffy’s has carried since my youth. 

The Flavors of Anna Maria I Can’t Get Enough Of…

It might seem strange to book a vacation rental in a town you already know well just a 45-minute drive from your home. But honestly, I’d be hard-pressed to think of a better vacation. I got to enjoy quality time with my family, revisit old favorite beaches and burger joints, and discover a world of new culinary wonders. This town has grown up as I have, and now I get to experience that change once more through my daughter’s eyes on what I hope will be regular vacations there. 

The flavors of Anna Maria have long been a part of my life, and I’m so glad I get to keep experiencing them.