A week in October in Lake Como

Best to ask about the funicular schedule in October and payment options.

https://www.myswitzerland.com/en-us/experiences/monte-bre/

You can buy your train tickets at the Milan station - just don't validate (time and date stamp) them until shortly before you use them.

I suggest getting the Trainline app. Just buy them on your phone and show the barcode to the conductor. Very easy app and website. We used it in both France and Italy

I believe Trainline now has a service charge.

Hi, you were incorrectly advised that Varenna train station doesn't sell train tickets. there is an agent, just during normal business hours. When you get off the train, on the platform ,looking at the station its on the left hand end of the station building.
Varenna to Milano depart on the XX.37, so 7:37, 8:37, 10:37, 12:37, 13:37
Milano to Varenna depart of the XX:20 so 9:20, 10:20, 13:20,14:20, 16:20, 17:20, 19:20 tickets 6,70E.

'm going to say this because there was yet another tourist on one of our trains into Milan, who did not validate his ticket, and got a fine, so look for the box and stamp your tickets on regionals.

Fwiw,
I'd recommend booking Ristorante il Caminetto, its in RS book, they will come and pick you up /drop you off at the end of the evening.
Not in RS Book but recommended by our apartment owner was Al Prato (I think) its by itself in a little plaza off Largo Enzo Venini.
make a booking the night before.
Also along Contrada Scoscesa, is a small restaurant , also with outside tables, but I can't remember the name, but look for their red awnings above the ground floor windows.
All were very good and recommended.

regards

The ticket seller at the Varenna train station is actually a travel agency and they are very helpful. There is also a tabaccheria which is an "official" ticket seller a few doors south of the piazza, on the right hand side as you go towards the Villas.. We used both last week, no problems.

The two best meals we had in Varenna were at Ristorante Il Cavatappi and Al Prato. For Cavatappi we had to reserve several days in advance, as there were 4 of us. There is only space for 14 people inside, plus a few more outside.

And...it might be chilly there in October.
We were there mid September in Menaggio, for a few days a few years ago, and I had to wear every layer of clothing I had with me to keep warm.
Think bag-lady look.
It was sunny and clear, but windy and cold, especially while out on boats on the lake.
As long as you have layers, and a good rain/wind jacket you'll be fine.

Just a word of caution about staying in Milan with an early morning flight, if you plan on taking the train from Milan Central to the airport:
That was our plan in April, and the train we wanted was suddenly cancelled! We obviously had to wait for the next train, in about 30 minute, and had extra time, but were SO stressed that the subsequent train might also be mysteriously canceled. We were fortunate that everything from then on went well, we navigated thru the Milan airport quickly, and made our flight. The irony is that we were at the station early enough for the preceding train, but they wouldn't let us on with our later-timed tickets. However, we learned that our tickets were good for trains AFTER our ticketed route.
SO-
if going by train in Milan, arrive EXTRA early.
OR-
stay out by the airport. On our next trip, that is what we will be doing.
Safe travels!

Thanks everyone for the advice and recommendations!

My wife and I were at Lake Como Sept. 4-10 and visited just about all the Villa's you listed on a ala carte no reservation basis. If you hit Balbianello on a busy day you may have to wait a bit for a guided tour inside the Villa which are limited to about 15 people each. All the others Villa's were pretty wide open with nice gardens. We did our first night in country in Bergamo and walked from the train station to our hotel nearby, dropped our bags, then walked to the funicular base about a mile or so up the main drag. Be sure to buy R/T funicular tickets at the funicular base otherwise you'll be walking down and it turned out the down-steps were closed for work -- which caused us to have to detour onto the streets jutting out way out to the side further lengthening our walk. Loved City Alta though! Also, if you have the time and your train logistics allow, a stop in Lecco on the way back would be a good for eats, shopping, and some nice views of the Lake from a different perspective.

Take an umbrella and a sweater.
It will start getting wet and a little cold over there.
I would have chosen southern Italy or the islands at that time of the year.

I think Fall would be a lovely time to visit; just wear warm clothes especially while cruising the lake; the weather should be in the mid 60oF. At that time of year you won't have to line up to visit the Villas. Enjoy, loved Lake Como; we toured the lake but rented a car from Milan and dropped it off in Venice. So much more convenient! I'm sure the funicular takes credit cards?
Cheers,
Jean