Florida Trip 2026

We just got back from one of the BEST weeks our family has ever experienced together. And you know me, I have to document everything because this is my journal and scrapbook :) So, buckle up... it's a long one!

 After weeks and weeks of waiting (in hindsight, I told the kids about our Florida trip WAY too early) we finally made it to Florida! Michael's grandma and family have a condo on Longboat Key, which is an island near Sarasota. Michael and I used to go every year since we were dating, but we haven't been back since I was pregnant with Isla (7 years ago!). We have missed the place and were so excited to share it with our kids. 

(the last time me and Isla were in Longboat Key)

We are so incredibly grateful to Michael's Grandma Fred and the family for letting us use the condo and for encouraging us to take the trip as a family. We made some really special memories that will last our family's lifetime.

 I'll just share our trip day by day because I don't want to forget any of it!!

Sunday:

We waited around ALL day for our nighttime flight, which was the hardest part of the week. We drove over to Peoria and introduced the kids to a whole new world at the airport. They watched planes fly out, they went through security like champs, and they did great even though our flight didn't leave until just about their bedtime!

Eleanor was a little nervous when the plane took off, but a sucker helped. 

We were prepared with snacks, games, audiobooks, and activities.

After the flight, Isla asked the pilot to sign her flight logbook. He invited the kids into the cockpit and even let Isla "turn the plane off". How exciting! Sometimes, all you have to do is ask and you get to do cool things ;)

Here's Isla still reeling from getting to turn the plane off :)

While we were waiting for Michael to get the rental car, Isla screamed "Mom, get a picture of us with our very first palm tree in it!" And I thought, wow I really need to get these kids out more haha.

The kids were excited to be in booster seats all in a row. Then we drove off to the island at almost 11:00 p.m.

We arrived at the condo and the kids immediately dashed outside to see what they could see. The place is a beautiful top story condo that overlooks the ocean and the bay. It was hard to see in the dark, but they were so excited anyway! Then they all went right to bed without a hitch!

Monday:

We all slept in a little bit after such a late night. But I was reminded of the beauty of waking up above the ocean. The kids were so excited to come out of their rooms and see the blue, blue water!

If you had been around Eleanor for the month leading up to the trip, she would have told you she was most excited for "donuts in Flo-da". So Michael ran out to the store extra early to make sure she had some donuts first thing and grab our grocery pickup order. Although the real "Flo-da donuts" were still to come.

Our first day was slow and relaxing with an ALL DAY beach day. I think we spent 7 hours swimming the first day. There is a pool and a beach, so we had plenty of options!

And to christen our trip, a dolphin swam RIGHT IN FRONT of us. I think Isla called to the dolphin or something, it just knew she was there :) I think Isla's whole week was made on the first day.

We decided to take a break from swimming and grabbed dinner at a family-favorite- The Old Salty Dog.

Ewan and Eleanor almost definitely fell asleep at dinner. We were all pretty tired.

Isla ate her body weight in "dog bites"!

But dad said, "let's get ice cream!" and everyone perked right up.

One more snooze in the car, then it was off to bed!

Tuesday:

On the second day, it was breakfast over the ocean and morning porch views before heading inland to Myakka River State Park. 

Our main goal with this excursion was to see alligators, which we did! Can you spot them?

Then we hiked out to a canopy walk in the trees, which we learned is only 1 of 75 in the world. Fun fact, I guess?

SO many lizards and geckos! The kids tried all week, but they never did catch one.

We also learned it was love bug mating season the week we were in Florida. These harmless little lovers were EVERYWHERE!

Heat and hunger started to get the best of us, so we drove to the bay for some yummy lunch. We found (and by "found" I mean, "heavily researched beforehand") O'Leary's Tiki Bar and LOVED it so much that we almost went back later in the week. It was right on the bay, in the sand, with live music, a park right next door, a marina out back, and the BEST food we had all week!

Then, of course, it was back to the condo for more swimming!

