There is no one simple answer.
When a CG inflatable
came alongside my boat while I was under sail, they came to leeward. But their boat was low, and the wind was light, not lee rail down by any mean.
When I wanted to swap crew with another sailboat while sailing, I had them approach on the weather
quarter. We only overlapped slightly...the crew jumping from their bow to my quarter. I held a steady course. The overtaking vessel could head
up at any time, which would avoid collision
and slow his boat too. His "racing" boat had trouble catching up to my cruiser (to my delight), so I eventually had to spill the main a bit (with great aplomb, to my friend's chagrin). The two crew members transfered were only 10 years old, but the maneuver went smoothly. So much so that the crew insisted on repeating several times, until they realized I had the better/faster boat (with tv), and they stayed with me.
When a powerboat, adrift, needed a jump, I rolled up the jib
and sailed slowly upwind to him. Once we had a line, I let the main luff, in irons. Being a calm day, we stayed like that for 10 minutes or so while I removed a battery
to send him...his jumper cables
being only a few feet long. I now carry extra long cables
, since this seems to happen a lot in my area.
The big thing to keep in mind is not to foul the rigging
. So two sailboats underway should stay away from each other. Be very careful around square rigged ships, as their "yards" protrude aloft quite far.
For boats at anchor
, for just a quick GAM, I like to buzz the stern while under sail. With no engine
running, you can actually hear each other. Also, you eliminate the risk of catching their anchor
line on your underbody, which is a very real risk. When approaching in a dinghy
, I also approach from the stern, so they can see me coming, and shut off the outboard
as soon as possible. If they offer to take my line, I know they are keen to chat, otherwise, I just drift away....