Northern Italy in October

I live in Milan. It’s not your “typical” charming italian town. Since it's your first time in Italy, I'd bypass it and go straight to Venice as you suggested. Which airport do you fly into? If Malpensa, take the Malpensa Express straight from the airport to Centrale station (make sure it's Centrale and not Cadorna as Cadorna is an option too) or if it's Linate you can take the shuttle bus to Centrale. Buy your train ticket when you arrive at Centrale and not before. Too many things can make you late getting to your train to Venice. There are plenty of hourly trains to Venice through Italo or Trenitalia and you arrive early enough to have a lot of choices. Download the Trainline EU app and you can purchase from either line directly from your phone and you don't have to fuss with ticket machines. FYI, there's no free WiFi at Centrale so make sure your cell data will be working.
In October, Venice isn't as crowded as spring or summer but do expect some rain.

Hi Jane,
I would definitely fly to Milan (don’t stay in Milan, there is not much there for the first timer) and then jump straight on the train to Varenna (Lake Como). Varenna (1hr on the train from Milan/ 10 euro each-way) is a fantastic spot to base yourself on Lake Como. There is plenty of accommodation that is relatively cheap, within a 5-10 minute walk from Varenna train station. Also some great local restaurants, all without the crowds - and it’s a beautiful spot. There is a great ferry service that will get you from Varenna to a host of villages (including Bellagio) dotted around the lake, in about 20-30min. I spent a week in Varenna in Sep 2018 and am returning (from Australia) to Varenna for a week, coincidentally on the same date, October 2. We are catching the train (Naples) up after a couple of weeks on the Amalfi, at Atrani. Personally, I’d rather spend two extra nights in Varenna than 2 in Venice. However, I have been there, and it’s a bit like an Aussie travelling to NY and not going to see the Statue of Liberty, or Paris and the Eiffel Tower. Those crowds you have read about - they are worse :-). I don’t have any suggestions for a base in Tuscany, other than you don’t need/won’t a car in Florence. I would suggest you book accommodation for Varenna now if you are going there, as it is a relatively small village and vacancy’s dry up. I also recommend using the rail system (300km per hr trains) if travelling between Milan-Venice-Florence. A great and simple app for booking rail journeys in Italy (and throughout EU) is Loco2. The earlier you book your train tickets the cheaper they are, journey time (Milan-Venice) is about 2hrs 30min.
Mark

Jackie's plan is exactly what I would have given you. Assuming you are arriving from the US, your first day is not a "real" day, hours to get through the airport lines, jetlagged, sleep-deprived haze. You might as well spend those hours on trains, get to Venice with time to drop your luggage at your hotel, walk around a little, have dinner and crash. Venice is the perfect place to being an Italian adventure. There are no major sights to absorb, it's romantic, you can soak up the atmosphere while you recharge your batteries. Ride the vaporetto up and down the Grand Canal (early morning and after dark are the best times). Go to the high-tourist areas, mainly Rialto Bridge and Piazza San Marco early and late to avoid the crowds. It's surprisingly easy to find quiet charm here. 3 nights gives you 2 full days.

Verona is one of my favorite towns. It's worth spending a night there on your way to Varenna. I haven't been to Lake Como. Do you plan on a lot of (real) hiking in the CT? If not, it may not be a good choice in early October, especially for "hubby" who doesn't like crowds. The CT can be very very crowded with daytrippers even in early/mid October. Some here have suggested staying in other coastal towns where tourism is much lower. Or consider a few days in Bologna, where you have a slew of possible day trips by train to many great towns - Parma, Modena, Padua, Ravenna, Ferrara come to mind immediately. It's not a big tourist destination, so crowds will be less.

In Tuscany with a car, an agriturismo is a good choice. Be aware that when visiting towns, you will have to park outside the historic centers which are ZTL's (limited traffic zones - limited to residents). Learn the sign for them. There are usually no barriers and it's all too easy to drive into one by accident. The areas are photo-enforced and fines are considerable. Consider staying somewhere on the "border" between Tuscany and Umbria (just as beautiful, similar landscape) and lots of small towns to explore. Assisi is a good destination by car because it's very time-consuming to get to by rail (on a subsequent visit).

Try to avoid Florence on the weekends when it gets very crowded.

We visited Venice last October and it was not unbearably crowded. Venice is beautiful and magical and was our favorite city in Italy. We took a food tour our first evening there and our tour guide told us that walking lost was the best thing to do in Venice ... and she was right! We would walk back streets, visit churches, find gelato shops and stop in little restaurants off the beaten path. Most times we were the only ones on the streets. The major sites such as St. Mark's Square and the Rialto Bridge area get crowded with tourists but are worth seeing. If you are there a couple days, I would get a vaporetto pass. It's nice to just hop on a vaporetto whenever you want or take an evening ride down the grand canal but make sure to validate it every time you get on.

Thank you all for you input! We’ve definitely decided to go straight to Venice from Milan. Will stay 3 nights. Got a hotel reservation. When we check out, we’re going to Lake Como. We’d like to stay in Varenna. Any suggestions??