Snapshots from Anna Maria Island

Thanks for your love on Little Miss’s room reveal! She’s beaming with joy from all your kind words…especially on her artwork. And after only three days of school, her new desk area is already coming in handy!

We’re falling back in to the school routine and rhythm, but I am missing that family vacation bubble! You know the one, where everyone is happy and relaxed, and there’s uninterrupted family time with minimal distractions (and bickering). 

There’s just something about Anna Maria Island that instantly triggers that magical bubble, and a trip I look forward to all year. After four years, there’s a familiar comfort to it we all crave, and it’s a week of fun, food, relaxing, and good friends.

Her Swimsuit | Similar Straw Totes

We never have an agenda when we’re here…just days filled with beach walks and fish tacos, and nights of chasing crabs and playing cards. And sunsets take the place of Netflix.

We actually went back-to-school shopping before we left…and hit the jackpot at JCPenney! We found Vans tees and rompers for $10, huge selections of jeans and shorts, and even their favorite Converse sneakers on sale (low tops and high tops)! 

I assumed they’d save their new finds for school, but they wanted to wear them immediately and packed much of it for our trip.

Vans Tee | Adidas Shorts | Mermaid Tee | Knit Shorts

my outfit

We adore this precious family, and love seeing them every summer! Our kids have practically grown up together, and have the best time. Can you believe Jen and I met through our blogs?! She’s just as sweet as she is online, and then some!

Watermelon Tee | Adidas Shorts

We’ve taken this exact picture four years in a row…it’s so fun to look back at the past posts and see how they’ve grown and changed!

Vans Tee | Adidas Shorts | Mermaid Tee | Knit Shorts

Vans Tee | Knit Romper (only $5!)

Her Swimsuit

Vans Tee | Adidas Shorts

Vans Tee

We hit up all our usual spots, you can find our fave eats and things to do in these previous Trip Reports.

But we did stay in a new rental, 2901 Avenue F on Holmes Beach…this one was a little newer and larger, with incredible views from multiple balconies. It was a great location on the island, at the end of a quiet beachfront street.

It does has a narrow spiral staircase leading to the bedrooms upstairs, but that wasn’t a hinderance for us. You can find rental info here.

Vans Tee | Her Romper | My Romper | Color-blocked Tee

I’m holding on to that vacation feeling as long as I can, and cherishing the memories we made this Summer. Hard to believe we’ll be moving our son to college next year!

See everything I packed and wore in this Sugarplum Style post. And find our full Trip Reports on Anna Maria Island here.

[Shop our Beach Style]



*All photos captured on my iPhone by us. This post is created in collaboration with JCPenney, but all styles, opinions, and sappy-mom thoughts are my own. Thank you for supporting Hi Sugarplum sponsors.*



Leave a Comment


  1. What a great trip, I love the photos! Your family is the cutest 🙂

    Charmaine Ng | Architecture & Lifestyle Blog

    Posted 8.16.18 Reply
  2. Sandy wrote:

    Awesome pics! It’s like going to Disney World. One of the reasons you go is everyone else is relaxed and happy too. The pic of Little Miss and the turtle-adorable!
    Some of those properties seem awfully close to the water (think rising sea levels). The attitude down there must be Oh Well!! Don’t worry, be happy, ha,ha.

    Posted 8.16.18 Reply
  3. Sevahn wrote:

    Totally adorable turtle and Little Miss!!! Great sunsets and views. These are the types of family vacations we never forget as we grow older. My family would go on annual summer trips to Cape Cod and the memories never fade. God bless you and your family and your wonderful friends.

    Posted 8.16.18 Reply
  4. Marti Gommermann wrote:

    How blessed you are, Cassie. Such a lovely family-everyone is so cute, and you all seem to really enjoy one another. Wonderful to see-
    Thank you for sharing!

    Posted 8.16.18 Reply
  5. Kristin wrote:

    We were just in AMI a month ago and loved it. What is the name of the place where you are viewing the boats from the sidewalk? Thanks!

    Posted 8.16.18 Reply
    • Cassie wrote:

      That’s in Sarasota! We have family there and were visiting…the docks near Marina Jacks.

      Posted 8.17.18 Reply
  6. Debi wrote:

    BEautiful! Did you have any issues with red tide?

    Posted 8.16.18 Reply
    • Cassie wrote:

      It started creeping in the final days of our trip…it was so sad to see!!

      Posted 8.17.18 Reply
  7. Jen @ iHeart Organizing wrote:

    Missing our favorite family and counting down the days until we can see you all again next year! I can’t believe our boys will be graduates! ♥︎

    Thanks for the good laughs, chats, memories, and intense Phase 10 matches! #campers

    Posted 8.17.18 Reply