Big-boy breeze, that’s what we had today for the one and only race of the day before the heavens opened up and the squalls came whistling through Key West. That big-boy breeze is big-time fun, though, ...

The Southernmost Regatta, powered by Sailing Inc, took place this past week from January 19th to 23rd, 2026. The fleet of ...

It’s Day 5 at Key West Race Week and the forecast is for breeze and rain, increasing to more breeze and more rain. Awesome! Every sailboat is more fun to sail when the breeze is up and there will be ...

new video loaded: A first in 50 years -- race sets sail from Key West to Cuba First U.S. to Cuba sailing race in more than 50 years departs from Key West after thaw in US-Cuba relations. Rough Cut (no ...