My Fiance and I are planning a trip to Italy in May 2008. We have narrowed the places we want to stay at to Tuscany, Venice, Lake Como and Cinque Terre. In Which order to do so I cant figure out. Any suggestions??? Also I want to go ahead and buy our airline tickets now, but am worried that I should book my rooms at the same time? Is that going to be an issue? We want to stay in Farmhouses/ Villas to experience the real Italian Life. Any one know any good and not so pricie ones in the area we are planning to go?
Of your destinations, the two major airports are Milan (Como) and Venice. You may want to fly into one of those and out of the other. I'm sure others will have good advice on which order to do them in.
My wife and I actually chose Verona for our departure due to the cost of early morning water taxi to the Venice airport compared with just taking the train into Verona the day before we fly out (also early morning), staying the night, then taking a cab to the airport. Plus it gave us one additional location for our final night.
Our goal was to fly on the new Air France route from SEA direct to CDG (Paris) instead of doing our layover in the states. The only other option was British Airways, but we didn't want to do a layover in Heathrow.
Do you already have the dates for your trip? If possible, be flexible and it can save money on airfare, although it's a little early to expect May airfare to be near it's bottom.
Try to book an open jaw ticket - in to one city and out of another so you do not need to backtrack. One option could be flying in to Venice and out of Pisa. It really depends on what airpors & airlines service your home city best. May is peak season in Tuscany & Venice so be prepared to pay.
Your major issue is going to be that Lake Como and the CT are going to feel like the same type of place. Of course, they're different. But the pace of travel is much slower. It's may be tough to do, but if you can separate those two from one another, that would be best. This would be the only time I would suggest flying into and out of Milan. This is how I would handle those places assuming that you have 2 weeks:
Fly into Milan
Train to the CT - 2 days
Train to Florence, see Florence 1 day, 0 nights (unless you're a HUGE art buff), Florence is very expensive, pick up a rental car.
Drive to Siena, stay in or around Siena - 4 days
Drive to Venice, drop off rental car, stay in Venice - 4 days
Train to Lake Como - 2 days
Fly out of Milan
Of course, you could get a rental car for the entire trip, and that would make you a lot more flexible. Compare the cost of a rental car (including parking!) against train tickets for your entire party. You'll want a car in Tuscany.
I would start looking at airfares now, but not get concerned about buying until January or even as late as February. Make sure when comparing that you are including all taxes and fees, those can add $150 to $200 per ticket. Try different airports and days to get the lowest price, with your route, you could either do open jaw, or as a poster suggested a big circle. You can wait even longer to book rooms, I would book Venice ahead and your Tuscan destination if you are planning an Agritourismo. The CT and Lake Como, you could even wait until you get to Italy to book, or call ahead a day or so before.
Unless you really like to rush from location to location, seeing Florence in one day is like seeing Rome in one day. I would give it at least 2, one reason being commute time from Milan to Florence, whether by car or train is several hours. I would take a day off Venice. Also, not far from Florence is Lucca, a lovely walled city.