10 Must-Do’s in Anna Maria Island, Florida (plus HUGE giveaway!)

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Things to Do in Anna Maria Island, Florida

It’s been a bit quiet around here lately for many reasons, one of which is that I’ve been traveling a bit– including scouting out the best things to see and do in Anna Maria Island, Florida. However, ahhhh I’m so excited for this, I want YOU to be able to experience it too! So several of my blogging friends and Anna Maria Island Home Rentals are GIVING AWAY an Anna Maria Island getaway! And you won’t even have to share a bunk bed with me, it’s all yours to enjoy! Read on…

Win a dream vacation

This was my first trip to Anna Maria Island, and I had no idea what to expect. I must say, I was blown away by how much I loved this island from the get-go. It’s small but super friendly, and the beaches are spectacular. Plus the house… THE HOUSE…

Beautiful vacation home

It was beautifully decorated. Which was a big deal for us home bloggers!

Gorgeous interior decoration

Beautiful beach decor

Beach decor

Beautiful Florida vacation home

Vacation home

Guest room decor

Florida beach home

I loved the little details the owners incorporated into the home’s style like these oar railings.

Stunning oar railings

Hmmm… where does this ladder lead?

Fun ladder on the wall


Florida vacation home

The owners also rent out the neighboring home (and another on the island, too). We took a peek of the pool area before the renters arrived. Also spectacular.

Things to Do in Anna Maria Island, Florida

I went with 5 other blogging friends, and it was the perfect mix of people. Totally relaxing and fun. I shared a room with the lovely Roeshel from DIY Showoff and was hoping she’d spill her styling secrets in her sleep. Diane from In My Own Style was my flight-mate, we must have talked from the moment we took off until the moment we landed. Okay, longer than that actually. 😉

Here’s my favorite things to see and do in Anna Maria Island Florida, in no particular order:

1. Lounge by the pool. Drink Malibu with OJ and pineapple juice, preferably made by Karah from The Space Between. Swim and drift and chat and confess deep secrets. Bonus points if you can convince Kelly from Eclectically Vintage to push your float around the pool.

Lounge by the pool

Relax poolside
Re-enactment of how you can snuggle poolside if you so wish. Karah has issues with personal space.

These Shadepops came in handy poolside:

Poolside Shadepop

2. Eat out at the local places, in particular at Eat Here. The wait staff was hilarious and very patient with us, our waiter Matt even busted out a freestyle rap for us to enjoy. The food was fresh and delish, we had an amazing dinner out with many (MANY!) laughs.

Delicious food

3. Sing karaoke with the locals at Drift In. Okay, I don’t sing but Beth from Unskinny Boppy sure does. Stand by your man, Beth!

Sing karaoke

Karaoke bars are fun
I got so wild at the bar I EVEN TOOK MY CARDIGAN OFF.

Karaoke bar

From here on out, mark my words– every time I travel I’m going to ask the locals I meet about the best dive bar around. Then I will go there, and hopefully have as much fun as I did at the Drift In!

4. Rent a golf cart and pray for your life while you drive to dinner. This was a HOOT. And also? I WANT A GOLF CART. Can you imagine if I went through preschool car line in a golf cart?! I’d be all like, “that’s how we roll, people!!

Girls trip to FL

5. Bike to the beach. Hop off and grab coffee on the way there. RELAX.

Bike to the beach

Anna Maria Island, Florida

6. Take a kayak tour of the mangroves. I’m pretty comfortable in a kayak, but having a tour guide assure you there’s no alligators where you’re going is priceless.

Take a kayak tour


(thanks, Fun & More Rentals, for the rentals of the golf cart, bikes, and kayak tour too!)

7. Take a drive. Ford provided the wheels for the drive from the Tampa airport (about 1 hour and 15 minutes) and for use while there. It was handy to have a car for trips to the grocery store and such.

Rent a car to get around

8. Walk out on the pier. You might spot a manatee and most certainly a pelican!

Anna Maria City Pier


9. Eat breakfast on the canal (Sirenia cove has a beautiful dock next to a deep water canal, so lovely). Watch out for cranes spying on you.

Birds in Florida

10. Stroll or relax on the beach. This is the first time in 6 years that I’ve been on a beach sans kiddos. I read a book for an hour just to say I did it, since it’ll probably be 15 more years until I can do that again!

Beach toes

Florida beach

We did a ‘favorite things’ exchange too. We each brought 5 low-cost gifts to give the others. It was like Christmas to give and receive such sweet sentiments! I gave the girls personalized notepads from Pear Tree Greetings:

Anna Maria Island, Florida

Here’s the notepads, with blog names used to protect the (not-so) innocent.

Drumroll please… AND NOW… it’s your turn!!! We’re giving away a stay on Anna Maria Island so you can experience it for yourself. Here’s what you could win, it’s BANANAS y’all!!

Prize Package includes:
• 4 Night stay at Sirenia Cove on Anna Maria Island
• 1 ~ $60.00 Gift Certificate to Eat Here Restaurant Group
• 1 ~ Free Golf Cart Rental for 4 Days from Fun and More Rentals
• Free Beach Bike Rental for 4 Days from Fun and More Rentals
• 2 ~ Paddleboard or Kayak Rentals for 4 Days from Fun and More Rentals
• Free use of Beach Chairs for 4 Days from Sirenia Cove
• 1 – Portrait by the Sea value of $100.00 from Photography by Billi
* Photos to be purchased based on selection from proofs
• 2 Free Shadepops


Enter using the Rafflecopter below:

a Rafflecopter giveaway

I absolutely loved both Anna Maria Island and Sirenia Cove. It’s the perfect spot for families too! Who would you take along on this dream trip to AMI if you won? Tell me all about it below, and GOOD LUCK to all who enter!

