Since you mentioned brews, you may want to make a stop at Stone Brewing Company in Escondido, CA. They have everything from light beers to their Vertical Epic series, which is close to mead. They are my second favorite brewer in California behind Lagunitas, which is another hour north of San Francisco in Petaluma. Petaluma is a cool spot, because they have the Lagunitas Brewery with a cheap motel 2 doors down, and are near Drake's Bay Oyster Company, which has the biggest and best oysters in the country, IMHO.
Santa Cruz will be a cool stop for a skater. I grew up just over the hill from there. When you leave Santa Cruz, consider taking the long way out: Highway 9. It leads up into the redwood rain forests, complete with banana slugs and salamanders. At the top of Hwy 9 you'll find Skyline Blvd., which is the sport bike mecca for the SF Bay Area. The famous Alice's Restaurant is up there.
Your timing is pretty good as far as the Sierra mountain passes opening. Tioga Pass (Hwy 120) is scheduled to open May 11. If there is still ice or bad conditions when you get there, just keep heading north until you find a clear pass. Each one is different. Hwy 120 is stark and rocky with huge cliffs; about as opposite from FL as you can get. Hwy 108 (Sonora Pass) is forested and rocky, with some great views of alpine meadows and lakes. Hwy 4 (Ebbets Pass) is a crazy one lane supermoto haven. That's where the redwoods are, and they have Snowshoe Brewery in Arnold. Further north, you'll find Highways 50 and 80, which are the main corridors, and pretty much open year round. Lake Tahoe is worth a look too. You can ride the tram to the top of Heavenly Ski Resort, but it is rather expensive.