reconsidering travel plans

Personally I would drop Venice to two days and drop a day from Lake Como.

Haven't been to Sienna but definitely don't short change Venice - the longer the better there. I wen to Lake Maggiore, not Lake Como, but I think you could drop a day there, and probably CT as well.

As I understand you have 16 days total (4 days at 4 different locations). I would recommend 3 days at each city/ location with a partial travel day in between. This will leave about a day and a half to squeeze in Sienna - worth the short trip from Florence in my opinion.

Stephanie, Siena is definitely worth a visit, if you can fit it in. As someone else mentioned, you could either take a day trip from Florence or adjust the duration of your other stops and spend a few days in Siena. One option to consider would be to spend three days each in Venice, Lake Como, CT, Florence and Siena. Keep in mind that you'll have to allow for travel time of at least half a day, each time you change locations. Happy travels!

If you are going to add Siena to your plans, you will have the same transportation time getting there, no matter how many nights you stay. I would suggest 3 nights in each location, adding the extra night to the place of your choosing.

Venice can be hectic. If you can put up a copy of "Walk and Talk Venice" by Allessandro Giannatasio and Chas Carner. It is perfect for IPod or IPhone. We used it extensively and saw the hidden corners with out the crowds. it is available from Amazon or Audible. Como is beautiful. Visit Maggiore also. Italy has so much, it is a sin to rush.

Even in high season you can avoid the crowds in Venice - just get off the San Marco - Rialto - Frari route march and wander the back streets. Visit the Ghetto. Take a boat to the islands. September should be better than July and August.

We LOVED Sienna, one of our favorites in all of Italy. I think you could cut to three nights to add two in Sienna. Three nights is still a comfortable pace for Como and CT and Sienna, being so close to Florence, won't include much travel so you can enjoy it in the morning and evening after the tourist leave. I think it is worth the time.

If you have not purchased your plane tickets yet, I would suggest flying into Milan, then go to Lake Como first to get over jetlag, then Venice........ We have stayed in Siena for a few days as well as visited Siena as a daytrip from Florence by taking the bus a couple of times. We also like Florence and there's a lot to do there. In addition to spending a few days on several trips, we rented an apartment for a month in 2000 and again in 2003. We spent a relaxing week on Lake Como in 2007 but only two days in CT in 2003 and hiked all five villages. Altho we enjoyed our two days in CT, we have no desire to go back. Venice we love but you have to spend time there and get away from the main tourist spots/byways to appreciate it. We have spent 9 months altogether there since 2007 and plan to spend three months again starting mid-October (this is in addition to staying there for a few days several times since 1990). We love it that much! I guess what I am suggesting is, determine what is important to you and then plan accordingly. Happy travels.

I haven't been to Lake Como or Milan so I will not comment on it. I would reduce your time in the CT to two nights and Florence to 3 nights. I would add the extra days to Sienna. From Sienna (or Florence for that matter) you can take day trips to the other hill towns. It seemed that each hotel in Sienna or Florence has brochures for guided tours of Tuscanny, they would usually include going to a few vineyards for some wine tasting which is always fun. You can usually book them the day before. Florence is rather small and you can certainly see everything in two days. The CT is charming and but some of these towns are quite small and you can see them in an hour or so. I personally would never spend 4 nights there. I also would probably never go back to the CT. It's charming and I'm glad I went but it is discovered now and it can be crowded.

Thank you all for your wonderful perspectives
Happy Traveling to all who generously took your time to respond

I agree with several posters...at least 3 days every location. Siena is magical...a "must see" in my opinion. I also recommend Lake Maggiorie. It is wonderful. I have stayed in Stresa, Baveno and last month I stayed in Cannobio. You can take a boat from Stresa and Cannobio all around the lake.
If you are interested and need hotels or details, please send me a private email and I will provide that information

I was just in Venice, Florence, Siena and CT. I spent a lot of time in Venice, could have spent more, did 3 nights in Florence and CT and 2 in Siena. I enjoyed Siena but I would take time from Florence not CT.