I'm 75, and still sailing.
You haven't told us where you are now. If there is a lake or bay near you, you can start now. Time on the
water can be a good thing in your life, on so many levels.
Are there
sailing lessons available where you live? That would be a good start.
Look into
marinas close enough so you could use a
boat for day
sails. I would say an hour's drive, maximum.
If the above possible for you, I would suggest that you get some basic sailing skills, then buy a 20 foot
trailer boat, with a swing
keel. Moor it in a marina with similar
boats for the sailing season, and store it on the
trailer in
winter.
As long as you keep your
head out of the way if the boom swings across unexpectedly, and you stay in deepish
water, with basic sailing and
navigation skills, you can learn a lot in a short time. If you're in a marina with similar boats, you'll have a sailing community. (Beware of 'my way is the only way' syndrome from fellow boaters. We are an opinionated group. Don't spend time and
money on anything unless you really need it)
You can sail, with very little effort on
roller furling jib alone! Don't be afraid to
motor sail if you need to get in before dark, or it's just time to be anchored for lunch.
The real sailors on the list may have things to say about this, but a masthead rig with a 110 to 145%
genoa jib, and
roller furling, can be sailed on jib alone. That's what I have done most of the time for over 40 years, if
destination is not important.
Just to get out, for a day sail, or for a distance if there's enough
wind.
At 75, I just want to get out there, go from point A to point B, and enjoy it.
I roll out the jib, put on the auto pilot, and sit back and relax. I won't win any races, but the boat points high enough to tack upwind.
You can do everything from the
cockpit; roll out the sail, roll in some sail if there's more
wind, roll in the sail when you're done for the day.
Of course, you do have to be prepared to go forward and deal with things, when something goes wrong. With a properly installed
roller furler, that seldom happens.
(I an a big fan of no swivel furlers, like the CDI)