Hi,

My wife and I recently took a trip from Paris to Amalfi and fell in love with Florence. We land in Milan on October 12th at 5 am and fly out October 23rd..

Here's what we would like to do.

Land in Milan and either take a train to Cinque Terre or go straight to Florence. (not sure if it's best to go to Florence for a few days then Cinque Terre, )

We would like to rent a car at some point to explore the small towns of Tuscany.. I was thinking about getting the car just outside of Florence...

Should we go to Cinque Terre first and spend 2 days there? Then head to Florence for 2-3 days, then to Tuscany?

I would go to the Cinque Terre first, because your chances of bad weather increase the further you go into October. In Florence or rural Tuscany, a little rain won't ruin your day, but there's not anything to do inside in the Cinque Terre.

Just FYI, train from Malpensa to the CT will take 4.5-5 hours, depending on your destination. You'll likely arrive before you can check into your lodging, so you'll need to be able to drop your luggage there before exploring the town. Bottom line: Unless you spend 3 nights in the CT, you'll have less than 2 days there. One and a half days would be enough for me but perhaps not for you.

I would head to Tuscany after the CT. Pick up the car in La Spezia, although that would mean spending 3 nights in the CT as rental offices in La Spezia are not open on Sunday. If Lucca is in your plans, you could train from the CT to Lucca on Sunday and pick up the car there on Monday or Tuesday.

If you went to Florence first, you'd arrive on Sunday or Monday. Both days are difficult for sightseeing as many of the main sights are not open every Sunday or Monday.

After your time in Tuscany, you could return the car in Chiusi, Siena, Lucca or Florence, whichever makes the most sense for your plans.

Unless your flight out of Malpensa on Oct. 23 is in the evening, I recommend you spend the last night in Milan.

I meant to add that there is train service to Florence from each of the car rental return towns I mentioned. Make sure you know the hours for these offices as most will be closed for a few hours in the middle of the day.

Thanks for the responses! Great to know that most sights are closed Sunday - Monday...
My wife and I traveled to Positano last summer. Do you think we would be missing out if we skipped CT?

If this was my trip, I'd skip the CT. But that's easy for me to say as I've visited the area a few times over the years.

You have 10 sightseeing days. For me, that would be the bare minimum for exploring Tuscany plus a few days in Florence. Even a week in Tuscany won't give you enough time to explore the entire region which covers 9000 square miles.

Do you know what you want to see/do in Tuscany?

October is a very iffy time to go to le Cinque Terre, and if you enjoyed Positano in summer, then maybe in October le Cinque Terre will lead to disappointment.

If you fell in love with Florence, you could have a fabulous time in autumn visiting other Renaissance towns near Florence, even before you rent a car. For instance, if you head first to Florence, and spend a couple of nights there, before you rent the car, take a day trip to Arezzo or Lucca by train.

Or, in the alternative, if you are landing in Milan, head first by train to Parma for 2 nights. It won't matter if it is raining -- Parma will be beautiful & delicious, and you will see a side of Italian genius that is just as amazing but different from Florence. (Likewise in Arezzo & Lucca).