Europe Train Advice Btw Austria/Italy

You are correct about which websites to use. Be sure to use the correct Italian names on the Trenitalia site: Venezia (S. Lucia), Milano, Firenze (SMN), Roma (Termini). Where in Lake Como? Varenna? Yes, if you're taking a Freccia from Milan to Rome, you would need 2 separate tickets if you want to stop off in Florence.

There's usually no need to buy tickets ahead of time for regional trains, like the one from Milan to Varenna. But for the high speed trains you can save quite a bit of money by buying in advance for nonrefundable tickets for a specific date and departure time.

Also, Vienna to Salzburg you can use Westbahn (I understand you can just buy tickets on board.)
Hope your hotel reservations are refundable/changeable -- there might be an airfare sale, but might not.

Jason: I have been watching your other posts, but you have never mentioned what your home airport is. With that info, we could possibly give you information on airlines, etc. to serve your travel needs.
Distances in Europe can be farther than you expect. And going from Vienna toward Venice with a detour thru Salzburg requires crossing The Alps.

Hi David. Sorry I thought I mentioned that. I'm leaving the Washington, D.C. metro area. So likely either BWI (first choice ) or IAD.

Airfare isn't looking good right now though. Other than WoW or Turkish, most open jaw are well over $1000.

And Salzburg is part of my planned trip (staying there 3 nights) so it would be Salzburg to Venice, not Vienna to Venice. Figured I'd go through the Brenner Pass.

Laura, yes all my hotels are able to be cancelled.

If I were forced to place a bet, it would be that airfares will just be going up.

Just be sure to know when the 'no penalty' cancellation date is for your hotels

You can get all over the world from Dulles. But no real budget carriers going overseas from there--or out of Baltimore. I guess so much travel out of your region is governmental and they aren't getting the best deals.
The NYC--Boston--NH region is getting the real deals.

Have you checked flights into Munich? When I've looked in the past, it was substantially cheaper than Vienna. Whether there would be enough difference to make up for the train fare and travel time, I do not know.

Although my plans later changed, I set up a fare alert a number of months ago for a flight into Munich in early May and back from London in September. That fare has bounced all over the place: up $500, down $500, up over $2000, back down. I don't know what they're feeding that computer, but it is one sick puppy. I'd be watching every possible combination of origin/destination every day, hoping to catch a downward adjustment.