The Southernmost Regatta

The Southernmost Regatta Sun, steady breeze, and fast fleets collide in this iconic winter regatta set on crystal-blue Key West waters.

We had so much fun in 2026, we’re planning to do it all again next year! 🌊🌴⛵️🥥🍹🌬️Join us back down at Mile 0, January 18...
01/28/2026

We had so much fun in 2026, we’re planning to do it all again next year!

🌊🌴⛵️🥥🍹🌬️

Join us back down at Mile 0, January 18-22, 2027! New registration link is in our bio! We’ll see you there!

A few of the faces that help make this event possible! Thank you race committee!🌊☀️🌴⛵️🥥
01/24/2026

A few of the faces that help make this event possible! Thank you race committee!

🌊☀️🌴⛵️🥥

Headed upwind on those clear blue waters of Key West!🌊☀️🌬️
01/24/2026

Headed upwind on those clear blue waters of Key West!🌊☀️🌬️

Cheers to our winners!🍹⛵️Congratulations competitors! We saw some amazing racing this week with lots of close races & he...
01/24/2026

Cheers to our winners!🍹⛵️
Congratulations competitors! We saw some amazing racing this week with lots of close races & here are the results:

🏆J/111
🥇Bravo
🥈Spaceman Spiff
🥉Fireball

🏆Cape 31
🥇Sitella
🥈Cool Breeze
🥉Hobbes

🏆ORC
🥇Sitella
🥈Azulito
🥉Interlodge

Let’s hear it for our day 5 winners!🏆☀️ORC🥇Zammermoos🥈Sitella🥉Azulito🌬️Cape 31🥇Sitella🥈Warrior Won🥉Cool Breeze🏆J/111🥇Chi...
01/23/2026

Let’s hear it for our day 5 winners!🏆

☀️ORC
🥇Zammermoos
🥈Sitella
🥉Azulito

🌬️Cape 31
🥇Sitella
🥈Warrior Won
🥉Cool Breeze

🏆J/111
🥇Chips Ahoy
🥈Spaceman Spiff
🥉Fireball

One final day of racing to shake up these standings! Here’s what day 4 results looked like: ☀️ORC🥇Zammermoos🥈Azulito🥉Int...
01/23/2026

One final day of racing to shake up these standings!
Here’s what day 4 results looked like:

☀️ORC
🥇Zammermoos
🥈Azulito
🥉Interlodge

⛵️J/111
🥇Spaceman Spiff
🥈Bravo
🥉 Leading Edge

🏆Cape 31
🥇Sitella
🥈Cool Breeze
🥉Hobbes

Heading into our final day of racing here in sunny Key West!☀️Who will bring home the win?
01/23/2026

Heading into our final day of racing here in sunny Key West!☀️

Who will bring home the win?

Big thanks to our sponsor ! Thank you for making this week down in Key West possible! ⛵️🌊🍹🌴☀️
01/22/2026

Big thanks to our sponsor ! Thank you for making this week down in Key West possible!

⛵️🌊🍹🌴☀️

Powered by 🍹🥥⛵️☀️🌴
01/22/2026

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🍹🥥⛵️☀️🌴

Sailing into day 4 down at Mile 0!🥥🌴🦜⛵️☀️
01/22/2026

Sailing into day 4 down at Mile 0!🥥🌴🦜⛵️☀️

01/22/2026

On board with J/111 Bravo!🌬️

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Key West, FL

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