Italy and Switzerland or Austria?

How much time do you have for this trip?

About 2 weeks.

2 nights Venice, 3 nights in Rome, maybe 1 night in Florence but that's still iffy. 2 nights Milan with a day trip to Lake Como. And maybe 2 or 3 nights somewhere in Switzerland.

Jason, Florence fits in geographically between Rome and Venice or Milan, the trains go via Florence.

Where are you actually flying into and out of in your current plan?

If you are in Milan, a loop into Switzerland you could do is train Milan - Tirano - St Moritz. This route goes up the side of lake Como, then the Bernina Pass route over the Alps. Overnight in St Moritz.
Then there is a once a day bus from St Moritz to Lugano, going down the other side of lake Como. Then Lugano to Milan is easy by train. The bus runs daily to 21 Oct, and Friday, Saturday and Sunday only thereafter. The bus requires a reservation.
Timetable here: http://www.fahrplanfelder.ch/fileadmin/fap_pdf_fields/2018/90.631.pdf

Yeah that's why I might stop in Florence since I have to take the train through it anyway on my current plan.

Well my Austria/Italy trip was flying into Vienna out of Rome, but that airfare is outrageous and I'd have to take the train from Salzburg to Venice which is a pretty long trip.

If I switched Austria to Switzerland, I'd probably either do Round-trip to Milan or maybe fly into Zurich, out of Milan.

My starting point is Washington, D.C. area.

It's just tough logistics to figure out whether to do Austria or Switzerland with our Italy trip. I was leaning towards Austria since it's cheaper in the country, but getting there and then to Italy is more of a hassle/expense.

With just 10-11 nights, I think you may be better off to spend it all in Italy. It gives you more time to really stop and see things and reduces the logistical hassle you are battling.

I agree with Joe. When I run into complex logistical issues, I start cutting things out of my itinerary, because it's a strong indication that I've been planning a trip that has too much traveling and not enough actual sightseeing.

Q: Would it make more sense to go to Switzerland instead of Austria? A: Not particularly.

A day on the train doesn't bother me and the train from Vienna to Venice can be done without connections. I would "get over" this concern. Of course, you could also fly, or take a sleeper train.

Trains from the Berner Oberland to Lake Como (e.g., from Lauterbrunnen to Varenna) won't really be faster and will require a few connections. If you spend time in Switzerland, there are plenty of lakes to choose from, instead of Lake Como, or as you approach Italy you could stop at Lugano or Stresa (on Lake Maggiore) with a little less travel time.

If you want to visit Italy as far south as Rome, then I would not backtrack to Milan to fly home, unless you earlier fly from Zurich to Rome and then work your way north within Italy.

Looking Up Train Schedules and Routes Online gives you the Deutsche Bahn train schedule link and tips for using it.

Hi joe,

It will probably be about 12 nights/13 days. Big trips for us are quite rare, so seeing 2 countries is kind of a must. We're not the type who spend long days just relaxing. We do a little more whirlwind, see as much as we can type trips. I was originally planning on Austria to see Vienna, Salzburg and the Alps before going to Italy. But now I'm thinking 4-5 major cities in Austria and Italy might be too much in 12 nights.

So I'm considering changing the plan to Switzerland and flying into Zurich. We don't need to spend an entire week in Switzerland like we planned in Austria, so we can get the Alps experience and spend more time in Italy. Something like 3 nights in Switzerland and 8 or 9 in Italy. Originally it was 5 in Austria, 7 in Italy.

And then hopefully someday we can plan another trip to do Austria and Germany which seems logistically easier than Austria/Italy.

My last three trips included these countries.

My first family trip landed in Milan, then up to Berner Oberland, 3 days, then back to Rome( 3 days), Venice(3 days) and home from Milan. Rushed, lots of rail time but airfare from Milan worth it. It you want a sneak peak into these places of check them off your list, then you are all set.
Last summer spent two weeks in Austria, Vienna, Hallstadt, Melk, Salzburg. Much more relaxed but the mountains not like Switzerland. I like your last trip, fly into Zurich, then BO then Italy.

Have fun.