Northern Italy itinerary help

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Do you have 10 nights actually on the ground in Italy? How big is your travel group, what is your pace of travel, are you into art and museums, hiking, food, etc. ?

I'd definitely include Venice and Lake Como.

Have a great trip.

You didn't say where you are landing. Milan? Rome? Venice? That will affect how you structure your visit.

I fell in love with Venice at first sight, walking out of the train station and seeing the Grand Canal at my feet. See it before is totally overwhelmed and sunken. Probably going to have a tourist fee. Get a multi-day pass to ride the "water buses" and go to the other islands, or even something we did--entirely circled Venice on a vaparreto.

Spent about 10 days in and around Varenna on Lake Como, took ferries almost every day, loved the area. Lots to see, great gardens. The other lakes have things to recommend them also.

From Varenna--but also do-able from Milan--we caught the trains to St. Moritz, Switzerland. Lovely trip, also in September. Discovered Laderach Chocolate in St. Moritz-branches in Europe and a few in USA. Best dark chocolate I've ever had.

Milan has a lot to offer, can definitely recommend the Duomo tours (including the roof if still available). Fees charged, but worth it. Some of our group went to the Canal District and enjoyed it.

You can drive to Switzerland from northern Italy, Haven't done it myself, but if that fits your car rental period, something to think about.

Bologna? Florence? The Dolomites? Trieste? So many possibilities! Have fun!!!

I’m undecided if I should fly in to Milan or Venice. I’m coming from NYC. either is an option depending on the itinerary

If you end up flying into or out of Milan, Bergamo would be a convenient choice of medieval town, though there are other options. I'd probably leave that as the last decision after pinning down the lake stop.

If you rent a car in Italy and drive it into Switzerland, you'll probably need to buy a Swiss highway vignette. Only an annual vignette is available, and it's pricey for a short visit at CHF 40 (currently about $47 US). I'd take advantage of one of the scenic Swiss rail routes--another decision I'd make after knowing the lake plans. You'd want to select the rail trip carefully to avoid those that spend a lot of time burrowing through mountains rather than going around them.

It’s easier to fly IN to Venice than out of Venice so I would opt for in to Venice, out of Milan

How many NIGHTS will you have in Italy?

If you fly into Venice that needs a minimum of 3
You could stay 4 and day trip to Bassano del Grappa

Then a lake stay of choice -3 nights

If you fly out of Milan you will need to spend 1 night there before departure

That’s 8 nights

Not sure you can fit Switzerland unless you plan to fly out of Zurich
Maybe work your way thru Switzerland on one of the Scenic trains

Don’t see any need for a car
Renting in Italy then dropping in Switzerland will add a huge drop off fee

Definitely fly into Venice and back from the area of your last stop (perhaps Milan). Will save a lot of time by not backtracking. Suggest spliting the time between Venice (you'll love it) and Lake Como, with perhaps a little more time in Venice. You can do day trips from each, and that will eliminate time lost relocating.

If you like medieval towns, consider adding South Tyrol to your travel plans. The region has 800+ castles and is riddled with medieval villages. The village of Glurns would make a great stop as it is in Val Venosta, which is en route to Switzerland. It is one of the few communities still fully surrounded by a medieval wall. Merano and the surrounding valley make a wonderful base to explore the region. Be sure to walk the enchanting Tappeiner Promenade to take in several historic sights: https://throneandvine.com/merano-italy-promenades/

I love that idea Kate!
How is it driving in that area? I’d probably drive up from lake garda

If you head up into that section of the Dolomites, you might like to check out Chiusa/Klausen, which is between Bolzano and Bergamo (closer to the latter). It looked intriguing as I passed through the village on the train, so I hopped off and walked around for a while. Definitely medieval.