Northern Italy Trip in September, Milan or Como as Hotel base before heading to Venice?

For Lake Como, I would not stay in the town named "Como." Varenna is on the train line and thereby ideal for a day trip via the Bernina rail route into Switzerland as well as for short ferry rides to Bellagio and other places on the lake. Although it is doable, I would not want to travel from Lake Como to Milan for a full day of sightseeing in Milan and then head back to the lake for the night. These trains are sometimes quite crowded with numbers of people standing. I appreciate the desire to minimize hotel/city changes with one base, but I would find it much more enjoyable to stay at least one night in Milan for the Milan sights. If you want to see DaVinci's Last Supper, you need to reserve timed entry tickets several months in advance. If you have at least a full day or parts of two days, your changes of getting tickets will be better. You might stay in Milan the day you arrive since you would need to take a train into Milan to get one to Lake Como (if you are going by train). Or you could stay in Milan the night before you go to Venice as you will need to take a train to Milan to get the train to Venice, again, assuming you are traveling by train. If you are renting a car, you won't want to have the car in Milan.

It may not be an popular choice, but I would consider staying in Como city; you can tour the lake from there by ferry and it's. lively city with great restaurants and shopping....and much less jam-packed than the ocular towns that have easy access to Milano, like Varenna.

You can take a ferry and reach Bellagio in an hour or so...

You will need to be in Milan or near MXP the night before departure.
I would spend first few days at Lake Como- day trips to/from Milan from there would be a pain as transportation is limited and extremely overcrowded
Next train to Venice
End in MIlan- give Milan at least 2 nights.
If you are interested in the Last Supper be sure to stay on top of when those tix go on sale. They sell out almost immediately.

Another option is Venice- Milan- then end at Stresa on Lake Maggiore. There is a direct bus to MXP from Stresa (actually closer than Ilan)
Stresa won't be near as crowded as Lake Como. Take the train into Switzerland

Venice hotel
Hotel Ala- can't beat the location, just steps from vaporetto with no bridges to cross. In a quiet campo, excellent bkft, great staff and roof top terrace. Quick walk to the sights
https://www.hotelala.it

I suggest staying in Varenna on Lake Como. There is a train station there. You could either walk to your hotel or take a taxi or uber. We loved staying at Hotel Albergo Milano. An easy walk to the ferry terminal. And they have an awesome restaurant, La Vista. You should make reservations.

In Venice, we stayed at Hotel Agli Alboretti located in the Dorsoduro district, which is a much quieter area than San Marco Piazza. We loved staying here. It's about a 1-minute walk from the vaporetto stop at the Accademia Bridge. About a 5-minute walk from the Zattere (seaside promenade on Guidecca Canal). And about a 20-minute walk from St. Mark's Basilica.

Thank you for the advice and recommendations. We will have a driver for most of the trip so train lines are of less importance. We will be staying the last night in a hotel close the MXP to make the next morning's flight home much easier or maybe we could end our trip in downtown Milan and cover the main attractions at the end of the trip. Any recommendations for hotels in Milan?

Staying on the very busy Grand Canal can be noisy. We love the Cannaregio area, and the hotel Ai Mori d'Oriente, in such a charming area, without the crowds. Have a great trip!

Milan hotel
Duca di York
https://www.ducadiyork.com/en/

I second the recommendation for the Hotel Gran Duca Di York. Convenient location, a good-size room, and a delicious breakfast buffet. It was about a 5-minute walk from the Milano Cathedral. We stayed there twice: 3 nights at the beginning of our trip, and then our last night before we flew home from Milan. They have a happy hour starting around 4pm or 5pm.

If by "two days" in Venice you mean two nights, I think that is really too short, unless you've been to Venice before. It takes time in Venice to see the totally overrun highlights (Piazza San Marco and the Rialto Bridge and market) and have extra time to wander the back canals where you can really feel the atmosphere. Otherwise, it's akin to visiting Disneyland. Folks who make really short trips to Venice often end up disliking it.

