Itinerary advice please?

That is, we'd rather see two towns slowly than race through 8 of them.

Well, by my count you already have 8 or 9 destinations on your list. You will do a lot of travelling during your month.

But first of all, what's wrong with stopping for the night in Tirano?

• images of Tirano

I bet that no one you know has ever stopped there, so that will give you something to talk about. Also, the culture is different from what you will experience in the south, so there is that, too.

Milan warrants at least a couple of days, even if there is nothing specific that you want to see. It's not a place for an overnight stop.

Matera is something special, so either make sure you get there early enough to spend a full day or plan to spend one day and one night to see the light changing on the Sassi (the old complex of cave dwellings).

As for Venice vs. Santorini -- flipping a coin may be your best method as you cannot compare the two.

Thank you! Very helpful emmeff!

I would also spend that first night in Tirano - since you have to do a transport change there anyway, but if you added Milan or elsewhere, that is an additional transport change prior to reaching Turin - and just an avoidable overhead.

Florence is of course outstanding for a few days - but don't expect any solace whatsoever - it is extremely busy.

Naples is a bit trickier - it's a very interesting city for a couple of days, but would you expect to use it as a base for visiting one or more of Ischia, Pompeii, Herculaneum, Sorrento/Capri, or the Amalfi Coast? If none of those appeal (and again they will be busy), then Naples might not be the best option available to you.

And I think Venice above Santorini - and there is a lot else in the region too.

Santorini is a one-trick pony, and that's fine ... we've visited there 2-3 times as a part of cruises, and it's been a pleasant day-trip excursion (but again, incredibly busy - even in April), but I'm not certain it warrants the time and expense of a stand-alone trip there - that includes nothing else in the Aegean.

Tirano is fine to stay in for a night,why not? No point going to Milan with the time you have available.

The rest of your plan looks doable,though I agree it is not particularly slow or leisurely..you are basically covering the entire country.

Florence and Venice are two of the 'Big 3' (along with Rome),Matera is something different (though becoming ever more touristy)and Naples is a very ntresting city and a base for the Almafi Coast and the bay...you are going to be in VERY busy and tourist filled places.

Thank you all very much; this is tremendously helpful. We will spend that first night in Tirano. After hanging out with our Italian host in the Turin area, I think we’ll spend a few days in Florence. No, I don’t see us going to the Amalfi Coast and the bay or Pompei etc. . .. maybe I just want a pizza in Naples (!), get the car there and then find a smaller place to hang out for a few days on the way to Nova Siri.

Santorini is one of those “bucket list” places for me. Kind of silly but I want to gaze upon it with my own eyes, and hike up and down those hills for a few hours. It’s super-helpful to know that it doesn’t merit multiple days. I think I’ll look for a less-traveled island to spend a few days exploring, or . . . Leave Santorini and Greece for another time - maybe an October visit some year - and simply go to Venice, which makes better sense on this particular trip.

I appreciate everyone’s time and help.

Santorini is great indeed ... but much more logical n a longer Aegean / Eastern Med trip (Rhodes, Crete, Mykonos, etc). In fact - why not do a Med cruise? There are worse ways of spending 10-14 days.

Tirano is not a main tourist destination but it's a decently sized town in a marginal, border area, and a transport hub to reach Switzerland and wonderful Alta Valtellina. It would certainly be cheaper and quieter than Milan.

The baroque church deserves a visit. I found its baroque rather overwhelming.

The Bernina train homepage lists some accommodation in Tirano that may come useful. The old town centre on the Adda river can be good for a stroll and to find a restaurant for dinner - try pizzoccheri, sciatt, slinzega, because they are typical of the area and hard to find in the rest of the country.

In any case, I happen to be going to Tirano next Saturday so if you need more info I'll be happy to give it.

After your arrival at 12.49, you will most probably have lunch at Tirano. Then you may walk around this small city and visit the places suggested by Chiara. But what will you do after that?
May be you are interested in the rock carvings of Capo di Ponte (bus to Edolo plus train)?
Or you may skip the visit of Tirano by boarding there the 13.00 train to Colico and go on by Lake Como boat up to Como (ar 18.49).

We'll be spending the month of June in Italy

Literally? From the 1st til the 30th?
If not, what are your exact dates?

Also, what are the exact dates of the house sit?
And your time in Torino?

Are flights out of Venice already booked?
Also, where do you fly into Europe?
You mention the train to Tirano but you don't say from where.

Just trying to get a sense for how many days are already spoken for, when they're spoken for, and what might make the most sense to do with the remainder.