Headed to San Fran the week of NYE for Anniv.

You can dine at The French Laundry for $800 pp on NYE

Yeah... I’d be shocked. We went to Gary Danko 20 years ago, and I’m going to try there again. Reservations open 60 days out, and they are not open NYE, so will try 12/30 on 10/30.

Try to stay around Coit Tower, Telegraph Hill, if you can. At least one meal at Boulevard and a sunset at Lands End park.

A drive down 280 to Los Gatos, up the mountain, then down into Pescadero to eat at Duarte’s. Their cream of green chili soup is the jam. Down the coast to Santa Cruz stopping at 7 mile beach. There’s a natural bridge and this cool ‘light house’ cave. I asked my wife to marry me in there ~19 years ago.
https://m.youtube.com/watch?v=j4T3dXv9GFw

The Pulgas Water Temple and mountain towns La Honda and Ben Lomond are other things that can be wrapped up into that drive.

Just south of Stinson beach is a beach called Red Rock that is unreal, as is the short drive up the 1 from SF. To the right of this outcropping.

Some people may not have clothes on. Lunch in Stinson then you’re less than a couple hours from Napa Valley.

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Another question: is the homeless problem that bad? Planning on getting out of the city 2/5 days

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Depends where you are... I'm in SF every few weeks and, I won't lie, drug addicts and homelessness is a problem, but pretty confined in three neighborhoods - Mission, SoMa, Tenderloin. There are plenty of other areas to check out (i.e. Noe Valley, Bernal, Haight, Potrero Cow Hollow, Presidio, etc.). That said, I wouldn't say to avoid neighborhoods like Mission, which have plenty of history and awesome places to eat.

Arriving Sunday night 12/29. Leaving Thursday 1/2.

Leave SF gng over the golden gate and head to Marin county. You can go to the original Hog Island Oyster Co. Then, head east to Healdsburg for a day/night. Tons of great wineries there. J is our favorite. It’s a Pinot Noir valley. Healdsburg is a cool little town. Then, head east again to Napa. Tons of threads in Napa already.

I must be missing the non-deadly route to the cave.

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You can go to the original Hog Island Oyster Co.

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We ate at the Hog Island Oyster Co. at the Embarcadero a couple of times a few weeks ago. Local oysters - very salty, small, strong tasting. I prefer Gulf coast ones. Their oyster poboy was actually very good as was the grilled fish. A couple of us asked for Diet Coke and got lectured "we will not serve you a diet drink or a Coke, we do serve a locally sourced cola". Well, frick you too .

Walking the streets 25 years ago the hookers were everywhere and the homeless were low key. Now the homeless are everywhere with a few pretty obnoxious and the hookers are not to be seen.

Monterey/Big Sur was great as always. We stayed at an Airbnb in Marina which was not too far away.