Sarasota Sailing Squadron

09/09/2026

Wind might have been in short supply on Sarasota Bay, but there was no shortage of enthusiasm with young sailors at the two-day 78th annual Labor Day Regatta.
https://www.yourobserver.com/news/2026/sep/08/youth-sailors-regatta-tradition/

09/08/2026

🍹⛵ Another Parrot Head Regatta is officially in the books! 🌴🎶

What a fantastic day of sailing, fun, music, poker, rum, and plenty of Parrot Head spirit! 💙

A HUGE THANK YOU to all of our amazing volunteers who worked behind the scenes and on the water to make it happen. We couldn’t do it without you! 🙌

Thank you to our incredible vendors for being part of the party and helping make the day such a success. 🍹🍔🎶

And, of course, THANK YOU to our members for showing up, participating, volunteering, cheering everyone on, and bringing the fun! ❤️

It truly takes a village to pull off an event like this, and our Squadron family showed up BIG!

Until next time… Fins Up! 🦜🍹⛵

09/07/2026

🌴🍹 TODAY’S THE DAY! 🍹🌴

The 2nd Annual Parrot Head Poker Run Regatta is HERE! 🏝️⛵️

Over 70 people are registered and ready to PARTY! 🎉🍹🃏

Boats, friends, music, rum, and a whole lot of Jimmy Buffett vibes! 🎶🌊

Come ready to sail, play, laugh, dance, and have one hell of a good time! 🥳 Launching around 11:00ish

🌴 It’s 5 o’clock somewhere… and today, it’s at the Squadron. Live music starts at 2:00pm

09/06/2026

https://www.mysuncoast.com/2026/09/05/sarasotas-oldest-regatta-returns-78th-year/

125 athletes set sail in region's longest-running sporting event

09/05/2026

⚓️ Our members make the difference! 💙

A big thank-you to our amazing volunteers who spent the day washing down the docks! 🧽💦

Because of you, when our sailors come back in from the water, they’re welcomed by clean, beautiful docks. ⛵️

We appreciate everyone who gives their time to help keep our Squadron looking its best. It truly takes a village! 🙌

09/03/2026

💦🔧 Getting the Pump Fixed!

Behind the scenes, there’s always something to keep the Squadron running! Today we’re working on the well pump to get our water back up and running.🤞

Doing what it takes to make sure the Squadron is ready for a busy Labor Day Regatta weekend! ⛵️

09/01/2026

Labor Day Regatta is this weekend! We’re gearing up to put on a great event- register now! ⛵️🇺🇸

09/01/2026

🏝️🍹 RAIN OR SHINE — WE’RE READY TO PARTY! 🍹🏝️

Join us Monday, September 7th for the 2nd Annual Parrot Head Poker Run Regatta! ⛵️🌴

🃏 Poker Run
🎶 Live Music Starts at 2:00pm
🍔 Food
🏆 Prizes
Massages
🍹 Plenty of Parrot Head fun!

We’re celebrating the spirit of Jimmy Buffett and keeping the island vibes alive! 🌺🎸

11:00 AM — Let the fun begin!

🌧️ Rain or shine, this party is happening! 🌞
Grab your friends, wear your best Parrot Head gear, and come make some memories with us!

Let’s make Jimmy proud! 💙⚓️🍹
Sign up today on Rechub or call the office at 941-388-2355