Siesta Key, Florida

I set out 2018 writing out my goals, and one of them was to visit somewhere I had never been this year! The past couple of years I have saved up my vacation time and taken one big trip around the August time frame, but this year I wanted to go about it a little differently and take small trips throughout the year, because sometimes you need a little getaway more than you know!

I booked this trip October 2017, and I didn’t know this girls retreat was going to fall right when I really needed it!

(some of the most amazing women that were on the retreat)

(some of the most amazing women that were on the retreat)

This trip was an organized girls retreat with about 40 girls, so we were responsible for booking our own flight and accommodations if you weren’t staying in the main house that had limited space (which was absolutely gorgeous!).

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Money Talks gift bag.JPG

If you ever plan a trip to Siesta Key with a big group, I would highly recommend this rental property! You can find it HERE

Siesta Key Beach.JPG

I flew into Tampa International Airport, which is about 70 miles from Siesta Key. It wasn’t the closest airport, there was definitely other options (Sarasota or Ft. Meyers), but this was the cheapest option. I always tend to use Southwest for travel because they’re typically the cheapest option, and from Austin it’s easy to get a non-stop flight to most places. I split an Uber from Tampa to Siesta Key with a girlfriend, so it wasn’t too bad ($80 each).

We booked a HomeAway rental and stayed walking distance to the beach. Since I was going with a group of about 40, yes 40, a few of us planned to stay near the main house for easy access to weekend events.

To be honest, most of my time was spent between the main house, that I really only went to my place to get ready and sleep. I will say, in the future I would definitely look for a rental that also has a pool, but in this instance- it wasn’t necessary since the main house had a pool, and the beach was walking distance!)

To get around Siesta Key there are some free shuttle transportation options, you just need to tip! Some of these options were-

Jonny’s Free Ride,
Jerry’s Free Ride
Surfside Free Ride

There was also a nearby market, Morton’s Siesta Market, where we were able to buy snacks for the house, and booze, of course!  

Most of our meals were catered, so I didn’t get out much to eat- but I did stop at a decent breakfast spot one of the mornings, called Another Broken Egg Cafe.


Local Bar

The Beach Club- This was the happening spot on Friday & Saturday night, we liked it so much the first night that we went back for a second round! Its a decent sized spot with live music and a fun atmosphere if you’re with the right crowd!

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(this babe put our retreat together, through her Master Your Money Look Course-

Overall, it was a fun weekend and a good start to my year of mini getaways!


Xo, Stephanie