First trip to Italy - early March. Looking for feedback of locations and itinerary

Whatever option you pick, you need to stay in the city of the departure airport the night before your flight. I couldn’t tell if that was implied in your count of a week’s time.

As much as I absolutely love the smaller cities of Italy, I wouldn’t pick option 1 for the month of March. Those locations are more enjoyable if you can eat outdoors, so save that for a different trip.

I don’t think option 3 has enough variety, so I would pick option 2.

Of the auxiliary cities you’re considering, Siena & Montepulciano are higher on my list than the others.

Looks like you have 7 nights?
I would also pick Option 2 but do
Rome 3
Orvieto 1
Florence 3

You can always day trip to Siena from Florence

Since you have never been to Italy, I can’t imagine not seeing some of the major sites especially with March weather. I would take your option 2, delete either Orvieto or Sienna and add the time in Florence. Of course, after having been to all the places you listed, it’s just my opinion based on my interests.

Your other post about both Italy & Spain just disappeared when I wrote this reply, so I will just place it here:

“I think I just replied to your Italy question on another post. : )

I love Italy & have stayed in 49 cities there. So, I think it’s always a great choice!

But, I am going to Spain again for the third February in a row to the Andalusia region, so that’s also saying something. : ). It’s a fantastic location for that time of year! The three cities you listed are very easy by train. Last year I flew into Malaga and immediately took a train to Cordoba. (It takes three flights for me to reach Malaga.)

If Spain, reserve your timed entry to any of these that appeal to you: the Sevilla Alcazar, the Night Light Show at the Alcazar, the Cathedral, the Cordoba Mezquita, the Malaga Picasso museum. Also, the Hammam Bath/massage combos are an excellent way to relax!”

Agree with Christine,
Still, if you want to see smaller cities, I would go with #1. You don't need to overnight in San Gimignano. Do it on a day trip from Sienna.
San Gimignano is always very crowded. Hate to think how expensive a hotel there would cost.

Take train to Orvieto (stay for 1 night)

I drove from Naples to Siena and did a stopover in Orvieto for lunch and a little exploring, which seemed like enough. Maybe transfer that night in Orvieto to Florence so you don't have an 1.5 hour trip to the airport, which will already be a hectic day. Although if you're taking the train and can't stash your bags, maybe that won't work.

I like option 3 because it minimizes the hotel changes and Florence and Bologna are good hubs. Florence gives you the option of a day trip to Lucca. Bologna gets you into Parma/cheese/balsamic country as well as Lambo and Ferrari museums nearby. The only thing I don't like is having to double back to Florence for your departure which will require a train change. Departure days are always hectic so keeping it simple is always better.

Any of these would be fine, but as mentioned, weather could be a factor in small towns. Mostly, you need to take logistics into consideration, like being close to an airport for last night, not driving too much on arrival with jet lag, that kind of thing. What do YOU envision?, because it does not have to be what others envision for a first, or tenth, trip.

Very difficult choices as all cities on your prospective itineraries are worthwhile. I have traveled and studied in Italy and recently did a three-plus week trip, and that was not enough time. With seven days I would also choose number 2, that way you can explore three regions, Umbria, Lazio, and Tuscany, a bit and avoid long travel days. Alternatively, you could stay in one of those regions the entire time in one location and take day trips. I would return to Montepulciano and Pienza (I only had two hours there). Florence is amazing if you love Renaissance Art but be prepared for very long lines everywhere, even in March (same with Rome). I was in Rome in early November 2025 and there are now metal detectors in place (and a long line) to enter St. Peter's Square, which was a bit shocking. It's never easy planning a trip to Italy because everywhere is so full of art, architecture, amazing food, people, beauty. Also, someone mentioned above that it is advisable to stay in the city in which you are flying out of the night before your departure otherwise it's way too stressful. I once flew from Catania to Rome and Rome to Los Angeles in one day. That was a mistake. Buon Viaggio!