Feedback on tuscany/ rome itinerary

Realize that you are getting my preferences here. Flying into Rome is probably your best solution - you'll probably get in early enough to salvage the day. I'm tempted to suggest heading straight to Florence and work your way south to Rome. The Freccia from Rome to Florence is relatively fast so you can probably check into your hotel, freshen up, walk around, eat a leisurely dinner and get to bed by 10 or 11. That's help the jet lag . . . a bit. That's your 1st day on the ground. you have 1 more day in Florence before you move on to Val d'Orcia. (So much for 3 days in Florence!). You repeat the same kind of schedule for you 3 days (really maybe 1 1/2) in Val d'Orcia. It happens again in Rome BUT you're down to 1 full day. Most US return flights leave by noon (is your's later?) so getting to the airport in the morning is much easier if your last night is spent in Rome.

Sorry, it really looks like you want to do a whole lot of traveling in a very short period of time. I think both of you will feel a bit 'cheated.' You don't mention when you are traveling. Remember that summers can be very hot and humid and crowded - all of which will slow you down and cut into your 'must see' check list. Any chance you can start planning your RETURN trip while planning this trip?

Hi from another Minnesotan, Jason.

Do you feel the trip doesn't seem to congested, or burdened with
traveling?

Arg, sorry but I think you're trying to cram way too much into way too little. As previously pointed out, one of your two days in Rome is likely arrival day so it's only a partial, and a jet-lagged one at that. Whatever time you have on that day won't be much good for more than a walkabout to try and stay awake until bedtime ROME time. That leaves you only one full day in the city: you'll barely get your head around it with that little bit of time.

You'll lose 1/2 day or so with your other two moves plus you " would like to visit Pienza, Siena, and Montecello (Monticello Amiata?) while in Val d'Orcia." That's a lot of day tripping, and very little time at a "luxury agriturismo" you're asking about. As noted on that other thread, you would need to rent a car for your stay in Val d'Orcia, and do you homework regarding the ins and outs of driving in Italy: specifically, where you are and are not allowed to drive a rental. People do it, of course, but, well, do the homework.

With just 7.5 days to work with (I'm subtracting that partial day from Rome), I don't think I'd choose more than two bases. For a first-timer, I'd say add time to Rome and spend the rest of it in Florence, taking day trips to Siena (bus) and Lucca (train) as a substitute for Pienza/Monticello.

I know, not what you wanted to hear but IMHO, it sure would make things easier and less rushed.

Some thoughts for your consideration ( in no particular order)

If I could not spend at least 2 weeks, not sure I would bother with such a short whirlwind trip.

If your locations are 'set in stone' I would go directly to Florence and work back to Rome if you must fly in/out of Rome.

If you can fly into Rome and out of Florence ( or the reverse) for a little more than r/t Rome it may be worth it to save you some travel time and backtracking, and give you a bit more time 'there'. Going one way saves some train fare so factor that as well.

Pick 2 locations and enjoy them, rather than be rushing through 3. If you want a day trip to somewhere may be an option, and save another hotel transfer.