If you're in the right city for it, sailing can actually be a really cheap thing to get into - some rich guy buys the boat and wants to do a bunch of races on it but it's really hard to keep a consistent crew so they're always looking for blow-ins. On 30-50 foot boats there's room for people who maybe don't know much but can mostly act as extra weight to hang over the side while they learn, and there's usually casual beer races that are less serious and don't have spinnakers upping the stakes. You can get on lists at a club for callup whenever they need people, the price of entry is really a six pack of beer and a pair of boat gloves. And the rich prick who owns the boat gets stuck with all the bills when all the expensive shit inevitably breaks. Fair warning though, you have to put up with a LOOOOT of chuds.

Offshores have a higher cost of entry cos of all the gear you need but honestly I reckon the sucky bits outweigh the good bits in offshores generally. But if you get to know the right people you can hitch a free ride on deliveries as a spare pair of hands, which is a lot more chill