Perche

I agree, an early train from Venice to Milan to catch a flight that morning is doable, but grueling. I'd never try it. You'd have to take the 5:40 or 6:20 train from Venice, and it's a four or or so ride to the MXP airport with train changes thrown in, then going through check in at the airport then flying. Not good. I'd have lunch in Venice, do some last sightseeing, then take an afternoon train arriving at the Sheraton MXP in the evening, changing trains but not stopping in Milan itself. Get up, relax, and go to your flight well rested. Right now the Sheraton MXP is showing only 109 euros on your date. That's a steal that's not going to last.

Perche

For Venice, you are going when it's still doable as far as crowds go. The most important things is to not stay at any hotel that advertises itself as close to San Marco, or close to Rialto. Those are the areas where you don't want to stay. They are packed with tourists, tourist merchandise, tourist food, tourist prices. Certainly don't stay near the airport either, in any of these cities. There are places where you can get away from the tourists in Venice, and the easiest place to do that is in the Castello area.

Hotel Bisanzio is in Castello, close to San Marco, but isolated enough to allow you to breath easy, and has a decent price for what you get, at least most times of the year. See San Marco and Rialto early in the day or in the evening. A great thing to do is to just keep walking, getting as lost as possible. There are no unsafe neighborhoods. Just find the narrowest alleyways, and head down them without a care. It's beautiful.

In Rome, the most central location, where it is easiest to get to everything, would be staying around the Pantheon. It's a long walk to some places, but you really can walk anywhere from the Pantheon area. Albergo Cesari is in that area and is also very nice, and a good value most parts of the year.

JMN57

You don't have to spend the day before you leave at an airport hotel.

Personally, I would take a late train from Venice to MXP and stay at the Sheraton which is basically close to what I did last November but we started in Florence. We took a 4:10PM train from Florence to Milano Centrale that got in at 5:50PM. We then caught the 6:25PM Malpensa Express that got to MXP around 7:15PM or so. This would allow you to have a nice lunch in Venice before leaving.

I have stayed at both the Sheraton and in Milan the night before flying out and I, having done both, would always stay at the airport. When you factor in the time it takes to get out the door of the hotel, to the train station, out to MXP and being there in advance to check bags and check-in, you have to be up VERY early when you stay in town.

I agree with Slawecki that an open jaw would be good but I think you mentioned the good fares to MXP so that's probably not in the cards.

exilencfc

We stayed at the Hotel Orion in Venice which is in San Marco but not too horrendous in terms of tourist numbers - it was handy for disappearing down back streets if nothing else. I agree with Perche though that the best thing to do in Venice is wander the backstreets and get rather lost.

holbropa

Make sure you pre-buy tickets for the bigger stuff - such as the Uffizi museum in Florence, the Colosseum, Vatican Museums. Buy from the official websites and not someone selling those tickets.

I'm doing a similar trip with my family in late March/early April. We too are flying into and out of Milan because it was much cheaper than the other cities. I have two kids though and we did not want to have to get on a train after a flight. The airport train is still a 45 minute train ride to Milan Central. So, we are staying at a hotel near the Milan Central train station. I bought tickets for the Last Supper the day we arrive so we will hopefully nap, see the Last Supper, and then visit the Cathedral there. The next morning we take a train to Venice.

We are taking an evening train from Rome to Milan when we leave Italy. We'll probably get to the airport hotel around 8 PM. Our flight leaves the next morning though at 10:30 AM so we wanted to get to the airport early.

Perche

Agree completely. Have a great lunch in Venice, and get to the MXP Sheraton in the evening, then relax and reminisce about your great vacation before the flight home in the morning.

pavlovb

Thanks a bunch. New itinerary:

4/19 arrive MXP 10:45, take early afternoon train to Rome (4 nights)
4/23 morning train to Florence (3 nights)
4/26 morning train to Venice (4 nights)
4/30 afternoon train to Sheraton MXP
5/1 depart MXP

Hotel Info:
Rome - Pantheon area (Albergo Cesari)
Florence - Oltarno, Duomo area (Ganduomo, Hotel Lungarno)
Venice - Castello area, not San Marco or Rialto (Hotel Bisanzio)

Food recs? Let's say one high end restaurant in each city and then some nice affordable dinner spots and/or good spots for quick bites with coffee/wine and view. Or anything else that you think would be fun.

Really appreciate the feedback.

exilencfc

Just a quick warning that budget hotels in Europe tend to have small rooms, no aircon or ice machine and quite often no elevator or American style breakfast. So if those things are important to you do your research very thoroughly.

JMN57

In Florence - right down the street from the Lungarno is Trattoria Cammillo - whether that's high end or not depends on your perspective. Have always eaten well there. BTW - Lungarno is our favorite hotel in Florence - get the river view if you can.

