Our Family’s Guide to Anna Maria Island, Florida

This past summer was the 2nd time we visited Anna Maria Island, Florida, and I have to say is that this place is SO INCREDIBLE!  We’ve already booked a house for next year, this island is so fantastic!  I got a ton of questions about our trip, so I wanted to answer some of the questions I received and share our family’s favorite spots on the island.

What’s so great about Anna Maria Island?

There are so many things that make this place great, here are a few of my favorite reasons!

  • First, it’s really easy to get to, which is a huge plus for me.  It’s about an hour away from the Tampa airport, so traveling here is so convenient.  We can fly direct from Indianapolis, so basically a few hours after we leave Indy we can be on the island.
  • It’s such a quaint island!  Instead of high rises and crowds, you will find tons of quiet tropical vacation homes for rent.  The downtown shopping area is adorable and perfect for strolling.  They also have a free trolley that will take you around the island!
  • The sand is like powdered sugar and the waters are turquoise – you just might think you are on an island in the Caribbean ;)
  • The entire vibe of the island is friendly and laid-back.
  • Whether you want to hang out at the beach or your pool, go shopping, enjoy yummy treats, or do fun activities (check out the ‘scootcoupes’ or even book a charter), there are activities for everyone!


Where did you stay?

The first year we went, we booked a house through VRBO and really enjoyed it.  We went with my parents and my sister’s family, so there were 10 of us total.  The first house was great, but we were looking for something a little closer to the beach when we went this past summer. We found another house through Anna Maria Vacations that worked out great!!  Here is the link to the actual house we stayed in. (I would have taken better pictures had I known I was going to put them on my blog, ha!!)

Anna Maria Rental House


Anna Maria Rental House


Anna Maria Rental House


Sunset Paradise Anna Maria Island House

It was newly remodeled, has a great pool and outdoor patio, and it has several outdoor porches and balconies.  I think the day we were leaving, we found another balcony we didn’t know about the whole week!  The BEST part about this house is its location… literally footsteps from the beach, and we could walk to the quaint shops and restaurants on Pine Avenue, one of the main shopping areas in town!

Beach parking is tricky because although the beaches are public, there aren’t really parking lots unless you go to one of the big, main beaches!  We preferred the quiet, off-the-beaten path beaches.  So staying literally footsteps away from the beach so we could walk instead of having to pack up the car and find a side street to park on was awesome.

What did you do?

Ahh!  So much!


As I mentioned, the beaches are fabulous.  The sand is soft, the water is turquoise, and they are very clean.  If you go to one of the main, public beaches, they will have facilities (bathrooms, showers, etc.).  The ‘off the beaten path’ beaches do not have facilities, but in my opinion are so beautiful and quiet, it’s worth going!  One tip… rent a tent!  The sun gets hot and there is no shade.  Having a tent makes it so much nicer to enjoy.

Anna Maria Island Beaches


We rented a ‘scootercoupe‘ and it was AWESOME!  We rented it for the day and took turns driving it around with the kids.  This is basically a low-to-the-ground scooter that 2 people can ride in, and it’s SO FUN. Tip – bring a towel to sit on if it’s been sitting in the sun or you will burn your buns!!

Scootercoupe Anna Maria Island

If your house doesn’t have bikes (several have them included) and you are in a residential area, renting bikes and biking around is so enjoyable to get to see all the houses and get to know the area.

If you are into fishing or water sports, there is plenty of that, too!  My sister and her family took a dolphin-watching trip, and the dolphins were following their boat, jumping in the wake!  Her kids loved it.

You can also rent golf carts as a fun way to get around!  You obviously wouldn’t take these from one side of the island to the other, but depending on where you are staying and what you want to do while you’re there, you could use your golf cart to get around during the week!


Ahhh!  They have some of the cutest shops here!  As I mentioned, we were right by Pine Avenue (our house was actually ON Pine Avenue) which is this cute strip of quaint, fun shops.  As much as I don’t like to shop in real life, I love strolling through these adorable shops on vacation!  Because it was our 2nd time back, we knew we wanted to hit up our favorites.

One shop we could not WAIT to go back into was the Shiny Fish Emporium! I don’t know how to explain this place other than a whimsical gift store that makes you happy!  She has the most unique gifts, and if you’re there you MUST check it out!

