Trip Report | Anna Maria Island

After three Summers vacationing on the sleepy little island, it’s safe to say Anna Maria has stolen our hearts. We visited the quiet little island for the first time two years ago, and fell in love with the slow pace, sugar-white sand, and clear waters. This year when we left, my heart ached a little.

I don’t know if it’s the memories we’re making there, the fun we have, the joy on my kid’s faces, Mr. SP’s relaxed posture…or all of the above, but this island has become a special part of our family. Several years ago, we moved our family vacation to the end of Summer, and it was such a great opportunity to reconnect before the crazy days of school schedules began again. The tradition stuck, and now it’s something we look forward to all Summer.

anna maria island

beach umbrella

beer can island

We rented the same little cottage in the trees, just a few yards from the beach, so we could have our toes in the sand whenever the mood struck, and quickly fell into our lazy routine of beach, sleep, eat, and repeat. Anna Maria doesn’t have miniature golf, movie theaters, or even a McDonalds…but it does have 7-miles of walkable beach (the sand never gets hot!), clear water that’s a new shade of blue and green every day, and cotton-candy sunsets that make you stop whatever you’re doing and stare.

The speed limit is 25-mph, nothing is over 2-stories tall, and dressing up for dinner means putting on a shirt. Or pants in my case (I lived in a swimsuit)! The entire island is family-friendly…including the casual restaurants, and the flat, shallow beaches.

rod and reel pier
His Tee (on sale!) | ‘Beach Bunny’ Tank | Her Flip Flops | Chambray Shorts

sunset anna maria island

We met our dear friends there again this year (they stay in their own home a few miles away), and I think it’s safe to say a new annual tradition has been born!

anna maria island

anna maria island beach anna maria island sea urchin

Her High-Neck Swimsuit (only $25!)

anna maria island pink door

anna maria island

One rainy day, we found a huge back-to-school sale online at Bloomingdales, and the kids begged me to have it shipped to the beach house….then proceeded to wear their haul the rest of the trip! It’s been years since I shopped Bloomingdales, and I was so excited to find crazy-good prices on so many name-brand pieces (including Ralph Lauren, Hurley, Converse, Splendid and Havianas). We’re talking Ralph Lauren dresses for girls under $20, and boys 2-pack of designer tees for $15! It’s a literal jackpot of kid’s clothes.

Sentimental Sidenote: Growing up, my grandmother would take me to Bloomingdales once a year to choose my back-to-school outfit. We’d drive to Dallas in her humongous Cadillac, have a fancy lunch, and she’d buy me a new head-to-toe outfit (usually Esprit!). It was always the nicest outfit in my closet, but even better, one of my favorite days all year. 

mote laboratory
Her Jumper (40% off!) | Her Flip Flops | His Flip Flops

biking on anna maria island
My One Piece Swimsuit | His Tee | Her Tee

anna maria island storm
His Tee | Her Tee

anna maria island chapel anna maria island changing station

beer can island
My One Piece Swimsuit | Similar SarongSimilar Romper

anna maria island

grouper sandwich

anna maria island
‘Mermaid’ Tee

Striped Hoodie Cover-Up

beer can island

{Where We Stayed}

You won’t find any big resorts or high-rise condos on AMI, but rather lots of rustic cottages, swanky homes, and small condos & townhouses for rent. Location is key for us, so we opt for beachfront, and this simple, little cottage fits us perfectly.
It’s located on Holmes Beach, the quietest area on the island, and close to restaurants and the one grocery store. There were a few beach items left behind by previous renters, but you can rent chairs & umbrellas from a local shop, or pick up inexpensive ones at CVS or Publix. Everything else is provided.
Travel Tip: Tampa is the closest major airport, and an easy 1-hour drive away.

