Where Do I Start?

[Weyalan]

Different strokes suit different folks.
Personally, I recommend looking for a GRP boat. Overall, GRP is the lowest maintenance.
I'd definitely stick towards the bottom end of your size range. 50' is an awful lot of boat for 2 novice sailors to handle. In the 35-40' range you will be able to get a boat with 2 decent sized cabins, a decent galley and saloon, and plenty enough storage. If in doubt, go for a smaller boat, not a bigger. Maintenance and upkeep cost do not increase linearly with boat length, but probably increase by the square of the length (a new mainsail for a 44' boat will probably be more than double that for a 36' boat).

[carstenb]

The bigger the boat - the more difficult things become. Just as an example - docklines. Big steel boat - very heavy boat - docklines will be minimum 25 mm (probably more) 25mm docklines weigh in at say 1 pound per meter. Now think about carrying a 40 meter line around (40 pounds - can you hold/swing 40 lbs in 1 hand?)

Docking a 50 footer is not easy and requires a lot of practice. So doing it single-handed is extremely difficult.

PM Dockhead - he has a 54 footer - I know he thinks singlehanding is very difficult.

Better to stick with something around 40 feet. This can be handled and is spacious enough for you and your son (if not - then you probably shouldn't go sailing).

I sail a 40 footer can do so singlehanded, although when docking in strong winds, I'm very happy indeed that we are two persons

[tomfl]

Originally Posted by Vasco

SNIP

I don't know where you are but a good start would be to join a boat club as a crew member and get some sailing in. Also you'll be able to see a lot of different boats and learn what you like and don't like.


As boats get bigger everything on the boat gets bigger, sails,sheets,halyards, winches, standing rigging, mooring lines, anchors, etc., etc. And replacement costs for wear and tear items gets bigger. I would stay just under 40 feet.

SNIP

Agree with this.

Reading about steel boats can be much different than sailing on one. Not saying it is not the right boat for you, just that you really don't have the real world experience to make that choice right now.

Same goes for cruising to Greenland. Nothing wrong with that destination, but sailing on someone else's boat in even a normal Florida winter will at least give you a feel for what it is like to go out in cool/cold wet weather.

Just hanging out at a sailing club and talking can help you get up to speed.

[dohenyboy]

How much of a learning curve do you want? To cruise on a sailboat long distance takes lots of preparation.
You might think about the heresy of lets say a 43' Hatteras.. Under $50,000..more room.. Hang around the Exumas or Abacos. Less brain damage, more fun than bashing to windward. Lots of sailors motor more than sail due to weather.


Sent from an undisclosed location on the high seas or from the lounge chair by the pool, you decide.

[7yrsorless]

Since you have a year why not go to the crew wanted section on here or your local marina/club and try that first then buy yourself a cheap small boat (lots $2000 to $3000 range ) and see how you like it... This is the rest of your life your talking about and taking courses is an excellent idea but actual experience is priceless. Smaller boats can be lots of fun and then you'll know for sure if it's what you really should be doing with your life not just a dream. Don't get me wrong is an excellent retirement plan..mine starts at 46 too!! My husband and I have been working towards this for 10 years now..we started with a 25 footer...way to small but lots of fun and an excellent boat to learn on. Now we have a Seafarer 38 and it's just the right size for us. With a bigger boat docking is a huge challenge...though if you where just planning on using it as a floating condo then go for it but it doesn't sound like that's your plan.