Where you look will probably be a function of where you live and what your budget is. The larger the budget, the more sense it makes to look further away. Obviously, if you live in the midwest like me, you are not likely to
purchase a boat locally.
I purchased my last boat in
Florida because the sheer number of boats there affords more selection and helps keep the
price down. It was also close to my likely cruising grounds. Related to something Maxingout said, is that most boats I looked at were not maintained from cruising - by far most on the used market I saw had been day sailed or let go since their cruising days. This probably relates in part to size as well. The
Caribbean probably has a higher percent of boats that are cruise ready, but obviously traveling to the
Caribbean to look at boats, hire a
surveyor, etc. will have it's costs. If you are looking at budget boats, it may be cheaper and less headache to spend more on outfitting.
What you need to get a boat ready, is not just a function of money, but also of your time, so you need to consider that. A
GPS charterplotter is an easy add on.
Wiring upgrades may be simple if you do it yourself, but take much longer. What you need will also depend on where you intend to cruise and your own priorities.
For coastal cruising, you may be able to take a boat used mostly for
day sailing, but in good shape and be ready to go with a few simple upgrades. Obviously most people will want more gear and a better reliance on boat systems for
offshore work.
The thing I learned in my first two boats was that it's not just about what the boat has, but the conditon of the systems than can make the difference between
day sailing and coastal cruising.
My first boat was a capable boat, but had only been used for day sailing.
I immediately added the following for coastal cruising: (Pocket cruiser sizes)
Autopilot,($700)
Solar Cells ($400), Second
anchor and
rode, ($400)
GPS ($150) increased
water carrying capacity (5 gallon jugs), Added
fuel tank ($80) Those things were fairly quick to add and the lack of them was reflected to some degree in the boat price. For about 2K I had added the gear to go crusing and doing so was fairly quick and easy.
What I had given less thought to at
purchase was that many systems had been let go which did not matter so much for daysailing, but needed to be addressed for cruising:
Head tank back siphoning when
holding tank filled.
Wiring an absolute mess which I eventually completly tore out and replaced. Some
plumbing not working well including 2 thru-hull replacments,
stove not working right, awkward reefing system,
storage needing to be modified for greater cruising gear needs and organization., new
VHF antenna, bimnii
repairs, anchor light, clanking wires in
mast, painting, window
leaks etc.
These items were present on a boat that had been day sailed, but not up to snuff. Identifying the issues and fixing them took a great deal of time, time that could take away from cruising time. Most fixes were not all that expensive, but added up.
Of course, that was just the first year....