Possible Itinerary?

Overall looks ok, but unless you're flying out of Milan I'd drop it and add more time somewhere else. One nite in a city isn't long. So either move that nite to Cinque Terra, or consider using your extra nite in CT. The train from Sienna to CT is 3.5 hrs, add in time to get to the hotel, etc. and your left with about 1/2 day the travel day. Assuming you want to hike some of the trails, visit some of the 5 towns, ride the boat between towns, relax on the beach, etc. that's a lot to put into 1.5 days.

You will get different views on how to travel, but I'm moving more and more into the "less is more" camp. In 14 days you're trying to work in 6 places. You can do it, but realize that just about every other day once you leave Rome is going to be getting to the train station, a ride of a few hours, finding the hotel, etc. with your exploration of the new town beginning in the early afternoon. Which leaves you the next full day before the cycle repeats. If it were me I'd try to stay 3 nites in fewer places (Siena is smaller, 2 nites would be ok)

Thank you for the reply! We are flying out of Milan which is why we have a night there.

We had considered spending the extra night in the Cinque Terra... we've heard wonderful things!

I wish we could spend more nights in each city... we had a hard time narrowing down where we wanted to go this trip and this is what we came up with. I don't know what we would cut from here!

Jen

Jen, I tend to agree with Mike's advice. While your suggested Itinerary is feasible, that's a lot of stops in a 14-day trip.

Your timing for each of the cities looks reasonable, however I'd also suggest adding one night in the Cinque Terre. With such a short trip, I'd delete the stop in Pisa and use the time in Florence.

In order not to waste any time, be sure to plan your rail links carefully. I usually depart each city after breakfast (since in most cases the cost of breakfast is included in the room) and try to arrive in the next city in the early afternoon (rooms aren't usually ready for check-in until after about 13:00). Of course, this method has to be adjusted slightly depending on the travel time between towns.

I wouldn't bother trying to find somewhere to use the extra night. You'll need to allow for travel times to reach the destinations you have. If you arrive in Milan fairly early and have the option of leaving your luggage at the Hotel, a quick day trip to Lago di Como would be one possibility as it's only an hour to Varenna (that is, if you're not interested in having a look around Milan). Be sure to note the time for the last train back to Milan!

Happy travels!

I think it looks reasonable. Remember that the distance between Venice and Milan is pretty long, so the travel will take awhile.

I could see adding a night in Rome and doing only one night in Siena. Two nights in CT is plenty for a two-week trip, it's more of relaxation stop than a place to see and do a lot.

I'd drop Milan and make it up to Lake Como for 2 nts.

We are flying out of Milan in the morning which is why we have to end our trip there. Thanks for the suggestion though!

This will be a controversial and highly subjective suggestion, but if I had to plan my Tuscany trip all over again, I would skip Siena and spend more time in Florence or the Chianti. But, but, but, if someone had told me that before I went to Italy I would have been reluctant to take that advice. Also, I may not have the best choices in Siena and that may have colored my perceptions. Mind you, I enjoyed Siena and found it amazing, but it was my least favorite part of my trip.

Take this advice with a huge shaker of salt... It's so subjective and personal..