Siesta Key Staycation

Siesta Key Staycation

Last Fall, my husband and I began thinking about what we were going to do for my upcoming birthday. This was to be a milestone birthday and we wanted to do something big. Initially we thought about a destination party but with Covid, travel restrictions, and the uncertainty of the future; to plan something like that seemed more of a headache than pleasurable. One weekend last October, we were strolling Siesta Beach as we so often do and I turned and looked at my husband and said, “Let’s have my birthday celebration here”!

Although I live here, there aren’t many places that wow me more and so it was decided we’d find a place on Siesta Key to throw my birthday. I noticed when using google to try and find a rental, the options seem limited in terms of all the actual options available. We chose to drive the 20 minutes it takes to get there from our home and searched for a place on foot. We walked all throughout the streets that were close to the beach and walking distance to Siesta Key Village. As I passed homes I liked, I took pictures of the property management signs and/or contact info. After compiling a few of my favorites, I noticed a majority of the properties I liked were with The Cottages on the Key. On October 11th we chose the perfect place and left a deposit.

It’s amazing how the time flew as just this past week on May 29th, we checked into our place. The week was pure magic, from the house, to the family members that flew in and stayed with me, to the weather, and the places we enjoyed while there. I could not have picked a more perfect place to celebrate. The house was located directly across the street from the beach and within walking distance to the village. The views from our 2 balconies were to die for. Waking up each morning to that view was pure heaven. We enjoyed our coffee and conversation on those balconies. We spent our days on the beach and our nights at the village.

Some day time highlights not including the spectacular weather, was finding 4 perfectly intact sand dollars which from what I understand is pretty rare at Siesta Beach. We saw a mating pod of manatees which at first looked like a sea creature. We enjoyed long beach walks and a fun ride on a banana boat.

Some evening highlights were Gilligan’s Island Bar and Grill, dancing at the Daiquiri Deck, Star Thai & Sushi, the Fudge Factory, and the birthday dinner at Summer House Steak and Seafood. The Summer House was spectacular and deserves its own write-up as well as a shout out to the best waiter ever, Jeffrey!

The week was a girls only trip with family members comprised of mothers and daughters, aunts, cousins, and sisters. There were 8 of us, some I hadn’t seen in over 2 years due to Covid and because I was local we enjoyed special guest visits from my local friends who were able to enjoy the house and my family with me!

As all things eventually come to and end, so did this week. It is always so hard saying goodbye to family. I am so grateful for Siesta Key, although in my own back yard, it provided the perfect backdrop for a birthday and memories I will cherish forever. I could not have been more proud to share this special place with my family who now love it as much as I do!