caltexflanc
Guru
Trekker--- Something you might want to consider before getting all wrapped around the axle on trying to decide what kind of boat, how big of a boat, blah, blah, blah ad infinitum, is charter one somewhere for a week or two. Particularly if you are unfamiliar with this kind of boating but have a good friend who is and who will split the charter with you.
While chartering isn't cheap, it's damn near free compared to the purchase price of even an older used cruiser and worse, the annual ownership costs of these kinds of boats that never stop as long as you own the boat.
Chartering gives you the opportunity to see if you like this kind of boating and this kind of boat with no risk to you and no obligation other than paying the charter fee.
On the advice of a good friend and long-time boater that's what we did when, inspired by countless trips flying a floatplane up and down the Inside Passage, my wife and I began thinking it might be fun and a whole new kind of adventure to explore the same area by boat.
Chartering convinced us that we liked being out on the water in this way and that a cruising boat was what we wanted. So we bought one and 14 years later here we are sitting on it in a beautiful tiny bay all by ourselves this weekend out in the San Juan Islands; we still enjoy the hell out of using it year round just as much today as we did the first year we had it.
Chartering in my opinion is the best way for a "newbie" to discover for him/her self if this kind of boating and boat is right for them.
I second Marin's suggestion about chartering with a BIG thumbs up. Worked for us perfectly.
And yes, you will be having work done to your boat forever, how much only depends on your pride of ownership level, seaworthiness and safety concerns. Believe it or not, based on what we ended up buying, we fully support the "Don't buy the biggest boat you can afford, buy the smallest boat YOU can be comfortable in" dictum from Skipper Bob. It is a very personal decision, as is the definition of "comfortable". Only by spending extended time on the water cruising in different boats will tell you this with certainty.
If you only really boat a total of a month or so every year, renting/chartering is by far the cheapest way to go. You can get a captained charter the first few times, and learn a lot, especially if you take care to hire someone who is a professional teacher of new boaters.