Itinerary Help - First Trip Abroad

TT, have you considered booking your flights as multi-city (aka open jaw) so you don't have to backtrack to Rome? It would be much easier for your itinerary to fly back to the US from Milan Malpensa. Varenna to Milan is a much shorter trip than the all-day it will take to get back to FCO.

Or fly into Milan and finish in Rome?

If you must do r/t to Rome, perhaps continue on to Florence on your arrival day and do Rome at the end.

I like to look at itineraries in terms of number of nights in a location: how many nights will you lay your head down in XX city? Here is how I see your itinerary -

• Rome, 3 nights
• Florence, 2
• Siena, 3
• Montepulciano, 2
• Varenna, 4
• Rome, 1

That is a lot of moving around. Assuming you arrive at FCO early in the day, go immediately to Florence or Siena, eliminating one transfer by putting all of your Rome nights at the end. I would combine Florence and Siena. Spend 4 nights and day trip to one from the other. Add the remaining night to Montepulciano, a decidedly different part of Tuscany and worthy of three nights. Varenna seems heavy at 4 nights, so look carefully at how you would spend three full days there (I think 3 nights/ 2 full days is enough) as it would not be overkill to spend 5 nights/4 full days in Rome at the end of your trip. No need for an airport hotel stay,

Thank you for the suggestions! After looking at it, I think the right move would be to book an open jaw and just fly back from Milan.

I also tend to recommend open jaw flights, but as you are flying from a major airport, it doesn't hurt to consider round trip if it saves a lot of money. Just watch some seat sales in the next few months and do some comparable date open jaws to see the savings (or not). Personally, I would spend more time in Rome and Florence but it looks like major cities are less of a draw for you so this is realistic.

And if the flight home from Milan is significantly more expensive than returning from Rome, then certainly continue on to Florence on your arrival day, and end your trip in Rome, so you have one less hotel change. I've continued on to Florence, Lucca, and even Venice upon arrival day at FCO. Frecce trains (the really fast ones) can get you from Roma Termini train station to Firenze Santa Maria Novella train station (the main one, in the center of town) in a couple of hours. Laurel's suggested itinerary changes look great!

If possible do the reverse itinerary.

Fly into one of the two international airports in Milan (Malpensa or Linate) then work your way down to Rome, from where you return home.

So:
Upon arrival to Milan go straight to Varenna.

Varenna: 3 nights
Florence: 2-3 nights
Rent a car in Florence and head to Siena area, preferably through the beautiful Chianti Road (2 hr drive). You can stop at wineries along the way.
Siena area: 3-4 nights. Visit Siena, Montepulciano, etc. from here.

Finally head to Rome, if you wish visit Orvieto and/or Civita along the way
You can return the car in Rome, upon arrival.

If you want you can return the car in Orvieto and proceed to Rome by train. However only HERTZ has an office in Orvieto.

If you’d rather skip Orvieto, Civita, etc., and head to Rome by train, do not return the car in Siena. Rather return the car in nearby Chiusi (not far from Montepulciano along the Florence to Rome rail line). Then from Chiusi you can take a train to Rome.