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A Week in Paradise: Siesta Key, Fl

For those who have been following me for a while and/or know me personally, you know that my family and I go to Siesta Key every year. It’s the one vacation I look forward to most, all-year-round, because Siesta Key is my happy place. So let’s recap my week in Siesta Key!

We go to Siesta Key the same week every year, and it happens to usually fall on the last week in June. In my opinion, that’s the best week to go because it’s post-Juneteenth and pre-4th of July. Our party, specifically, makes up roughly 40-50 people who are part of my immediate and extended family. Basically, we take up 12 units at the resort.

For the most part, we all stay in the same condos each year (if we like it, that is) so we’re already set for next year. Our condo specifically is a 2 bedroom, 2 bath condo. The master has a king bed, my room has two full beds (this is where my aunt and I stay), and then the living room has a sofa-bed. Chinaberry 415, as our condo is known, is on the first floor looking out towards the pool and beach (we stay beachside, not Gulfside).

Photo Credit: VRBO

The first thing we typically do when we drive in is go straight to Captain Kurt’s for lunch. This year we were so behind and it was absolutely pouring when we arrived that we headed to Publix for groceries. $300 and several full carts later we were done and unpacking our stuff. My sister had basically just arrived from Tokyo, so we had an early night and hung out in our condos.

Sunday morning, my cousins came over and made a feast for breakfast while my parents played pickleball. I spent the morning reading and getting ready for the day, and then in the afternoon I headed out to the beach. The waves were actually very rocky this year, so I think I spent the least amount of time in the ocean.

On Monday I woke up with a rash from being in the sun, so I decided to just stay in. I had a few calls to take care of for work, so I knocked those out and just stayed in reading. I read five books while I was in Siesta, which is a pretty good number.

The weather held up really nicely the rest of the week so we got lucky. Wednesday night was bowling night, which is the best. We’re super competitive and take bowling very seriously. It’s one of my favorite things to do.

The rest of the week was pretty chill. We hung out at the beach, watched the sunset, ate, read, etc. I did give my nephew’s my Go Pro and they went wild. It was such a cool thing to witness how much fun they were having taking pictures of things.

Honestly, Siesta Key is my favorite place on the planet. Even more so than Disney, and that is saying a lot. I love it there and I definitely will continue this tradition for the rest of my life.

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