I would stop in Montalcino en route if you can. Some of the best food I ate was there and Siena. The picci bolognese at Trattoria Pozzo in Montalcino was the single best dish I had in Italy.
For bistecca fiorentina, I would check out Buca dell'Orafo in Florence. We went there on a whim and it was the finest example I've had.
This past weekend I had the in-laws in town, which meant a lot of wine, mainly for me to get through it.
2009 Palama Salice Salentino
2004 Chateau Redortier Gigondas
2005 Chateau de Beaucastel
2001 Chateau Pradeaux Bandol
2009 Leitz Ein Zwei Dry Riesling
Some daily drinkers mixed with some stuff that I had held for a bit. I'm going to a Loire Valley wine tasting on Thursday night and will report back.
Here's what I was thinking tentatively:
Friday lunch: Katz's
Friday dinner: Ssam Bar
Saturday lunch: Gaia
Saturday dinner: Le Bernadin
Sunday lunch: Grimaldi's
Sunday dinner: Awash (wife wants Ethiopian one night)
Is Le Bernadin worth it? Any place you would go instead? Anyone know a better Ethiopian place?