Anna Maria Island – A detailed review of Florida’s fun family vacation destination

Travel Edition: Anna Maria Island

by Alicia in New posts, Travel

6 Flares 6 Flares ×

Thanks to guest blogger, Desiree from Bottles to Britches, for providing us with this detailed review of her family vacation to Anna Maria Island & Longboat Key in Florida.

Want a family vacation that seems a little slower than regular life? Maybe a relaxing beach? There’s a string of towns along Florida’s southwest coast that still hold that Old Florida charm…a place where you can ride bikes with your children through the streets or take a quiet trip down the river and get up close and personal with nature. Situated just south of Tampa Bay, Anna Maria Island and Longboat Key, Bradenton and Lakewood Ranch offer that walk back in time that you can really embrace. Don’t get me wrong—this is no sleepy little town. The options for food and entertainment are assorted, from funky diners that double as antique shops to top-knotch restaurants with historic ties to the area’s first settlers. I was invited by their visitor’s bureau recently to come see what the area offered and have to say the trip was a special treat for my entire family. We did it all, from learning to paddleboard to “horse surfing”, and ate some very memorable meals. Nothing is more than a short walk or drive on Anna Maria Island, but there is a free trolley that makes stops along the island if you’d prefer. We had a blast and can’t wait to go back. And here’s the beauty of South Florida—it stays warm pretty much all year, so a trip in October or November should provide a comfortable beach climate.


Not sure where to stay when visiting the Anna Maria Island area? What makes this area special, in my opinion, is you don’t have to go grand. You can have lots of space in a fabulous little package without twenty story condos. We stayed in a great little rental house on Holmes Beach, almost at the tip of the island. The home didn’t look like much on the outside, but the inside really surprised us. It was classy and casual and truly set up to be a home away from home. Set up by Island Real Estate, this four bedroom home had its own heated pool—complete with a built in table IN the water with shaded table for in-pool (not poolside here!) drinks. It was just two blocks from the beach and an easy bike ride (the owners left bicycles in the garage to make things super simple, though there are places you can rent bikes). The home we stayed at had been remodeled and was so well-done my husband, the realtor and home-flipper, decided to take photos with hopes of duplicating some of the special touches. Three of the four bedrooms were equipped with king-sized beds, and the fourth had bunks. It was decorated well, super comfortable, and completely stocked with family games. The home was ideal, but we didn’t have much time to spend there to be totally honest. That’s because we wanted to be sure to check out all the special things that make this area unique, including the cool restaurants and activities.


The afternoon we arrived we had lunch at Mattison’s Riverside. We had some pretty nasty weather (afternoon showers are a regular thing in Florida, but these were on the heavy side), so it was nice to have a place to have lunch inside with a wall of windows to watch the rain on the water outside. I had the crabcake and a fabulous salad. The hubby ate the catch of the day and the kids tried a burger and calamari. Yum all the way around! The kids loved the fish tank in the lobby and that helped keep them occupied while they waited for their meal. The chef, Paul Mattison, is known for combining his Mediterranean flair with a hint of Asian flavor while focusing on fresh seafood, lamb, duck and beef. There’s a sushi bar too. You can dine indoors or out with a 140-seat deck and outdoor bar featuring live music nightly (though we just hit the lunch crowd so I can’t tell you good the music is). I got the impression this is the place where groups of people who work on the island go for business over lunch.
We had dinner that night at Mr. Bones BBQ. If you’re looking for something fancy, keep looking. If you want something delicious, park the car at this place. I have to say, they served up the best ribs I have ever eaten. Ever. Really. I’m typically good after 2 or 3 ribs but in this case, I ate at least four times that much, right along with my five year old daughter who chowed down like I’ve never seen before. The food was that good. The atmosphere was even better. It’s eclectic, very funky—you even pick your drinks out of a coffin. And drink selection is tough because they have so many options. They offer more than barbecue ribs, like chicken, Indian, Mexican and vegetarian food, burgers, sandwiches, burritos and a variety of salads. But I’m telling you you’re missing out if you don’t get the ribs. ‘Nough said.
The next morning we dined at Ginny and Jane E’s at the Old IGA, or the Anna Maria Café. Roberta Schaefer, the owner, was kind enough to meet us for breakfast and even arranged for a birthday muffin for my daughter who turned 5 that particular morning. She’s a super sweet owner of very neat place. There’s a café/bakery in the back of the store and the front is packed with antiques and unique furnishings. It’s a different concept, yes, but it works in Anna Maria Island, where you just go with the flow. This place honestly offers a little bit of everything, including yummy eats. I personally tried the pecan sticky bun (Roberta said it was her grandmother’s recipe) and loved every bite. Oh, and I had the B-12 fruit drink (good thing, too, because I needed the extra energy during our fun events later in the day!). Then I spent a bit checking out all the cool stuff stocked up front.
For lunch, we had the most beautiful view combined with some incredible food at The Beachhouse Restaurant. Their tag line is “Great food, great beach, great fun”. They are right. Just thinking about the meal gets me drooling again. The Beachhouse is located at Bradenton, the other end of the island from where we were staying. The food was amazing. It was pretty–served with small orchids on the plate—but the meal was also delicious. My son ordered the crab sandwich and the meat really looked like a crab, right there between the bun. I have to say that was the most impressive crab sandwich I have ever seen. And the food wasn’t the only thing that was impressive. The view is unbeatable. They actually hold hundreds of weddings here each year (yes, HUNDREDS) because it’s the combination of everything ideal for a really unforgettable evening. They’ve been recognized repeatedly by The Knot magazine as a top spot to host a wedding ceremony. And the staff is superior, too. The waiter went above and beyond to make this family of six more than satisfied and picked up on the birthday celebration, treating us to a massive brownie and ice cream sundae. My only complaint about the entire experience would be the insects that just don’t want to leave you alone when you’re at the beach this time of year. Consider it the price for paradise I guess, but also pack some repellant.
Dinner was set for The Waterfront Restaurant in Anna Maria overlooking the Bay. I’m a sucker for old buildings with interesting history behind them and The Waterfront has a great story. It was one of the first homes built on Anna Maria Island, back in 1922. The main room of the cottage had walls paneled with wood that came from the inside of an old ship and a fireplace made of stone and brick (the fireplace still stands but the majority of the original home was destroyed in a fire in 2004). It served as an art gallery, ice cream parlor and restaurant before being turned into The Waterfront. The food was divine (I picked the crab cakes—my favorite meal when dining out on the coast) and my husband tried the Bahi Rib-Eye, the signature steak. It was all wonderful but we were pretty exhausted at this point and the good food made us want to get right back to the house for sleep.


