Join Date: May 2011
Location: Auckland New Zealand
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Single handed sailing under 45 foot
2 boats to consider: the Dufour 405 Grand Large, this was European boat of the year in 2010. The other is the Jeanneau 409 which was European boat of the year in 2011.
You can have a self tacking jib on either of them. You can also add a motorised winch to help putting up your main or have in-mast furling.
Both are great boats,I have actually just bought a Dufour 405 to sail on my own when required.
The two boats also have very good headroom and are configured to sail single-handed with all controls in the cockpit at hand.
Another option but bigger and pricier would be the Hanse 445. This has a self-tacking jib as well.
There are others but the 2 I have listed have a good reputation and are well built production boats and well priced.
I have to admit I have just acquired a Dufour 405 having spent months researching the boat to suit the same purpose you have listed.