Portugal - Spain - Italy

A few random thoughts . . . In my opinion, your time and money would be better spent somewhere other than Milan. It's an expensive city without nearly the attractions your other destinations have. Given your stated interests, Madrid merits another day; so does Florence. Remember that realistically, your number of days in a city is one less than the number of nights. I would check on air fares to see if trains are really much of a savings. Vueling is one of the budget carriers that flies to and from many Spanish cities. Milan's airport is also quite far from the city. The others are not too bad. Actually looking back at your plan, I think it wouldn't be a bad idea to scrap Lisbon, as well. If you distributed those days to your other cities, you would have time for some terrific day trips; e.g., Toledo from Madrid, Padova from Venice, and Orvieto from Rome.

I am taking trains from one city to another.
Is this feasible in terms of logistics? (i.e. getting from one place to another)

From Lisbon to Madrid its up to you. you already know the time by train. By air it about an hour?. Cost will be a factor too. But dont forget to add getting to/from airport and security on both sides. Im doing the same leg, but right now, I'm wishy-washy on what. Im leaning towards the overnight train, but again, on the fence. dont forget by taking the overnight train you are traveling and sleeping at the same time. Also, the $$ you would spend of a hotel night could be directed or used for your overnight train, if you want to consider it that way. If you 2 can share a double bed cabin, it could be less expensive for both since if i remember correctly they are double occupancy.

if i was going from Madrid to Barcelona, i would do the train since the 5 hours is about the limit for me and then i would look at planes. As far as whats in between, I'm not sure since I'm not going there. Im sure others will chime in.

Sienna, you may want to think about getting a copy of Rick Steves books on Portugal, Italy and Spain. Your local library may have them too. Or use google and research the airports servicing the cites you wish to visit. The individual airport web sites will tell you the logistics on how to get from/to the airports into the cities. One bonus of RS books is that it also has CONNECTIONS listed so for time and cost (sometimes) it will give you an idea on what you are facing and may give you the answers.

One other thing about using some guide books is that they should have admission prices and open/closing times. Even if the prices are not up to date (UTD), you can still use the book prices to figure out your budget and if you will be over/under by choosing what you would like to do/see. If you really want to get UTD prices/hours you can visit the web sites.

all of the info can be input on a spreadsheet. Easy to manipulate. Easy to save. And if you have a smart phone, you can save individual (areas of the spreadsheet) cities in PDFs and use it on your phones desktop as a daily itinerary.

as far as where you end up in Italy, you may want to look at flights back home from all of those cities and see which ones can be done. Im sure some or one will be better than the other in terms of layovers somewhere on your journey home.

keep up the good work, you're getting there.

happy trails.

Some random thoughts. You mention "scenic" train rides – if you're on a high-speed train, you're not going to see much, and if you're on a slow train, it's going to take forever to cover such large distances. So I would suggest making your decisions based on travel time and cost, not worryng too much about scenery. For a number of the routes identified, I think you will find the discount airlines to be cheaper than the train; check skyscanner.com. Make sure you factor in the cost to get from the airport to the city, but typically there are low-cost busses.

Since you're covering such large distances, I would suggest you drop one or two destinations. I would drop Lisbon, because it's such an outlier geographically. Milan has some fine galleries – the Brera and the Ambrosian come to mind – but you could do those in 1 day, so I would drop 1 day there. I've been to Milan several times, and I've not seen the type of closures that you mention. In fact, it is the best organized Italian city I've ever visited.

I would suggest taking 1 night from Madrid and doing an overnight in Toledo for wonderful architecture and amazing art. Finally, you mention 5 hours to go from Madrid to Barcelona – I think there is a high-speed train that does it in about 3 hours.

High-speed trains aren't all that fast. You do see the scenery. I've even taken some pretty decent photos on the train from Madrid to Cordoba, which I thought was scenic.

You'll be traveling during Easter Week. That's a busy time. Book early! Start by using rome2rio.com to look for flights from Barcelona to Italy. I just took a peek - no specific date - and Bologna seems to be a cheap option. It's between Venice and Florence and a good, relatively inexpensive place for a couple of days.

I would stay one day in Milan and put another day either in Florence or Rome.

I agree with Sherry about Milano, it's very well-organized and worth a night or two. The Duomo has great art and architecture and there are some very good museums.

Flying might be cheaper between some destinations, to compare transportation modes check rome2rio.com, although their estimated costs seem high, you can compare time and distances. The site also has links to transportation sites where you can check prices, including super-economy fares for trains.

There are hundreds of great stopovers between your cities.

In Venice, get the vaporetto pass, it saves a lot of money if you are staying for three days. The Roma Pass might be a good value in Rome, depending on what you want to see. If you are on a tight budget, walking by the Forum might be as much fun as walking through it, as an example.

In Florence by the Florence tourist card which will give you free access to most museums and also public transport within the city .
Should I know the budget you have for your accommodation in Florence or Rome I might be able to help you.

In Florence by the Florence tourist card which will give you free access to most museums and also public transport within the city .
Should I know the budget you have for your accommodation in Florence or Rome I might be able to help you.

Try a site called goeuro.com, it compares, flight, rail, bus and car travel times and costs between points. Clicking on each mode of travel gives you things like bus times, airlines and Includes transit costs/time to and from airport
Very helpful in making decisions

Also, for the Portugal segment of your trip, check out a blog at gailatlarge.com. Lots of info about Portugal. She offers couchsurfing and walking tours of Porto if that is on your radar.

Madrid to Barcelona is less than 3 hours on the AVE (Spanish high speed train). And your trips within Italy are also short on the train. So, for these segments the train is by far the most logical way to go. If you dates are fixed, you will save a fortune with advance purchase, non-refundable tickets, bought online. Some details of how to do that are on the Man In Seat 61 website. Here's his Italy page: http://www.seat61.com/Italy-trains.htm and his Spain page: http://www.seat61.com/Spain-trains.htm

However, Lisbon to Madrid and Barcelona to Milan are longer trips. It's up to you, of course, but I'd fly those legs. Be flexible with alternate airports for the second leg; there are flights from both Barcelona and Girona (a great town, by the way), and there are flights to Milan Linate, Milan Malpensa, and Bergamo. As suggested above, look at Skyscanner, and figure in all the angles before deciding (time to get to and from the airports, cost to get to and from the airports, will you get a good night's sleep in an overnight train, how much will the sleeper accommodations cost, etc).