There are lots of answers to similar questions about what boat to get or how to go about deciding what boat to get in the archives, so if you feel like doing a search you'll unearth a lot of really good advice already on this forum.
We went from a 2,000 poundm 17' outboard fishing boat to a 30,000 pound, 36' twin-diesel diesel cruiser in one step. However, we chartered a diesel cruising boat first to see if we even liked the power cruising "thing." We did, so after a bit we bought our own boat.
So the charter approach mentioned by others in this thread is a very smart way to go in my opinion.
However, my view on the "what boat to get" is perhaps a bit different than a lot of people's in that I put the type, make, and model of boat dead last in the quest for a boat, particularly for someone new to this kind of boating (as we were some 17 years ago).
I treat the whole thing the same way I would if I'd decided I wanted to get a computer and was trying to figure out what to get.
The first thing I'd do is draw up a list--- and it should be a long and detailed one--- of exactly what I wanted to accomplish with the computer. Write? Illustrate? Draw/paint? Financial stuff? Business management? Scheduling? Photo manipulation? Video editing? Internet exploring? Movie streaming?
Once I had completely defined what I wanted to do, then I would find out which applications were best for doing them. Microsoft Office? Photoshop? Adobe Premier? Illustrator? And so on.
Finally, when I had compiled my list of the ideal software to do all the things I want to do with a computer, I would find out which computer would do the best job of running the software I wanted to use.
To me, getting into cruising with a powerboat is no different. Forget makes and models for now. Instead, define what you want to do with the boat. Where are you going to boat? Where do you want to go? How many people will be on the boat? What kind of people will be on the boat? Just you? Kids? Grandkids? How about pets? Do you want to explore out of the way places or are you primarily interested in visiting the big and popular harbors and marinas? Do you want to live on it or do you want to just take short (or extended or both) cruises? And on and on and on.
Once you have defined exactly what you want to
do with a boat, then it's time to start listing what you want your boat to be
able to do, and what you want it to have on it.
Does it need to be able to take open water for long periods of time with it's changing and sometimes nasty conditions? Or does it need to be simply a good coastal cruiser? How many staterooms will it need? How many heads/showers? Will a full walkaround deck be beneficial? How easy does it have to be to get a big dog on and off? If you want to visit more remote places, how strong, versatile, and reliable does the anchor system need to be? Do you want to cook with gas (propane) or electricity? How fast do you want or need to go to destinations in the region(s) you want to cruise in? How many engines will best suit your requirements?
How efficient in terms of fuel usage/cost do you want the boat to be? (A lot of cruising folks want a boat that can go fast to get somewhere and then bumble along slow while they're there, and then go fast again to get home. This maximizes the time they can spend in a location if they have busy schedules or their boating time is limited.)
Is a flying bridge important to you for the view and socializing? Do you want big windows to look at the view or small windows that heavy spray or water from big waves won't break? Do you want large living spaces for comfort and guests or do you want smaller spaces that you won't get thrown across in rough water?
And on and on and on.
Once you have defined what you want a boat
to be like, which is based on what a boat
should be able to do in terms of your first, what-I-want-to-do-with-a-boat list,
THEN you can start finding out what makes and models of boats offer what you need.
At that point, in our experience and opinions, the search actually becomes quite easy because if you drew up your two lists accurately and completely, a huge number of boat types and models will have already been eliminated. All that's left is to check out the survivors and pick a winner.
This is sort of what we did after we chartered a boat to see if we even liked the whole idea. However, we had been creating partial "lists" for some years prior to this as we discussed off and on the idea of getting into cruising.
Starting by trying to decide on a make and model of boat first is, to me, the backwards way of approaching the whole thing. To someone new to this kind of boating especially, it can be very confusing and frustrating.
Done the other way round makes the whole process, at least in our experience, a hell of a lot of fun and relatively short. Our feeling is that we'd rather be boating than looking for a boat.