anna maria island can't wait house anna maria island

{Where We Ate}
For such a small island, there are a surprising number of yummy spots. Some are a little more upscale than others, but nothing requires more than a sundress & sandals.
Little more than a road-side shack, but delicious burgers & ice-cold draft beer. Plus, you can go in nothing more than a swimsuit.
All-natural & organic taco shop with made-to-order chips. Need I say more?!
Made-to-order donuts worth waiting for, in tons of inventive flavors.
Tide Tables
Right on the marina, you can eat indoors or out…with the best fish tacos & key lime pie on the island!
Rod & Reel Pier
With only a handful of tables, it fills up fast. Watch the fishermen while you devour the grouper sandwich of your dreams.
Smoqehouse BBQ
Darn good BBQ (this coming from a Texas girl!), in a darling little spot.
This marina-side spot is about as authentic Florida as they come. But go early, because they sell out of fish tacos every. single. day.
Beach House 
Best ocean-side bar with delicious cocktails…a little piece of Miami in AMI.
One of only 11 restaurants in the U.S. to receive the top-score from Zagat. So basically it’s the Top 10 restaurant in the entire United States. It’s crazy-expensive for dinner, but a fun spot to splurge on desserts.

Travel Tip: There’s a free trolley that runs the length of the island, and many people rent bikes or golf carts to get around (the top speed limit is 25-mph, so it’s safe!). We rented a car, but you could get by without one if you stay on-island.

anna maria island pier popoos taqueria

{Favorite Anna Maria Experiences}

Rent bikes (and chairs & umbrellas!) from Beach Bums (they offer free delivery & pick-up!), and cruise the neighborhood streets of colorful houses.

Spend a morning boating and snorkeling with Captain Kathe. We saw sand dollars the size of our faces, and so many dolphin we lost count!

Tour the Mote Marine Laboratory where you get to touch stingrays and sharks, and see the reproduction of jellyfish and sea horses.

Explore Beer Can Island with the towering driftwood & secret trails. To find this spot, take the first right after the bridge from AMI to Longboat. Park at the beach access point, and walk down the beach to the right until you dead-end. From there, follow the un-marked trail through the trees until it opens up. But warning: The currents are too strong for swimming, and high-tide can make the hike a little tricky.

Park yourself on any beach as the sun is setting….it’s better than anything on Netflix!

Icy cold draft beer at Skinnys, piping hot hush puppies at Starfish, the fish tacos from Tide Tables & a raspberry drizzle donut from Donut Experience. What? Travel is all about food for me!!

anna maria island

sunset fishing on anna maria beach

anna maria island

family anna maria island
My Striped Racerback Dress | My Flip Flops | Little Miss Twist Tee

No schedules or agendas, minimal bickering and nagging, and lots of laughing and relaxing…it’s our perfect retreat! I wish I could bottle that lifestyle…or at least the feeling of peace that comes with it…and keep it with us all year long!

Did your family get away this Summer? Have you figured out how to keep that slow pace and easy-going attitude during the school year?! Check out our previous AMI trips here and here, along with my Tips for Staying Stylish at the Beach.

{Shop Our Beachy Styles}


FOOTNOTE: Our hearts continue to ache as we watch the horror in South Texas linger on, but we are not helpless! There are countless ways to help and give back…check this post for places to donate, and if you’re in the DFW area, check this post for specific ways we can help the evacuees coming here. If you’ve been impacted by this devastation, just know we’re praying for you and will keep praying and helping as long as it takes! #texasstrong



*This post is created in collaboration with Bloomingdales, but all styles, opinions and online sales-stalking are my own! Thank you for supporting Hi Sugarplum sponsors.*

Leave a Comment


  1. Your family is possibly the most photogenic family ever!

    Charmaine Ng | Architecture & Lifestyle Blog

    Posted 8.30.17 Reply
    • Cassie wrote:

      hahah!! thank you! We’re certainly hams! 😉

      Posted 8.30.17 Reply
  2. Sandy wrote:

    This place so reminds me of the Turks&Caicos Islands when it was unspoiled, before it was developed and crowded w/touristas!
    Thank you for sharing your special place, awesome photos, and fun times. So very kind. And loved the line-minimal bickering and nagging-ha,ha! The island of St. John will remedy that too! : )

    Posted 8.30.17 Reply
    • Cassie wrote:

      Oh yes, St. John is a slice of heaven, too!! Mr. SP and I went for a wedding several years ago, but would love to go back and take the kids!

