Flight Options

First of all, I would not drive in Italy, at least for city-to-city transport. If you want to take some excursions in the country, rent a car for that portion.

In the mean time, research all the pitfalls of driving in Italy.

Need International Drivers permit for all drivers. Not a biggie, get them at your local AAA.

ZTL's, forbidden zones in central areas of cities and towns. Guarded by cameras that photo your license plates as you enter, then send you tickets 6 months after you get home. The car rental company will ding your credit card to the tune of 40 to 50 EUR for each violation, and that is just their fee for telling the police where to send the ticket.

Automatic speeding cameras that send you tickets for exceeding the speed limit by a couple KPH.

Tickets for driving in bus lanes.

Train tickets are pretty cheap in Italy, and the Autostrada tolls are high. Fuel is high too.

As far as going early to Amsterdam and taking a discount airline to Milan, yes. But I would stay at least 3 days in Amsterdam before going. Contrast Amsterdam to Venice, two historic commercial powerhouses based on water born trade, built in a swamp.

Assuming one itinerary, Amsterdam is a great airport in which to change planes to a connecting flight to MXP. I would do this over connecting in BRU.

If you choose to have a separate itinerary to a discounted airline to MXP, allow a minimum of 4 hours in AMS in case there are any delays of your transatlantic flight.

Only you can decide if the added hassle is worth the savings.

Be sure to factor in the "what ifs" (what happens, and what would be its impact to you, if you miss your connection in AMS).

This is the most critical part of your question:

I'm curious whether the added hassle is worth the savings . . .

Well, that depends on what is worth more to you - time or money, and of course how much the money difference is. A non-stop flight to your destination that saves a day of vacation time, is worth the money to me. But you have to do the math, recognizing that its always a moving target.

Less than three weeks ago I got back from my trip starting in Trieste (flew into VCE) and then to Padova, Bolzano, Bologna, Barbaresco and Torino. Just a few points. If you have the option to fly into Torino, do so to save time in getting to the Piedmont and a small easy to deal with facility. The only part of the trip you’d need a car for is to tour the Piedmont (my new favorite place in Italy) and possibly to visit Bolzano and the Dolomites. Alba and the other cities in the region are charming, manageable and welcoming. We stayed at the Agriturismo Tre Stelle in Barbaresco and it was terrific. Only four rooms, all with terraces overlooking the hills and vineyards. Convenient for touring the area, great breakfast, wonderful hosts!

PM me if you have any questions.

I've connected through Amsterdam numerous times on separate tickets. Delta has a direct flight from Portland to Amsterdam - used to be the only one from here to Europe but other airlines have since added more. I've done the inbound connection (to Venice, Gdansk, Vilnius) the same day a few hours later - risky but I made it without issue each time. Ideal layover would be 3-4 hours for me though I've done less. If you can find a 5-6 hour layover that would minimize the risk. I certainly wouldn't need days in Amsterdam to connect.

I always make sure I understand the consequences of missing the connecting flight if my inbound is really late. Would I be able to buy a ticket on the next flight to my destination and arrive the same day? How much would that cost - cost of additional flight, cost of a hotel if I have to arrive a day later? I "war game" - it out in a sense - it's kind of fun, though I've never needed to use any of my contingency plans. Yes, it might cost you a few hundred euros if you miss your connection and have to buy a new ticket, though some travel delay insurance plans may cover some of the cost. Because I've done this numerous times (not just in Amsterdam), I figure that the cost of one missed flight averaged out over several flights isn't very much.

On the way back, depending on the flight schedules, you might plan an overnight in the Netherlands - doesn't even have to be in Amsterdam. The risk of a missed flight home from Europe is probably a lot more expensive than the risk (extra cost) of an intra-Europe flight, though I have done it (with about a five hour layover in Paris flying home.) The Netherlands has a great rail system with direct trains to the airport from numerous other towns e.g. Delft, where I spent a night a few years ago before flying home from Amsterdam after a trip elsewhere in Europe. I agree that Schiphol is a terrific airport for connecting in Europe.

Thank you for the input.

We'd have plenty of time as we would plan on spending the night in Amsterdam prior to the connecting flight. An upside would be that we'd have time to explore a bit of Amsterdam.

