Advice - Two Week Itinerary (In and Out of Milan)

Hi Daniel, lived in Tuscany for a while! I'm glad you choose it! But, tell me something about what would you like to do? Arts, adventure, countryside relaxing things...let me know, I can better address my tips ☺️

I don't know where you've been on previous trips, so it's hard to give advice. One point: are you trying to go too many places? Remember that a travel day isn't really a "being there" day.

Other than that, here are a few thoughts:

• I assume you are going to Florence just to get to Siena? If not, why aren't you staying longer there?
• Cinque Terra is my third favorite place on the planet, and you are very smart to go in September rather than July.
• Avoid Milan. It's a wasted day. Have you considered flying directly into Florence instead?

I'd start your trip in Florence and do Milan at the end, so you don't split up your nights. Fly into Milan and take a train from the airport to Milano Centrale then a train to Florence. I like the other didn't really care for Milan either, but some people do like it. I had one night there and it was plenty.

I organize my trips by where I spend the nights not days, so I'm not quite sure where you would spend your nights based on this. But I might do it this way:

Fly into Milan, train to Florence
Florence (3 nights) - day trip to Siena (or three nights in Siena, day trip to Florence)
Tuscany (rent a car, take a tour?) (3 nights)
Drop car and train to Cinque Terre (might drop car at La Spezia I guess instead of near Florence)
Cinque Terre Town (3 nights)
Train to Lake Como
Como (3 nights)
Milan (2 nights)

That's 14 nights. How many do you actually have in country? A "two week trip" might be leave Monday morning, fly home Sunday night, which would be only 12 nights in country plus 1 night flying overnight (presumably). Leave Saturday morning fly home two weeks later Sunday night would be 14 nights in country.

Monty, Thanks! What are your other two "favorite" places? Is the Cinque Terre even better in October because it is less crowded? Reason we're including Florence is because we are absolutely in love with it and can't imagine visiting Tuscany without at least one full day and an overnight stay in that magical place. Having been there already for multiple days we don't want or need to stay longer than that, so that's why we're deciding to move on quickly. We've never been to Siena/Montalcino/Montepulciano/Lucca/etc.

Yves, Thank you! We have already visited all the important historical and cultural sites in Rome, Pompeii, Sorrento, Venice, Florence, and the Amalfi Coast. This trip is mostly about relaxation, so our primary aims are eating well, being blown by the natural beauty of Italy, eating well, and seeing new places!

Andrew, Thanks for your suggestion. I like your idea of starting the trip in Florence (that opens up an extra day essentially) and your other suggestions are also on point! Appreciate the help!

Should we just skip the second night in Milan? If we can see everything there in one day, we'd rather get the extra day in Como, Tuscany, or CT.

Daniel, you'll have to decide what you want to see in Milan before deciding whether you can get away with only one night. And because that would be your final night, if you follow my suggestion to do Milan at the end, you might not have any time the final morning. So what time would you likely arrive in Milan the day before?

Many people want to see "The Last Supper" - something you need to reserve well in advance. I did not even try to do this or go to any museums. So all I really wanted to do in my single day / one night was wander around Milan and see the basic sights. If you want to see museums and more, it might be tough to fit it all into a single day (or even less than a day - assuming you'd arrive mid-morning from Como).

I love the Cinque Terre - I just got back from my third stay there. My first stay was in October, and we had warm weather (almost too warm for hiking). This was some years back and though it was fairly busy on the trails even then, I think it is much worse now. On my most recent trip a few weeks ago, I did some of the less-known hikes: Levanto (where I stayed) to Monterosso, and Manarola to Corniglia via Volastra - a very difficult hike with a steep climb (up steps to Volastra) but with breathtaking views down, so very rewarding. Some of the more popular trails (between Riomaggiore and Manarola and Manarola to Corniglia, at lower elevation) are closed now and probably still will be in October. The trails between Corniglia and Vernazza and Vernazza to Monterosso may still be open (are open right now) and are the ones likely to be the most crowded - even in October. The Volastra trail was not exactly empty either but no tour groups on it - just individual hikers.

Daniel,
My other two favorite places in Italy are (of course) Rome and Venice. But like Cinque Terra, I prefer them in the off season. CT will be MUCH nicer in October than in July.

I'd still recommend flying into Florence rather than Milan. Milan was the most miss-able city in Italy for me.

Siena is weird and interesting--sort of like Venice in the long narrow "roads". Get a room that looks at the back garden rather than the street unless you love the sound of Vespas. It was cool to compare its medieval charm with Rome's antiquity and Venice's color.

But truly: skip Milan.