Anna Maria Island, FL

Hi all! So excited to tell you all about this trip! For Thanksgiving my family and I went to Anna Maria Island, FL. John and I headed on a 17 hour road trip to bring the pups….YES….we drove 17 hours just to bring the pups with us. It was exhausting.

I know Thanksgiving, November 2019, was SO long ago but what better time than now to post this and relive all the beautiful moments we had before the devastating COVID struck our world! I hope everyone finds enjoyment out of this post during such a crazy time.

Just as an FYI this post probably has the most photos I have ever posted. I feel like I just took SO many more than usual and I hate picking and choosing when sharing, so I chose them all! It was our first family vacation (my mom, dad, brother, and now John) in years so I felt it was extremely important to document it.

John drove through the night and I mostly slept. A road trip that long can be dreadful but there were actually a couple of fun stops we could make along the way.

One of the most popular and well known places, for my family at least, is called “South of the Border.”

This famous roadside attraction has been around since I was a kid. Surprisingly there is actually A LOT to do here. You can do the Sombrero Tower which is basically a glass elevator that goes 200 feet high. There’s a Reptile Lagoon, miniature golf, bumper cars, a restaurant, gift stores, hotel, and more. I personally have never spent that much time to do any of these activities but hey maybe one day.

Finally we arrived, half alive, but excited to start our vacation for the week! We had a beautiful house right across the street from the beach. It made for the most stunning sunset views. We rented this house through Vrbo.

This was such a wonderful home to stay at. It had 2 bathrooms and three bedrooms. The room we stayed in had a balcony and California king bed. The pool in the backyard was secluded from the other homes and fenced in which was perfect for the dogs to run around and play. We had a grill and bikes we could use as well. This island was HUGE on bike riding.

The dogs loved the pool! Had to share these cute photos.

The first thing we did when arriving to the house was head out for some food! Anna Maria was great when it came to outside dog friendly restaurants. About a ten minute walk from our house they had a cute beach strip mall and the restaurant we went to was called “Poppos Taqueria.” If you know me I’m a sucker for Mexican food so this was right up my alley.

This was definitely an island version of Chipotle.

We sat outside and had a great time with my family and the dogs. Definitely can be either a small or big lunch depending on what you order.

This restaurant also had the cutest furniture, such as this swinging chair. The other shops around this restaurant were clothing stores and a fun donut shop! This donut shop was called, “The Donut Experiment.” Basically here you get a card with a bunch of options to create your own donut. Each donut is freshly made and you choose which icing you want on the donut, which glaze, and any toppings.

This shop is ALWAYS packed. I think we waited at least 30 minutes for our donuts.

One of the most memorable ways to travel on this island was called the “Monkey Bus.” You call the bus number, tell them where you need to be picked up and dropped up, and they’ll arrive anywhere from 1 minute – 40 minutes out.

Inside the bus was blasting fun music, good vibes, and different sayings/ jokes all along the inside of the walls of the bus. It is definitely an entertaining time and such a great resource to use considering everyone can drink and still get a fun ride home! It was the island’s version of an uber, except rides were free and all you did was tip.

The first night on Anna Maria Island, we took the Monkey bus over to the “The Waterfront Restaurant.” This is definitely more on the expensive side but was super yummy.

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I highly recommend the “Queso Cheese Drip” for an appetizer. It was delightful! This was a great way to end our first day.

Sunday, day 2, was a chill day. Hanging by the pool and beach, snacking on chips and dip with cocktails. The beach across from our rental house was called “Bean Point” which is the most quiet of all the beaches on Anna Maria. It’s definitely one of the most prettiest as well.

In the middle of the day we decided to grab a late lunch at a Brewery called “Motorworks Brewing.” This was a fantastic brewery with outdoor games, beautiful decor, and a great social environment. It is also Dog Friendly for all you dog lovers out there!

They do not make any food, however they do have a food truck off property you can order from. They also have more than just beer so don’t fret non beer drinkers (like myself). I ordered a cocktail and it was delicious!

Monday we stopped relaxing and got up to explore the area and do a bunch of activities, such as explore the towns off Anna Maria! One town we decided to head over to was called Bradenton. Bradenton is only 20 minutes from Anna Marie. Here we walked on a nature preserve called “Robinson Preserve.”

This was a great place to walk around and explore. There was a lot of wildlife including jumping fish in the water! I highly recommend this for a nice morning walk. If you happen to be a photographer you could get some great shots!

After a morning of exploring we went and grabbed lunch at a place called “Island Time Bar and Grill.” This was a great place to grab a quick snack. Buyer beware, I ordered the drink called the “Painkiller” because it had coconut rum and pineapple puree but this drink is only for the strong. Be smarter than I was, lol. That drink was STRONG.

Close to this restaurant joint was our Dolphin Tour. I am HUGE on dolphin tours and try to go on one every chance I get because I may be slightly obsessed. The sad part is I can’t seem to remember the exact tour we went on since there are so many but I bet any would be feasible. The tour we went on was definitely one of the better ones I have tried. We got SO close to the dolphins you could touch them (which we of course did not).

Below are AMAZING shots I got on my camera.

Bradenton also had miniature golf and local stores to hop in and out of. It was a street of stores, restaurants, and miniature golf. The street wasn’t large but it was worth walking around and checking out. The miniature golf attraction was called “Fish Hole Miniature Golf.”

