Two of us are approaching an obstruction — who decides which side we pass?

Whoever holds right of way at that moment. While one boat is clear ahead she is right-of-way under Rule 12 and chooses the side under Rule 19.2(a). The instant the trailing boat draws level and an overlap forms — making her the leeward, right-of-way boat under Rule 11 — the choice passes to her. The outside boat still owes the inside boat room at the obstruction under Rule 19.2(b). (World Sailing Case 124.)

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<iframe width="560" height="315" src="https://www.youtube.com/embed/hPV2Wr6ixYQ" title="Sailing Kiwi" frameborder="0" allow="accelerometer; autoplay; clipboard-write; encrypted-media; gyroscope; picture-in-picture" allowfullscreen></iframe>
<p><a href="https://sailing.kiwi.nz/v/hPV2Wr6ixYQ/">Source: Sailing Kiwi</a></p>

Recommended reading

  • The Rules in Practice 2025-2028 by Bryan Willis — The clearest guide to the racing rules around the racecourse — updated for the current 2025-2028 rulebook.
  • Advanced Racing Tactics by Stuart H. Walker — The classic deep-dive on racing tactics — starting, beating, reaching and mark rounding.

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Next on this shelf — The Upwind Beat