Shiny Fish Emporium


And how awesome is this… they carry Young Living!!!  I knew I loved this place. ❤Shiny Fish Emporium


Shiny Fish Emporium


One of the things they are known for is that you can paint your own sand dollar here!Shiny Fish Emporium


This is a pic of our kids the first time we visited, painting their sand dollars.Shiny Fish Emporium


I’m also sucker for the olive oil/balsamic vinegar shops, and that’s exactly what the Olive Oil Outpost is!  They usually have something tasty out to try (like gourmet cheese and crackers!), and of course you can try their olive oils and balsamics.  Stop inside if you are nearby.  :)

Olive Oil Outpost


This Jalepeno Lime balsamic is AWESOME.  I bought it the first time we visited, and then bought more when we went back this past summer!  It is SO good on wateremelon!!!  And also on arugula or vegetable salads!Olive Oil Outpost

One of the new places we found this summer was Pineapple Junktion – a fun, funky group of little independent shops set up all in one place with lots of treasures!  My favorite thing I found was my diffuser bracelet from The Babe Cave Studio!

Babe Cave Studio Bracelet

There are so many fun places to shop and look for trinkets to bring home, we realized there is another whole side of the island to explore next time we go!  But the shops on Pine Avenue are definitely a hit.


In terms of dinner, there are lots of restaurants around the island, as with anything it’s helpful to read reviews :)  Because there were 10 of us and we stayed in a house, we cooked in about half the time and went out to dinner the few other nights.  There are lots of casual restaurants and of course some nicer ones if you want something fancier.  As for nicer restaurants, we enjoyed The Waterfront Restaurant.

Another gem we stumbled upon last time was Mr. Bones BBQ – this is a super funky restaurant with an extremely diverse menu, but everything everyone got was delicious!!  Heads up, this place is more expensive than you think it would be from the looks of it, but we’ll likely be back it was so good.

One of the quicker, more casual restaurants we enjoyed was Popo’s Taqueria for fresh Mexican food.  This one is right on Pine Avenue.


There are SO many places for treats, ha!!!  Pretty much everywhere you turn, you will find an ice cream or treat spot… they’re all good, we don’t discriminate. ;) Basically you can try a new place every night.  The picture below is one is from Dips Ice Cream.

Dips Ice Cream

New to us this year was The Waffle Press.

The Waffle Press

Order your hot waffles topped with a variety of decadent toppings – oh my goodness.  I’m a plain type of waffle girl, but pretty much everyone else got some extravagant toppings on theirs.

The Waffle Press


And you will hear people talking about The Donut Experiment for sure!

The Donut Experiment

There will likely be a line in this little shop, but if you like donuts, this will be worth it.  You get to choose which toppings you want on your hot donut, options range from Reese’s to sea salt to bacon!

The Donut Experiment



The Rod and Reel Pier seems to be a must-see spot, because it was in all the literature we came across!

Rod and Reel Pier

You can rent fishing poles here and fish off the pier, but as a non-fisherman, one of the best things about this spot is watching the pelicans! We sat out here for about an hour and a half the first time we were there and just watched the pelicans fish, they were an arms-length away and it was amazing to watch them dive and do their thing!  I’d say go in the morning before it gets too hot to enjoy, we did go once when the pelicans weren’t there which was kind of a bummer.  But these guys are SO entertaining to watch, and if you like to fish, you can do that, too.  If you’re staying close enough, you can ride your bike here in the morning to check things out. :)

Rod and Reel Pier


The end of the day sunsets are spectacular, be sure not to miss them!  You will find that on some of the beaches, people start coming out in droves to watch the sunset and to take pictures.  We saw some truly breathtaking skies!

Anna Maria Island Sunset


Anna Maria Island Sunset


Anna Maria Island Sunset


Anna Maria Island Sunset

One of my most favorite things to do is to walk out at night to the beach at Bean Point, after dark.  It is so surreal and breathtaking.  Bring a flashlight because it gets pretty dark, but it is one of my favorite experiences!

Well that’s a wrap!  I just love Anna Maria Island and can’t wait to go back next summer.  If you’ve been there, share in the comments other places we should be sure not to miss next time!

Anna Maria Island

Our Family’s Guide to Anna Maria Island, Florida