I plan on retiring very soon and am thinking about a new boat as a reward to myself for many years service, a gold watch so to speak. I am sort of thinking about building a Pygmy, but on the other hand that would delay using it, another option is a Current Design, probably a Caribou.
thoughts? waters would be the typical places people go here, not ocean although yeah, Great Lakes

If you can buy a production model you're happy with and don't have a strong desire to build then you might as well buy one, assuming the price doesn't bother you. It will hold its value better in case you decide to sell it and you can also look around for a used one.

If you have a strong desire to build then I say do so.

Alan

You'd have better resale value buying a well known brand rather than a hand made one if you think you might try a different design in a couple of years. But building one is very rewarding, good for the soul.

I would build your own check out of a Chesapeake Light Craft kit.

CLC Boats

FYI: A Chesapeake 18 is a big kayak. :-)

I have a clc chesapeake 18. I used the standard plan with the addition of a rudder and two rod holders for trolling behind the cockpit. I take it out on Lake Michigan all the time and it has been in the BW/Quetico maybe a dozen times. While a kayak is a pain at portages, there is nothing like it on big open water. Handles wind and waves far better than a canoe. The clc 18 is very stable and easy to handle, and holds me (225 lbs) and a lot of gear. It is not that heavy and there are plans on the net for making a portage brace for it. It was well worth the investment and time. One note - a wood boat required a bit more annual maintenance than a glass one.

I built a Chesapeake 17 about 15 years ago. I too put the rudder kit on it. Mounted a compass on the deck just in front of the cockpit. It has elastic straps on the deck to secure larger gear that will not fit in either of the storage compartments.

It's a fast boat and built like a tank.

It's been to the bw about 3 or 4 times.

If you are planning a bw trip with minimal portages it's an OK boat to take along.

I would not take it on trips where you are portaging all the time.

Have a CD Caribou. Off the shelf. That said I have paddled the original Caribou from Barry Buchanan out of Bass Harbor ME. The original is basically a plywood craft.

Barry is into motorcycles now and sold the Caribou design to Current Designs some years back. Its tried and true in Maine in the ocean.

Lake Superior behaves for the most part like the Gulf of Maine.. the former is a bit choppier..the latter tends to 6 foot rollers with the fetch from Africa.