I`m perfectly happy with my 250. I have owned bikes up to 1000cc (Ariel) and as small as 200cc (Bultaco). In August I took a trip to the Gaspe Peninsula with two friends on much larger bikes than mine. I had no trouble keeping up with them. Their only comment besides, "That`s a fast little bike." was that I had to shift much more often. It may have been a little more work to keep the bike in the "sweet spot" (8000RPM) in the mountains, but I certainly had great control. The only reason I can think of where I would need abigger bike would be if I were contemplating a sidecar rig. I can just visualize a Ninja 650R with a Lime Green Jawa sidecar.
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