All right, quick and dirty version which I can get more specific with more information to the above questions.
4 People, noobs, I normally recommend a varied experience. Go somewhere big, somewhere small, somewhere boutique, and take a tour. Plan on 3 wineries, with room for a 4th that doesn't require reservations. Keep your day sort of flexible, worst thing to do is try to fit in too much, and then get stressed when your behind schedule because you had fun somewhere. Even more worse, to get shit faced and get a DUI from over tasting. Remember, tasting wine does not mean you drink. There are spit buckets at every winery for a reason. Taste the wine, if you don't like it, dump it/spit it. They will not be offended. If you find a wine you like, by all means finish the glass, but if you're a red fan who doesn't like chardonnay, try the wine, you may find something you like, but if it's not your thing, dump the glass, spit out the 2nd mouthful, and move on. You'll have a much better/longer day. Bring your own water as well, hydrate hydrate hydrate.
Once you've taken a tour, you've pretty much taken a tour of most wineries, the info is usually the same unless they have something different to experience, or do something different in the process. Red wine vs sparkling wine kind of thing.
July 17/18th is going to be a busy weekend around here, so plan now. Restaurant reservations, winery tours/reservations, going to fill up fast so plan early and profit.
For a tasting, no tour, just belly up to a bar and drink type experience, plan on 15-30 a person. You can split the tasting between two people to save on money, and sobriety.
Tours are usually 50-75 per person, and not able to be split, nor should you at that price.
Start with a tour in the morning, you'll have more energy to walk around and be less drunk to take in the information. Also it'll be a good chance to learn, and you'll be able to use that knowledge for the rest of your day. Pine Ridge, Domaine Carneros, Far Niente all do great tours.
Big wineries I usually find out what you normally drink first to recommend. There's something to be said to go to the place of the wine you like to buy at home to try wines you might not know they produce. Chateau Montellena is a favorite of mine and after your first tour, and if you make a picnic (see below), has a 2 billion gallon koi pond out back that you can enjoy AFTER your tasting. Also watch the movie BottleShock before you go and you'll know more about the history of Napa and the winery.
Small wineries/Boutique wineries tend to be more fun IMO, you get more of a one on one experience, they help guide your questions and will probe you to see what you know and want to know. Vincent Arroyo, Hagafen, Failla, O'Brien, Goosecross, Envy, Cade. All a lot of fun. Hagafen and Vince Arroyo are my two favorite wineries in Napa. Vince for Reds, Hagafen for whites.
There are also "tasting rooms" which are pretty much wineries without squishing grapes on property. Some stay open past the 5pm cut off for wineries so they're a great option if you're still thirsty. Hope and Grace, Priest Ranch, 1313 Main St, Ceja vineyards are some good ones.
Restaurants, for lunch, I usually recommend deli's. Most wineries have a picnic bench or area to enjoy some food AFTER your tasting. If you wanted more of a restaurant to enjoy, somewhere like Travigne, Farmstead, or Hurley's is a great spot and not hard to get into.
Dinner, depends on what kind of food. Yountville is the mecca for restaurants, so Bistro Jeanty or Bouchon for French are my gotos. Ciccio's for out of this world Italian, but they dont' take reservations so get there early, get your name on the list, go across the street to R&D kitchen for a drink and wait for your table. It's well worth it IMO and absolutely the best Italian I've had this side of the pond. Steak, Rutherford Grill, Brannans, or Redd (though Redd is nearly impossible to get into nowadays).
So as a basic itinerary for you.
10:30 tour at Pine Ridge of caves/vineyard/wine making process.
Pick up Picnic supplies at Sunshine Market in St Helena
12pm Tasting at Chateau Montelena
12:45 Picnic at the pond at CM
2pm Tasting at Vincent Arroyo
3:30 Tasting at O'Brien Estate
Drive to Yountville
Walk in tasting if still thirsty at Hope and Grace.
Walk into Ciccios, put name on list, cross street to R&D, order well made cocktail, wait 25-45 minutes for table, return to Ciccios, enjoy amazing meal, profit.
Return home after an amazing day, PM i_am_the_koi to arrange delivery of a thank you bottle of Port from Vince Arroyo.
This can be molded to fit your desires a bit more but should give you a good idea. Feel free to PM me with more questions or I'll watch the thread too.