A quick dinner upstairs, then it was back downstairs for a sunset walk along the beach.

Oh wait! But first, ice cream bars :) We might have had ice cream every night.

It was windy enough to struggle with fly the kite.

The amount of shell-hunting we did all week was insane. I can't even begin to tell you how many seashells, coral, crab pincers (yes, you read that right), rocks, and other unknown things we came home with.

A dead stingray, that I'm sure the kids wanted to bring home and dissect.

Isla identified every bird we came across.

Even Michael joined the shell-hunting fun ;)

There is NOTHING like a beach sunset.

Wednesday:

I'll be honest, Wednesday morning was not our best day. Everyone was tired and we had to get up early to head to the aquarium for our ticket time slot. It was really busy, really expensive, everyone was hungry, and it was a lot of walking. But it was still cool to see manatees, sharks, and a huge octopus!

Afterwards, we drove to St. Armand's Circle to stop at one of my favorite restaurants- Columbia. The sangria and salad were just as good as I remember. The kids actually ate something other than french fries too! That aquarium really made us all hungry.

And a trip to the circle is not complete without some kind of little treat :)

Then it was back to our regular programming of swimming, swimming, swimming! Somehow, the days were so long in Florida and we could squeeze so much into them.

The waves were so good. We spent a long time jumping and diving in them. I'm pretty sure my sinuses got the best saline rinse of their life. I didn't have a single sinus headache the entire week (one of the many reasons I want to move to Florida!)

Another quick dinner upstairs and we were back down for a walk on the beach and a night swim. The kids had been waiting all week to swim with the pool lights on :)

Thursday:

Finally we reached Eleanor's favorite day... donut day! After first breakfast, we piled into the car and headed north to Anna Maria Island for the day. In my opinion, AMI is quintessential island life and one of my favorite places. There are colorful beach houses, restaurants in the sand, cute little beach shops, and a family-friendly and fun beachy vibe. And fun fact, my mom used to spend her spring breaks on AMI :) and I imagine not much has changed since then with how relaxed and preserved the island seems.

Michael and I used to visit the Donut Experiment every time we vacationed in Florida, so we knew we had to take the kids! It's a cute little place where you get to mix and match your frosting, topping, and drizzle flavors. Eleanor had been planning the kind of donut she wanted for weeks. And I think her dreams finally came true.

Michael, ever so smartly, brought a cooler along so we could take donuts home for the next day too!

Have you ever seen someone look at donuts so lovingly?

After donuts, we wanted to take advantage of the free island trolley. The trolley, while really cool, soon became the bane of Michael's existence. It was never on time or where it said it was supposed to be. Twice we waited for a long time in the hot sun for our ride. The kids and I had a blast hopping on and off all day, but Michael could have done without.

We got off multiple times to check out beaches, trinkety/souvenir shops, parks, and anything else we came across that looked fun.

Ewan got a little 3D printed octopus that he now sleeps with :)

When we got hungry, we headed to lunch at the Wicked Cantina, which was also a favorite of ours for the week. The most delicious food and margaritas, right across the road from the beach. 

Oh look, more waiting in the hot sun for that darn trolley. We found shade in a cute beach shop next door and the kids got free shell necklaces!

When we finally got on the trolley, kids were starting to fall asleep on me :) We were all a little tired and hot.

Ice cream helped :)

By late afternoon, we were so tired that we headed back to the condo. Eleanor just couldn't make it much longer. Here she is dreaming about that rainbow sprinkle donut she had :)

She was still sleepy back at the condo.

No one was tired enough to not swim though. The kids practiced their diving and synchronized swimming. They are definitely ready for pool season after this trip!

The kids did not like a lot of the restaurant food all week, so eating was kind of difficult. Also one of our kids is really picky. But pizza will always be a winner. So Michael went out and grabbed us all a pizza for the beach. They gobbled it up and got right back to swimming.

Ewan's favorite part of the whole week was the pool. He was upset every single night when we told him it was time to stop swimming :) Such a little fish!

