Planning for Northern Italy in May 2025

One thought I would offer is to go immediately to Venice upon landing in Milan. The trains are frequents and efficient and Venice is a lovely place to spend 4 nights recovering from the flight and enjoying the sights. Then build your itinerary moving back toward Milan so you can spend your last night or two there.

Ok that's something to think about and consider depending on when my flight leaves. Most flights to Europe leave in the evening or late night and I don't sleep or sleep very little when sitting upright so I would be very jetlagged and sleep deprived.

What about flying into Venice and out of Milan?

I'll need to do more research. I know RS always recommends the open jaws flight. My old research shows that flying out of YYZ and flying into and out of two different cities is much, much more expensive compared to flying in and out of the same city.

My brief check of Air Canada autumn flights to Milan shows that there are no non-stop, direct flights from YYZ to MXP - they stop in Montreal or somewhere in Europe.

There is a charter airline that flies into and out of Venice but it doesn't allow for a one way flight when searching a booking

We don't have as many flight options as the USA.

Taking a look at Air Canada and picking random non weekend dates in September October since it's too early to check for May flights- one way flight from YYZ to Venice ~ $300 more compared to price of arrival flight when flying in and out of same airport. One way flight from MXP to YYZ is $2000 in October! This is economy.

Wow, that IS quite a difference. One way flights definitely can be more expensive than round trip. Does the search engine allow you to look at Multi city tickets? Those generally are similar in price to round trip, at least in the U.S. So you'd put in Home airport to Venice and Milan to Home airport.

I'll need to play around some more.

Unless there are changes for spring flights, it looks like the only way is a flight with one stop. If the flight stops in Frankfurt- looks like layover time is about 1h 30 minutes, I suppose that means you are stuck sitting in the plane on the tarmac for that time?
It's been a few decades since I've had a European flight with a stop over so that is why I'm asking.

Hi Susan,
I’ve used AC for most of my 20+ trips to Europe, and almost always fly “open jaw”. It’s rarely much of a price difference, if any, and any difference is less than the cost and trouble of getting back to my first arrival city. Do not look at the cost of one-way tickets though- that’s always crazy expensive. Click on the trip type “Multi-city”, and look at YYZ-MXP as Trip 1 and VCE-YYZ as Trip 2 (or reverse).
Edit: I just read your most recent post, and no, the stop in FRA does not mean you sit on the runway. You will deplane, go through passport control, and make your way to your connecting flight. With AC’s record of late arrivals, and the size of Frankfurt airport, 90 minutes is outside my comfort zone for such a connection. On the other hand, I see that some flights from YYZ to FRA show a stop in Montreal. That MAY be one where you don’t deplane- if the flight number doesn’t change, you probably stay on the plane at YUL.

Thanks for the mental reset. It's good to get that perspective and to hear from a fellow Canadian!

Read your edit- makes sense that the Montreal stop is for new passengers embarkation only and don't have to deplane. I will keep that in mind when book.

That is kind of early to book flights for May, in my experience. Keep monitoring prices, but generally you might find favorable price changes after August/September.
Go to Kayak or similar search engine (for example Google Flights).
Then select Multi-City trip.

1st LEG:
From YYZ to VCE (select also nearby airports)
Select date (if you are flexible select the +- 3 or 2 days option)

2nd LEG:
from MXP to YYZ
(select also nearby airports)
Select date (if you are flexible select the +- 3 or 2 days option)

The website will show you a grid with all the options at the various prices.

If you can't find a decent price, then go with the round trip to MXP. Since your flight is likely to arrive in the morning, going to Venice by train from Milan is simple (train from MXP to Milano Centrale, then train from Milano Centrale to Venezia Santa Lucia). If you are jetlagged you can always doze off on the train to Venice. There is no risk of missing the Venice stop. Venice S.L. is the last station, so the journey stops there.

By doing so you save time, because you will need to sleep in Milan on your last night before coming home, so it is better to aggregate your Milan nights at the end. Do not select to fly back from Venice. The VCE airport is not near the city center, and since flights to North America depart in the morning, flying out of VCE would require getting up super early.

I would consider starting from Venice preferable. Venice is small and walkable, and you don't have to worry about being run over a car while you are walking half asleep like a zombie. The worst that can happen is that you fall asleep while walking and fall into a canal. That would certainly wake you up.

Miuccia, thanks for the recommendation regarding the food and markets - I look into that more as I do more intensive research and thanks for the warning about the Venice airport.

I'm fairly sure I wouldn't want to take another flight/ journey from where I land. I know from other European trips just how awful the sleep deprivation is for me on the first day and not being able to get into the hotel room for many hours and how to spend those sleep deprived hours.

Roberto, I know it's too early to book. Just checking tail end of vacation season to get an idea about flights. I've already had another warning about flying back to Canada via Venice.

Early morning flights back to Canada certainly make for fewer options.

Hi again Susan,
I am going to have to disagree with some of the suggestions posted above in that they do not necessarily apply to your specific circumstances. I too am planning a trip to Italy next May/June, into Rome and likely home from Venice, so I have been spending a lot of time researching my options, most of which involve AC flights. First off, AC offers a direct, non-stop flight from Venice to Toronto at 12:40 p.m., so the issue of getting to the Venice airport early in the morning is not a factor. Even to be at the airport three hours early, you can still depart from Venice after 8:00 a.m. Just make sure you have made your travel arrangements to the airport beforehand. For you’re in bound flight, even though Malpensa Airport is way outside of Milan, if you wanted to start your trip in Milan the Malpensa Express is a train that runs multiple times per hour from the airport to the city. It takes an hour to get to the central station. From there there are plenty of hotels nearby, or within a short taxi or metro ride. As I said in my previous post, I’d be hesitant to book a flight through Frankfurt airport with only a 90 minute layover (speaking from experience here). Passport control can be very busy, and moving between terminals to connect to your Lufthansa flight can involve a lot of walking and a shuttle train. I’d opt for the 16:15 flight from YYZ with a 2:45 layover in Frankfurt just for the extra peace of mind. It also gets you in to Milan earlier and, if your flight from Toronto is significantly late, gives AC more options to reschedule you from FRA to MXP.

Lastly, while Roberto may be right about prices dropping in September, they have gone up $200 per person on my itinerary since I started looking at the beginning of July.

Thanks Ottawawanderer. Today is the first time I've explored flights and I haven't searched a wide variety of airport and airline options. Nice to learn that there is a non-stop direct flight to Venice- always better than a flight with a stop.