Last minute seat-of-pants tour of Italy

Hi,
I'm in Italy right now and there are definitely places to book last minute but less available on weekends. I would encourage you to skip the car and use the excellent train system. Easily booked at last minute at the station and much more convenient than trying to drive into the cities.

A possible itinerary with 8 nights I would suggest 3 for Rome, 2-3 in a smaller town ( Orvieto is lovely and quiet if you want a countryside feel, and easily accessible by train. Then your last two in Milan.

Unless an hotel in the center puts your plate number on the cops' white list, you can't drive into any city center because of ZTLs.

This is not a problem in the hill towns where you can easily park outside the ZTL and walk in, but thousands have been fined in bigger towns like Florence and Pisa.

You are highly unlikely to get into the Borghese Gallery or the Vatican Museums if you don't look for tickets now.

For the Vatican, there will probably be options for $$$ tours if you are willing to pay extra, but even that should be investigated ASAP. The Vatican Museums have been selling out well in advance recently. You can check the status of the days you hope to be in the city here: https://tickets.museivaticani.va/home. Your best bet is probably a late entry on Friday or Saturday, and the experience is likely to be somewhat less miserable (in terms of crowding) at that time of day.

The Colosseum underground level is also a hot ticket.

The Last Supper in Milan sells out even farther in advance than the Vatican, but sometimes if you show up first thing in the morning, you get lucky (based on comments here and elsewhere). You just cannot count on it.

There are of course dozens of great things to do that do not require such pre-planning.

I should add that we only would stay over in Milan for flights...not interested in really seeing it.

When I worked for the airlines, it was impossible to fly in and out of IT as a stand-by so I flew into Zurich. Milan was better than Rome but still, why take that chance when you need to get back to work. Zurich is a 3h 30m direct train ride from Milan so keep that in mind.

Seeing the Last Supper was one of my greatest travel moments. Just me, a guard and the painting.
Pre booked via Viator….this was a decade ago.

My point, one of the most famous paintings is in Milan.

Lastly, fabulous pasta at Trattoria Sabbioneda da Romelo.

Hidden gem; the Church of San Bernardino alle Ossa, or Church of Bones.

Safe travels!

My only bit of advice is that I love Milan also, it’s great and I think sometimes gets overlooked. If you do decide to spend some time here- I agree with above poster regarding seeing “the Last supper” if you are an art lover. We booked a tour with “Walks of Italy” tour and loved it! Tour of The Last Supper and the incredible Duomo, as well as little tour of the tourist area of the city. The Duomo is just breathtaking.
We stayed at Hotel Gran Duca du York, a reasonably priced and centrally located hotel near the Duomo. I think this place always contributes to my love of Milan, because it’s always so sweet and the breakfast is so good and the people that work there are just great.
Just my $0.02 😄
P.S. the hotel I suggested is always so booked up- very popular so may not be able to book last minute, just saying…
We spent 2 days here and loved it.
Happy travels!

This sounds like an exciting way to travel even if it runs against my tendency to over plan.

My take: If you assume Rome <> Milan in some fashion it should be easy to figure out 8-9 days and put together a plan of highlights you wish to see. It sounds like a car fits your "free as the wind" travel style but it does not fit into large Italian city travel.
Do no rent a car for use in Rome or Florence as it will be a huge burden. All large cities are served well by trains and if you want to put together a Rome (3), Orvieto (1), Florence (2), Lucca (1), MIlan (1) trip alternating large and small cities that is easy by train.

The exception to the train rule being the famous hill towns of Tuscany. So you want to do something more rural I would suggest something like:
Rome (2/3) train to Orvieto (1), rent a car and tour Tuscan hill towns - 3/4 nights: Cortona, San Gimignano, Montalcino, Volterra, Montepulciano, Pienza etc.
Return the car in Siena or maybe Pisa/Florence airport - somewhere outside the city center - have a last night in city if time permits - Florence? - and then train to Milan.

Your limiting factor may be where you can pick-up and drop off a car - the agency needs to be in both locations - but I strongly recommend not using the location in the city center in any large town.
Nearly all well known Tuscan towns have a dedicated parking area outside the city. Trust them and use it rather than risk any internal city craziness and potential ZTL violations.

Whatever you decide have an exciting trip!
=Tod

I was just at the Borghese yesterday (Sunday) and they had a sign posted at the ticket office saying they were completely sold out through Oct 28. I’d originally booked a tour with Walks of Italy but they canceled about 6 weeks ago saying their reservation was canceled by Borghese.