Friday:

Michael and I both agreed this was our favorite day of the week. First things first, we spent the morning swimming. 

We did lunch and then headed out to the bird sanctuary. If you know Isla, you know she LOVES birds. She could identify most of them.

A quick caffeine pick-me-up for the afternoon ahead.

Then it was time for our boat tour.  The kids had never been on a boat before (they aren't Michiganders, after all), so that was exciting enough, but the boat tour was a learning experience too. The tour was lead by a marine biologist. She shared all about the bay with us and pulled ocean critters into the boat by net. We were able to touch and learn all about really cool fish, seahorses, and crabs. And to top off the tour, a couple pods and nurseries of dolphins swam right up to our boat. 

The rocking boat and sound of the waves put Eleanor right to sleep. Best $30 nap Florida has to offer :)

We went by a bird rookery, which Isla really enjoyed.

Isla answered every question that was asked on the tour, asked some of her own good questions, and shared all she knew about marine life. Afterwards, she went right up to the marine biologist and asked her what she had to do to become a marine biologist. She was really helpful and explained all the steps. If we ever doubted her ability to socialize as a homeschooler, we won't after this trip. 

For dinner, we ate at a little hole-in-the-wall place that was half grill/half bait and tackle shop. The kids loved watching the boats and we even spotted the ice cream boat that we tried so hard to hunt down on AMI.

And no day was complete without a little beach stroll and night swim. We found what we think were cowries everywhere!

Late night snack and off to bed!

Saturday:

On Saturday, Isla and I wanted to sneak out and see the sunrise and do some tidepooling at low tide. Eleanor had been holding Isla's hand when I woke her up, so Eleanor woke up too and joined us. Unfortunately, this made for a crabby toddler as we were up super early. But we still enjoyed having the whole beach to ourselves that morning.

For our last full day, we declared it a full-day-swim-day! We played in the HUGE waves and when the current became too strong, we played in the pool. 

Lunch and naps and swimming :)

After a long day, we headed back to Anna Maria Island for one last hurrah dinner at the Daiquiri Deck. Look at those sleepy, tired faces. They got a good snooze in as it took us an hour to get onto the island. Everyone was trying to leave because a big storm and tornado warnings were rolling in, but we braved it anyway.

Lobster pasta, daiquiris for everyone, and Ewan actually ate a burger... success!

Isla begged to do something else, so we stopped at a place we had seen earlier in the week for her to get her hair wrapped. 

And of course we had to get ice cream on the last night, even in the rain!

Ewan found a really cool hat and t-shirt to remember the trip by. 

Sunday:

 

And then the saddest day of all, it was time to go home. We spent the morning cleaning and packing up then we headed to a really cool park with an ibis bird to crawl through. I love that the parks in Florida are surrounded by oceans and not cornfields. 

And to reaffirm the socializing homeschooler thing, Isla and Ewan asked a lady if they could pet her dog. They then continued to have a full conversation with her and a whole crowd formed with Isla leading the conversation. Ewan and Isla then thanked her for allowing them to pet the dog. 

Fear of strangers/stranger-danger: 0/10

Ability to talk to adults: 10/10

We finished with lunch at the Toasted Mango and walked some trails before heading to the airport.

Our flight was delayed and the pilot chose a longer route, so it was a long travel day home. Everyone did great though (except for a few squirrelly moments from the littlest).

We had the very best time. It was one of my favorite weeks ever! When we were leaving Eleanor just couldn't believe we had to go back to Illinois. She told Michael he could go back to work and we'll just stay in Florida. And we did actually get on Zillow to see if we could get a second home down there, but alas we can't afford it ;)

We ate such good food (well, except for Ewan who mostly ate peanut butter and jelly sandwiches all week), we logged over 50 hours outside in one week, we spent so much fun time together, and created the absolute best memories. We can't wait to go back and I'm already planning our next big trip because travelling is just so fun :)