As you are asking the question on the Cat. 36 web site I have to believe that you are considering this make and model.
As a fairly recent entry into the world of sailing I can't speak from a broad base of experience but I can talk a little about the C36 from my personal experience and perspective.
I looked at a lot of boats to buy and in the price I was willing to pay and the C36 became the front runner mostly because of the level of value for the money. Additionally, the large fleet size and solid reputation of the company played into the decision.
This is an easy boat to sail, one I have sailed single handed in a variety of conditions with ease if not elegance. I'm sure I don't wring every knot out of any given condition and I know I am often ham fisted when handling the boat, but I have never felt endangered or out of control.
I have cruised all the grounds you are talking about and have found my 36 to be a pleasure to sail and live on while cruising. It is easy to take out for an hour or for weeks at a time.
As to four people, it is just my wife and I or even just me, and the boat is plenty big enough. It sounds like you are accustomed to a smaller boat so the 36 should be a great trade up.
My 36 is several years older than what you are talking about , so there are some differences but don't let age be the only deciding factor. I decided to reserve 30% of my purchase money to fix and upgrade my purchase and though I haven't spent the whole 30% I have come close. No doubt a newer boat would need less upgrading or fixing but that is a large variable with condition of the boat, wish list and, yes, luck influencing the outcome. As you are not new to boats, I'm sure that you know what I'm talking about.
Should you get a 36, get some good "one on one" instruction from an experienced source on handleing both in the marina and out. Don't skimp on this. Practice on all the safety related issues that are unique to sailing in general and sailing a medium cruiser in general.
There are many choices out there. If stability, safety, ease of handleing, availability of parts and expertise, comfortable accomodations, good looks and reliability are on your list, then the Catalina 36 fits the bill.
Give a wave if you see me on the sound.

Hi Marcelo

I’ll be the first welcome you to the light, when you do actually make the switch.

I have two points,

1) Family issues - You mentioned you’re a family of four. How old are your kids? If they are older teenagers or young adults, perhaps you may find 36 feet a little confining after a while. If they are younger, I think there will be enough room for the grown ups plus room for the kids and an occasional little friend or two of theirs. Ultimately though, weather or not 36 feet is too small or too large for a family of four depends on the family and how much “togetherness” they’re comfortable with.

2) Going larger – If your family is younger, you probably should stay at 36’ or perhaps go smaller, say around 32’. Depending on your family’s age and/or their sailing experience, you may find you’re more/less solely responsible for operating, sailing, navigating, etc. the boat. Between that and keeping the little ones safe, it may be too big a job on a 36’ or lager. Another downside of going larger is everything (nuts, bolts, cleats, sails, light bulbs, etc etc) is one or two sizes larger, or, there are more of them so repair, replacement etc, not to mention the usual ongoing maintenance is going to be much more expensive.

Bottom lines, if the little ones are just that, stay at 36 feet or perhaps go smaller. If the family is older and (especially) if the crew can keep themselves safe and assist with navigation and your pocketbook allows, you may want to look at larger boats.

Let me second Neil's comment about obtaining instruction. It pays off not only in terms of safety, but also in terms of the overall enjoyment of the sailing (as oppose to motoring) experience.

Good luck with your search.

Another thing to keep in mind is speed. A sailboat is quite a bit slower than most powerboats. That can be an issue with some kids (adults too).

It is a different experience. You have to accept the fact that it will be a long ride to go anywhere. With tight schedules, it can become an issue.

You have to think about what you want to do out there.