Southernmost Regatta 2026

Southernmost Regatta 2026 — Key West Sailing Competition & Island Culture

The Southernmost Regatta 2026 returns to Key West, Florida from January 19–23, 2026, bringing together elite sailors and enthusiasts for five exhilarating days of racing and island festivities. Powered by Sailing Inc., this prestigious event blends high-level competition with the laid-back spirit of the Florida Keys, making it one of the most anticipated winter regattas in the United States.

Five Days of Racing Excellence

Sailors will compete in multiple formats, including:

• One Design Course — Precision head-to-head racing for one design keelboats.

• ORC Course — Intense battles for racing and cruising keelboats.

• Daily Distance Races — Scenic offshore challenges designed for ORC cruisers.

With up to two races scheduled daily per course, participants can expect a mix of tactical windward/leeward contests and open-water adventures east of Key West’s main shipping channel. A maximum of 10 races is scheduled across all classes, ensuring every competitor gets ample time on the water.

Back to the Spirit of Key West Racing

The mission of the Southernmost Regatta is simple: return to what made Key West racing legendary. That means fierce competition on turquoise waters, reconnecting with fellow sailors, and celebrating the vibrant island lifestyle. As longtime racer Rob Ruhlman notes, “Racing in Key West had an epic 30-year run. To reignite that flame, even on a smaller scale, is worth it.”

Regatta Schedule Highlights

• Saturday, Jan 18 — 12–3 PM: Check-in & sticker pick-up (Galleon Sunset Tiki Bar)

• Sunday, Jan 19 — 11 AM–3 PM: Check-in; 12:55 PM practice race; 3 PM Welcome Reception; 5 PM Skippers’ Meeting

• Mon–Fri, Jan 20–23 — 9 AM radio announcements; 10:55 AM first warning signal; 2 PM Friday cut-off; 5 PM daily awards & shore activities at the Galleon Sunset Tiki Bar

Rules & Scoring

The regatta follows the Racing Rules of Sailing (RRS), ORC rules, and One Design class guidelines. ORC scoring will use official wind mix scoring models. A minimum of three races is required for class scoring, with one discard allowed after six or more races.

Island Vibes & Social Scene

When the sails are down, the festivities continue ashore. Daily award ceremonies and evening gatherings at the Galleon Sunset Tiki Bar ensure the regatta experience is as much about community as it is about competition.

Registration

Spots fill quickly for this premier winter regatta. Register now at the Southernmost Regatta website to secure a place in one of America’s most unique sailing competitions.

Lodging

Website