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Hiking and sightseeing Milan to Cinque Terra

Would this be a good loop? Fly to Milan from US, Lake Como, Venice, 2 days hike in Dolomites, Siena, Tuscany area, 2 days hike in Cinque Terra, fly out of Milan. What type of transportation would be feasible, car or train? This would be a 10 day trip in September 2012.

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It's good that you are staying mostly north in such a short trip and not trying to see the whole country, but that's a lot of stops for 10 days. You will not experience much except transport and check-in/check-out. Each change of location takes about 1/2 day. This itinerary has 6 or 7 changes of location in 10 days. That's 3 of your 10 days just spent changing cities. Perhaps you could no more than 3 locations and build your trip around 3 night stays in each. (10 day trip = 9 nights?) If you actually have 10 nights, stay 4 in the one place you most want to experience. Trains are generally the best unless you want to tour the hilltowns extensively in Tuscany. But a train into the Cinque Terre can make for a long day, further eating up your daylight hours with transportation. You seem to like hiking. Maybe you could confine your trip to Venice, the Dolomites and a Tuscan hilltown: one city and two more rural experiences with unlimited outdoor activities. (There are great hiking guidebooks for Tuscany.) You could fly into Venice and out of Pisa or Florence and avoid having to spend a night in Milan just to fly out of there. Alternately, you could fly into Pisa, go to the CT, then the Dolomites and Tuscany, flying out of Florence or Pisa. Be sure you plot your trip out on a map, then check transport times so you understand the impact on time. It will usually take longer than you think.... Good luck!