Assuming you're starting out bright and early in San Francisco for your trip to Napa, your first move is to grab one of the city's exquisitely brewed coffees--take your pick between Blue Bottle, Four Barrel, Ritual and others. If you don't have time or patience to wait for pour-over action (totally understandable), no one will blink if you hit up Starbucks. Then, head toward the Golden Gate Bridge. Going under those orange arches is an experience, and if it's not too foggy, make sure to take a peek back at the city as you traverse the bay; it's an unbeatable view.
Once on the other side of the bridge, take a quick detour to the Marin Headlands. Take the Alexander Street exit and follow the signs to the coastal route, going only as far as the first or second lookout points--it's a perfect photo opportunity, with a view that captures the bridge and the city behind it.
Muir Woods — Photo courtesy of Stepan Mazurov
A little farther north, you can swing off route 101 and snake your way along to Muir Woods. It's easy to pop in and marvel at the giant redwoods without walking very far. Alternatively, there's plenty of hiking in both the Marin Headlands and around the adjacent Tamalpais State Park and Muir Woods, if you want to get in some miles before heading the rest of the way to wine country. Continuing north, Mill Valley has a charming downtown, with lots of restaurants and boutiques. Mill Valley Beer Works is a good place to stop for lunch, and there are lots of playgrounds around if you have little ones who need to work out a little energy.
If it's a Thursday or Sunday, the farmers market in San Rafael can't be beat for fresh California produce--it's where San Francisco's top chefs shop for fruits and vegetables. Still hungry? If you do nothing else, be sure to have breakfast or lunch at the Fremont Diner--it's one of the true wine country treats--excellent comfort food (chicken and waffles, fluffy biscuits, BLTs) made with ingredients from right down the road. The picnic tables looking out over the vineyards don't hurt, either.
Fremont Diner — Photo courtesy of Brooke Lewy
From there, continue east to Napa. Stop at Domaine Carneros to start your true Napa experience with some bubbly. Next, you'll pass by the Carneros Inn on your way. Stop in for a game of bocce ball or a massage, or continue on and cut to the chase--head to downtown Napa and the Oxbow Public Market, or veer north toward Yountville and the rest of the rolling hills of wine country.