Milan to Rome, 2 weeks itinerary check

I'd have to spend some time looking at this, but a couple of points that stand out.....

• Are you planning to stay in the town of Como, or somewhere else along the lake? You might also consider staying in the small town of Varenna, which is in the mid-lake area. It's a big favourite with many here.
• Wherever you stay on Lago di Como, you might head there as soon as your flight arrives and not waste a night in Milan.
• Are you planning to stay in Orvieto? One night stops are mostly a waste of time as there's not really much time to see the town.
• I assume you're planning to travel by train? If you haven't travelled by train in Italy before, be sure to do some research as there are some potentially expensive caveats to be aware of.

Those are just a few initial impressions.

I don't know if your airline ticket's been purchased. But have you checked into flying open jaw'd into Milan and home from Rome?
Backtracking is inefficient and expensive. And distances in Europe can be pretty far.

Remember that your first and last day of the trip is wasted. Also is every day you move to another city.

You have booked two nights into a Firenze agriturismo. Firenze is Italian for Florence. Farm stays are very difficult without renting a car. Tuscany is a place that's easiest seen with an automobile since roads are well paved and easily to travel on--if a little crooked.

Thank you @Ken and @David

The tickets are already purchased, otherwise yes I'd have done an open-jaw. I will fly out from East Asia in the late evening and fly into Milan at 930a, so I expect to be rested on arrival- at least to do some city walking and meals. Flight out is 7:30p, so have most of the daytime to use up.

Is Milan really that bad that its a "wasted" night lol? I will be staying in Varenna, not Como.

The firenze agriturismo is a 30 min bus ride out of Florence. I wanted to do a few agriturismos but yes, the transportation looked impossible with my timeline (and expensive!). I cant drive manual and dont want to be stuck looking for one in stock so I decided to give up the rental idea.

I will sleep in Monterriggioni, Siena, and Orvieto, so three nights. I figure that will give me at least two meal times and a relaxed evening in each place.

I will travel by train and bus where possible and Ive seen the high speed from Rome to Milan is comparable with my current city (~USD $50-100). Thankfully thats only one trip. I assume the rest of the stops are EU$5-15 and the buses are probably negligible cost. I did hear theres something about activating tickets or other for the trains, so Ill be sure to understand those procedures and where to actually purchase tickets if I cant do so in advance. I have TrenItalia app on my phone to better understand the times and prices.

I've never stayed in an agriturismo; Is it on a frequent Florence city bus line? I admire your lack of a car, but some of these distances seem time consuming (e.g CT, Siena, Orvieto), even if they only take a single public transit "seat." (?) Have you DONE all the bus research, or is it seat-of-the-pants? This is a very ambitious itinerary. Have you been to Rome before? Monteriggioni is very pretty but small and isolated. I wouldn't stay there without a car. I don't think it has any "art". Siena is a very rich destination, so I'd only do the dinner if it is after everything is closed for the day.

you should be able get train fares as low as 19€ or maybe 29€ from Rome to Milan, but they aren't out yet for September.

Where are you looking for fares? Since you are quoting in US$ it seems likely you are not familiar with Italo Treno or how to get decent fares on Trenitalia? Have you studies Man in Seat 61?

@Tim thanks, I did some preliminary google maps routes. The trip from Florence -> Monterriggioni -> Siena -> Orvieto -> Rome seems to be a fairly quick and straight shot by bus and train.

Besides, it was either a night in each or one of those day tours with only 45min-2 hours allotted for each place.

The Florence agriturismo has two bus lines about 30m away from the city, and the owner helps visitors call taxis when needed.

@Nigel, I used the trenitalia app for that estimate. Sorry if its confusing for me to switch between USD and EU, I actually live in Asia but use USD to "compare" between my current city and these travel numbers as USD is just the easy base for me to work off of.

Be sure you understand the whole picture for your transportation to and from Monteriggioni, Siena and Orvieto.

The walled town of Monteriggioni is about 1/2 mile from the train station at Colonna di Monteriggioni.

The train station in Siena is located well below the city, requiring extra time to get up to what you want to see. A lot of inter-city buses take you to a better stop, but a few of them only go as far as the train station.

In Orvieto the train station is below the historic town; you take a funicular (or a bus if the funicular is out of service) up to the top. The funicular upper station is on the opposite end of town from the Duomo, a fairly substantial walk.

So the bus or train times you see really do not paint an accurate picture of how long you will be in transit. Those trips are certainly still manageable, but I think you won't find you have as much sightseeing time as your are assuming. Monteriggioni looks minute. Siena and Orvieto have tons to see and do.