For dinner, Anna Marie Island has a lot of places to eat. One place we were told to try was “The Ugly Grouper.” This was probably the best place we ate the whole trip because of the atmosphere alone. It was all outdoors with games. The games consisted of cornhole, ring toss, jenga, and more! They also have live music at night which I always find appealing. Lastly, for all you dog lovers out there, yes you can bring your pooch!

The food wasn’t bad either! My fiance John raved about the wings saying they were some of the best he ever had. I think they had a mango sauce on them that he enjoyed. I was rather basic and ordered flatbread which wasn’t out of this world but bread and cheese is always good to me.

The biggest tourist thing to do at this restaurant was take a picture with their very own “Ugly Grouper” statue. Here I learned the Grouper is an actual fish in our ocean. I had no idea!

Out of all the places you can eat at, the “Ugly Grouper” is our highest recommended.

Bradenton was not the only location we tipped our toes into off the island of Anna Marie. We also explored Saint Petersburg, FL for half a day to bring our dogs to the beach. Anna Marie Island surprisingly does not have many dog friendly beaches, even though they have a lot of dog friendly restaurants. In which case yes we drove an hour out of the way to spend half a day at this beach and I am so happy we did. It was Maverick’s first time in the ocean and they had a blast! Maverick also learned not to drink too much salt water as it can really upset your stomach, whoops!

For dinner that night we went to “Swordfish Grill” in Cortez, FL which is only about 30 minutes from Anna Marie Island. This was a great place for food and having seating outside.

I recommend coming to this restaurant on a Tuesday. Every Tuesday they have Crab Racing! You’re probably thinking of those big red crabs with pinchers but they were actually hermit crabs!

You pay $1.00 to be in the race and pick out a crab. Each crab has a number on their back. This is how you can tell your crab a part from the rest. Then there’s a table you place the crabs in the middle of and whichever crab walks past the finish line at the end of the table wins! I will admit we got really into it. We came in second place! So sad we didn’t come in 1st but that’s okay.

If you did come in first you won all the money that everyone paid for the crabs with. It’s a really fun lighthearted family place to go!

Wednesday was all about exploring the Island! Everyone on the Island bike rides to their destination so it was great that our rental property had so many bikes we could use. We rode all around the island and they had fun shops you could park your bike at and walk inside.

After our morning bike ride we headed over to “Manatee Beach” to grab some lunch. This beach is super busy and crowded so make sure to go in with that mindset.

As you can see the food here was your run of the mill beach food. This probably wasn’t my favorite beach due to how crowded it was but the food and bar was a plus. You can’t bring alcohol onto every beach of Anna Marie so if you want to drink definitely go here, but if you want less crowds and to relax I would stay at Bean Point which I referenced above.

I really just felt like we ate SO much on this trip, but I guess that’s typical for a vacation! The rest of the day was resting up by the pool before getting ready for yet another dinner!

For dinner that night we ate at a place called “Harry’s Grill” on Anna Marie Island. This restaurant was voted for the best bar, grill, and burger on the island. I will be honest, no where had any burger that was super spectacular, including this restaurant. I could see how on the island it was “the best” but it doesn’t necessarily mean it was an amazing burger in general.

Here is a picture of one of their burgers. It was good but to be honest nothing to write home about. If you are however craving a burger and staying on the Island this would be the best place to go.

Here are their onion rings that were on “HGTV.” Again, personally nothing special about them to me but hey you may think otherwise.

For dessert that night we went to an icecream shop on our way back to the rental home called “Two Scoops.” I highly recommend the “blueberry pie” flavor. It was AMAZING. Actual pie chunks in the ice cream. Yum!

The next day was Thursday, which was Thanksgiving! We did not, by any means, have a typical Thanksgiving on our Florida vacation. John and I wanted to explore more of Florida before our 17 hour car ride home in the morning and my parents wanted a pool day. With that being said, John and I were off for a fun adventure about an hour away!

For breakfast we went to “Ginny’s & Jane E’s Cafe and Gift Store.” This was a cute place that had great food!

My favorite part about this meal was the yummy apple sticky bun!

We drove to “Myakka River State Park“, home to the alligators! There was SO much to do. You can go boating, camping, boat tours, fishing, horseback riding, hiking, etc. We decided to take a boat tour on the “Myakka River Queen.” You did have to pay for this boat tour but in my opinion it was worth it. On this boat tour you’re in the middle of a lake with hundreds of alligators swimming past you. It really was kind of scary and surreal all at once.

They even brought the boat closer to land so you could see them sunbathing on the dirt.

Additionally, there was a bridge you could walk across which was pretty cool. The bridge led to a tall tower with a beautiful overlook.

Overall this was a fantastic family vacation. There was SO much to do and it was very relaxing. It is such a crazy time right now during this pandemic and writing about our experience here makes me wish our world was normal again.

Anna Marie Island, FL is a beautiful escape I highly recommend once the craziness of this world goes away.

Anna Marie also had so many beautiful sunsets.

Let’s end this post with one last beautiful sunset photo of my little family. Thank you for reading and keep dreaming with me that life will soon get back to normal so we can continue to share our travels with you! Stay safe everyone!