Will you be looking for new or used? If used - how old?
If used: With hindsight after about 2-3 years of fruitless search in the early 2000s, and having found my 1st boat on c-list, I would recommend starting making rounds at you local boat yards, assuming you live in an area with active boat yards. 2nd step would be searching though sailboatlistings.com, they have an extensive selection FSBO. 3rd wold be active brand/make specific forums
. Only as a last resort I would look at brokers' listings or megasites such as yachtworld as they don't do a great job with older, less expensive boats and concentrate all their efforts on more recent boats, i.e. more profitable for them.
If new, the boat shows are probably the best place to start and even buy as I know a few buyers who picked up quite deals on close out models or someone else's cancellations. A friend of a friend a few years ago got a brand new decent brand 36 footer for $140K all equipped and ready to sail. It had a list price
of around $200K but was at the boat show
for $169K boat show price
. Then someone gave a non-ref deposit on it and couldn't/wouldn't follow through with the purchase
. So the manufacturer and the dealer wanting it to move quickly, let it go for the remainder of the price. Of course the fact that this was shortly after 2008 also helped.