A very long time ago we were rafted up in Honfleur and got invited to have tea and cookies on a Westerly Tiger. It's a nice memory of a half-dozen people chatting about boats inside a very nice, small boat.
As it happens, I saw a Westerly Tiger for sale up in Seattle for $1K and a lot of my positive reaction to the boat is related to that one evening of drinking tea, eating biscuits, and pleasant conversation.I mention this because most people feel a 25-foot boat is far too small for any sort of cruising and should be just for day-sailing and the occasional weekend at anchor. I'll even go along with them and suggest that if carrying around a lot of 'stuff' is an important part of your cruising style, then a 25-foot boat is not going to work for you.
On the other hand, if you're on a budget, a 25-footer is going to cost you a whole lot less to buy, cruise, and maintain than a bigger boat.
Size matters.
One of the reasons you see so many nice boats selling for not a lot of money is the simple fact that marina and associated costs are nuts in most places. So they go on the market because the outgoing costs are greater than the value of owning a boat they only use once in a while. A situation so bad, in fact, that far too often it makes more sense to give away a boat to stop the associated hemorrhage of money.
The problem, of course, is that cruising boats of any size are not a great vehicle to sit in a marina and run up bills. They're designed to cruise.
While it's going to cost you money to cruise, you won't have the monthly slip rent taking a huge bite out of your budget. For the most part, you'll be able to anchor, and while more and more destinations are starting to charge for anchoring, the beauty of cruising is that it's surprisingly easy to sail to places that don't.
Maintaining a smaller boat is a lot less expensive. Looking at the cost of haul-outs and bottom paint it does not take a math genius to figure out that a couple of weeks on the hard is going to be a lot less painful than a bigger boat. Our CAL34 reminds me of that fact every time I even think about the current costs involved.
There are a lot of 25-30-foot boats that will fulfill the sleeps two, feeds four, and drinks six checklist of what you need in a small cruising boat, just like the Westerly Tiger, providing you are not addicted to carrying around copious amounts of stuff you seldom use.
Worth thinking about...