[Don Plumley]

With my caveat about Sonoma v Napa; we have lots of friends that visit and am routinely asked for information. Aggie93 did a nice job above, there will be some repeat. Here's a summary of SF and Wine Country:


SF:
Here's some ideas for a couple of days in San Francisco. The key is to avoid the super touristy stuff while still taking in the quintessential San Francisco. First, don't call it "Frisco" or "San Fran." Only tourists do that. SF or San Francisco.

California Academy of Sciences - very worthwhile, plus it's in Golden Gate Park which is beautiful.

Golden Gate bridge. Everyone and their uncle wants to see if and walk across from the visitor center on the Northeast side. Big lines to park, etc. Two ways to see it - drive to the Marin headlands exit (photos above);(one more north, or approach from the north side headed south), and drive west to the Marin Headlands - beautiful view. You can also see it from the SF side down at Crissy Field. Consider taking a city bus to the Golden Gate stop on the South side and walk across.

Fun idea: Rent bikes in SF, go across the Golden Gate, down to Sausalito, take the ferry back (puts you in the Ferry Building).

See a show: Beach Blanket Babylon. Changes constantly for current events, even our son thought it was fun.

Twin Peaks: On a clear day, nice view of SF

Alcatraz: On a nice day, it's pretty interesting, on a cold day it is beyond misery. Given your limited time, maybe next trip.

Cable Cars - pricy but a very unique thing to do. The trick is not to board at the main stops (Union Square, 1st/Market, Fisherman's Wharf); Top of Lombard Street is where lots of people get off, good spot to get on.

Union Square - visit in the evening, will be very pretty; plus nice shopping if you need that too.

Pier 39 - really touristy. I'd avoid. I'm not too keen on the Fisherman's Wharf area either, other than for crab from the stalls. Avoid most of the restaurants around there.

Coit Tower - probably not worth the walk/wait

SF Food:

Ferry Building (Market @ Embarcadero). Food Mecca. Sweets (gelato, artisan chocolates), Cheese (Cowgirl creamery), Bread (Acme Bread), Meats (Prather Ranch "Praise the Lard"; Bocallone "Tasty Salted Pig Parts"), Seafood (Hog Island Oyster Company); plus great Vietnamese food (Slanted door - probably too busy to get in, but great take out adjacent "Out the Door"). Get your burger at Prather Ranch instead of Gotts roadside

Cotagna - Amazing wood fired foods. Good lunch, Pacific Ave near downtown

Perbacco - Northern Italian food. Might be a nice last dinner, or a nice lunch.

Other restaurants worth a visit: A16 (Marina District); Farallon (union square, seafood); Zuni Cafe (Mission, amazing roast chicken); Anchor and Hope; Salt House; Town Hall; Range; Rich Table; Spruce; Quince; La Folie; State Bird Provisions


Wine Country:


First, there are the two big regions: Napa and Sonoma. They are roughly similar to Bordeaux and Burgundy in France as far as general philosophy, vibe, etc. To be fair, I live in Sonoma County, I'm a burgundy guy, I make Pinot Noir, so I'm not the best qualified person to give substantive Napa advice. But I'll do my best. However, I do have the food thing nailed, so no problem there. And there's lots of good food in Napa...

Oh - we talk about Napa and Sonoma interchangeably when they both refer to a City and to the larger County. So caveat emptor

Most wineries have tasting rooms (though you should always double check on the website), but only some have tours, and of those, some of the more fancy pants one require an appointment. Later on I can get into "how to get the most from your tasting room experience." (short answer: pay for the reserve room)

From my perspective, there's definitely a limit of how many tours you can go on, because frankly, once you've seen one winery, they are all highly similar - some are prettier, some are more detailed, etc. But definitely do a few.

I think four wineries a day is a reasonable goal depending upon how far apart they are - most tasting rooms are open only from 10 to 5, so you have to plan the logistics/distance well. After all, it's a vacation so your goal is to relax! Some wineries have picnic grounds - consider getting a lunch from one of the many gourmet grocery stores and having lunch at a winery.

Napa (city) is about 30 mins from Sonoma (city) and 1 hour from Santa Rosa. If you drove way out into the Russian River Valley in Sonoma, you are about 1.5 or so hours from Napa. But it's worth the drive, as are the passes between the north parts of the valleys. Many good driving roads (but be careful with the drinking).

Here are a few ideas:

Napa:
Domaine Carneros - close to Napa, nice way to start your first day with a Sparkling toast - nice views (or they stay open late too)
Robert Mondavi - while the wines today are pedestrian, they have a great tour and anyone in the wine biz owes thanks to Bob Mondavi; but they are a tourist mecca, so be forewarned
Grgich Hills / Heitz / Peju
Robert Sinskey
Chateau Montelena - Famous place (the 1973 tasting)
ZD - Tour/Tasting (might need reservation)
Clos du Val - apparently they have a nice tour and picnic grounds
Rubicon Estate
Hall - I don't think their new Frank Gehry designed winery is open yet however.
Frank Family Vineyards
[Sterling: now way overpriced, don't fall for it]



Sonoma:
Lynmar Estate - Our favorite spot to visit; well crafted wines, setting; has it all
Chalk Hill - Amazing Place (not a fan of Lancaster Estate nearby, however)
Gary Farrell - The prettiest setting for a tasting room in the world - heart of the Russian River Valley
Gundlach Bundschu - Eclectic, cave tour, more bohemian and casual than Napa (true of much of Sonoma)
Marimar Estate - Nice
Copain
Chateau St. Jean - go the reserve room (used to recommend Arrowood nearby, but last experience was sub-par)
Benziger (not beringer) Family winery - great biodynamic program
BR Cohn - the former manager of the Doobie Brothers, they have a great concert every year
Rochioli
Silver Oak - well known Cab
Valley of the Moon
J Vineyards & Winery - the bubble room...

Places to Eat:
Napa:
Bouchon - my favorite. In Yountville, French Bistro (owned by Thomas Keller). If you like bistro food, please go here.
Redd - Also in Yountville (their casual place, Reddwood is great for wood fired pizza)
Bottega - Napa
La Toque - in the West in Napa, close to you.
Ubuntu - Napa
Morimoto - Napa (very special)
Gott's Roadside (formerly Taylor's Automatic Refresher) - in Healdsburg and Calistoga, sometimes you need a burger and fries

Sonoma:
Dry Creek Kitchen - Healdsburg, part of the Charlie Palmer Group
Bistro Ralph - Healdsburg
K&L Bistro - Sebastopol
Central Market - Petaluma (where we live). Tell Tony you know Don.
El Dorado Kitchen - Sonoma (the city)
The Girl and the Fig - Sonoma
Cafe La Haye - Sonoma
[Don't fall for the General's Daughter]


Happy to provide any suggestions, trade-off choices, etc.