21 day itinerary first time to Italy September 2009

Our suggestion would be to pick several "bases" from which you daytrip, to avoid frequent travel. We would also suggest eliminating Milan altogether, as it is a commercial city without atmosphere. During a 2004 trip of 30 days, we were in Rome,Florence,Assisi,Sorrento , Verona and Venice.

You're planning 8 cities in 21 days, and that's probably the most you want to consider. Itinerary might flow better if you fly R/T to Rome and book a separate flight morning of arrival to Venice on Air One (no premium for one-way flights - watch for sale fares). Venice deserves more than 1 long day. Consider going Venice - Milan - CT - Lucca - Siena - Orvieto - Sorrento - Rome. You could add time for Venice by spending only 4 days in Rome at the end or by staying in Siena for 4 nights and day tripping to Lucca and Pisa. You can use train for travel between most areas, but bus is either the only or the better public transportation option for Siena to Florence, San Gimignano, Volterra and Orvieto to Civita. Those are my thoughts, but I'm sure other Italiaphiles will have some great ideas to add.

Ditto to Paul n Sara!

I agree, less stops. I just got back from A three week trip in Italy and Paris with a large group of family and friends. Trust me, the less big travel days the better. We stayed in the town of Lerici/Tellaro, near the Cinque Terre for a week near the end of the trip. It's very close to many places on your itinerary. I would suggest keeping your itinerary the same up to Milan, but instead of Going to the CT and hop skipping around to Lucca, stay in Lerici for one week (It Is WAY Less crowded, and incredibly Beautiful). From there you can do full day trips to the CT (Bus, Train, or Ferry), Lucca, Pisa, and some hill towns very easily. Public transportation is cheap locally, but to get to more secluded areas of tuscany, rent a car or vespa for a few days. Take Train to Florence/ Siena spend a while there, day tripping by bus from one to the other. From there you can get to Orvieto and other hill towns pretty easily for day trips. Then Train to Rome for the two nights, stopping at Pisa on the way.
Recap:
Your Itinerary up till Milan,but w/ extra day in Ven.

Train to Lerici-day trips to: CT, Lucca, Pisa, nearby hill towns, stay about five days

Train to Florence/ Siena- day trips to Hill towns, about 5 days

Train to Rome with stop in Pisa

Have fun on your trip, and feel free to send me a message if you want suggestions for Florence, Venice, or along the coast. Ciao!

thank you all for your very helpful info. Milan is out - we can catch a Serie A soccer game in another city. Will check out Lerici/Tellaro as a CT alternative.

September is the perfect month to travel in Italy, but your itinerary is way too much. You have 8 days of train travel and hotel changes; meaning you really have only 11 days of vacation - day coming into Rome and day going out of Rome are also travel days. With this schedule the only thing you will see in Venice is tourists. Venice needs several days staying in the city so you can see the main sites when the day trippers are gone and the rest of the city when they are there (9:00 am to 5:00 pm). I would cut this down to Rome, Venice and a homebase city in Tuscany where you can rent a car and tour the hilltowns - several of which you mentioned. Fortunately, you have plenty of time to fine tune youe schedule.

Its doable but I'd say in my experience travelling for all but the shortest trips seems to eat up 1/2 the day or more. For the trip to Sorrento I'd suggest getting off the Circumvesuviana train at Pompeii on your way to Sorrento, see the ruins, then get back on to Sorrento. This avoids the out-and-back trip.

The RS Italy book lays out a good, if ambitious, itinerary for 21 days. Check it out.

On our trip last October we flew from Naples to Venice, a one hour flight on Alitalia...left our hotel in Sorrento via early (6:00) AM taxi to Naples airport and were at Venice airport by 10 AM. Water taxi from airport had us in San Marco Square by noon (with half a million other tourists). Venice is worth at least 2 nights...same for Florence.