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Old 08-05-2011
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I'm not one of those people who thinks you absolutely must have a 50' ketch to go cruising, but the Newport 27 seems like a small, inefficient boat for what you want to do, even if it is tough and reliable.

I have a Coronado 25, and this boat looks a lot like that, only a little bigger. The cabin layout is inefficient, the sail area/displacement ratio is low, and the boat doesn't displace much. Like the Coronado, it appears that they pushed the cabin out to the hull, so you don't have a side deck which can be a real inconvenience.

I submit to you that the Newport is a great training sailboat but that you shouldn't put another penny into her, and start looking for something at 30 feet. The boat market is pretty bad right now, and if you can unload your Newport, you'll be in the driver's seat when you purchase.

On another forum I frequent, we were discussing the Columbia River, and what happens when you sail "outside the bar". From what I've been told, it's not for the faint of heart, and you want a solid boat that you can trust.

In my opinion, 30 feet is the magic number. It'll have enough storage, enough wateline to go fast, enough displacement to sail comfortably, yet small enough to keep maintenance costs affordable, and small enough for either of you to handle alone. Of course, these are all generalizations, I'm sure that there are crappy 30 footers out there that don't meet these criteria.
Do your research and figure out which boats are good for offshore, so that you don't have to do a lot of "beefing up". Look for a cabin layout that makes smart use of space. Where is the galley? Where is the storage? Is there a lot of wasted space? You'd be surprised what 3 extra feet will get you: Standing headroom throughout the boat, 3,000lbs more displacement, more tankage, 2 more feet of waterline, more sail area.

While you're boat shopping, like others have said, learn "dead-reckoning" navigation (using paper charts), some engine repair, how to splice lines, basic damage control procedures, man-overboard recovery, etc, etc. Basic seamanship stuff.

Face it- when you're out in the Pacifc, pulling over and calling AAA when things go sour isn't going to work.

Good luck!
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