ToC shadowing or Mt. Hamilton hillclimb.
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One of these.
Shadowing Tour of California 2015 queen stage. 106 miles, ~9K ft climbing. Milpitas - Livermore - Mines Rd. - Mt Hamilton - Milpitas. Pros do it in 4 hours, I would ride for the whole day; ~13 hours.
Mt. Hamilton hillclimb; ~4K ft climb, same descent. Descent into San Jose is outright spectacular :)
I would plan for 4 hour climb, 1 hour descent. 20 or 26 miles one way depending on starting point.
Contact me for preparations necessary.
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