Italy August 2015

Congratulations! You'll have a great time, as long as you're prepared from some pretty toasty temperatures. Do you have a good guidebook? If not, the Rick book on Italy is outstanding for first time travelers. As for Rome, Piazza Navona is a great central location but it can be a bit pricey. Rick's book gives you information about other neighborhoods as well. And for those three destinations the train is the way to go. No need to deal with the hassle and expense of renting a car.

And just FYI, it's Cinque Terre, not Cirque Terre. That could make a difference when you're looking for info.

Happy travels.

I had a couple of thoughts. Are you absolutely set on being in Italy on your real birthdate? If not, waiting 'til September would relieve you of fighting crowds, a lot. For either month, I recommend getting to work now on your hotel reservations. You'll be surprised how many of the really nice, reasonably-priced places are already fully booked. I like using booking.com. You can see immediately if a place has rooms available, and you get instant confirmation. It also has reviews from people who have actually stayed in the listed accommodation. It's not too hard to check whether a Milan departure has any advantage over one from Rome. First, figure out your final destination, CT? Then find out how long it will take to get from there to the two airports. My guess is that you will need to spend the night prior to departure at a hotel in the airport vicinity, either way. Personally, I cannot tolerate the stress of having to get to a different city the same day as departure. Finally, look on your airline's website to compare cost and convenience for the two departure cities. You might even find that leaving from Milan saves you some $$.

United flies non stop to Rome (FCO) in summer. There are no non stop from IAD-MXP.
If the price is right, flying non stop is a big time saver.

From the Cinque Terre to Rome (by train) it's a 4.5 hours. From the Cinque Terre to Milan it's 3.5 hours. So not much difference. In addition MXP is far from Milan city center, so you have to get up very early in the morning when you return home. FCO is only 30 min from Rome city center.

Leaving your intended destinations unchanged: Rome, Tuscany (Siena), Cinque Terre. This is how I would do it.

If you fly back to the US from Rome, I would leave Rome for last.

When you land in Rome, it's going to be in the morning, therefore I would take a train straight to the Cinque Terre. That would be a perfect place to unwind and get used to the time zone (+ 6 hours from DC). I would choose Monterosso because it has more accommodations. However in August you are likely to find places all booked very early and you might be forced to pitch a tent in the woods. Book now and if already booked, try nearby Levanto.

Then after the Cinque Terre, you could go to Tuscany (Florence, Siena, or wherever), by train.

Lastly you would go back to Rome for your 3 or 4 nights before returning home. From Florence to Rome, the fastest is with a high speed train. From Siena you can go back to Florence (by bus or train) then take the same high speed trains. But there are also buses that connect Siena directly to Rome (buses stop at Rome Tiburtina station).

Regarding a sea-front hotel in the CT, look at La Spiaggia in Monterosso:

http://www.laspiaggiahotel.com

No way about it, CT hotels in high season are going to be pricey, and especially so for those with a view but this one had better rates than many others we looked at, and an excellent location. Just be sure to specify a sea-front room, and do be aware that payment is cash only so make sure you have the euros in hand. Rooms are quite small and breakfast is a little basic but you couldn't beat the view from our little balcony, short walk to/from the train station, and access to restaurants and other amenities. Maria - who handles the desk - is a gem!

I had one further thought re: lodgings. IMO, one of the great charms of traveling in Europe is staying in small, family-run lodgings. However, we are now at the time of year when many of those folks close up for a few months and don't check reservation requests regularly. It's less of a problem on booking.com; however, even there you may see indications that a place has no availability, when it means they haven't set rates yet. Or, it can mean they haven't decided how many rooms to release. I suggest you get reservations, now. If after Jan.1 you see something you like better, it's really easy to change or cancel on booking.com. Just be sure you read the cancellation policy carefully when reserving.

In Vernazza, try:

http://www.elisabettacarro.it/

Rosalyn's suggestion to wait until September if you can is an excellent one.

Agreed with Rosalyn and Michael. That was my first thought when I read your post.

I don't think there's much difference between Milan and Rome for your return. You may save an hour on train travel if you're staying in Monterosso, but if you're in, say, Riomaggiore, it may not be much longer to Rome via La Spezia than to Milan via Monterosso. It's a usually little faster/easier to get to FCO than to MXP. It would be better if you found a flight from Pisa, Genoa, Florence - somewhere nearer.

Edit - I just did a cursory flight search. It looks like the only non-stop flights between Washington DC (including Baltimore) and Italy are to Rome. If it were me, I'd choose a non-stop flight.

And as Roberto advised, leave Rome for last. You'll want to spend your last night there before your flight anyway.