Re: How to go for 1 or 2 year cruise?
First know that I departed Lk Michigan out the St Lawrence in 2008 and just completed an around the world. I loved the Gaspe, NF and NS!
Your question is really a big one, so many variables. Purchase price of 20-30k limits the field a lot making it difficult but is doable. If you want a strong sea-going vessel look for something like a Baba 35 or Cabo Rico. Problem will however be finding even a 20 year old boat of this quality for under 50k without having to put a lot of work into it.
The "plastic fantastics" like benny's can be fine but do require better sailing skills in heavy seas. The spade/fins do not heave to like the traditional boats but you can get a lot of boat for the money. My personal take however would be stay away from the older Hunters. The discussion of what boat could go on and on but you will be challenged to find a sea worthy boat in that price range if looking for 35 ft or larger.
The route to the med is not that difficult from NF or Halifax but in the normal passage period of May and June you can get slammed my strong gales north of about 39 degrees so some experience would of course help, thus a crew perhaps??
To get your feet wet so to speak consider going through the Bras d'Or Lakes and then down and around Nova Scotia to Maine and then down the US eastern seaboard working your way to your first winter cruising in the far Bahamas. You will love it and that is a good distance for a one year cruise from where you are.
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