Italy in September

I think Genoa will be a let down. You have 4 nights in the Cinque Terre for your coastal time so not sure why you’d add more especially in the same general area, the Italian Riviera.

Where are you flying into and out of? The Cinque Terre will be at least as crowded as Venice and Florence, BTW. But if you can fly into Venice, transfer to Florence then to the Cinque Terre, it might work… Depends on where you need to go to fly home.

Another thought is to extend your time in Florence and do some day trips like Siena and perhaps a hill town.

Thank you Laurel. We have no set plans, flights. We do have a stay in Vernazza booked. Maybe more time in Tuscany would be the way to go. Lucca, Pisa, or other suggestions? I suppose we could fly into Genoa (closest airport to CT?), spend our time in Cinque Terre, and then off to Tuscany with departure from Florence. Is 4 days too much in CT, where maybe we spend 3 nights CT- 2/3 nights in Tuscany somewhere - 3/4 nights in Florence?

How do you want to spend your time? Are you hikers? Unless you have day trips identified, four days might be a bit much in CT for all but the avid hiker or someone who has an abundance of time to devote to natural beauty. You could just do more time in Florence, choose a smaller Tuscan town if you want to drive, or stay in Lucca, which is close enough to fly out of Pisa.

Hi Jamie, I love the local festivals in Italy because they’re so different than what we can experience in the US (if that’s where you live).

Check out Arezzo for the jousting festival (June & Sept), or Lucca’s festival on September 13, or I just attended the Asti Palio which will be Sept. 6 in 2026.

I was just in Venice a few weeks ago for the 6th time. Just stay away from the Rialto-to-San Marco day tourists’ path during the day, and it’s fine. I took my daughter out to Burano Island, and we explored the other neighborhoods during the day, toured a palazzo, had the earliest timed tickets for St. Mark’s, etc. and enjoyed the lovely piazza sitting at an outdoor table at the Florian for an evening beverage & listening to the music - a magical atmosphere! Of the 49 cities I have stayed in Italy, it will always be #1.

I haven’t stayed in Genoa. My niece taught school there for two years. For a first trip for them, that’s not where I would choose.

If you want to avoid crowds, think about Torino. There’s a lot to do there, and is beautifully underrated, so it’s not crowded. I highly recommend the food tour & bike tour I did, plus the hotel where I stayed when I recently returned there. Send me a PM if you want details.

Thank you for such great insight everyone. Jean, I fell in love with Venice as well. Absolutely amazing city. La Spezia to Siena is a 3 hr train ride. It’s a bit of a crisscross but Florence to Pisa(day trip) to CT(3 instead of 4 nights) to Siena to Florence? Thoughts?

I second the recommendation for Torino - great museums, no crowds. If you want to be on the Ligurian coast, instead of Genoa I suggest Camogli.

Jamie, Siena is very nice, and Florence although very busy is an iconic location. Be sure to purchase timed tickets way ahead for anything in Florence. Pisa is so touristy, but if you’re in the area, they will want to stop there at least briefly. Yes, I think three nights vs. four in Cinque Terre will be a good amount for your group. Enjoy!

Jamie- I highly recommend the small towns of Montalcino, Pienza and Montepulciano. If you and your group are into wine, then this is the time to go as it's harvest time for some of the best wine on the planet! I think that Genoa might be a let down. Tuscany is amazing and there is so much to do there. I must ask how you are not going to Rome? If you have 9 days, I would recommend doing the following- flying into rome.
Rome- 2 days
Tuscany- 2 days
Florence- 2 days
Cinque Terre- 2
fly out from? This itinerary is pretty ambitious, but would allow you to see alot in a short time. I recommend doing tours for the main sites to avoid wasting time in line and also food tours to not waste time on tourist traps. If you are not into wine, then you could skip tuscany and spend more time on the coast as you said. Hope this helps.

I would do 3 nights in Cinque Terre, then go to Venice. You can depart from there, or, consider Milan, depending on what your flight options are. Train to all.

Since you have been to Venice, consider Lake Como, always spectacular.

I'll add yet another perspective: we didn't really care for the Cinque Terre villages. Are they pretty? Definitely, but they are absolutely overwhelmed with tourists, and they lack the infrastructure to deal with the tourism effectively. Trains along the villages are very unreliable, as switching systems are antiquated and passengers share the same track with freight trains, which apparently have priority.

Genoa is an entirely different place to be. It's certainly gritty, and it's not a great place for photo ops. But the history of Genoa is very important, especially as the port where the great Italian diaspora to America largely originated. And oh, my heavens, the food! The seafood and pesto in Genoa are like nowhere else.

Just an alternative point of view. Full disclosure: we dislike going to Venice now, too.

Florence will be packed out at that time. I’d leave it for when you can visit off season.