Northern Italy mid October
 

We are flying into Milan mid October 2024 on our way to Trieste to join a cruise. Our current plan is to head straight from the Milan airport to Lake Como for 2 nights, then to Cinque Terre for 3 nights, Florence for 4 nights and Venice for 3 nights (then one night in Trieste). My questions are as follows:

1. Does it make sense to go to Lake Como for only 2 nights just upon arrival? I'm debating saving this for some future trip and just staying in Milan for a night or 2 and then heading south.
   
2. Has anyone stayed at the Grand Hotel Portovenere as a base for Cinque Terre? I currently have a reservation at Hotel Porto Roca (in Monterrosa) but am debating changing it to either Grand Hotel Portovenere, Grand Hotel Miramare (in Santa Margherita Ligure closer to Portofino) or Grand Hotel Bristol (in Rapallo) and just doing a day trip to some of the Cinque Terre villages. We do NOT plan on renting a car but rather taking trains/ferries etc. Would be interested in anyone's thoughts on best place to stay.
   
3. Looking to do one day trip/private tour outside of Florence - probably to some wineries but would be interested in anyone's off the beaten path suggestions on this one as well as good private tour companies.
   

Thanks in advance for the input - much appreciated.

October can (but must not) be rainy in Val Padana.
What do you intend to do along Lake Como and in Liguria?
As long as don't know your reasons for the choice of Lake Como and 5Terre and we can hardly give any good advice.

Is this your first trip to Italy?

I would question spending time in the CT. What do you plan to do there in October? Hiking?

I liked GH Miramare in Santa Margherita (among few with heated pool) but Camogli is a more charming town.

If you are on your way to Venice and Trieste, is there maybe another place more on the route that interests you?
Verona? so many options in a more direct route to your ultimate destination....


I am always in favor of fewer destination with more time in each one.....

Where on Lake Como? Apologies if I missed that.....

What about all the places near Venice? Padua to name one.......must be terrific in October....

For me, and for me only Piemonte makes more sense in October.....can you see if you might go to Turin and tour around the Langhe and then head east towards Verona and Venice......truffles!

One full (and likely a bit jet-lagged) day at Lake Como won't give you much time to see/do anything. You're limited by ferry timetables and where you decide to stay. The train ride from Malpensa to, say, Varenna takes nearly 2.5 hours, the journey from there to one of the coastal destinations you mention will take between 3:45 and 4:30 hours. Onward to Florence will take between 4 and 4.5 hours. That's a lot of time sitting on trains and not sightseeing. Florence to Venice is a relatively quick 2:15 hours.

Before you start planning day trips out of Florence, plot out your 3 sightseeing days. To make the best use of your time, get entry reservations for any sights that offer them. Most of the "main" sights are not open every Saturday and/or Sunday, so you may have to do some difficult prioritizing.

And before your decide to stay in Porto Venere, check the transport options and timetables for your particular dates as I think ferry schedules change sometime in October. IMO, Porto Venere is a lovely spot but not particularly convenient for exploring the Cinque Terre and the coastal towns beyond during a short-ish stay, so much depends on your priorities for these days.