Two weeks in November

Please tell us how much time you'll have outside of watching tennis in Milan. Even if you have the full two weeks, your plans are overambitious. Even in November Venice and to a lesser extent Florence could be crowded.

A car will be a liability in big cities like Milan and Florence. If you want to wander through small villages, some of your big sites will have to be skipped.

One possibility would be to leave Milan, train to Lake Como for a few days, and return to Milan and rent a car. From there drive south hitting Parma, Cremona and maybe even cutting over to catch Lucca and Pisa. Then spend a few days in Florence before catching the train back to Milan.

We really don't like changing locations more than every four nights to have three full days in an area. You really need to triage your interests. and forego about half the places you mentioned.

Thanks for your reply. Just one evening for the finals on November 9. We did consider a train ride to Lake Como, possibly a day trip or an overnight stay. We'd like to see Florence and Venice, spending a few night in each, possibly Siena. Is that too much for two weeks?

We did consider a train ride to Lake Como, possibly a day trip or an
overnight stay. We'd like to see Florence and Venice, spending a few
night in each, possibly Siena. Is that too much for two weeks?

A lot depends on how much time you have before and after the Nov. 9 event. You could take a train to Venice immediately upon arrival, then work your way back to Milan via the lakes depending on how much time you have. That can be done by train.
After the tennis match, head to Florence, spend time there, then rent a car and explore rural areas before dropping the car and returning to Milan by train for departure. Get a good Tuscany book to help you pick out villages, such as the Blue Guide.

I like that idea and will pick a blue guide.... possibly a green guide too! Any suggestion about accommodations?

Does this seem reasonable? 2 nights, 1 before and 1 the night of tennis. Next day train to Lake Como, sleep 1 night Lake Como. Train to Venice, sleep Venice 3 nights, train to Florence, sleep Florence 3 nights. Rent car somewhere(?) outside of Florence, drive to Siena and other parts of Tuscany. Return car and travel by train back to Milan. Any ideas on accommodation and car rental location?

Consider taking a day trip by bus to Siena (it's better than the train) from Florence. Expect that the historic center in any Tuscan town will be off-limits to cars of non-residents, the dreaded ZTL's. They are all monitored by cameras and any infringement will result in a hefty fine. There are no-entry signs, but it's easy to miss one when you are distracted by traffic, unfamiliar roads, and interesting surroundings. That means you have to find parking outside the ZTL and walk in. You can also visit Pisa/Lucca in a day by train and San Giminagno by bus. Or you could spend 3 nights or more in Bologna and day trip by train to any number of nearby towns - Ferrara, Modena, Parma, Padua . . . . Also, I don't know how scenic Tuscany will be in November, maybe fall colours, maybe too late for them - like fall in New England or tulips in Holland, I'm told autumn is weather-dependent in Italy.

Trains for November are (or should be) on sale. The cheapest tickets are limited in number and sell out so booking as soon as you have your itinerary in place will save you money. Reduced price tickets are usually no-refund-no-exchange.

Even in November, it's a good idea to book ahead for some sights. In Florence, the Academia and the Uffizi; in Venice, the Secret Itineraries Tour at the Doge's Palace if you choose to take it. (I liked it very much)

Does this seem reasonable? 2 nights, 1 before and 1 the night of tennis. Next day train to Lake Como, sleep 1 night Lake Como. Train to Venice, sleep Venice 3 nights, train to Florence, sleep Florence 3 nights. Rent car somewhere(?) outside of Florence, drive to Siena and other parts of Tuscany. Return car and travel by train back to Milan. Any ideas on accommodation and car rental location?

That sounds reasonable if you can work out the Lake Como logistics. Is your plan to leave early in the day and spend the rest of the day, that night, most of the day at Lake Como, then train late afternoon/evening to Venice? That would give you two full days in Venice.

Be sure to factor in travel time from one place to the other. Checking out, traveling and checking in can eat up hours of time. I like the suggestion of staying one more day in Florence and day tripping to Siena.

You can rent a car in Florence and head straight out of the city. If that concerns you, you can go to the airport and rent there, but there will probably be extra fees and you'll burn up time getting there.

If you really want to get a taste of Tuscany, instead of staying in Siena, stay at an agriturismo and use it as a base to explore the small towns and countryside. Somewhere near, but not in Siena would be a good choice. From there you can go north to San Gmingnano, Volterra or even Lucca at a stretch. Then you can go south and explore Montalcino and Montepulciano. Go east and drive the famed SR222, the Chiantigiana to Greve, catching Radda, Castellina and Gaiole on the way.

the dreaded ZTL's

The ZTLs are not dreaded by people who can read and follow simple directions. Please don't let the exaggerated stories of ZTLs dissuade you from renting a car for Tuscany. Some common sense, such as not driving in major metropolitan cities will keep you out of trouble. The rule of thumb for hill towns is to assume anywhere within the walls (they are pretty hard to miss) is ZTL. In towns like Castellina, Radda and San Gimignano, there's plenty of parking just outside the walls. These towns are small enough that walking is not a problem.

In our 10 days driving all over Tuscany, we had absolutely no trouble avoiding ZTLs. We also strictly observed the speed limits (who wants to drive fast in the gorgeous scenery anyway?). Whenever a local wanted to go faster, we found the nearest place to turn off and let them by.

Thank you for sharing your experience and giving suggestions. My Saturday morning will be filled with research and reservations. I will look into the agri-tourism idea. I think I'll add a night in Venice! We are starting to get excited about this journey!

We are starting to get excited about this journey!

Planning is half the fun! You are going to have a great time. Italy is wonderful and November is a great time to be traveling there.