      Posted 8.30.17 Reply
  3. Jana wrote:

    We love AMI too! We also have vacationed there 3 times. Its low key environment invites you to just relax. We always rent a house with a pool so the kids are happy from sun up til the beautiful evening sunsets. Riding bikes on the island is a joy too especialky with the 25mph speed limit. One of my favorite things we did this year, was rent a pontoon and go out on Tampa bay. It was fabulous! Thanks for sharing your trip.

    Posted 8.30.17 Reply
    • Cassie wrote:

      Your trip sounds blissful!! Thanks for the tip about cruising the bay!

      Posted 8.30.17 Reply
  4. Dora wrote:

    Hi, lovely vacation!!!
    In one of the pics, the one with your daughter, you are wearing 2 pieces bikini, just the top is showing. The one with stripes and flowers. Where did you get it from?

    Posted 8.30.17 Reply
  5. Looks like such a fun trip, and you got some great photos! Makes me want to pack up and take one last summer vacation! 🙂

    Posted 8.30.17 Reply
  6. Jennifer wrote:

    This looks like such a wonderful vacation spot. I’m always amazed at the blue water and white sand beaches on the west side of Florida!
    Continued prayers for all affected by the devastation in Texas.

    Posted 8.30.17 Reply
    • Cassie wrote:

      In my opinion, they’re the most gorgeous beaches in the world!! Or at least, the best I’m able to get to! 😉 Thank you for the prayers, so many of my closest friends have been impacted.

      Posted 8.30.17 Reply
  7. Heidi wrote:

    What gorgeous photos! You have me sold on AMI! This summer we road-tripped Transylvania as our vacation (before a week in England), and while it was amazing, it was more “traveling” and less “vacationing”. Plopping on that beach all week would be ideal! And I love your first day of school shopping memories with your grandma! I’d always get Esprit for my first day outfit too! Continuing to pray for the people of Texas!

    Posted 8.30.17 Reply
    • Cassie wrote:

      Oh yes, I know those trips well, too! This is a definite sit and veg trip!! Thank you for the prayers, it’s been so inspiring to see so many people eager to help and pray! xo

      Posted 8.30.17 Reply
  8. Beth Fink wrote:

    We went to Anna Maria Island this year for the first time (it caught my eye on your blog two years ago) and our whole family (including the grandparents) absolutely loved it. We went to many of the same restaurants (Beach Bistro – unbelievably amazing!!, Star fish – we got take out from there twice at my insistence!) and just had a wonderfully relaxing vacation (last week of June) – looking forward to going back again!! Thanks for the wonderful trip reports that helped us discover a new favorite vacation destination as well 🙂

    Posted 8.30.17 Reply
    • Cassie wrote:

      I’m so happy to hear that!!! It’s a magical little spot…maybe we should stop talking about it!! 😉 xoxo

      Posted 8.30.17 Reply
  9. Liz wrote:

    Just when I thought I had seen your best-ever post, you outdo yourself; it is beyond gorgeous!! I’m thinking I may have to twist my husbands arm & book a place on AMI next spring!
    I seriously cracked up at the mention of Esprit. In the hoity-toity town I grew up in, that was the ‘must have’ brand to have on the first day of school!!

    BTW, your IG story on donating items to help those in Houston was nothing short of inspiring. I’ve had to limit my watching of the news and Weather Channel because all I want to do is cry. Wishing I was closer so I could volunteer, but we sent a donation in it’s place and am encouraging anyone who crosses my path to do the same. 🙂 It’s truly inspiring in these times to see such an outpouring of kindness to others. The folks of Dallas should be proud.