Girl time in Florida
Heading to dinner with Karah, Kelly, & Roeshel

HUGE thanks to Anna Maria Island Home Rentals, Ford Motors, Eat Here AMI, and Fun & More Rentals for the wonderful vacation! This post was not compensated however I did receive the previously mentioned services in exchange for writing about the experience.

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  1. OH my gosh!! Those karaoke pictures are making me LOL! I hadn’t seen the eyes-closed one. LOL!! I loved, loved, LOVED our night out at the Drift In. It was such a blast! Excellent post, Carrie! I wanna go back today!

  2. I’d love to say the first thing I’d do is run straight to the beach, but to be completely honest – I’ll probably check out the room first and unpack a bit. Then straight to the beach and kick of my flip flops!

  3. As soon as we unloaded the car, I’d grab the kids and head to the beach. I really need a family beach get-away!

  4. I love Anna Maria Island! We usually stay on Lido Beach when visiting that area, but always drive to Anna Maria Island to enjoy the beauty there. First thing I’d do is head to the beach!

  5. I will order some delicious cocktails to put under my shadepop drink umbrella 🙂

  6. This would be a dream come true! I would absolutely love to go with my man and just get away for a few days. We work so hard and don’t get to get away …ever!

  7. Run to the beach and sink my toes in the sand! Thanks for a great give away!

  8. wow, how gorgeous! i live in jacksonville, fl and have never heard of this city!! i’d bring my husband and kids so the first thing they would want to do is check out the water!!!

  9. I’d love to try paddleboarding, but that whole reading a book on the beach without the kids- that would be amazing!

  10. Looks beautiful and amazing! What a great spot to spend time with friends and make wonderful memories

  11. Pretty sure I’d have to lounge by the pool first and then do all the other fun things on your list! Sounds like it was a wonderful trip and great place to visit!

  12. Toes in the sand…that would be my first thing to do. I love Anna Maria Island!

  13. I Love Anna Maria Island….it is such a great place! I would head right to the beach!

  14. I would definitely take a dip in that pool and then head for the beach!!! Love Anna Maria Island!

  15. I had never heard about Anna Maria Island until this article. It looks amazing!! I love the house, and the beautiful beach. I would love to win this giveaway.

  16. Thanks for all the great details! I’m adding Anna Maria Island to our “must visit” list!

  17. I would cry of joy that I won such an amazing trip, then I would jump into the pool with all my clothes on.

  18. If i won, honestly I would break down in tears just because my family and I need a vacation! After that I would probably call and rub it in my sisters face lol just kidding but she always wins stuff and I don’t.

    1. The first thing I would do is explore the house and then relax in the hammock!!!

  19. I cannot even imagine winning. I would hold my children, and enjoy every second with them. My husband and I would just never get over something so nice. We have had a hard year….both losing parents…and I would love to have a nice break with our little sweethearts! Good luck everyone…your stories made me cry!


  20. I would love to win this. Although others would probably take other adults, i would take my children. This is a vacation we probably otherwise wouldn’t get to take . Who else better to enjoy it with then my children. What memories this would make!!

  21. Dear Anna Maria Beach Lovers………The first thing I would do when I got to Anna Maria Island is throw my luggage down and run around the beach house and admire every little nook and decoration! Then I would shriek in sheer delight and grab my husband and son and have them admire it all again with me. We would jump and hug and take pictures and hug more. We would make plans while changing into our swimsuits and running for the ocean. We would be so happy we would jump the waves and scream in sheer delight! This would be the best prize ever.
    xoxo – Marsha Young and Family

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  23. If I won this trip, I would run out to the beach right after settling in, just to get my toes wet! Heaven!

  24. These pics look so inviting, I would kick my shoes off and put my toes in the sand with a stroll along the beach. This vacation home is beautiful! I love the decor and the attention to detail, kudos to the owners of that property!

  25. First thing I’d do is dip my toes in the water! What a beautiful vacation spot!

  26. If I won, I’d kick off my shoes and go to the beach and never leave! 🙂

  27. Oh my gosh, what beautiful pictures!! I’m so happy you got to experience this! The first thing I would do is probably take pictures as well!

  28. Thank you for the shout out! We are glad you had an amazing time. Hope to see you next year 🙂

  29. Carrie,
    I LOVED your blog post about Anna Maria. My family is going there in a couple of weeks. I cannot wait to get out of the cold weather and into the beautiful sun. You had so many great ideas about things to do! I definitely want to try Eat There, it seems super yummy. We actually looked into the kayak tour! It seems kind of scary to do it without the guide because of all the alligators. We are staying on the north side of the island, its only a few steps away from the beach. The house you stayed at is stunning, it must have been so hard to leave! Thank you so much for all of these helpful tips on things to do!

    1. Have a wonderful time! It’s been a few years since I visited, but I hope to go back again soon and bring the family. The kayak tour was so fun and the entire community was really welcoming. 🙂

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