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.
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.
His Tee (on sale!) | ‘Beach Bunny’ Tank | Her Flip Flops | Chambray Shorts
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!
Her High-Neck Swimsuit (only $25!)
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.
Her Jumper (40% off!) | Her Flip Flops | His Flip Flops
My One Piece Swimsuit | His Tee | Her Tee
My One Piece Swimsuit | Similar Sarong | Similar Romper
{Where We Stayed}
Right on the marina, you can eat indoors or out…with the best fish tacos & key lime pie on the island!
With only a handful of tables, it fills up fast. Watch the fishermen while you devour the grouper sandwich of your dreams.
Darn good BBQ (this coming from a Texas girl!), in a darling little spot.
Best ocean-side bar with delicious cocktails…a little piece of Miami in AMI.
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.
{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!!
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.*
