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Took offshore sailing school's basic keelboat certification, stretched out to 5 days so my waifu would have plenty of time to learn the basics. It's pricey but good, and the colgate 26 really is forgiving. The solo sail when it was just she and I hove to and having a picnic off in the middle of the BVI was fun af. We did some sailing on a relative's 31' hunter last year and hope for more this year, maybe even without 'uncle john' on board. There's a local sailing club on the Hudson River that one can join for ~1000/yr, but their equipment is super old and basic. 21' daysailors with no outboards, etc, so you hope that the current is right and you're not up against a lee shore.
We're saving for a world cruiser of some kind but in the mean time want to drill rigging, muscle memory, helm control, so I'm just building a sailing dinghy this spring from a CLC kit. The options for a first boat seem to be:
1) Buy a lazer/sunfish and hope the glass is in good shape, seems to be 2.5-8k
2) Buy an old trailer sailor and any problems it might have for 4-10k
3) Build a cheap sailing dinghy from a kit for ~3-4k
4) Go balls out on your first boat and hope for the best
Option 1 was surprisingly more expensive, and some of the sunfish I've seen for the lower end of the price range were really ate up and 70s-models.
Option 2 seems to be rife with cheap daysailors but you need something to tow with and a place to launch, and they also have more potential problems than a smaller boat. If you spend more than a few grand, you risk distracting yourself from buying a real boat down the road by dumping cash on your training boat.
Option 3 is what I went with, for a few reasons. You'll get experience dealing with wood, epoxy, and fiberglass, setting up your own rigging, understanding how the boat is assembled, and using basic hand tools. You'll have a cheap boat that you can throw on top of a car and sail almost anywhere. Looking forward to summer.
