Napa Valley is a truly amazing destination, and world-famous for a reason, but it can be big, crowded, and sometimes overpriced. As a Bay Area resident, I will fully admit to frequenting the neighboring Sonoma Valley for it's quieter & friendlier vineyards, but over the past few yeasr I've had the chance to get to know Napa as well, so I though I'd pass on some tips from a "local" to help you with your planning!
Places to stay: There are plenty of tours from San Francisco if you're thinking of doing a day trip, but to get the full effect of the joys of the valley, I highly encourage spending a night (or more) up there, and luckily there are tons of choices! First there is the very convenient Westin Verasa, which is located just up the street from the Oxbow market, and across from the famous Napa Valley Wine Train (a lovely, if slightly overpriced way to see the vines!). It is just a few blocks walk from downtown Napa, so you could get away with a visit without a car pretty easily. It's a lovely, relaxing property (as most Westins are), with huge rooms -most of which are suites, great programs in the lobby (like free wine tasting every evening), and of course a wonderful spa and year-round heated pool. Not to mention a Michelin-starred restaurant on-site (Le Toque)! With all that said, I might prefer my other go-to downtown hotel of choice, the Andaz Napa. This is a very cool, hip new brand (created by Hyatt) that is all about featuring the location, so the restaurant serves locally sourced foods, the award winning mixologists at the bar serve locally produced alcohols (& wines & beers, of course!). It is located right downtown, and is more of an "urban" hotel, in that it doesn't have sprawling grounds or a pool or anything, but for a quick getaway, this is the place I'd stay. Then there are some pricey & smaller inns as you continue north up the valley into Yountville & St. Helena, but there is one more property that I want to encourage you to check out if you're really celebrating something or want a flawless few days, and that is the Calistoga Ranch Resort. This may be the finest hotel I've had the pleasure of staying at, and that's saying something. Each suite features amazing indoor/outdoor living, with gorgeous kitchens, fireplaces, and ridiculous bathrooms (including outdoor showers!!). You would think that being outside in our own private dining/lounge area &/or our own secluded hot tub would mean you'd encounter other guests, but some how the ingenious design prevents you from all of that, other than a glimpse of a neighboring suite's wall or perhaps the sound of a golf cart whisking others to their room. Yes, you heard me, after you arrive at the front lobby house, valets take care of your car & luggage while a golf cart brings you to your suite. Needless to say, this place deserves it's own post & review, but you & your loved ones would NOT be disappointed with a stay here. (I'll come back & add photos when I can- they're sadly not available right now!)
Places to Eat! Before I get to some suggested winery stops, let's focus on Napa's other treasure, and that's great food. Downtown Napa does have some fairly decent restaurants, and of course Le Toque, which boasts a Michelin star, but to me it is more of a place to grab snacks after a full day of tasting, or perhaps to fuel up for the day. Oxbow Market is a newer addition to town, and it is a fabulous sort-of full-time farmer's market. There are lots of neat food & non-food suppliers, and of course some spots to get an after-tasting-hours glass or two. My absolute favorite picnic supply spot, however, is outside of town, up the valley: Oakville Grocery. Really amazing for products can be found at this little "old" roadside market, including a wide selection of delicious fresh sandwiches and prepared salads. It's really as you get into Yountville, however, that the real stars show up. The most famous is of course the French Laundry, but unless you're willing to go through the really difficult process of getting a reservation, paying $300+ per person for a meal, and having a (sublime) multi-hour meal experience, it may be best to try one of the other, excellent options in town. Bottega, for example, also boasts a celebrity chef (Michael Chiarello) and of course excellent food, but mere mortals can get reservations and afford a three course (delicious) meal. St. Helena has some nice spots as well, like the Culinary Institue of America's Greystone restaurant, and then Calistoga is a bit more relaxed & casual, for example the tasty Busters Southern BBQ. There are also the standard spots along highway 29 like Rutherford Grill, Mustard's, and Press, which are all better than average, but nothing "extra" fancy/special. Note that there aren't nearly as many options up & down the Silverado Trial (the "backside" of Napa), but there are far fewer crowds there- so definitely pack a lunch if you'll be doing tastings along that part of the valley!
Places to Taste!! I do not pretend to be an expert in wine, or even in Napa Valley, but if you want to get off the beaten (and pricey) path, here are a few wineries I've been to & really enjoy. Some of the famous spots are way overpriced & not that fun, but some are worth the visit. For example: the tours at Robert Mondavi are really well done. He really is the father of wine country in many ways, so if you're an amateur learning about wine for the first time, this should be on your list. I also think the champagne tasting over at Mumm is wonderful, especially for a sort of newbie. I tend to prefer the smaller wineries over on the Silverado trail overall: Chateau Boswell, Paraduxx, WM Harrison, and Casa Nuestra run the gamut of "fancy" to "relaxed" over there, to name a few. On the main road, I've enjoyed my time at Peju Winery, and of course if you want my favorite ever it was at Cakebread Cellars, but that was years and years ago before they became what they are now (get an appointment & plan to buy!). Some of my faves that are really a bit out of the way include Bremer Family Winery (on the way up Howell Mountain- free, but requires appointments!), Lava Vine (super fun, relaxed place in Calistoga), and Hendry Winery (tucked into the space between downtown and the mountains separating Napa from Sonoma; appointments required as well).
Overall, you can't really go too far astray when visiting Napa Valley, just expect tasting fees of $10-$20, with stiffer buying requirements to waive those fees (sometimes they make you spend $50-$100 before they waive the fee!). Use your hotel's concierge- they are amazing sources of knowledge. Designate a driver, or better yet hire someone to drive you around! And finally, my biggest tip: try to come on Sunday-Thursday! Nearly all hotels have two-night minimum requirements on weekends, especially in the summer/fall, and wineries in general are FAR more crowded on the weekends. In fact, coming after the harvest (November) through the beginning of spring (March-early April) will be your best bet for affordable rooms & more relaxed tasting experiences. The weather then is generally lovely, and seeing the vines with red/orange leaves is a treat! Here are just a few shots from around the valley to tempt you!