I suggest this book, which has a lengthy section covering the peninsula.
Keep in mind that this is one of the most active cycling places in the country and rides go all-year round. If your BF is into training rides, they can be found every Saturday (Donut Ride), Sunday (Kettle Ride) and Tuesdays/Thursdays (Pier Ride).
The most popular recreational/scenic ride is the PV Loop. For hill climbers, you can go up and down hills and get a good 5-6k feet in about 50 miles. For a totally flat ride, you can ride on the bike path that extends 22 miles along the beach.
If you want to drive a bit, you can park at Malibu Bluff Park and take a scenic coastal ride (rollers) north to Ventura. For more ballsy stuff, you can hit the Santa Monica Mountains, where you might see the pros training. Every experienced cyclist should take at least one trip up Latigo Canyon Road.



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