If you’ve been around here for awhile, you probably already know how much we love a good beach vacation! This summer we headed back to Anna Maria Island, Florida, and this trip was one I had been looking forward to for months!
We stayed in a house just a block from the beach with my parents, rented a golf cart for getting around the island, and basically spent the week rotating between the beach, pool, ice cream and food. Which, honestly, is exactly how vacation should be.
I tried to jot down little notes each day because I knew I wanted to remember all of those random moments that are so easy to forget once you get home.
So here we go with Part One of our Anna Maria Island vacation: Days 1-4!
Day 1 | Saturday August 8: Travel Day + We Made it!
Vacation officially started with a 10am flight, although traveling with kids means vacation doesn’t really start until everyone and everything successfully arrives at the destination. We had a pretty long wait at the airport, so Hadley got a refresher drink at Dunkin. Hadley sat by herself on the plane, while Huxley had the window seat, Kevin was in the middle and I was on the aisle.
Huxley did SO GOOD on the flight! He happily ate his snacks and provided some in-flight entertainment for everyone around us. At one point he announced, “It smells like smoke, Dad. The plane might be on fire.” The people sitting in front of us cracked up. Nothing like a four-year-old casually alarming an airplane full of people! The smoke smell was just the air ventilating throughout the plane and happens occasionally.
Once we landed, my dad went to pick up our rental van while we waited for our luggage. Then we headed to Chick-fil-a for lunch because we still had about four hours before we could check into our house. After lunch, Kevin drove us around Anna Maria Island for a while. The kids were DONE with being in the car at that point, so we made a stop at Baskin-Robbins before finally getting into the house.
I had also placed a Walmart grocery delivery order ahead of time for between 4pm-6pm, which may have been one of my smartest vacation decisions. Our groceries arrived around 5pm, the kids immediately put on their swimsuits and jumped into the pool, and we officially switched into vacation mode. Our house was so nice, and I even made a little snack tray for the kids once we got settled.
We kept dinner super easy that first night with burgers and mac and cheese, and after a full travel day, we were very happy to be there!
Day 2 | Sunday August 9: Our First Full Beach Day
Started Sunday morning with a walk with my mom, which became one of my favorite ways to start the day on the island. Afterward, Kevin, the kids and I took our first golf cart ride! Hadley and I drove the golf cart to Publix to pick up ice, and then it was time for our first full beach day!
Poor Huxley got absolutely fried despite us reapplying sunscreen multiple times. We couldn’t figure out if it was the spray or sunscreen we were using or what happened, but his little face and lips got so read. Parent fail moment for sure, and we switched things up after that!
Before dinner, I took the kids out for another golf cart ride. We had steak and potatoes for dinner, which tasted extra good after spending the day outside. After dinner, obviously we needed another golf cart ride because I quickly learned that the golf cart was basically part transportation, part entertainment on this trip. Hadley took pictures of houses around the island while we drove around, and then my mom, Hadley and I headed to Dips Ice Cream. And OH MY GOODNESS. Dips was so good. Spoiler alert: this would definitely not be our only visit of the week.
Day 3 | Monday August 10: Donuts, Pool day + The Ugly Grouper
Monday started with an early morning golf cart ride to The Donut Experiment! Hadley picked a glazed donut with oreos and Huxley chose one with sprinkles. The donuts were super fresh, which apparently was not what my kids wanted because neither of them liked theirs. Kevin and I happily took a few bites for them and thought they were delicious!
Next we stopped at the Blueberries Cafe. Hadley got a strawberry banana smoothie with peanut, and I tried a chai tea. Unfortunately, mine was not a winner. It tasted like fresh tea, and I’m not a fresh tea kind of girl.
Once we got back to the house, I took a solo walk and then we settled in for a pool day. We ate lunch by the pool, and just hung out and relaxed. The pool was soo nice at the house!
After Huxley’s nap, Kevin took him down to the beach because he had promised him they would go. While they were there, Hadley, my dad, mom and I took the golf cart to The Ugly Grouper for dinner. It’s one of our favorites for dinner on the island, the vibe is fun but it is all outside seating so bring a little mini fan!
Afterward, we headed home, picked up Kevin and Huxley, and went right back out on the golf cart for ice cream. This time, everyone got to try Dips. My dad got caramel swirl, my mom got latte ice cream that tastes like coffee haha, Kevin didn’t get any because he’s insane, who doesn’t get ice cream on vacation? Hadley and Huxley both got superman, and I got peanut butter cookie dough because apparently vacation Mandy believes one ice cream flavor is simply insufficient.
We made a quick stop at CVS afterward so my dad could grab some readers. Huxley got a key chain, and Hadley got a travel wet brush. Just one of those random little vacation evenings that ended up being so much fun.
Day 4 | Tuesday August 11: Beach, Mom’s Solo Pool Afternoon + Sunset
Started Tuesday with a walk in the morning, and then Hadley and I spent some time tossing the softball in the ocean. Because even on vacation, softball follows us to Florida. Then it was another beach day! Huxley wasn’t feeling the beach after an hour or so, so I took him back to the house for lunch and a nap. Once he fell asleep, I packed myself what I call a mom bag for the pool: vodka, three Zevia’s, sunscreen, and a towel.
I spent the afternoon hanging out at the pool complete by myself and it was glorious! I made some videos, swam a few breaststroke laps and eventually just laid out in the shallow end. There is something about being alone by a pool on vacation with nowhere you need to be that is just perfection.
We grilled chicken at the house for dinner and then, naturally, loaded everyone onto the golf cart again for dessert. This time we went to The Fudge Factory. My parents both got black cherry, I got brownie batter, Huxley got superman. And then we waited in what felt like the world’s longest line so Hadley could get a Dubai chocolate bar.
We ended the night by driving down to the beach to watch the sunset around 8pm. Kevin had started drinking at 10am this day, so I was officially the golf cart chauffeur for the evening. Huxley had the best time taking pictures of the sunset with our phone, and it was the sweetest way to end the day.
And that wraps up the first four days of our Anna Maria Island vacation. By this point, we were fully settled into the island life; slow mornings, beach days, golf cart rides, way too much ice cream, and nowhere we really had to be. Basically, my favorite kind of vacation. And we still had plenty more fun ahead of us!
I’ll be back with part two soon to share the rest of our week on AMI, including more beach time, more good food, more sunsets, and of course, more golf cart adventures!
Stay tuned for Anna Maria Island 2026: Part two!
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