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It's important to remember that we have different kinds of cyclists here and we may not all be talking about the same thing.
In north america, I think Portland is probably the best city besides Chicago as a destination for a laid-back bike vacation (e.g. riding a bike around a city). I wouldn't put Seattle on the list-- I was there in September and in terms of seeing people on bikes it was like Chicago in 1990 (plus unless you're a gym-rat the hills will wear you out in a 20-minute ride.)
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