Fun in the Sun at Anna Maria Island, Florida

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Anna Maria Island is known for its beautiful beach coastline along Florida’s Gulf coast.

stone crab and oysters
Anna Maria Island, Florida

A girl’s weekend is good for the soul. Sometimes there is nothing better than surrounding yourself with longtime friends, laughter, good food and of course, the beach! And Anna Maria Island is an ideal place to get away from it all. It’s a piece of paradise where you can enjoy hanging out in your flip flops, dining out on local seafood, seeing the perfect Florida sunset over the Gulf of Mexico and to watch the dolphins play. It’s been a while since I’ve written a travel post about Florida, so I thought I would share some highlights of out weekend.

Anna Maria Island sunsetgirls trip anna maria island

Anna Maria Island Restaurants

As most of you know, I am all about the food and getting new inspiration! Thank you to all of you who commented and gave me ideas on where to go, I could have stayed a whole month and still not gotten to all your recommendations!!! We definitely found some gems—on Saturday we went to the Sand Bar for lunch—-what an awesome place!!! Right on the beach (which was beautiful), great service and stone crab appetizers that were fabulous!! Do plan to wait for a table if it is a weekend- but grab a drink and watch the waves- you will not be disappointed!

Another favorite was The Chateau, which we went to for dinner one night, and is located at the Waterline Villas and Marina. The ambient was great, our food here was very good too, with a mussel’s appetizer and mushroom ravioli entrée being one of our favorites.

Do not let the appearance of The Ugly Grouper fool you—this was by far one of our BEST finds!! Fun atmosphere, great service, and some of the best fish tacos ever!!!! If you are in the area you should really check them out- we ordered the Island Grouper Kabobs, Avocado Caprese salad and Grouper tacos with the cheese fan shells- these shells make the meal as does their mango sauce! Everything we ordered was delicious!!

ugly grouper capreseugly grouper fish tacosthe chateauthe chateau ravioli

How to get there

Flying in from New York and Tennessee, we met up with our Florida friends on beautiful Anna Maria Island.  The closest airports to fly in for your Anna Maria Island stay are Tampa International Airport (TPA) and Sarasota-Bradenton International Airport (SRQ). Once we landed, we drove to the island which is accessible by car. While we did not use it since we had our own vehicle, there is also a free trolley on the island to make travel (and parking) easier. The closest major city is Sarasota, which you can reach in about 40 minutes by car.

Where we stayed

Anna Maria Island is quaint, with lots of cute hotels and rentals along the island. You won’t find high rise condos and fast food restaurants in this quaint town. We rented an Airbnb right across the street from the beach which was close to all.

What to do in Anna Maria Island

In between eating we were able to check out different beaches, the Anna Maria City Pier (where you can see manatee and dolphins) and check out some cute shops. We were lucky and had beautiful weather, sunset on the beach was of course mandatory and did not disappoint!

I highly recommend the sunset cruise we booked it through Anna Maria Island Dolphin Tours, it was reasonable priced, pontoon boat (no bad seats!) and we had great captain- Tristan! Even though this was a sunset cruise we still saw quite a few dolphins. The history lesson on the area dolphins, music, and boat-wide sing a longs made this cruise a highlight of our trip.

We ended our weekend with a mimosa and breakfast at The Sage Biscuit on Cortez Road. Good food, big menu, and options for gluten free which was nice since one of us has a gluten allergy.

So, while our trip was too short (always is!), it was a wonderful weekend in a beautiful area! I am always grateful for time spent with my family and friends, making new memories, and enjoying every second together. If the pandemic has taught me anything it is that life is short and tomorrow is not promised. Enjoy today, surround yourself with loved ones and laugh- there is nothing better! Hope to see you again Anna Maria Island- thanks for the memories!

airbnb anna maria islandanna maria island piersunset tour

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32 comments

  1. Love AMI! We used to go there in the early 90s with the kids.  There was a great restaurant called Pete Reynard’s and it had a revolving Mermaid Bar and All You Can Eat Seafood Buffet! Does anyone remember that place? You can get there by boat. Thanks for sharing your pictures! It’s still so beautiful there! 

  2. Such a wonderful place. Wearing my sweatshirt right now. We have booked 2 1/2 months next year.  I miss it so. Vinny’s is awesome Minnie’s for breakfast. Grubs barbecue. North shore cafe. Just to name a few. We also stayed on Siesta Key which was so much fun as well. Love the sunshine. We are back on our beautiful Keuka Lake. 

