Help planning city route?

Good order. Do fly out of Rome rather than back-tracking if at all possible. Staying in 6 locations is a lot for 2 weeks, though. Don't add any more!

After you take into account the flying days, this leaves you with about 12 days. IMHO 5 stops, 3 of them larger cities, is too much. Keep in mind that even if Trenitalia lists something as about a 2 hour ride, you need to leave the hotel and get to the station in time for the train and then find your new hotel at the destination. Each time you change locations it takes about half a day in my experience. Much of your trip will be an afternoon plus all of the next day, repeat. I prefer spending 3 days in a smaller place, 4 in cities. This lets me use each stop as a base to explore not only that location but to take day trips, plus allows me flexibility to adjust my schedule based on the weather, energy level, serendipity, etc. Also I noticed most of your trip is in the northern parts of Italy, so for starters I'd drop Rome and save it for another trip. 4 days in Florence lets you explore the museums and city, plus make a day trip out to visit a hilltown or two. Many tourists don't find Milan that interesting (I haven't been there personally) so if you drop Milan as a destination where you spend time and fly into Venice you can work your way towards Florence, then fly back either from their or Milan. Depending on how much time you want to spend in Verona, you could even do that as a day trip from Venice (1 hour train ride on the Eurostar each way). There's lots of combos you could consider in ordering the travel; you might want to look up travel times between the cities on trenitalia and see what combo works best (for example, maybe fly into and back out of Milan).

I think its a good plan-you'll definitely want to fly back from Rome. If there are only a few things you want to see in Verona, I would just do it has a day trip from Venice, to minimize the packing/unpacking. The first time I went to Italy, I only spent 2 nights in Venice and Florence and 4 in Rome; you'll just have to be selective in your sightseeing. I recently spent three nights in Stresa (Lake Maggiore) and had a good time-don't miss the beautiful gardens in the area and the isole borromeo.

I agree it's too many places to stay in, but the order is good (Assuming you're not actually spending the night in Milan, but rather just arriving there.) You could do Verona on your way from Lago Maggiore to Venice, as a long stopover.

Thank you all so much for the advice and posts. I only plan to 'arrive' in Milan, I hear there isnt really much to do there. I am thinking of renting a car to do the Lake maggiore / Verona / Venice travel. 2 days at the lake 2 days to do Verona & Venice 3 days in Florence
3 days in Rome The balance of my days I am devoting to travel (trains). It seems people have a love/hate with Venice. I am hearing people either hate it or love it. Is it worth going to? Maybe the better question is: Is it worth going to if you are travelling alone? Any good hotel suggestions in these locations? :)

No car. At least not for Verona which is right on a hi-speed rail line as is Venice, nor for Venice where the car isn't much good unless it floats and has a propeller. Venice, as you've noted, is love/hate. Mine was hate, but others will of course differ. All I can say is that before accepting a drink at a cafe, be sure to ask how much it is! A car might be useful for getting to/around the lake, but I don't know from any personal experience. Just to reiterate what I wrote earlier, you seem to have 12 days on the ground and now list 4 places, but just allocate 2 days to train travel. Not sure how that will work :-) If it was me, the 2 days you have for Venice and Verona would turn into a "don't bother" for me. That's one day in Venice which I personally wouldn't do if I wanted to visit it. I'd suggest taking those 2 days and adding 1 apiece to Rome and Florence, although if I was your travel advisor I'd actually say drop Rome and add the days to Venice and Florence.