Milan/Florence in October

The plan of day tripping everywhere is not my favorite but seems feasible. Your longest roundtrip is about 1.5 hours each way for Milan-Genoa. If you don't want to be on the train every day, then I'd cut Genoa and Parma. You can buy tickets as you go to maintain flexibility.

Thank you for your input Laura and I agree that day trips every single day will get to be too much. Having been to Florence before, and having seen most of the things I wished to see, perhaps it might be best to limit Florence to three nights with one day trip to either Siena or Lucca and then on to Milan where there seem to be more day trips that would be worth doing.

The real rub here is the return draw of Venice. Have been there twice but have fallen in love with the city and am torn between revisiting and exploring something new......No wrong answer and both would work I am sure.

If you stay in Venezia you can daytrip to Padova and Verona. From Milano you can go to Pavia (Certosa and the town of Pavia), Bergamo, perhaps some other place as well. Perhaps save Tuscany for the next trip?

Weather at that time, whether October or April, is somewhat unpredictable with a fair chance of rain, so certain locations (like coastal or lake areas) may not be desirable in case of bad weather.

Florence is an excellent location for day trips via public transportation. Siena, Arezzo, Pisa, Lucca, Pistoia, and other smaller towns in Tuscany are all within about 1 hr. Bologna, although not in Tuscany, is only 37 min. away by high speed train. Even if you've seen Florence before and don't need to see anything else in Florence itself, I would still recommend Florence as your base.

Milan for five days would be an overkill. You will probably need to spend the night before your flight back there if it's a morn flight, so I would plan to leave Milan for the last couple of nights before returning home. You still might have extra nights. Lake Como for a couple of nights is a possibility assuming weather cooperates.

I don't know what you've seen of Italy before. How about Venice or Verona? I don't know Turin, so I'm not giving you advice on that one. For sure I'm not fond of Genoa. I've never found it particularly beautiful, although there are a couple of things to see.

Seconding Roberto on his thumbs down on 5 nights in Milan.
I can't remember anyone, reporting in here, who did 5 nights in Milan. It's a financial and business center with a lot of tall buildings: You can see Last Supper (if you reserve in advance), the Duomo including the rooftop, and the Galleria diagonally across from the Duomo. Those will take less than a day.

I'm planning my trip to italy for this fall and I like the Milan to Venice rail line. You could land in Milan, see that, go to Turin, then backtrack a bit to go to Verona, Padua and Venice. You could stay in a Milan location and make trips to Turin and verona, then make venice your next stopover and do day trips from there to Padua.
You could then base yourself in Bologna and go to Lucca, CT, and Pisa either on day trips or an overnight. Or perhaps Florence with day trips to Sienna and Azizzi.

We're planning to hit those spots except for Turin in the first 24 days of our visit, so maybe you can pick and choose parts of the itinerary. Best of luck.

Awesome input from everyone and I thank you all so much.

The reason for 5 nights in Milan was to allow one day to see the city and then without a change of hotel, to be able to do day trips to Turin, Genoa and Lake Como. The priority there would be Lake Como followed by Turin and then Genoa.

I did love Florence when I was there and still remember the view from the top of the Duomo and the stairs leading to it.

Florence would allow me the time to see Lucca and perhaps Siena and make a quick return trip to Pisa.

I have been to Venice twice but will admit it is my favorite city in the entire world.
I could see myself spending a few nights there walking and getting lost and just relaxing. If Venice is included, I certainly would take the Milan to Venice train as I seem to have learned the secrets to making reservations on the Italian train system. Also seems that if there is to be a local train strike, it occurs on a Sunday so those days would be the best to remain local.

I know this will not be my last trip to Italy and while there is so much to see and enjoy, I find myself drawn back to those places that I first fell in love with.

I probably will try to perfect the trip throughout the entire planning stage but at least I know that no matter what I decide and no matter where I wind up in Italy, I will have a great time.

So, where might one find some ideas for inexpensive hotels in Florence, Venice or Milan? And by inexpensive, I would like to stay under $80 US if at all possible. Just want some place clean and safe with ensuite bathroom.

Being retired, I am free to go any time in 2016 but would rather not do cold weather. Crowds are ok and I expect them anyway.
Have been to Italy in early September and it was extremely warm everywhere while the last trip was in April and it was a tad cool.

October is my favorite month in Italy. Probably a bit cold in the Dolomites, but delightful everywhere else we have been from the Cinque Terre to Ravenna.

You have plenty of good advice above, but I do have a hotel for you in Firenze: Hotel David. I have not had the pleasure of staying there but good friends did and enjoyed it immensely. Free breakfast, happy hour, mini-bar and WIFI.

You mentioned an interest in exploring churches. That could argue for spending at least a couple of days in Milan. There are some really lovely very early churches founded by St. Ambrose in the late 300s.

And as far as weather goes, while there's no sure way of predicting -- I've had good luck in N Italy in late September/early October on the last 4 or 5 years. Only a day or two of isolated showers. Nothing that really affected my activities.

Another idea - stay in Bologna and day-trip to Ferrara, Padua, Ravenna. I really enjoyed exploring Bologna for a couple of days and it is one of the cheaper places for rooms.

Do you have a choice of this October or next spring? October probably has better weather, early spring would have fewer tourists.

Paul, I spent Oct 2013 and May 2014 traveling in Italy, spending one or more nights in probably 20 or more different towns, and the only one I would NOT love to return to is Milano. I know others may disagree, but like some others here, I can't see spending five nights there, unless you have a special reason. I think the northeast part of Italy has so much see and do, not just Venice which you say is your favorite place in the world (and you're planning to skip it ???), but Verona, Ravenna, Padua, Lake Garda etc. If you like to visit churches, Verona and Ravenna both have various beautiful churches in very walkable towns. The mosaics in the churches of Ravenna are out of this world. In this kind of trip, I see there are two competing, even conflicting, desires: one is to not be packing up and moving hotels every night or two, but settling in for a few nights; but the other is not to limit yourself to many day trips, where you end up just visiting a town when other day trippers, bus tour groups and cruise boat visitors are all there with you. The most magical time in both cities and small towns is so often in the early morning and the evening, when everything is quieter and slower. Just for instance, I arrived in Siena in the early afternoon, finding everything so crowded and hectic that I couldn't understand why everyone said it was so special; once the sunset hour came, the crowds of both tourists and busy locals disappeared, things quieted down, and the lights illuminated the public squares and buildings, and only then, I really understood.

The relies are beyond awesome and my mind is flooded with ideas to make this an even better trip. And it will not be my trip if I have anything to say about it.

So it comes down to either going back to places that captured my heart and mind, or looking for new and perhaps even more exciting adventures. Or......perhaps a combination of both????

But I will be flying into Milan for sure as the cost difference is great between there and Venice or anywhere else. And as I remember, the cost of trains, other than regional, does drop the future out you buy. Now I know a lot of folks will say that since I can not be sure of what time my flight will arrive in Milan, that buying a greatly discounted ticket may not b wise. But since I will only have a backpack with me, and since the flight is due in just before 9 AM, I was going to look at say a 2PM train to Venice and if I am early, I will walk around and perhaps check the bag at the train station and go see the Duomo and a bit of the city before going to Venice.

Last question please. As I am a new poster and certainly do not wish to step on anyone's toes, and am not familiar with the protocol here, I was wondering if there is a policy on sending someone a private message if I have questions on something they might have said?

I was wondering if there is a policy on sending someone a private message if I have questions on something they might have said?

Feel free, Paul. That's how it's done!