Docking a sailboat under sail can be one of the trickier maneuvers you'll ever need to make, and many sailors with boats with an engine never even try it. Obviously a small, engineless sailboat must be docked under sail, making this an essential skill when you first learn to sail, but owners of larger boats with engines should also develop this skill if for no reason than the engine can die at an unexpected moment.
Besides, docking well under sail can be a source of pride and impress other sailors as well!
Docking under sail can be difficult due to wind direction, dock layout, currents, etc. Yet if you always think ahead and follow the steps below, you can learn to dock almost anywhere under sail.
Step 1: Consider Your Boat
Because docking under sail requires complete control of the boat in a variety of wind and current situations, it's essential to know your boat's abilities well. How quickly does it coast to a stop when no longer propelled by the sails? How tightly can you turn it? Even at low speed? In a pinch can you stop its forward momentum by backing the mainsail, braking with the rudder, or in a last-ditch effort throwing a line over a piling or cleat and gradually tightening it?
Consider also your sails. It is generally best to make the final approach under one sail only, in part because you should need only one sail to keep moving and it's much easier to manage only one sail at the last minute. Many sailors with furling jibs prefer to dock with only the jib, since you can roll it in gradually to reduce speed while still maintaining control. On a boat without a furling jib, it's usually better to use just the mainsail, which can be luffed to slow down, sheeted in to slow if the wind is from behind, or backwinded to brake at the last moment. Because of these advantages, some sailors even with a furling jib prefer to use the mainsail to dock.
If you have never docked your boat under sail before, get to know it better first by practicing in open, calm water. Toss a fender or other float overboard and pretend it is the dock face; see if you can approach and stop just beside it (with the wind at different angles) without running into it. This is also a great skill to have in a crew-overboard situation.
Step 2: Plan Ahead
Before making your approach to the dock, study the wind and any current present. If necessary, practice once stopping in the water just outside the docks. Sailors are sometimes surprised by a following current that makes it difficult to stop at the last second before hitting the dock.
Also study the dock layout and consider where the wind will be in your final approach. If ahead, you'll need to approach close-hauled at an angle and then turn into the wind at the last moment to stop alongside the dock. If from the side, you can luff up or spill wind to slow and coast to a stop. If from behind, plan to approach very slowly with the mainsail in fairly tight so that you aren't blown forward at the end - and prepare dock lines that may be needed for the final stop.
Also prepare your fenders and dock lines well in advance. Put out more fenders than you think you'll need, in case the boat is blown at an unanticipated angle at the end. In addition to bow and stern lines, have a long line ready amidships as a spring line in case you need to loop it over a piling or cleat to assist in making a final turn.
Step 3: The Approach
As already mentioned, use only one sail - the best for the specific situation. If a furling jib, bring it in as much as you can while maintaining forward motion for steering; slower is better. If the main, plan either to luff up or trim it in to slow down as needed, depending on wind direction.
The ideal docking situation is an outside dock where you can coast in at an angle and stop alongside. Just approach very slowly at a shallow angle. If you must come in to an inner dock or slip, watch the wind very closely and approach at your slowest speed with a clear plan how you will make a final turn and stop the boat. If a current or the wind is from behind, particularly with a larger boat with more momentum, proceed very cautiously with a clear plan for how you will stop the boat. You may have to roll the jib in all the way at the last minute, for example, or harden up the main so that it does not draw at all.
Your crew should be ready with dock lines and, just in case you stop too far off the dock for them to step off, a boat hook that might be needed to grab a cleat and pull the bow over.
Assuming you know your boat well and have planned ahead, the last step is to bring the boat alongside the dock very slowly and stop. The stopping part is obviously the most critical. Roll the jib in all the way, flatten the main if the wind is from behind (or backwind the main by having a crew push the boom out if the wind is from ahead), and have crew ready with dock lines to step off and cleat the lines for the final stop. Remember that the rudder makes a good brake too: throw it all the way over at the last moment if you need to slow more.
As with most sailing skills, practice makes perfect. We've all seen old-timers dock boats under sail in "impossible" conditions - but they weren't born that way. Go out in some calm water and practice docking by a floating fender until you can do it well, and soon the real dock will be much easier to stop alongside.