Here is how I am learning to sail - and it is working very well so far...
I bought 5 sailboats in a "backwards" order. Instead of buying a small boat and getting bigger, I bought a big one and went smaller... haha! I retired early at only 29, so I decided to buy a huge Benetau 32 foot sailboat. Then I realized I only had time in passagemakers like my dad's nordhavn of 50+something feet. I took the boat out a few times with my dad to see how things went after about 5 books on sailing. I knew enough "book" knowledge to actually do everything properly, but had no physical time on the boat, so I didn't do as good as I probably could have. My wife and I thought we should get something smaller and less expensive to learn on and one which was easier to handle, so along came boat #2, a lancer 28 (which is my favorite by far).
I packed up the boat and trailered it home after 15 days on the water with a logbook full of to-do's and notes.
Next, I bought an 8 foot cat-rigged dinghy
with a loose-footed sail and a 2 hp kicker to get me out of times where I get caught a mile from shore without breeze. My 28' sailboat came with a clamshell dinghy
and sails but it wasn't "pretty" and that bugged me for a while.
I learned REALLY fast in the cat rigged dinghy
, and took what I learned back to the big boat.
A couple of weeks later, I went to a course for ASA which taught me basics (at that point it was a waste of money) and then worked up to higher winds and heaver keelboats. I finally took a course on Cruising in blue water and that was disappointing, as we couldn't have any practical time because I don't have any blue salty water around here.
So, I went on to purchase sailboat #5, hahaha! I bought a Dynamic 13 foot dinghy
with a 110 Genoa and main, all of the adjustments of my large sailboat, and this increased the ability to learn, and not be worried about tipping the boat over, or handling the boat inproperly. This boat, because it has all the same lines
and adjustments to the sails as my big ones, has really been the most beneficial.
I have learned how to sail in light winds, which I think is the most important, and I'm still figuring out my storm sailing. I like the smaller boats more so than the larger ones, that we have put the Bene back up for sale and we will use the money to pay for the final resotration on the older lancer.
The best thing I can say is that if you're in good health and can do tasks without "assistance devices" like anchor
windlasses, you'll be fine with sailing. There are a ton of people your age at my local marina and they are so cool to hang out with and learn from.
I've also noticed that younger sailors have smaller, less comfortable boats that have less draft, and more tenderness. Older couples prefer a Large comfy boat that has a beamier (over 9 feet), less tender hull. If I had to do it again, I would have bought a cheap daysailor with fore and mainsails to learn on for about 6 months, then bought a large liveaboard boat after searching out what I needed and what I would like about a large boat, besides the smell of new paint
and wood finish.