  3. We love Anna Maria Island and Longboat Key! your suggestions are spot on. I also liked reading other suggestions in the comments. Would you be able to share the AirBNB you stayed in? I’d also like to plan a girls get away. 

  4. I grew up going there in the 90s and early 2000’s. Actually named after the island, but haven’t been in a long time because the cost to stay is astronomically high due to it now being a very popular tourist destination and the drive from where I live. They did just add direct flights from my local airport to St. pete though

  5. How awesome! We came down here for a month and are staying for 3– looking for a new home now!! So many wonderful places on the island. I’m going to have to try your recommendations!   I just adore these beautiful beaches and sunsets. 

  6. Add Ginny and Janes to you list for best trip…best Cinnamon Rolls! Worth every calorie! 

  7. Loved learning about this super beautiful vacation spot and hope to go there too very soon. Thank you for sharing!!!

  8. Hi Gina! 
    Anna Maria Island is our favorite vacation place in FL.  We will be there next week.  We rent a place right down the beach from the Sandbar.  Looking forward to to trying some of your recommendations.  
    Best, 
    Mara

  9. LOVE AMI! Lucky enough to spend almost 2 weeks there in February and absolutely fell in love with it!🏝👙🍹☀️

  10. So glad you enjoyed your stay!! I am lucky to spend the winters here!  Wish I could have mwt you 😎

  11. I live on Longboat Key and agree with all of your comments!!! Especially, the Ugly Grouper😉 Looked like a great time. Cheers!

  12. We just booked a trip to Anna Maria Island for a few days in May (we’re staying at a hotel on the sound so it’s a bit more affordable), and I’m going to try and check out everything you mentioned here! I’m a horse rider so I really want to do a ride in the ocean as well.

  13. I visited the island 2 years ago in January. Beautiful island, loved the trolly. Parked the car and walked or used trolly to tour island. Highly recommended destination.
    Had to meet friends for dinner but appreciate your food reviews.

  14. I hope you do a Skinnytaste version of those tacos- yum! 🙂

  15. We love the Island for sure. However the cost of lodging are have skyrocketted in the last few years making unaffordable for families.
    We’re sorry but we can’t afford it anymore.

  16. 🙌🏼☀️🏖 all things Anna Maria Island 😎 simply thrilled you experienced the freedom and joy of life on the island with sweet people and places 😍
    My bestie worked at sandbar where I first visited 25 yrs ago and have been returning — not as frequently as I’d like but want so desperately to get back NOW! 
    Thank you Gina for your post and the other yummy places to try. My bestie is in the midst of fighting cancer— and doing a darn good job beating it so I’m trying to visit among many obstacles. This my friend —well, thank you ❤️❤️

  17. Thank you for posting this! My husband and I are going there Memorial weekend through the first week of June, we have never been there! I will continue to follow this for any reader recommendations as well!

  18. If you ever go back no need to swim on a horse at cponies.com The horses actually swim not walk through the water in Bradenton. Check out their website-all their horses are rescues. I did it in Palmetto where hey no longer go out from. Even experienced riders rave about this-incredible experience! And love The Sand Bar!

  19. Thank you for al the great suggestions. My husband and I will be celebrating our 30th wedding anniversary this Sept. In all those years, we’ve had ONE weekend away. No kidding. I always end up changing my mind and feel guilty about spending money on a trip and think that money could be better spent on home repair, some bill, or just saved. Oh, and my husband won’t fly so…..we will in GA so Anna Maria Island just might be feasible. 
    Thank you for sharing. 

  20. Whoo hoo Gina we are here now!

  21. Love, love, love Anna Maria. We just came back two weeks ago. This year we ventured around since we rented a car (not needed) but flew in to Tampa. We tried the Tide Tables Restaurant and Maria in Cortez for delicious fish tacos and my husband had the grouper sandwich. Fresh catch daily. Delicious and beautiful views of the inter coastal. Harry’s Bar and Grill (Anna Maria) is also a great venue on weekend nights, don’t miss Pam Ward awesome entertainer. But most of all don’t miss a single sunset, every night you will be wowed.

    • So many great places, thank you for sharing!! And agree, those sunsets were spectacular!

    • I second Tide Tables! My husband loves their fish tacos and the carrot salad (when it’s on the menu).
      Another hit is The Donut Experiment on Pine Avenue (for the occasional treat!). Custom-made, fresh, cake donuts still warm when handed to you! They are delicious!