What rental car company?
Restaurants are open on Sundays but wineries are closed for the most part. Especially the family run wineries
Doesnāt really matter tbh. It was two separate companies on the same day (and both are big companies that Iāve used plenty of times).
I had a different experience with a different company in Alba, but at the end of the dayā¦.lesson learned. Itās easier to pay $35 to get an IDL than have to cancel appointments you were dreaming of
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Actually it does matter as I rent in Italy reasonably often and have never been asked, and it will influence my next reservation. Also important to know if policy changes.
Please share the names.
We rented with Enterprise at the Florence airport in March and they required an IDL. Have also heard that if you encounter a random traffic stop in Italy, the police will ask to see your IDL.
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Theyāre two major rental companies. Thatās what matters. Iād that doesnāt work for you, thatās not my problem. Iāve already said which company I didnāt have a problem with in Alba.
Naming them doesnāt change the fact that I am not able to reschedule one appointment and canāt get the bells and whistles on the other with the reschedule I was able to do.
Simply put, just get the IDL.
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So we just did a more in depth look at flights from St. Louis and from a price and timing standpoint to limit layovers it probably makes most sense for us to fly in and out of Milan (with one layover in Chicago and NYC respectively).
Would it be reasonable to take the train from Milan to Florence, spending most of our time there, then rent a car to drive to Piedmont for a couple nights before returning to Milan the night before our flight out (dropping the car off in Milan)? Any other sequence that makes sense?
Iām a huge fan of focusing on keeping holidays logistically simple, and without additional downtime / annoying wasted unenjoyable time. Even if this means we donāt get to do everything we want, we get to do more of the things we want in the locations that remain.
So in that context, I think your new plan is a brilliant one 
. Flight complexity minimised & two locations, doing one in depth, but the other with enough time for it to be a decent ātasterā. Were it not a city location, having the car from start to finish would be worth considering, but I absolutely agree on this compromise of getting a car from near Florence, and ending up dropping it off at Milano Malpensa.
Flight time out will be a factor. If afternoon or later, then Iād absolutely recommend an extra night in the Langhe and not an overnighter in Milano. If in the morning, the overnighter in/near Milano makes practical sense.
I do have an alternative to a night in Milano. Ghemme is near to Milano Malpensa (about 30 mins drive IIRC), and weāve stayed a few times at Il Cavenago there. Itās a lovely old large farmhouse, where they grow and rear a lot of their own food (buying locally for anything else). At dusk the bats come out and give an aerial display in the courtyard. The food (not served every night - usually Friday & Saturday, but also any other night thereās a group booking - itās popular with locals) is very good indeed, probably the best risotto Iāve eaten, but all is good, and as typical with agriturismi, more than enough of it. Ghemme itself is most untouristy, with a criss-cross of streets, but these mostly not used any more since the bypass. As such it has a surprising calm. A good few wineries including Cantalupo, Rovelotti plus some good smaller places. A decent (but not great) gelateria, which however is lifted by the attitude of the lady who works there, who gave off the impression she was the luckiest person in the world to have the best job going. Thereās a smallish, but interesting historic centre, and a very old man-made watercourse, plus the river. Nothing youād go out of the way for, but for a few hours, rather enjoyable. It might also work out that you could fit a winetasting in there, so you donāt feel so bad about short-changing the Langhe, plus itās an interesting contrast of nebbiolo styles. As an alternative where thereās a bit more to see there, and arguably better wineries, Gattinara worth a look as well, but I donāt know any accommodation (the place in Ghemme is lovely, so weāve never looked).
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I would definitely recommend more than a couple of nights in Piemonte. Itās a 4 hour drive from Florence and you will regret not spending more time there.
Ianās suggestion for staying in Ghemme is a good one. And you can visit Gattinara, which is just across the river.
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Too much driving for just two nights in Barolo IMO. Thatās only one day really.
Weād be likely driving from Florence to Barolo 10/15 in the afternoon and leaving 10/18 in the afternoon to return to Milan. Due to limited return flight times weāll probably need to stay a hotel airport the night before.
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Much better!
I also would strongly recommend not short-changing your visit to Piemonte. Personally I would spend at least half the ten days in the Piemonte, including the northern area and maybe a day trip up into the Aosta valley.
Sheraton hotel at Malpensa is nice and is connected to the airport. Just walk over the morning of your flight
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Even though his wife doesnāt care for red wine?
Keep the wife happy Brian, Florence is amazing!
And plenty of excellent wine there too.
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Thereās plenty of good white wine made from Piemonte and Aosta grape varietiesāArneis, Cortese, Erbaluce, etc.
Florence is fine. Great museums. Loads of tourists. I personally prefer Piemonte. Itās been mentioned before that Torino is overlooked. Maybe thatās for the best. 
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We booked our flights in/out of Milan and our hotels (Grand Hotel Baglioni in Florence, UVE in La Morra).
For Florence, are there any small group or private tour guide companies people recommend for the more popular destinations?
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We used Walk About tours for a day cooking class as well as a private guided tour to Siena, Pisa, and San Gimignano (all in one day), and I gave 5 star reviews for both days. Our guide Antonio (Toni) was excellent on the private guided tour. Plus having a private driver to drop you off right where you need to be made things much better. I assume they run similar tours in Florence itself.
Also, your hotel spot for Florence is great; short walk to the central attractions. We stayed at the St. Regis, which was a very nice spot with excellent service (the A/C wasnāt up to par, but itās Europe). However, we were 15-20 minute walk to any spot we wanted to go, which isnāt bad but in 95 degree heat with a crazy amount of people, it made it seem twice as long.
For Florence we did a 4 hour walking tour with Francesca for our group of 6. She did a great job and you can customize what sites/areas you want to focus on. I think I got her name from someone else on the board