Join Date: Dec 2008
Location: Calgary, AB, Canada
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If a 34' boat is rigged properly, it can be single-handed. An autopilot is nice, but not 100% essential. You might prefer all lines led to the cockpit, I am quite comfortable going to the mast.
I might suggest that you charter a couple of different makes with different layouts and configurations to determine what you like. I have some biases:
Slab reefing with a ram's horn for the reef tacks (I have had some single-line systems jam on me.
U / L / or J shaped galley with a centre-line sink.
If 2 heads - one of each side. If 1 head - sink close to centre line
Rigged for gennaker
Fractional rig with adjustable backstay.
A ketch can be balanced very nicely, while a sloop can be a little tougher. Do you want a boat that points (fin keel) or a more solid boat the sails more readily off the wind (full keel)?
Cruiser? Racer? Racing cruiser? Cruising racer?
In the end it requires lots of compromises, as no boat can do it all.
I could go on, but I think you get the point - look for one with your preferred set up.
As a novice you will need to learn how to single hand, an instructor is good idea. They are required to to be able to single hand.
Where are you located? Can you drop by a few dealers with boats at the dock and check out what is available?
ISPA Yachtmaster Ocean Instructor Evaluator
Sail Canada Advanced Cruising Instructor
IYT Yachtmaster Coastal Instructor
ASA 201, 203, 204, 205, 206, 214
As I sail, I praise God, and care not. (Luke Foxe)