Emirates has a good deal to Milan, Italy. 2 RT tickets for 998 from JFK. I figured I can take Jetblue to JFK from here. Anyone been to Italy lately? Flying in a on Thurs afternoon and leaving Tues afternoon.
Haven't spent time in Milan, but plenty in Rome and Florence. I think there is another that about what to do (Pompeii etc) typical touristy stuff in Italy is always good is that's what you're in to.
The last time I was in Italy was in 1993... so not much help. But Italy in October sounds fantastic. Avoid the summer crowds. Decent weather, especially if you like fall type weather.
I lived in Milan for sometime in 2005, and was just back there earlier this year. Since you'll be arriving in the north of Italy and only have 4 days, I would leave Milan as soon as you arrive (I actually like the city, it was a great place to live, but there's far more to see/do in other parts of northern Italy for a tourist). I'd recommend Cinque Terre. It won't be peak season there, but the weather should still be very nice in October. Ideally, train travel is the way to go in Italy, especially when just traveling regionally. Having said that, I think you should rent a car from the Milan airport. This will allow you to get door-to-door from the Milan airport to Cinque Terre in 2.5 hours. By having your own car, it'll save you a lot of time on your first day (from the Milan airport) -AND- a lot of time on your last day (to the Milan airport). Saving this much travel time on two of your days is very significant when you're only going for four days. As far as renting a car in MXP, it's fine. I've done a weekend trip from NYC to Milan before and rented a car from MXP, drove to Venice and back to MXP for the flight back. It's definitely easy. This is what Cinque Terre looks like:
from milan you can take a 1hr train ride to lake como. or a 1.5hr ride to bologna. i also like genoa, which is 1.5hr as well. heard good things about verona and turin, which are also within reach. milan itself is crap (unless you want to shop for clothes).
Studied abroad in Torino for a semester in 09. With only 4 full days I would leave Milan as soon a Friday and focus on other cities in the north and possibly central Italy. Definitely take a train ride to Cinque Terre and maybe spend 1 night there to visit all 5 villages, Bologna has amazing food, and if you can stretch it Florence is a really amazing place.
Milan is the most modern city in Italy, so unless you're into fashion there's less "Italy" to see on the spot. Bologna is a nice destination, and Pisa is good to stay for the day or two. I'm not too sure about the northwestern side of Italy. Dolemites are a vacation destination for Germans. I guess that's heading further north into the mountains fur you. Just read you have four days. I'd highly recommend Florence or Venice but given that time table plus jet lag, I would do a country side tour near Milan.
I just spent a week in Lucca last month. Did Florence, wineries in Chianti, and Cinque Terre... If you're going to any of those areas - I can give you plenty of suggestions. Pro tip - don't bring a stroller to Cinque Terre.
Dear OP: I hate you. Die, die, die. Italy in October is PERFECT. It has been awhile since I've visited the country, and I'm more of an expert on Southern Italy (especially Sicily, where I lived). I remember the odd-sounding Italian dialect of the region---odd to me, who was used to the Sicilian way of speaking, to suddenly hear a German-flavored Italian. As one or two other posters stated, Milan itself isn't that great. Kinda like Houston in the sense that the traffic is bad, you can do a lot of shopping, you can eat good food....but you need to get outside of Milan to really enjoy yourself. I do know it's barely a 3 hour trip by car from Milan to Venice. The route would take you through Bergamo and Verona. So, if you can spare any time to make a side trip, it'd be worth it. Lake Como is also very close by. Although I do know it isn't always easy to make side trips when your stay isn't long to begin with.
good news. I just rebooked the ticket to fly out on Sunday (instead of Wed). That gets me into Milan on Monday afternoon + 7 full days + Leave at 4pm on tuesday.
In that case, go to Florence and Tuscan countryside. If you have time on your way back (assuming you spend Monday night at the end of the trip in Milan), be sure to go here.
I've been over to Italy a few times over the past 2 years and I'd 2nd the recommendation to go down to Florence. I stayed there 4 days and still didnt see everything. So 7 days there (with a day trip to Siena and a country winery) would give you plenty to see. Id skip the car and take the high speed train - driving in Italy is a bit crazy and the train would give you one less thing to worry about. The Cinque Terra would also be nice if you prefer hiking and the outdoors to museums and churches. Venice wasnt my favorite place and I cant imagine killing 7 days there. But some people really like it and you can always spend a night or two in Verona. Genova is a very cool port city but can probably be seen in 2-3 days. Finally, you can always get another cheap flight from Milan to Rome and easily spend a week there.
ive been twice. in october 3 years ago, and two weeks ago in august obviously. im jealous. it was freaking HOT 2 weeks ago. seriously my friend and i almost melted after a few days (i do think it was even hotter then normal). almost to the point that after walking 10-15 miles every day (pedometer on my phone) that we progressively got wore out later in the trip in budapest and amsterdam. still fun though.