Matthew loves Hog Island Oyster Company. Expect misty fickle weather and an awesome cliff-filled drive. Order the BBQ oysters. Best eating: Hog Island Oyster Company (reservations recommended), Cowgirl Creamery, Olive Oil Tasting at McEvoy Ranch (reservations recommended). Best hiking: Anywhere in the Point Reyes National Seashore. Alternatively, drive down the coast to Muir Beach & take a trailhead along the cliffs from there.
Los Gatos is pretty much home base for Erin's family. Nearly every day begins with an early morning run to the Lexington Reservoir followed by coffee. Best coffee: Manresa Bread (the bread outpost of the famed Michelin restaurant, Manresa), Cafe Dio, Great Bear, Los Gatos Coffee Roasting. Best eating & drinking: Los Gatos Cafe, Oak & Rye, Icing on the Cake, Left Bend Winery, Loma Brewing Company. Best trails: Los Gatos Creek Trail to Jones Trail to Novitiate Trail. Be aware of mountain lions, bobcats, steep inclines, and competitive runners.
Carmel is all about the coast. Take a drive. Wind through the art galleries. Find your way to the mission by following the mission bells. Go to the sea. Best doing: 17-mile drive, Point Lobos (look for seals, sea lions, otters, whales), Monterey Bay Aquarium, Carmel Mission. Best eating: At the world famous Monterey Bay Aquarium's wonderful displays of regional habitats, Matthew likes to point out how many species can be canned. For more fresh options, see https://sf.eater.com/maps/best-food-drinks-monterey-carmel.
There are closer vineyards (some very close) and it's a bit of a drive, but so long as you're here... Our favorite spots include the Oakville Grocery and Glen Ellen Star to eat, and tastings at Cakebread, Paraduxx, and Stag's Leap (you figure out which Stag's Leap).
San Francisco is a fantastic city and nearly every time we head out on a road trip in California, Matthew wants to make a "quick" stop at the Ferry Building. Two hours later, we're usually ready to leave, right on time ;) Best eating: Ferry Building, Pizzeria Delfina, burgers if you're lucky at Butcher Shop (by Niku Steakhouse), Bi-Rite Creamery, Tartine Bakery. (Other recommendations, https://sf.eater.com/). Best doing: San Francisco Giants, Alcatraz, Golden Gate Bridge. Best to buy: Heath Ceramics, Monocle Guide to San Francisco.
Update: As of Summer 2020, we're so sad to report the Big Basin's historic center is CLOSED due to wildfires. We just didn't have the heart to remove it from our list. Big Basin is the best place to see Redwoods. It's California's first state park & filled with tall tall trees. Most people head to Muir Woods (which is also awesome) but we like Big Basin a lot better. Consider it your hidden gem. Big Basin is a short but windy drive from either Los Gatos or Saratoga. While you're up there in the mountains, check out one of our favorite wineries called Loma Prieta Winery. For other local wineries, we recommend: Big Basin Winery & Ridge Winery. Keep going over the hill to Santa Cruz if you're surf bound. On the edge of town, Natural Bridges State Park is a beautiful (often chilly) beach and a layover on the monarch migration. Verve Coffee downtown pulls a decent espresso.