Italy mid-April to Mid-May: What's the Best Itinerary?

Generally people on this forum recommend starting north and ending south. If you fly into Milan, you could unwind in the Lake Como area for a couple of nights. Lake Como will be cool and perhaps cold on the water. Or spend the first couple of nights in Milano, it's a big city but very well-organized and not challenging.

Further along in your trip, Paestum has a beach, great temples, a very good museum. You might want to overnight there. Orvieto is worth a night as well, the city changes when the day trippers leave.

You don't mention Ravenna but it's a very nice place with great art and a beach nearby. You can also get to beaches from Rome.

I would fly into Milan and out of Rome; Naples to Rome is only a little over an hour by train, but I would spend the last days of my trip in Rome rather than trying to get to FCO from Naples on the day of a flight. If you fly out of Naples you will most likely change planes in Rome anyway.

Great advice from Zoe.

I would not "waste" time in Milan. There is so much more to see! You can go straight to Como (or Venice) from the airport.
Check about the Dolomites - April may not be a good time. Hopefully someone else will chime in.
I would not take day trips from Venice. It just takes too long to get around. You can see Verona as a stop on your way to Venice (arrive early, leave your luggage at the train station, late train to Venice) and Padua on your way to Florence. Or consider basing in Bologna for a few days and day-tripping to Verona, Padua, Ravenna. Then Florence/Tuscany. If you want to spend time in Florence, stay there. If not, day trip from a different base. Are you planning to rent a car for a few days in Tuscany or stick to trains and buses. With a car, you could stay in an agriturismo.

From Florence, you could go to Assisi, then Orvieto. I'd stay at least one night in each. It takes too long to get to Assisi to make it a day trip, but it is well worth 1 night and 1-1.5 days. Orvieto is only a little less time-consuming to get to, so again, 1-2 nights and one full day. Both these towns are on hills, so you'll need about 1/2 hour to get to/from the train station to them. In Assisi, you can leave your suitcase in the train station and just take an overnight bag up.

You'll use the better part of a day to get from Florence or Orvieto to Sorrento and 1/2 day from there to Rome. Sorrento is a good base for day-tripping by train to Pompeii, by bus/ferry to Positano, Ravello. Early May isn't swimming weather in Italy. Even if the air temps are warm enough, the water will be too cold (unless you like swimming at the beaches around San Francisco :-). Paestum is not that well-connected to Sorrento. You may want to stay overnight there. I'd plan on at least 5 nights (up to 7) in Sorrento. On the way from Sorrento to Rome (or as a day trip from Sorrento), I highly recommend visiting the archaeology museum in Naples - it's got all the gorgeous stuff from Pompeii and the other towns that fell victim to Vesuvius.

Sounds like an amazing trip! I think I'm a little different from RS and a lot of travelers in that I want my first day to be in a big city with lots to do. Otherwise, I find myself entirely too tempted to hole up in my small town hotel room and nap, which only makes jet lag worse. I'd fly into Milan and either stay there for a night, or store my bags at the train station while I did a quick tour of the city before heading on. Milan is clean and incredibly easy to navigate - I wouldn't consider it a challenging environment at all, but again, my personal preference is to beat jet lag by forcing myself to stay awake due to big-city stimuli.

I've only been to Lake Como once, in March when it was still pretty chilly, and it was picturesque, but there wasn't a whole lot to do because of the weather. And if I remember correctly, the city was pretty dead at night (we had a hard time finding a restaurant that was open). Again, that was 8 years ago and we were there in March. Personally, I'd skip Lake Como and head to Venice by way of Padua (which I prefer over Verona).

Florence is my favorite city in the world (I lived there for 6 months during a study abroad in 2008), so I'm biased when I say I think you should have at least 3 full days in the city; more if you're an art lover. I'd also take a few nights from Rome (which has some amazing sites but to me just wasn't worth the money - high cost of lodging/food - for more than 3 nights) and spend them in Orvieto, where you'll get more bang for your buck.

Sadly, I've never been south of Rome, so I can't help you with the rest of your itinerary. Have fun!

Thank you all for your valuable comments! I will skip the Dolomites this trip and try to see them another time in summer or fall. Apart from that, it sounds as if the weather will be fine for a north-to-south itinerary, with arrival in Milan and departure from Rome.

Zoe and Chani – Wow, great insights! There isn’t much in Milan that interests me, so I’ll take the train from the airport to Lake Como as Chani suggests. I’m going to take a little time to digest all your suggestions, but will definitely add an overnight in Paestum.

Erin – Thanks for sharing about your March visit to Lake Como. It sounds like the weather in mid-April will be OK, and enough activities to not be boring. I will take your suggestion and stay overnight in Orvieto, maybe with RS’s recommended side trip to Civita. I didn’t mention that I’m veryinterested in ancient Roman history, so I will stay several days in Rome – I can always wander, people-watch, and creatively “do nothing”!