Bachelorette in Siesta Key

In October, the amazing ladies in my life joined me for a bachelorette weekend in Siesta Key, FL–or what we liked to call “Kathleen’s BEACHelorette!” All of my friends know how much I love a quick getaway, so instead of having the bachelorette in our hometown, we opted to fly south for the weekend. My family owns a couple beach-front condos in Siesta Key, so it made it an easy and cost-effective spot to escape to for a weekend. If you’re looking for how to spend a low-key bachelorette weekend in Siesta Key, the below itinerary worked for us!

Three of us flew down on Thursday night to prep the condos and get everything in order. This also meant that we had time for a late dinner at Captain Curt’s–one of my faves! If you’re looking for a casual lunch or dinner and award-winning clam chowder, head to Captain Curt’s. The next day the rest of the girls flew in and we hit up the grocery store and the liquor store to stock up for the weekend.


The weather was amazing on Friday (and the forecast was not looking good for most of the weekend), so we had lunch at home and then spent the afternoon out on Turtle Beach. We stayed on the beach to watch a beautiful sunset and then went inside for a night of casual appetizers, comfort foods, and Uno.

Saturday morning we got an early start and went to a yoga class on Siesta Key Beach. Sadly, the yoga class left much to be desired, but we all had a laugh because the instructor was such a character. We spent some of the day on Turtle Beach until the weather chased us away. That night we went to Daiquiri Deck and sat on their awesome new sky-high deck that overlooks the ocean. The food was good and 2-for-1 daiquiris were had by all. To end the night, we went to Big Olaf Creamery for a tasty treat!

The following morning we went for the windiest walk ever on Turtle Beach. The strong winds really gave us a good workout! For lunch, we went to Siesta Key Oyster Bar and made sure to stick our dollar on the wall. Since it was Sunday, we ventured to Siesta Key Beach for the infamous drum circle at sunset. My friends and I had a blast dancing with the locals and I highly recommend everyone visit–it’s such a unique and fun experience! Finally, we closed with one last visit to Captain Curt’s as some of the girls hadn’t had the experience yet.

Sunday night drum circle at Siesta Key Beach.

Despite the crummy weather, my bachelorette was super fun. I loved that it allowed me to share one of my favorite places with my favorite people. While we didn’t get to hit all of my favorite Siesta Key spots (The Cottage, Ophelia’s on the Bay) or do all of the awesome activities (kayaking, SUP, bike riding), it just gives us a reason to go back!


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