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I have been riding somewhat regularly for the last 6 months using my mountain bike on the road. I would like to step up to a road bike, and have tried several and really like the feel of the Cannondale Synapse 5 alloy. My question is will it stand up to my weight (260 down from 300). I plan on 50 to 60 miles a week and building from there. On another note what is the largest tire size I will be able to fit on this bike.
 

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I think so, you won't have a problem at all.
I've riden Cannodales for years. Never a problem with my weight.
I was at 265-275lbs at my heaviest, these frames are solid, and they have an awesome warranty. ( They also helped me go from 275-225lbs, without an issue).

Side note: You will probably have more problems with components, especially rear wheels. I would recommend a 700x 23C perhaps a Vredestien Fortezza. Large and comfy tire. I would recommend triple cross spoke wheels, or 24 spokes in the rear at a minimum. Very solid!
 

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Try 700 x 25c tires and a 32 spoke rear wheel :)

And you'll be fine putting that weight on a Synapse. I started at 240 without any problems at all.
 
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