OK,here is the rundown on my trip to Tuscany - very long but only a fraction of what I could say. If people are planning a trip, feel free to write me - this is my second trip to Tuscany in 2 years - and I have lots of opinions!
Florence: Stayed at the Hotel Lungarno, reasonably expensive, small but exquisitely decorated rooms, cool balconies looking across Arno to spires etc. Good service.
Florence meals: Went to Cibreo at the advice of just about the entire world. Hideous service, very so-so food. First claimed we hadn't reconfirmed reservation (we had), then huffily seated us at awful table. Everyone in restaurant American and loud. Rushed waitress reels off menu in English at 100 mph. Tiny antipasti (you don't order) dumped on table. Good but truly bite sized. Wait almost an hour for first course. Keep asking everyone why it's taking so long. Everyone rushes off without comment. Other people have finished meal during our wait. Finally comes, unmemorable pesto and ricotta sformata for me - bland bland bland. Excellent yellow pepper soup for my boyfriend. Small saucer of paste consistency polenta as apology for delay. Salty second courses (tiny). Annoyed by end of meal. Completely unmemorable dessert.... So don't bother! Ignore the hype.
Much better, although still with a high (but not 100%) tourist content, was the Cantinetta Antinori. Similarly priced to Cibreo ($100 for two), but hearty delicious food. Particularly good was a baked eggplant appetizer, fettucine with cream and meat sauce, pot roast cooked in Chianti and onions, braised mushrooms and artichokes, a perfect peach poached in vin santo. Great wines. Only the risotto (really just rice) not good.
Siena: stayed at the Hotel St. Canterina, just outside the Porta Romana, nice simple rooms, gorgeous garden, affordable, friendly. Siena is terribly touristy by day, much better at night when all the Sienese come out and the buses leave.
Siena meals: Had one of our warmest, if not particulary gourmet meals, at the Ristorante Fuori Porta (the name means outside the gates, and it was a short walk from our hotel, in a residential area of Siena. Delicious pasta with cinghiale sauce, good asparagus, fun appetizer buffet, had a tasting of desserts - some excellent, some not, but fun. Dessert includes a bottle of vin santo and a bottle of grappa placed on the table- help yourself. Owner opened a bottle of wine for himself and a companion, and gave us glasses - very friendly -90% Italian diners - final check $36 for two - and we were stuffed.
Another Siena rec is the Antica Trattoria Botteganova, also outside the town, this off a highway heading towards the Val de Chiana. Hard to find, ask directions. Unlike many places in Italy, a truly worthwhile splurge - had a totally decadent tasting menu, changes every night, but the highlight was teeny weeny baby lamb wrapped in bacon and truffle pici. Very friendly waiter - great help with the wine list. Many tourists, but at least they were European (spanish and french in our room) and less loud. About $120 for two.
Cortona: What a beautiful town - many tourists but not as bad as Montepulciano or Pienza (where we had a delicious cheese picnic lunch - all the restaurants were packed with bus tourists - buy some cheese and sit outside). Stayed at Il Falconiere, an absolutely beautiful inn with gorgeous views, huge beautifully decorated rooms, about $225 a night but totally worth it. Don't however eat there, we did one night, and it was fine, but overly refined and bland for Tuscan cooking and the stuffy formal Relais Chateaux service just doesn't jive with the Tuscan vibe. Plus any restaurant that gives the woman (me) a menu without prices just turns my stomach. More expensive than its worth.
Instead, when in Cortona, eat at Castel Girardi, it's on the highway heading out of the top of Cortona, about 5 miles down the road on the right. Family run, packed with locals. We ate there three times. Great meat and cheese platters for appetizers, delicious crostini too. The pici al fumo (a tomato and cheese sauce) is heaven on earth, and the tris (a succession of three pastas) will leave you blissful and gloriously stuffed. Actually got to use some Italian. Cheap yummy wines, delicious berry dessert. About $20 a person to be stuffed beyond belief. Truly wonderful. Go. You will feel like you are (finally) in Italia.
After Cortona, went to La Chiusa for two nights. The rooms are spacious, a bit odd, and pricey - $300+. (Very parsimonious breakfast for that price). The food is perfectly delicious, all the raves are not wrong - just not particularly worth $200 for dinner. The multicolored swirls of sauce on the plate struck me as more midtown than Tuscan. Entirely American except one bewildered Italian couple celebrating a birthday. The service very warm in a very inauthentic practiced way. I know I won't dissuade anyone, but I think the glory days have passed.
Our second night we passed on La Chiusa and went to La Grotta just outside Montepulciano. Heavy local element (some Americans). Warm family-run place, very sweet, enthusiastic waiter. Heavenly cheeses, fabulous tagiolini w/ truffles, great wine, perfect salad, fresh plum cake (oh, those plums!) - total damage, $75.00 and a warm handshake from the waiter - who clearly loved food and loved seeing people enjoy it. Go!
Also really good in the La Chiusa area was Cantina Il Borgo, in the tiny very steep town of Rocca D'Orcia. No tourists made it up the narrow twisty road the day we were there, and we enjoyed a hearty Sunday lunch (pici and roast chicken) with a bunch of Italian families. Beautiful old room - not very expensive. Go!! Handmade pasta, double go!!!