This August marked my third trip to Anna Maria Island, Florida, and I wanted to shed a little bit of light on this unique, laid-back beach community. Upon returning from my vacation, I told a friend that I had just returned from Florida and his exact words were, “What, did you lose a bet?” I just laughed it off, and once he saw my photos he recanted his statement. Florida is the only “double beach” state in the union aside from Hawaii (which is pretty much all beach), but Florida is unique in the sense that it offers both Atlantic and Gulf beaches. The water is warm on both sides, but the Panhandle and Gulf Coast beaches offer soft white sand and beautiful teal waters. A few people asked if the pictures I posted of the beaches were from the Bahamas–nope! Just humble Florida.
While the beaches are beautiful all around Sarasota (in fact, Siesta Key near Sarasota was named one of America’s best beaches), we stayed 40 minutes north of Sarasota in a beachy community called Anna Maria Island. The island is actually a strip of land with the Gulf Coast on one side and the Anna Maria Sound on the other side. The Sound leads up into Tampa Bay.
Lodging
The quaint community is a vacationer’s dream. While there are hotels and beach bungalows for rent, most of the island is full of rental homes. This was ideal for us, since we like to stay for a week and having a house close to the beach is perfect for cooking meals in and taking breaks from the heat. This time we stayed in a beautiful three-story home with a pool that was just a short walk from the beach.
Transportation
Once you get settled into your place, there is really no need to get back in the car! We chose to rent a golf cart for the week to make quick trips to the store or to go out to dinner. You can also rent bikes and scooters. But if you don’t want to rent anything, there’s the “Monkey Bus” which predates Uber and only works for tips! Yes, it’s a tropical party bus that will come pick up your crew and take you wherever you need to go on the island. The town also has a free shuttle that runs until 10pm.
Eats
Unfortunately, a lot of restaurants on Anna Maria Island have what I like to call the “beach tax,” meaning you will pay a premium for mediocre food since you are dining on the beach. The beautiful sunsets and ocean views do make up for the so-so food, but a few places that do have epic food are:
The Waterfront: The Waterfront is on the Sound side of the island towards the top tip. They are known for their shrimp and grits. It’s super tasty but also super rich, so consider splitting the entrée to save room for key lime pie.
The Bridge Street Bistro: The Bridge Street Bistro is on the opposite end of the island from the Waterfront, and while you are not on the sand, the restaurant has an epic view of the ocean since it’s upstairs. We had the coconut shrimp and lobster dogs as appetizers. Both are amazing, but the lobster dogs are a must!
Skinny’s Place: While Skinny’s Place is fairly basic (think hamburger and onion rings type of menu), the vibe is great! It’s a little shack with a beer bar. They will serve you up an icy cold beer mug to go with your draft beer. The burger wait time is written on a chalkboard as “half a beer.” We always enjoy going by Skinny’s for an easy, no-frills lunch!
Cupcake Delight: If you want a sweet treat for your stay, swing by Cupcake Delight! We got some cupcakes to celebrate my mom’s birthday during our vacation and the lemon brulée and key lime were house favorites! It’s a quaint, family-run operation with fresh cupcakes made daily. They do close for the day once they’ve sold out, so get there earlier in the day to have the best selection.
Fishing
If you are like us and enjoy getting out on the water, I suggest booking a fishing charter. I first tried googling fishing charters and could only find overpriced charters leaving out of Tampa, but then I stumbled upon Fish Booker. It’s almost like the Airbnb of fishing charters–you put in your location and how many people you are, and it pairs you up with folks who run fishing charters. We went out with a guy named “Captain Rooster” who has been fishing in the area for 25 years. He knew exactly where to go and the charter included rods, licenses, and bait. It was a nice way to break up the beachgoing!
To conclude
All in all, if you are looking for a laid-back beach vacation, Anna Maria Island checks all the boxes! I will be honest, if you are the crazy adventure-seeking type or get bored lying around on a beach or by the pool, you might want to only stay for a few days. But if you love reading a good book with your toes in the water and butt in sand, go for a week and really unwind!
Looking for another epic vacation? Check out our two week run down on Bali!
