Winter Break In Florida

Over the winter break holiday we took a family trip to Florida to escape the cold Chicago days and to get some fun in the sun on the beach! We feel very fortunate to have been able to travel over the holidays and to get to spend extra time with our family.

We spent the week on Anna Maria Island in Florida and had the best time! This was a new location for us, and it did not disappoint! We were not sure what the weather would be like so late in the year but we lucked out with sunny and 70’s everyday.

Gap pajamas sold out – here are similar pajamas

In the mornings we mostly played on the beach in our pajamas (it was still kind of chilly at that time). Other days we took walks for coffee and exploring, went shopping at St. Armands Circle (adorable), and we even found the cutest little pirate ship park that all the kids loved!

After naptime we would head to the pool. Kylie absolutely LOVES the water and it was so fun to watch her jump in and splash around. Hunter has recently taken off with swimming so it was exciting to watch him try new tricks (like cannonballs). Grayson is timid in the water but still ventured out more than ever, it was wonderful to see his confidence grow as the week went on. Preston is not the biggest water lover – he was happier searching for salamanders!

boat ride and an ecology tour
Happy Anniversary!
fun evening swims

Places to eat:
The SandBar – the perfect place for lunch or happy hour in my opinion (especially if you have kids). The boys had the best time running around on the beach while we waited for our food. Definitely recommend The SandBar.
Mar Vista – Beautiful scenery! Another nice place with kids because the outdoor space is decently large and there is a dock to walk out onto as well.
Bayou Tavern – a quaint pizzeria on Longboat Key. We had a delicious dinner here, probably one of my (Kelly) favorite dinners.
The Ugly Grouper – this place is a must do for everyone. Great outdoor space (even a game section for the young, or the young at heart). I highly recommend the pretzel bites for an appetizer!
Viento Kitchen + Bar – at the Zota Beach Resort. We ate here on NYE and had a delicious meal. The restaurant was beautiful and the setting was lovely.

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