I was on port and could just cross ahead of a starboard boat — should I take the gain and cross, or tack underneath her and play it safe?

Both are legal: on port you must keep clear (Rule 10), and crossing ahead does that. The choice is tactical. Cross and you get to the right; when the wind swings right you're on the winning side, and here crossing won by about a boat length. Tuck in ahead and to leeward and you're safe on starboard, but the same right swing favours her and you end up only just ahead. Rule of thumb: if you can cross cleanly and you want the right, cross now — the next shift may close the door. Tuck in when you'd rather go left, and accept you'll be the port boat later.

📖 Want more situations like this one? Bryan Willis's The Rules in Practice 2025-2028 works through the rules as they happen round the racecourse. (affiliate link)

▶ Watch on YouTube ↓ Download (via YouTube)
<iframe width="560" height="315" src="https://www.youtube.com/embed/_aEf2XlnraA" 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/_aEf2XlnraA/">Source: Sailing Kiwi</a></p>

Go deeper: books and gear

As an Amazon Associate I earn from qualifying purchases. If you buy through a link in the list it helps fund the channel and keeps the videos coming for everyone.

Next on this shelf — The Upwind Beat