Help with Itinerary - 14-16 days

Gosh, there are zillions of options. If you do a single night in Venice, then it's going to be whirlwind on either side of that night (which might be way too much unless you've been there before). Cinque Tera at 2 nights seems fine... and you can day-trip into Pisa for the standard sites on your way in or out of the Cinque Tera; in that case there is an easy bus from the train station to the Miracle Campo... then it's back to catch the train into the Cinque Terra (as you only need a few hours in Pisa - and they have timed entries into the Tower). For me I'd probably not both with Bologna... and I'd spend more time in Chianti country (Tuscany), which we've used a car to zip around. 3 nights in Rome will make that part of the trip packed, so plan every day to the fullest there.

Hi Scott. At this rate, you're doing as much traveling between cities as you're spending in each city. Each time you move to a new city, you lose time and money. Since you have 14 days, I would spend them in Venice, Florence, Siena, and Rome. 1) Fly into Venice and spend 2-3 nights there. If 2 nights, take a daytrip to Padua, Vicenza, Verona, or Bologna on your way to Florence. (Padua and Verona are cool, Bologna was just okay, and I haven't been to Vicenza.) 2) Florence, 3-4 nights. If 4 nights, take a daytrip to Lucca or Pisa (I prefer Lucca). 3) Siena, 1 night 4) Rome, 4-5 nights and fly home from there. Or do the trip in reverse. There's so much to do in Florence and Rome. You aren't spending a lot of planning time and money on this trip just to try to cram everything into a couple of days in each city.

Hi Scott. This is a classic challenge for the Italian traveler: How do you see everything you want to see in teh limited time we Americans have for vacation? In Italy, less is more, IMHO. Each one night stop means 1/2 a day to see the place, then move on. So your typlical days are like this: Day 1: Ar Milan, transfer to Verona, 2-3 hours to "see" something, have dinner, fall exhausted into bed and get over jet lag with a 9 hour sleep. Day 2: to Padua, part of the day to see stuff Day 3: to Venice, part of the day to see stuff
and so on. Stay at least two nights in a place so you get a sense of "being there" not just passing through and ticking off the sites on your list. Scale back your number of locations. You will return! One way to approach your trip is to combine cities into groups and do day trips. Padua and Venice are close: Stay 3 nights in Venice and do both places from one lodging. Venice deserves two days (actually it deserves more, but that would take a longer trip). If you have to go back to Milan to fly out, you'll need to leave Rome the day prior, in all likelihood, so you'll have a night in Milan. You might be able to go Rome-Verona-Milan on that last day before you fly home if you leave Rome early enough. Research that (and all your travel times) on Trenitalia. You'll be amazed at how much transfer tiem cuts into your actual touring time. With 14 nights, stick to 4 locations: Venice (3), Cinque Terre (3), Florence or Siena (4-5) (daytrip between, and if you stay in Siena easy enough to daytrip to Montepulciano) and Rome (3-4). I'd add nights in Tuscany because there is so much to see, and you want to experience the Palio. You can see Orvieto on your way to Rome, since it is easy travel from Siena to Rome via Orvieto.

OK...with your help ive cut out a few things already. Im thinking of cutting out Assissi and adding a day to Florence or Rome. I will keep refining it...but its getting there for sure! Thanks again! Fly into Venice Venice (2 nights) Verona (daytrip) to Cinque Terre Cinque Terre (2 nights) Pisa/Lucca (daytrip) to Florence Florence (2 nights) Siena (2 nights) (Palio Horseraces on aug 15-16) Montepulchiano/Orvieto/Assissi/Bagnoregio (3 nights) Rome (4 nights)
Daytrip to Naples/Pompeii/Amalfi Coast from Rome

Something to keep in mind for going to Siena during the Palio is a lot of places require minimum stays of up to 4 nights during that time. So you might do some preliminary checking for accommodations. Since you want to do Montepulciano as well you should be able to combine total nights stay and daytrip as needed in the area.

Thanks for the tip about Siena! very helpful...So the plan has been cut again...anyone know of the cheapest ways to fly into italy? im finding airfares around $600 one way (boston to venice). that sound average? also does anyone know what goes on during the St. Lawrence Day in Cinque Terre? Fly into Venice Venice (2 nights) Verona (daytrip) to Cinque Terre Cinque Terre (3 nights) – St Lawrence festival Pisa/Lucca?? (daytrip) to Florence Florence (2 nights) Siena (2 nights) (Palio Horseraces on aug 15-16) Montepulchiano/Orvieto/Bagnoregio/Assissi (2 nights) Rome (5 nights)
day/Night to Naples/Pompeii/Amalfi Coast from Rome

Just a thought, but since you want to see the area around Florence, Siena and a number of day trips you could easily get a car and drive around Tuscany. More freedom and spontaneity, and you can then decide if Pisa is worth more than a quick lunch and a look at the tower. You can get a car at the airport in Florence and return it to the same location, then take the train to Rome to finish up your trip. I would also do 2 nights in Venice if possible.

IN Nov/Dec, I took my first trip to Italy. I had 16 nights. This is what I did and I firmly believe I gave each city the appropriate amount of time to be there. -Flew into MIlan for 1 night stay. Goal was to see Last Supper and Duomo -Off to Florence for 3 night stay. Wanted to side trip to San Gim but found there was wayyyy to much to do in FLorence to leave. -Off to Siena for 2 days. Got there in afternoon, toured the churches and some of the medieval museums first afternoon, Il campo sites the AM of the next day. For the afternoon, I took a guided tour of Chianti region with a stop in San Gimignano. I believe my 2 nights in SIena was enough to see what I needed to see. It is a beautiful little city. Tough terrain though, make sure you walk on treadmill with incline and use stairmaster. -Off to Assisi for 2 nights. Saw alot the first day we were there. Once again, treadmill and stairmaster train or else suffer. Next day it was soooo rainy we side tripped to Orvieto. -Off to Rome 4 nights. I saw what I needed to see. Found 4 nights perfect for what I needed. -Off to Venice 3 nights, and flying home from Venice. Did not want to leave for any day trips. I wished I had 7 nights for Venice, it was very awesome.
****Make your sidet trips an as needed basis. You may find that you do not want to leave the home base city. My side trips were based on that regions weather of the day, which was to our advantage. Think about those 1 night stays. May prove to be a waste of time with all the time you lose with traveling.