In Castello - a short (5 minute) walk from Bisanzio is Al Covo - can heartily recommend it. Somewhat of a scene and not cheap is the restaurant at the Gritti Palace. If the weather is nice, it is a decadent indulgence (particularly on a weekend day) to sit out there and have a meal (or at least a drink). My wife loves their fegato alla veneziana (which a good one is surprisingly hard to find in Venice).

yhm71

Is Milan +cost of train +lost travel time that much cheaper than an open jaw e.g. Rome Venice (and flying out of Venice is very cool, you can take a boat to the airport!)?

Your itinerary sounds good, except I think 4 nights in Venice is too many and would trim it and add the extra day(s) to Rome, there is so much more to see there. IMO 2 nights in Venice is enough for the main sights, 3 are plenty.

I would spread the sightseeing over the whole time you are there rather than trying to cram it into a single day (if that's what you mean), it can be pretty exhausting otherwise. A sight or two in the morning then relax the rest of the day.

Finally I would consider B&B/inn style accommodation in Rome over a traditional hotel, you will get more space, modern decor, and a significantly lower price. I would use e.g. Booking.com's map to scout the area for well priced and well rated places.

Enjoy the trip, a great time of year to be in Italy!

Perche

I agree with doing the open jaw and flying out of Venice if able, but definitely not to cut out time in Venice. There is superficial Venice, going to San Marco, the Rialto Bridge, the Doge's Palace, and Academia, and then going to the next city. Then there is seeing actual real Venice, where the people live, and the sights and sounds of the streets in the far out neighborhoods that are not any different from the way they were when Vivaldi and Casanova lived there, with the exception of electricity.

It's just not possible to travel to Venice and see it in two days. If a trip to Venice will only be two days long I'd recommend skipping it altogether because that's just enough time to see tourist highlights, not to experience the city itself.

Otherwise, I agree.

PWMTrav

Good rec.

Some of the recs I've thrown out there that other FTers have liked in Florence. This list is by no means exhaustive, I haven't eaten everywhere, but here's what I like:

Lunch -

Trattoria Sergio Gozzi (near the Mercato San Lorenzo). Only open for lunch. The location draws tourists, but it's a solid, reasonably priced, authentic Florentine restaurant, so the locals are there too. That means it gets crowded. Reservations not accepted, just show up. Soups are very good, meat dishes are outstanding, house wine is very serviceable. This is my single favorite place to eat in Florence.

Mercato Centrale. This isn't a restaurant, but the central market itself. There are food stalls mixed in with the purveyors inside, and it's great. Da Nerbone is an institution - try a sandwich with tripe. There is a good baker in there for desserts, but the name escapes me now. I'll update when I think of it.

Dinner (mid-range options in the historic centre) -

Giannino in San Lorenzo. This is really at tourist ground zero, but is an authentic experience. Prices are reasonable for the location. I would recommend pastas and meats here equally.

CipollaRossa. Fairly laid back atmosphere. Very solid pasta options - not entirely Florentine, but generally very Tuscan with some other regional influences. OK house wine. I haven't done meat dishes here, but they at least looked good.

Terra Terra. What the hell is a Sardinian family doing with a restaurant in Florence a couple of alleys off of the Duomo? Not sure but this is good food. Primarily Florentine food, but heavy regional influence, including Sardinian. Try the Gnocco Sardo if they have it on the menu. I enjoyed their antipasti the most of any on this list.

Wine -

Enoteca Pitti Gola e Cantina. You can have a light dinner here after 5pm or so, basically antipasti and primi. These folks know their wine and the best experience is sitting there for a few hours BSing with the staff and letting them pour glasses of whatever, along with some snacks. This is a multiple visit place for me each time we visit Florence.

Gelato -

Perche No! It's the best and I'm not open to other opinions on that

Honorable mention -

Buca Mario. Tourist traffic definitely fills this place, but it's good. If I was going somewhere specifically for dinner and bistecca alla Fiorentina, this might be it, provided the wait wasn't too long. Prices are on the high side. Really strong service though. It's an honorable mention because I don't go there every time I visit Florence, but the Michelin Guide includes it and it's not a tourist trap even if it looks like one.

pavlovb

I was just able to find a decent open jaw out of Venice so I'm adding an extra night in Rome on the front end of the trip!

I had considered getting a one bedroom rental home/apartment in Rome via AirBnB or VRBO near the Pantheon. There seemed to be some good options although I've never done it out of the U.S. so I'm a bit leery. I will check out your suggestion on Booking.com. Thanks!

holbropa

We're renting apartments in Florence and Rome off of VRBO. Florence I have a 2 bedroom, 2 bath place a block from the duomo and in Rome I have a 2 bedroom, 2 bath place right off a metro. If you use VRBO look for a place that has lots of reviews. Both the places we are staying at have plenty of reviews. I've had lots of contact with both owners too - both have sent me contracts, emails, etc. For my family of four the apartments are a better option than a hotel.

Perche

Apartments are generally way better than a hotel. They usually require a week, but if can do it, it's great. Just be careful about the location. They are usually very far outside the center of things. Location is very important, especially for your first time.