looking for my first boat

You may not want to hear this, but I don't think you are on the right track, because you are looking for too big and complicated a boat for your first boat. Lots of people make this mistake and end up not using the boat as they intended (or worse), simply because they lack experience in handling and maintaining such a large boat. You mention refitting.... you need to realize that even if you pay others to do the refitting, you will still need to make many decisions about what to fix or change, how to do it, what yard to use, who to hire to do it, how to monitor their work, whether or not they are delivering for the money you are paying them, etc.

My recommendation would be to start out with something 35 feet or less that is maybe 10 - 15 years old and well maintained, as judged by the best surveyor you can find. Then enjoy that boat while you become an experienced sailor, cruiser and boatowner. There is a lot to said for coastal cruising which is what you would be doing with a smaller boat. And if you are near the Caribbean, a lot of boats in this category would be very capable of cruising there.

Spend maybe $30-40k on this first boat and sock away the rest of your money until it's time to get the dream boat.

Learn how to maintain and fix the boat yourself. Get one with a good diesel engine and learn how to maintain and fix that engine. If you ever do long distance voyaging, you will have no one to rely upon but yourself to fix things when you are thousands of miles from assistance.

Then after a few years of this you will be better prepared to decide whether to buy that $160k boat to take you over the horizon.

thank aferlazzo. these is my thing, originally i wanted a benneteau but according to what i read it is not a boat for my cruising plans,regarding maintain and fix a boat:, i can do electrical ,plumbing,wood work and my brother works for contender which is a open fish power boat for 16 years he can do a lot on a boat from lamination to electrical and i can also buy most of the equipment at very big discounts(engine,electronics...). are they complicated because they are old, lot things to fix? or the way they sail?Another thing Buying a boat that i am not going to keep for long when is time to sell i will lose money and probably would take to long to sale .So , my thinking is buy something that i will use for long time and learn from the beginning with it.What do you think about beneteau??

Kind of reminded me of my recent aquisition

I had the bug up my butt to try something new, so on an impulse I ran out and bought a mandolin. But if I do not like playing it it is $150 I can afford to loose.

I have to agree to aferlazzo on this one. If you have just taken your first sailing courses and know nothing about boat ownership or whether or not your family will be scared the first time the boat heals past 10 degrees, a 40+ foot boat and a 160k is a lot to invest in an experiment of boat ownership.

The expense and complications of owning a boat of 40+ feet is magnified many times over that of one 30 feet. You could buy a Catalina 30 (not necessarily saying you should buy as C30 just an example) for less than 20k to learn to sail on while you learn about maintenance and what you like in a boat. If in the end of a few years you could give the boat away and be ahead of the learning curve and expense of buying a massive boat.

A smaller boat would be:
Cheaper to buy
Cheaper to own
Easier to fix
Easier to sail, without a large and knowledgeable crew.
Put the rest in the bank, no stock market, no, under your mattress so you can buy a bigger boat when your family also think visiting Brazil by sailboat is a good idea.

Donde esta?
I have only sailed on a Bene First 51' for 400 nm offshore. The boat had crossed the Atlantic several times before I got on it. I believe that the 'First's are racing models and the 51 I was on is an ocean racing boat. Not so terrible, in fact, a decent boat.
I like the other makes on your short list and with your budget you are looking to buy used. I also like older boats for less money but that is just me. You have to satisfy yourself ultimately.
Have you considered the rig? Sloop vs. Ketch vs. Yawl etc? Ketch and Yawl usually have shorter masts and heel a little less but may not point up wind as well.
I bet you could pick up a certain Allied Seawind Ketch that I sailed on which is in Miami for under 15K. It is pretty bare bones but has nice sails and a working engine.
There are a lot of boats out there.
Good luck.

je & after

you are making generalities that do not fit everyone.
I bought my first sailboat last spring. I did not take any asa classes nor any other sailing classes. I had about 10 days on the water on other peoples sailboats over my lifetime. I did own a 26' power boat for 15 years.

I'm doing very well sailing my Endeavour 42. At times I'm not happy with some aspects of the boat but ALL boats are a compromise and I quickly remind myself why I accepted the compromises I did. I researched sailboats for 2 years before buying this one. I have been putting in a lot of work on repairs and upgrades. There are no major issues with my boat, only routine stuff that needs tending to and some upgrades in electronics, like a radar & chartplotter.

We'll be heading out for long term livaboard cruising next year.

Vitor

Do you really need to stick with such a short mast? That will limit your selection, probably to ketch rigged boats only.
Keep in mind that you will find 5 times as many things to attend to as you think at the time of purchase. Do not discount the effort to do something as simple as changing out old hoses. I have not had to put in tons of money but I'm doing all the work myself. I have a lot of hours into simple stuff like the hoses. Save at least $30,000 of that money for the refit/upgrades. Plus taxes, survey, insurance, etc. It does add up!

Last thing...do not be in a hurry. Take your time and do the research on different boats, rigs, equipment, and go look at a lot of boats.

Some more considerations

Mandolin player and kitesurfer, you might be an alright guy.

I still think you should by a smaller boat to sail while you figure out what exactly you want in a 40+ foot cruiser. Get a good deal on a small boat and it won't be too hard to sell at a slight loss with a lot of learning and sailing in the mean time. In the mean time you can take your time to study up on bigger boats and choose the right type and the right boat. I have never owned a boat bigger than 22 feet but have spent 20 years sailing off and on and racing other peoples boats, hanging out at the marina and reading tons of stuff on sailing. I would not know what kind of boat to choose in this range as I have never aspired to anything bigger than 38 feet. I have read plenty of stories of people haven taken on too much boat and not ever leave on their trip or running into too many issues to make the trip enjoyable. As Xort pointed out a newbie can make a good first go at sailing a big boat. He did however take 2 years to figure out which boat he wanted and still contemplates the compromises he had to make.

I am not sure of your location and setup but it does not make sense to me to limit your boat's draft or mast height just to have it a few blocks from your house, when the long term goal is to take cruise it long distances. I would opt to have my boat and condo on the other side of the bridge if that is where the sailing is to occur. I would rather spend 20 minutes driving to my boat than 1 hour motoring the boat to the sailing area. You will get more sailing in that way.

Walk the docks and look at the boats you like. Maybe spend weekends scoping out the marina and if you find an owner on his boat they will most likely be willing to show you around and talk to you all day long about their boats.