Florence is wonderful. The museums, the churches, the open air leather market… wistful sigh Pisa is a short day trip from there – cheesy but worth it. You can see the tower from many places in town and its truly hard to take your eyes off it as the sense is that it could collapse any second. The actual tower is surrounded by vendors of almost indescribably tackiness - you’ll get my Leaning Tower of Pisa pepper grinder from my cold dead hands! I have yet to visit Rome or Pompeii; both are high on my list.
Maybe Sorrento, Amalfi, or Positano? All stunning places! Not Naples though, you will not be safe in Naples.
I live in Rome, it is wonderful… I’d also recommend Barcelona, Seville and Istanbul. I’ve never been, but many people I know say Prague is a magical place to visit.
As an English person I would say, skip the British Isles on this trip and come back another time. I love London, it is vibrant and has an energy that I have only ever felt there, and in Barcelona. Then you can walk in the Welsh hills, go to Scotland for whiskey, visit the Jurassic coast in England and hop over to Ireland before going home.
ETA: Yes, Ostia! Baron Greenback is right, if you come to Rome, spend a day at Ostia.
I am sure I am in the vast minority when I say I hated Paris.
Went there twice - once on the cheap, and once sparing no expense - and just disliked everything about the city; tourist trap, overcrowded, overpriced and just didn’t get the allure. (And yes, I know it is trite to say, but I did find Parisians quite unfriendly.) Then again, I am the guy who lived in NYC and never bothered to go to the top of the Empire State Building, even though I would walk through the building on the way to work. One of the reasons I love Anthony Bourdain is that he too can travel to a city and not feel compelled to stand in line with other tourists to do touristy things. I prefer to walk in off-beat neighborhoods and mingle with the locals.
I think as long as you have narrowed it down, spend almost the entire two weeks in Italy - take trains or rent a car and find some out of the way villages and towns. The people really are friendly there, great shopping and architecture, and even if you are not a big “food” person, you will become one while there! I don’t think I have ever heard anyone complain about spending too much time in Italy. Spending all (or most) of your two weeks there will give you time to really get the experience, soak up the culture and not feel rushed.
Let me put it this way; if you were a first time tourist to the USA for 2 weeks, would you rather hit NYC, Miami, Chicago and LA or would you rather just go to California, start in SF and drive down the coast, stopping along the way where your whim stops you?
The art museums in Paris are worth the trip, unless you aren’t into the old masters. A walk down the Champs is just something that should be done in one’s lifetime, particularly in the spring. A side trip to Versailles and Giverny is recommended. Personally, I prefer Marseilles and Bordeaux to Paris, but if time is a problem, Paris is good. In Germany, Schloss Neuschwanstein and the other Bavarian castles of Crazy Ludwig, such as Chiemsee, are well worth seeing.
Roderick, if you’re making it Italy-only and moving by train, see if you can edge Como in and take a boat tour as a day of rest in between two walk-to-lots-of-places cities. It’ll look ridiculously familiar because it’s been used in a lot of movies, but the reason it’s been used in so many movies is that it’s ridiculously pretty.
I mention “moving by train” because the drive into Como is complicated and can take a very, very long time. Rush hour between Saronno and Cuomo is just… my coworkers and I used to joke we could use the time to learn to crochet, including the driver. If you’re going to specific places, I recommend the train; if you want to be able to stop at interesting spots not described in any guide, then take a car, but keep in mind Italy “sells” less than 20% of the visitable spots it has.
Long before George Clooney made this the hip spot to be in Italy, I went to Como about 15-20 times (worked at a Swiss school nearby) and loved it!
A wonderful place to kill some time, see the sights, eat well, and roam the streets and get some great shopping deals. It is just beautiful there and you could easily spend a week or more just hanging out there.
Should you have a boatload of money or just want to splurge for a mid-week, one night stay, you might want to check out Villa d’Este. It is one of the top luxury hotels in the world, and when you see it, you will know why! Otherwise, some nicely affordable smaller hotels in Como as well. If I am not mistaken, you can also just take a commuter train from Milan to Como.
