How to Sail a Cutter

A cutter rigged boat, often referred to as simply as a "cutter," is a monohulled sailboat that has two or more headsails. The added headsails allow cutters a level of wind versatility and easy handling that few other boats possess. To sail a cutter rigged boat follow these steps.

Instructions

Difficulty: Moderately Challenging

1. Learn the difference between the foresails. The two or more sails forward of the mast serve different functions in different weather. The outer most headsail hangs on the jibstay and is called the jib or sometimes "yankee." The inner headsail hangs on the forestay and is called the staysail. The staysail is usually significantly smaller than the jib and so serves different purposes in different weather situations.
2. Tack the cutter like a sloop. Since a cutter is essentially a sloop with multiple headsails, all you need to do to tack is tend to the jib. Almost all modern cutters have self-tending staysails that act like the mainsail during a tack. So, perform your tack normally with one crew member attending to the jib and keeping an eye on the staysail to make sure it tacks without getting fouled.
3. Use the multiple headsail configuration for versatility. Couple cruisers and single-handed cruisers love the cutter rig because it allows for quick transformation of the boat in different weather conditions. If a sudden strong wind picks up drop the staysail to the deck (or furl it, if it's a furling sail) and sail on the jib.
4. Get the staysail out of the way downwind. On deep reaches or downwind runs, the staysail tends to create a layering effect that robs the jib of wind and create troublesome turbulence across the boat. If you need to sail on a deep reach or downwind (two non-ideal points of sail on a cutter), drop the staysail and fly wing-on-wing with the jib and main. If you don't want to drop the staysail for some reason, let it luff into the lee of the mainsail.