Lodging in the small mid-lake towns on Lake Como is extremely popular. September isn't off-season there. You should check immediately to see whether you can find something that meets your needs in the towns you are considering. Availability may affect which town you stay in. Booking.com is a good place for a first look at what might be available. You'll probably save money by making your reservation on the hotel's own website, however.

We are planning 3 nights in Venice. We have been before and loved it but our travel partners have not been. Last time we stayed there, we were in an Air BnB right on the Grand Canal, close to the Rialto Bridge and a vaporetto stop. Unfortunately, we didn't really pay close attention to any of the hotels along the way so would love some recommendations for 4 star hotels with a view. The hotel Ai Mori d'Oriente looks lovely and we will look into it.

Hotel recommendations in the Como area are especially appreciated. Heard good things about the Hotel Villa Flori but it looks to be out of the main downtown area of Como. Is that a big deal? Ideally, we'd like to be on the Lake with a view and within walking distance to restaurants and shops.

Thanks in advance for your help and advice!

hey hey Michael
do you have flights tickets bought already? you could do a multi-city, fly into venice and out of milan without backtracking. take train to the lake then spend last days in milan for flight home. or take train to venice first and work your way back
check-in times are 3-4pm and check out 10-11am. would not recommend staying on grand canal, it gets so busy, crowded and loud with every kind of boat going up and down it. years ago friends stayed at hotel olympia near train station and short walks to other places in venice. don't know what you want from "4* hotels", the stars are for more amenities you want, doesn't mean they are fancier.
(front desk available 24 houts, A/C, elevator/lift, views. if you find something you can email hotel if they have a better rate.
september is still high season and much of italy is crowded in big cities all year long. it's olive oil/harvest season for wine, many towns/village have fairs/festivals they are so much fun.
schezzini.it
alessandro does a chicetti bar crawl to small venetian bars with "local appetizers/small bites, wine & history of venice. email him/contact for more info. mentioned a lot here to enjoy.
so many travelers going here there and everywhere. do you activities/attractions you plan to see & do, book early direct at website. decide on what type of transportation you want. always look at route, pushing/pulling over cobblestones/bridges/stairs steps, if a platform right at hotel without stress with luggage. buying a pass 1 to 3 days getting on vaparetto any and all times. just roaming around, "don't fall in canal:)" getting lost with dead end calles/streets", walk the back canals/areas (canareggio, castello away from tourist central "st marks's square/rialto bridge), many daytrippers gone by 4pm, do you want to take boat ride to murano/burano (my favorite island) isoladiburano.it
good info for you is many restaurants closed mid-day 2-4pm, if having lunch look at times since you can eat.
[email protected]
well known venetian gondolier with many years in the family. we met him at the jewish ghetto area and cruised back canals & crossed grand canal, he sings opera LOVED IT!! fabulous guy and learn about history. email him for date you want. i think we did an hour, you decide daytime or nighttime which is more. we brought a bottle of prosecco with plastic glasses from apt to celebrate with 4 friends, 2 had never been & we have been 4 times. the "virgins" were in awe, yes it's touristy but we are tourists and lucky took selfie of us and him.
if staying on lake como, book early. it gets so crowded, long line to restaurants, ferries, walking the promenade sine lake como is like one of #1 places to go to. just renenber george clooney is now a frenchman! LOL
enjoy, have a great time, have gelato & tiramisu, prosecco (we took a private taxi tour to prosecco road, was gorgeous). ask more questions if need be
guruwalk.com milan
discoverwalks.com milan
aloha

@princess pupule, thanks for the additional information! Yes, we have locked down our flight already and the women want to travel via private care, especially while we are carrying our luggage. We are seriously thinking about spending the last couple of days in Milan to see the main sites and make it easier to get back to the airport for our flight home. My wife and I have been to Venice once before, 3 years ago but the couple we are traveling with, have not. Love the additional information on Venice and Como!