I assume you've read the reviews of the Osprey triple here - it sounds like people like it a lot. Of course most reviews are a 9 or 10, so must be taken with a grain of salt.
Having paddled many CLC and Pygmy boats, I would choose the Pygmy design without question. Newer CLC designs look good, particularly the Nick Schade designs, but the Chesapeake is a pretty old and boxy hull. The Osprey series is a more sophisticated design, in my opinion.
1 Canoe/Kayak Trailer
Recreational Kayak Paddle
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