I know this board is replete with Oliveto pros and cons, but I've always stayed on the sidelines b/c I've never made it there myself ... until last night. Anyway, I'll keep this short.
To answer first what always seems to be the threshhold issue: yes, I think Oliveto is worth it. I won't go through the litany of everything my wife and I ate b/c the food has been analyzed at length many times here (but if asked, I will tell). Suffice it to say that the quality and preparation of all the food was impeccable, with the Malfatti with Lamb Ragu and Grilled Pigeon with Roasted Cherries blowing me away. Yes, contorni must be ordered separately, but I did not find the portions to be too small for the price.
I had expected the service to be subpar and perhaps snooty given many comments I've read here. My server had zero attitude. He was friendly, mostly well informed and helped pace the meal perfectly ... right down to the all-important point when you start to send out mental waves to "bring the check, we're done."
We were even 15-20 minutes late because of traffic heading into the Bay Bridge, but when we called ahead to alert them they assured us we would have a deuce when we arrived.
Can't comment on the wines by the bottle, except to agree with other posters like Robert L. who have regularly noted that prices in general are pretty jacked up. My wife's not a big red wine drinker, so I stuck to the glass/quarto selection. I'd take advantage of the $18 corkage if I went again with a like-minded wino.
So, while it's out of our price range as a weekly stop, we'll definitely put it in the rotation.
(For those who have stayed away fearing an "exalted experience re: quality and simplicity a la Chez Panisse:" fear not ... Oliveto has quality and simplicity but the experience feels totally different. Not to say I don't an occasional visit to CP, but it's apples and oranges.)
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