20 days in Italy

The 3 nights for Sicily are just not worth the effort travelling to get there, only scratching the surface and in no way doing justice to your destination.

Arrive Milan
Lake Como (3N)
(Make your stop in Milan the day you travel to Venice)
Venice (3N)
Florence (5N)
- with days to Siena, Lucca+Pisa
Rome (4N)
(Make your stop in Naples the day you travel to Sorrento)
Sorrento (4N)
- with days to Pompeii, Capri, Positano
Fly from Naples to Paris

Thanks, David! How many nights would you recommend staying in Sicily? I actually planned 4 nights there (Sunday, Monday, Tuesday, Wednesday) and then the flight to Paris on Thursday but it's still only 4 days in Sicily--and it's so vast so that's probably still not enough. Would you recommend doing Sicily on a separate trip then in the future? I'm assuming it's worth it--my only problem is I have no idea when we'd be able to get back to Italy and I don't want to miss it.

I like David's itinerary a lot. I would leave Sicily for another trip. I know David's itinerary doesn't include the Cinque Terre, but you can only do so much. I do like that you would have three nights in Lake Como and 3 nights in Venice if you follow his itinerary. Venice is unlike any other in the world. Don't sell it short.

Hi Jenna!
I like David's itinerary too, and I would take trains everywhere except a day trip to Siena; easier by bus from Florence. And, of course, buses/ferries are how you'd get about the Amalfi Coast.

To my knowledge, there are no overnight trains to any of the villages in the CT, and no direct trains at all. Just doing a search by random time/town, the last one from Venezia S. Lucia to Monterosso on the 23rd leaves at 18:25 and gets in at 00:22 with 2 changes. Given that the majority of accommodations in the CT are small, family-owned properties without 24/7 desks, you don't want to be getting in at this hour. Also, if your trip is just 3 months from now, darn near everything in the CT is probably booked already; the place will be mobbed. I'd enjoy your time by the water in Como and the Sorrentine/Amalfi and use those days for something else (see David's suggestions).

I'd suggest skipping Sicily too as you just don't have enough time to do that one justice. If you end up planning to fly to Paris from Naples, I wouldn't book an early-morning flight; public transit from Sorrento doesn't start running early enough to get you there. There is a nice bus which goes directly from Sorrento to the airport that I highly suggest that you take; safe, comfortable, affordable and very easy; the next best thing to an expensive private transfer: Earliest derpature time is 6:30 AM.

http://www.curreriviaggi.it/eng/index.php
http://www.curreriviaggi.it/autolinee/images/AUTOLINEE_CURRERI.pdf

So why not sort a new itinerary and then tackle the "what should we do/see?" questions? Because you're coming from an archaeology class in Greece/Turkey, is this an area that you'd like to give special attention to in Italy as well?

Sicily would definitely be a trip all by itself. I spent 18 days there in 2015, and I did not visit key classical sites at Agrigento, Selinunte and Segesta, which I'm guessing you would want to see. With a rental car (which I did not have), you could cover a lot of Sicily in two weeks, but three would be better, especially if you wanted time for beach days.

I like David's itinerary, too.

Even if you keep the Cinque Terre in the plan, I'd still look at taking the direct Venice-Florence train and staying in Florence first. You can pick up or drop off a car in La Spezia, before or after the Cinque Terre. There are also direct trains from La Spezia to Rome (or an overnight train to Naples that departs at 1:30 a.m., coming from further north). Or flights from Pisa to Paris.

You have to assume that you will return and balance quality sightseeing time against too much transportation between destinations.

I love Sicilia but four days is short, considering travel time to get there. Save it for next time.

Thank you all so much! So helpful! Updated plan:

May 19: Arrive in Milan. Train ride to Lake Como.
 
May 20: Lake Como

May 21: Lake Como

May 22: Train to Venice

May 23: Venice

May 24: Venice

May 25: Train to Florence

May 26: From Florence, possible day trip to Cinque Terre

May 27: Florence

May 28: Car rental to drive through Tuscany

May 29: Day trip to Siena (use bus)

May 30: Florence. Train to Rome.

May 31: Rome

June 1: Rome

June 2: Rome

June 3: Train to Sorrento. Stop to visit Naples on the way.

June 4: Day trip to Pompeii

June 5: Day trip to Capri

June 6: Day trip to Positano

June 7:  Fly from Naples to Paris

Have you picked your Lake Como spot yet? You might want to ask here for suggestions.

Acraven, great question, I haven't! We actually just decided to do this trip yesterday (an unexpected opportunity arose) so I've got to get the ball rolling on finding accommodations. Please do let me know what your recommend! :-)

Also, here's another question: Looking at this itinerary now, I'm wondering if we should do it backwards (start in Naples, move to Sorrento, then Rome, then north). Any thoughts on that? I'm thinking it might be good to hit Rome at the end of May before school gets out for so many people. Just a thought. But these cities will packed no matter what, right? Also I just looked up flights and a Boston to Naples flight would cost $200 more than Boston to Milan, so budget-wise that wouldn't be a great idea.

Yes, the Ecstasy of St Theresa is absolutely worth seeing. It's about a 10 mi ute walk from Termini. Borghese Gallery features 3 additional fantastic Bernini sculptures. I also recommend the Pont St. Angelo for yet more Bernini sculptures.