Traveling to Italy end of October for 3 weeks

Just checking if you're going to these locations in order - Milan, Lake Como, Venice, Florence, Cinque Terra, Siena and ending in Rome, which would be the better choice given the weather. Personally, I think this is a fantastic time to travel with fewer crowds & cheaper accommodations. The weather will be changeable, and chillier especially east of the Apennines in Venice & north in Lake Como. You'd need waterproof shoes, layers, a down layer & rain coat, but why not?! Obviously the further off the beaten tourist path you get, the fewer places may be open but you're going mostly to famous cities, where things stay open all year, except Lake Como & CT. And if the weather is poor, there's always museums & churches to visit. Personally, I would skip Lake Como & CT at this time of year & spend more time in Venice, Florence & Rome. ( Ask others about CT, not sure when the trails would close.)

I am exploring Italy in the order listed above. I fly into Milan on October 24 and fly out of Rome on November 13. I put a three day hold on a United Airlines ticket because the price was very good. Having never been to Italy before I just wanted to make sure I was not making a mistake. I have been reading RS guide book and searching the forum and it looks like it may be cold but all the sites will be open. Thank you very much for your response. I will probably purchase the ticket tomorrow.

BTW, I agree with you. I will probably skip Lake Como and I will think a little bit more about CT. Thank you again.

WHAT fun!! Though it will be less busy, I would still book major attractions in Florence, Venice & Rome. Milan is OK for a night, but keep on going to the more picturesque places on your itinerary. Don't miss the Borghese Gallery in Rome, a peak experience IMO.

We went to Italy at the beginning of November, 2021, and we were really glad to go at that time. The weather was mainly pleasant--not too hot, although there was the occasional drizzly day and one big thunderstorm. Of course, there's no guarantee when it comes to the weather.

Crowds were manageable, except in Florence, although tourism was still lower than normal then. However, our daughter went to Italy in late November a few years earlier and found the same.

We didn't go to Cinque Terre and spent just a few hours at Sorrento, on a tour, because it wasn't really the season for that.

The only place we were cold was Venice, but only on the last day (out of 3 days). Mind you, we are from Canada, so YMMV.

We were also able to stay in places that would normally be out of our budget, because of the time of year.

The only places that were closed were in Civita di Banoregio. The duomo was closed for renovations, and there weren't many cafes open. But we thought it was well-worth the trade-off, having uncrowded streets.

We had a wonderful trip and would definitely recommend travelling to Italy at that time of year.

I’m not up on Cinque Terre trails being open or closed in late October, but if you were to go straight from Milan to CT, I think that time of year there might yield some delightful surprises. You may not get to hike the trails, but just being in the towns without the horrendous crowds would be a great experience. Of course, you have to keep in mind that it is later and all restaurants, the ferry, etc., might not be available. I’d still take the chance!

When you have a tentative sightseeing list, come back here and ask about where you need to get tickets in advance. In Rome you'll need them for any of these sights you want to see: Colosseum, Vatican Museums, Borghese Gallery and Domus Aurea. In some cases the tickets sell out a month or more in advance even in the dead of winter.

In Venice you can avoid a long entry line at St. Mark's by buying a cheap entry reservation ahead of time. I'd also recommend buying a Guggenheim ticket a bit ahead, because it's very popular and you could end up in a considerable line if you just walk up. The Secret Itineraries Tour at the Doge's Palace is very popular and calls for early purchase. I don't know what the situation is like for regular tickets to the DP.

I haven't been to Florence recently.

This is my favorite time of year to travel to Italy. Go. Enjoy yourself!

Thank you so much for the responses. You all eased my concern. This morning I purchased my airline tickets (I had fare locked a good ticket price) and now I need to work out the details, like where to stay and what to see 😀. I will be following your advice to get advanced reservations for the Borghese Gallery as well as other sites and museums. I am certain I will be reaching out to the RS forum again for tips and advice. I am very excited about this trip and I am looking forward to my first trip to Italy.
Thank you again.

People in the RS Forum are the best!

BTW I wanted mention that I decided to take a chance on visiting CT. I will be getting there on November 3 for three nights. It is a place I have been wanting to visit for a long time. Hopefully the trails will be open.

If you like cathedrals, you should spend a few nights in Orvieto or do a day trip by train from Rome. If food is important to you, you could consider Bologna. It's a university town, so wouldn't be shut down.

We are arriving in Monterosso on 11/4. We hope to hike if the weather permits. The trails are open all year [weather permitting], and the last day for trail fees is 11/6. Maybe we'll pass you on a trail. Basic info re hiking:

https://www.cinqueterre.eu.com/en/cinque-terre-current-situation

Edited to add: Also, while the ferries may no longer be running, I see there are a number of private boat hires that may still be working - again contingent upon weather. So maybe we'll try to put an ad hoc group together one morning to see the towns from the water.

Just left Lake Como and it was pretty spectacular.
I would recommend going there.
With the airlines chaos and jet lag, I would plan on staying in Milan your first night, don't try moving on. If flights are late, it's just too hard to make connections.
Have a great trip!

It sounds great! You'll have a wonderful time.

I just wanted to assure you that you made a good decision. We spent 8 days in Tuscany right before Christmas in 2015. The weather was fine, most days were warm (mid '60s) and sunny. A couple of mornings there was a little frost, but we were in shirt sleeves by lunch. Everywhere we wanted to go was open.

We love traveling during the off season. It's much less crowded.