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All Items are Medium. They fit me well at 5'8" and medium build (170 lbs) - KBC helmet (Dot/Snell) - 7.5/10 - Scorpion Gloves - 8/10 - Joe Rocket Textile Jacket with liner - 6.5/10 (missing a couple vent covers, a bit dirty) - Joe Rocket Mesh Jacket with liner - 9.75/10 (used only once)...

Been to Oahu, Maui and the Big Island (Hawaii). You can fly into Oahu or Maui direct (usually from LAX if you are starting in US, but flights between islands are cheapish and quick). Oahu - Waikki is like Niagara Falls. Depends on your thing. I spent a couple days there as a hub to explore...

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Here is a partial route I often do from Dundas. http://www.mapmyride.com/routes/view/44677622/ Edit: Messed that up just a little. Sulfur Springs to Mineral Springs, then to Binkley, Goveners to Wiers Lane. Sulfur Springs straight to Goveners turns into Gravel and Mineral Springs is a great ride.

It really sounds like you need a trail bike. Every manufacturer is building sub 30 lb, 5 inch, efficiently pedaling bikes now that a can take a beating (but as someone mentioned earlier, a smooth rider can get away with a 'lighter' bike). All these bikes will go fast with appropriate legs and...