    Posted 8.30.17 Reply
    • Cassie wrote:

      Haha!! Yes, the Esprit was the rage!! It was the nicest outfit I owned every year, and I wore it to death!! 😉 It’s been so inspiring to see so many people eager and anxious to help! xo

      Posted 8.30.17 Reply
  10. Kara wrote:

    This sounds so lovely. You have definitely made me want to visit!

    Posted 8.30.17 Reply
  11. Brandi wrote:

    I love AMI! The first pic, with all the colorful chairs, is that’s restaurant?

    Posted 8.30.17 Reply
    • Cassie wrote:

      I think it’s actually a rental home/event space! We stayed nearby and I loved seeing the lineup of colorful chairs on my walk!

      Posted 8.30.17 Reply
  12. Bilmo wrote:

    There is Miniature golf on Bridge Street!

    Posted 8.30.17 Reply
  13. Sharon wrote:

    It sounds like and looks like you guys had an amazing time! The sunsets photos are gorgeous. Isn’t great to have a relaxing vacation with no schedules and agenda just enjoy yourself. The beach is always so good for that. I’m actually headed to Florida in January. My parents bought a home in Venice and I’m helping my mom furnish and decorate it. We have a couple other trips before that and then we are attempting to get to Paris in April. Thanks for sharing your beautiful photos.

    Posted 8.30.17 Reply
  14. Jenny S wrote:

    I seriously can’t believe I have never been! I am only an hour north of AMI and didn’t realize what a treasure it is! I will be taking my crew for a day trip soon. Thanks for posting all of the recommendations, I like to know what to expect before I try a new food joint.
    May God bless you for your efforts to help your fellow Texans, my heart has been so heavy for everyone affected.

    Posted 8.30.17 Reply
  15. Chelsey wrote:

    My mom was raised an hour or so from Anna Maria, so my family has vacationed there for years. We didn’t make it down there this summer, so your pictures were a treat!

    Next time, I suggest heading towards Sarasota and St. Armands Circle delicious restaurants (the Colombian has absolutely amazing Cuban food and Sangria famous throughout the state), shopping, and sightseeing!

    Posted 8.30.17 Reply
  16. You all are just such an adorable family!

    Posted 8.30.17 Reply
  17. Ramona Howe wrote:

    Spent a month there in June, never had stayed more than a week. Hated to come home,it is so great there. Beautiful and relaxing there. Coastline adventures with Captain Kayse is a half day trip to Passage Key with bird sanctuary and on other side shells and sand dollars. Love it here!

    Posted 8.30.17 Reply
  18. Kim Crawford wrote:

    I love this place. First found it in the early 90’s, but have only been back 2 other times. It has grown in popularity since the first time I was there, but is still charming, old Florida.

    Posted 8.31.17 Reply
  19. My family loves AMI!! No other beach like it!! The Fish Hole is the miniature golf place on Bridge Street and it is apart of our yearly traditions. Cannot wait to get back to the island for our next getaway! ❤❤

    Posted 8.31.17 Reply
  20. Heather wrote:

    This place looks like paradise! I love your trip recaps!

    Posted 8.31.17 Reply
  21. Heather wrote:

    Espirit — i totally forgot about that brand! We must be around the same age as I would beg my parents for Espirit and Benetton. I would get one special outfit before school started. This island looks amazing!!!! I am going to look into this next.

    Posted 8.31.17 Reply
  22. RobertN wrote:

    Beautiful post.
    All the best!

    Posted 9.5.17 Reply
  23. Joyceev wrote:

    We love Anna Maria Island. There are some other places to visit on your next trip: Bean Point, Sandbar Restaurant right on the beach!, Ginny and Jane’s for the best breakfast ever, Spice Sailing Charters, and 2 Scoops for great ice cream!

    Posted 7.9.21 Reply
    • Cassie wrote:

      Woo hoo, thank you for all of these recommendations! We are itching to get back to AMI as soon as we can! xo, C

      Posted 7.9.21 Reply