Snapshots from Anna Maria Island

Thank you so much for the love and encouragement on yesterday’s Saying Goodbye post. I honestly feel like I have the best group of girlfriends guiding me through this season! I hope that reading my experience, and others that share in the comments, is helpful to those who are going through it, too, or will be soon.

Sharing my thoughts and emotions has been therapeutic, but this blog also serves as my personal scrapbook. I love that I’ll be able to look back at this time in our life, and have the photos and words take me right back. I know we’ll be sending Little Miss off before I know it, and I’m grateful to have the last 10 years of our life mostly documented here. And incredibly blessed to have shared it with all of you. You’ve always shown my family so much kindness, and I can’t thank you enough for that.

I refer back to my own posts all the time…What paint color did we use for the Kitchen? Where’d we stay in Paris? How old were the kids when we moved? Literally every milestone, adventure, victory, and many heartaches are all here. Ten years and more than 2,000 posts, and we’re still chatting! From the bottom of my heart…thank you!

Today is another scrapbook moment…our family trip to Anna Maria Island, Florida. After five years, there’s a familiar comfort to it we all crave, and it’s a week of fun, food, relaxing, and good friends.

Bodysuit | Skirt | Sandals | Tote | Bangles (look for less) | Tote | Sunglasses

This year was a little different because of our schedules, so Little Miss and I went on our own for the first few days…and it may have to be our new tradition! We loved the dedicated one-on-one time, and the chance to bond closer before the school year began. Eighth grade is an intense age for girls, so I love any opportunity to stay connected with her.

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.

My Swimsuit

Tank Swimsuit | Cut-Offs | Hat | Bangles (look for less) | Tote | Sunglasses

Ruffled Two Piece | Hat | Bangles (look for less)

After a few days, the boys joined us…and we connected with this darling girl and her family! We adore them, 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, and I treasure our friendship so much.

‘Good Vibes’ Tank | Cut-Offs | Flip-Flops

Cross-Back Swim Top | Full Coverage Swim Bottoms | Bangles (look for less)

Square Neck Tee | Shorts | Sandals | Bag | Bangles (look for less)

His Tee | His Sandals | My Embroidered Tee | Cut-Offs | Her Chambray Jumpsuit

Striped Swimsuit | Bangles (look for less)

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

His Tee | His Sandals | Her Chambray Jumpsuit

Ruffle Tank Dress | Hat | Bangles (look for less)

Striped Swimsuit | Swim Trunks

Palm Print Swimsuit | Tote | Hat | Sunglasses | Bangles (look for less)


[Where We Stayed in Anna Maria]

This year we stayed in a new rental, The Gulf Front, and loved it! It’s a newly remodeled condo (only 6 units in the building) with two bedrooms/bathrooms, a large comfy couch, huge TV, fully-equipped kitchen, and incredible views of the beach and sunset. It’s literally 10 steps to the sand! It’s a great location on the island, and even has a small pool.

It was our first time renting through Anna Maria Vacations, and we had a great experience. We’ll definitely be staying here again!

As for food and adventure, we hit up all our usual spots. You can find our fave eats and things to do in these previous Trip Reports.

Jean Jacket | Bodysuit | Skirt | Sandals | Striped Tote | Carry-On Suitcase

The trip was especially sweet this year since we took our son to college a week later. I’m cherishing the memories of this Summer, and hoping they sustain me until Christmas Break! Anna Maria holds a special place in our hearts, and we’re already counting down the days until next time.

Find our full Trip Reports on Anna Maria Island here, including everywhere we’ve stayed, our go-to restaurants, best beach rentals, and more!

Leave a Comment


  1. Great pictures! Great memories!

    Posted 9.4.19 Reply
  2. Shana wrote:

    Hi Cassie! This destination has been on my bucket list solely because of the amazing pics you post. Love! More importantly…your abs! Lol. We’re the same age and I’m also doing the intermittent fasting and it’s been incredible for weight loss. Are you still mainly doing Orange Theory? Is that how your core is getting so cut? It looks amazing!

    Posted 9.4.19 Reply
    • Cassie wrote:

      Thanks so much, Shana! Yes, I’m doing OTF 2-3 times a week and practicing IF. Some of those ‘abs’ are just where my loose skin creates a white tan line tho! For real! 😉 xo. C

      Posted 9.4.19 Reply
  3. Dee Nowak wrote:

    This looks like such a great vacation and fun with family and friends.. I love all your beach outfits – they look so put-together yet effortless.

    Posted 9.4.19 Reply
  4. Barb wrote:

    We are returning to Anna Maria at the end of October for two weeks. I always enjoy your posts with pictures of familiar sites!

    Posted 9.4.19 Reply
    • Cassie wrote:

      I would LOVE to go in the Spring or Fall sometime!! I bet it’s just glorious!

      Posted 9.4.19 Reply
  5. Ali J. wrote:

    Can you do a post on how you handle the mean girl issues with your daughter? My daughter is 11 and in 6th grade and sometimes I just am at a loss as to what to say at times. Like you, I have a good relationship with my daughter and want to keep her on the right path.

    Posted 9.4.19 Reply
    • Cassie wrote:

      Ugh…that is the WORST!!! I don’t have a magic solution either. Sadly, girls can be just brutal to each other!! But I try to listen a lot, and encourage her to stay calm and kind. I also validate her feelings and let her know she’s not alone…I’ve probably told her 100 times, ‘Middle school can be brutal, I KNOW, but I can also promise you it will get better.’ But also remember we only hear one side! 😉 xo. C

      Posted 9.4.19 Reply
  6. Kim wrote:

    What a lovely sounding vacation! My grandparents lived on Anna Maria Island but I never had the chance to visit them before they came back to England. It always looked so stunning! I am loving that palm print swimsuit too! Fabulous!

    Posted 9.4.19 Reply
  7. Valerie wrote:

    Woohoo! I’ve been dying for a dupe for the all weather bracelets. Just purchased. Thanks Cassie!!!

    Posted 9.4.19 Reply
  8. Teresa wrote:

    I always enjoy this post as we have vacationed on AMI ourselves several times. (We are in Miami.) So I know exactly where many of your photos are taken. It’s also fun to see Jen and her family. I actually found your blog by following hers, quite a few years ago. Trust me, your heart will soon heal from missing your son. All 3 of mine are on their own now, and 2 are 1200 miles away in Michigan, and 1 married and 6 hours away. Sigh! It’s not easy at first, but you will find a new normal with your “only” at home, and then with just the 2 of you one day. Unless you are lucky and they stay in TX!

    Posted 9.4.19 Reply
  9. Melissa wrote:

    Anna Maria island looks like heaven. I am looking for a white bodysuit ( haven’t worn one in decades) and am curious about your Amazon bodysuit. Not to get too personal, but I’m wondering how it fits around the bum. I’m not looking for a thong situation if you know what I mean. It looks great but I’m worried about comfort and “panty lines”.

    Posted 9.4.19 Reply
    • Cassie wrote:

      Hi Melissa! I love that bodysuit…I’ve worn it at least 10 times in the last month! It’s pretty cheeky, kind of a half-thong…but I just layer it over my reg undies and it’s fine! Odd, I know, but it works for me! 😉

      Posted 9.4.19 Reply
  10. Jen @ IHeart Organizing wrote:

    YAY! My favorite post of the year!

    I am already counting the days until we are back with our toes in the sand, a margarita in hand, and chats that are anything but bland.

    Love you guys so much!!

    Posted 9.5.19 Reply
  11. Loved this! Beautiful shots 🙂

    Posted 9.7.19 Reply