I have driven in Italy and agree that it can have it's drawbacks. The only reason I was considering the drive from MXP to Alba was drive time was half the time of a train. The more I think about it, the less attractive that the driving option is. We'll just have to look at our time budget and decide.

We are going to Northern Italy in the spring of 2019. We are taking a flight from Boston to Paris obtained with miles, then probably continuing on to Milan on a separate flight. In that case, we will stay overnight in Milan to recover from jet lag, then continue on by train to Padua.

Re: Flight home from Venice. Unless you leave Venice very early in the morning (which is a hassle), you flight to Detroit or Cleveland will arrive in the evening. Given that your body will think it is 6-7 hours later, and that you have to go through US customs and immigration, you may find it challenging to make it home that night.

At the end of our spring 2019 trip, we will be near Milan. We will fly from Milan to Paris and stay overnight there before flying home. The flight from Paris is non-stop to our destination.

Sounds like a fun and varied trip.
Many of us recommend NOT flying out of Venice though, because the flights that connect to the long haul flights home leave at o'dark in the morning. If you planned a connecting flight from Venice to another European city and planned on a day or two or three there (say Paris or Amsterdam or London) then you could take a later flight out of Venice.

The drive to Alba from MXP or LIN is easy enough. Whether you are jet lagged or not may be a consideration so overnighting in Amsterdam would help. Plus you'd get to explore one of my favorite cities before arriving in Italy. We fly internationally in and out of London LHR, stay overnight, and fly to our destination the next day without jet lag.
We loved our week in Alba! It is so easy to visit the various wine villages in the surrounding countryside. Much less touristed than Tuscany. Your trip sounds perfect!

You're not going to find anything out of Cleveland. Delta hubs in Detroit so there is good service to Europe. Delta also partners with KLM and flies non-stop to the KLM hub in Amsterdam; also Lufthansa and Air France fly out of Detroit so you might find some good deals there as well connecting in either Frankfort or Paris (which could help with the Venice issues others wrote about).

Actually, we found that by flying from Cleveland (on Delta) with a layover in Detroit saved us almost $800 compared to flying direct from Detroit for our October trip to Italy. I doubt I'll ever understand airlines...

Thanks again for all of the input!

Phrank - trying to understand airline pricing in the US is a PhD level class in ,"what were they thinking...." Dont know that I would drive in Italy, for reasons others have mentioned.

Much really depends on what you value the most - time, or money. If its me, I go the day early and connect. I would also choose AMS over BRU, and would be quite happy wandering Amsterdam to burn jet lag.

Thanks Tom.

I should have mentioned this in my original post, but I have driven in Italy. Probably not the best idea seeing that this was our first time overseas, but we used Waze and it helped tremendously. While it did point out speed checks I'm a bit on pins and needles as I didn't realize the margin of error was so tight. I did try to be conscientious. Hope it was enough.

Skyscanner.com allows you to search from Detroit or Cleveland to "anywhere" and by a whole month at a time. By doing this, you can find the lowest cost flight over. I just did and got DTW-LHR $502 on Virgin Atlantic, October 14. DTW-LGW via Keflavik was $310 on Wow.

To me it would be worth the hassle to save some money and see additional sites in Europe given the time, hassle and jet lag of getting over there in the first place. Amsterdam has some great museums (e.g. Rijksmuseum) to see if you have the time. They do recommend that you get to the airport in Amsterdam 3 hours ahead of time for your flight and we needed every bit of that time (and this was in April, traveling from Amsterdam to Ireland), Brussels seemed like an easier airport to me and there are certainly great museums (e.g. Royal Museum of Fine Arts) there too.

To put together multi-destination flight itineraries, it is both easier and more efffective financially to use a multi-destination search function rather than trying to patch together the flights individually. Skyscanner has one and it is good for short-hop flights in Europe. For trans-Atlantic I would compare the results from a more North-American-oriented source such as Cheapoair or Expedia. Perhaps the most comprehensive for trans-Atlantic is matrix.itasoftware.com (run by Google but more complete than Google's own Flights.) The difference is that the matrix only collections information without selling tickets. In your case I would look for connections all the way to Venice or Bologna on the first day, when you are going to be tired anyhow. Then fly home from the nearest international airport at the end of your circuit. To be clear, you can pick up cheap inter-city flights as single purchases, but for the long-distance connections you need a multi-destination search.