Paddleboarding is a new sport (technically it’s an old one that’s made its way back around) that’s making waves around the country these days and my family was eager to get a lesson on how to master this special sport. Native Rentals owner, Shawn Duytschaver (who just so happens to be an Anna Maria Island native) was a patient teacher as we hit the bay for our first experience with paddleboarding. Shawn has owned the shop for 15 years and handles everything paddle, bike or board on the island from rentals to lessons and tours (including eco-tours!). He’s not the only game in town but he’s the one I’d recommend based on our adventure. He explained quickly how to jump up on the board and then stay up, then make your way across the water getting incredible views of what lays beneath. Within minutes all the kids were on boards, including my husband and five yr old sitting at his feet). He made us masters (ok, that’s a bit of an exaggeration but you get my drift) in just an hour on the water. I honestly want to go buy my own board now so I can go paddleboarding all the time…sort of a problem since I’m landlocked. It was that fun! 941-779-2453, Shawn’s cell 941-527-6355
We also took a nice little bike ride on the island. We went by to pick out a cool set of wheels and ended up pedaling off with a family vehicle— something that only two people pedal but six people can sit on (if some of those six are little!). I felt a little like Fred Flintstone with my feet moving under the cart, but it was a great way to burn off some of the calories we collected from our incredible meals. It’s also something the children wouldn’t experience back home and I like it when they can try new things. It makes the trips more memorable in my opinion. And my kiddos are going to remember for a very long time how hard it was to stop that cart on wheels when we got to the stop sign, and how dangerous it would be if we had any real traffic on the roads around us. Lucky for us Anna Maria is not that kind of island. Bikes are perfectly acceptable on the roads and life just runs at a slower pace. It’s a nice change from my reality.
The highlight of the trip for my girls was the horse surfing adventure with Great World Nature Tours.  Both girls love horses and jump on any opportunity to ride. Both girls also love the water, so this was the perfect combination of thrill for them. ‘What is horse surfing,’ you say? Well, it’s really horseback riding in the water, except at one point, if you have the nerve, you can actually stand up on the horse’ back and surf. The entire excursion is more involved than that, but that’s the highlight (at least in my opinion). You start with a ride down the shore, sending tiny little crabs scurrying as the horses stomp by. Then you go for a stroll into the water, eventually up to the horse’s sides. If you’re feeling confident enough you will be able to stand up to try to surf. It’s no big deal if you fall since you hit the water. There are times during the excursions when the horses will swim and you can jump off and hold on by their tail, almost being whipped around in the water. And when they’ve had enough, you’ll race back to shore. I asked about the horses and whether this hurt them at all and was told the horses they use are retired from polo and the water actually helped them. I didn’t ask for any scientific evidence to back it up, but I knew some of you would want to know, so I figured I should share. This is the excursion my five year old talks about most and wishes she could do again. Some day she will, I have no doubt.

Website: Anna Maria Island & Longboat Key

Anna Maria Island TwitterAnna Maria Island & Longboat Key Twitter

Anna Maria Island on FacebookAnna Maria Island (Florida Gulf Island’s) Facebook

Disclosure: This post may contain affiliate links and I may earn a commission when you buy something. If you'd like to know more about the links featured in my posts, how I do and choose reviews, or choose advertisers, check out The Mommy Insider editorial policy.

Previous post:

Next post: