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Almost three week itinerary help

Hi and thanks in advance for your help. We are planning almost three weeks in Italy (mid September through early October 2025) and would like advice on our itinerary:

Leave Chicago, USA, Wednesday, arrive Venice early Thursday

Venice: 2 nights

Cinque Terre: 2 nights

Florence: 4 nights (with two day trips to Lucca and another place)

Tuscany: 5 nights (rent a car, explore the area, drink wine and eat pasta)

Amalfi Coast: 3 nights (day trip to Capri)

Rome: 3 nights (Saturday, Sunday, Monday - depart Tuesday)

I'm wondering if we should eliminate Cinque Terre and add another night each to Amalfi Coast and Rome. We would take trains to get from one area to another.

Thanks.

Posted by
11583 posts

The first thing you need to do is to add a day to
Venice. You are short changing this incredible city.

Posted by
2684 posts

You don’t say if you’ve been to Italy before. I’m answering on the assumption that you have not.

The outlier on your itinerary is the Amalfi coast, I think. You don’t say where on the Amalfi coast - but transit to a lot of those small places can be slow due to winding roads and high traffic volume.

You don’t have a ton of time in Venice - if you’ve never been there, I would consider adding a day there.

This is all specific to your interests - museums? Architecture? Food? Cars?

It’s hard to know what types of sites you’re after but very generally, you could consider this slower-paced trip with a smaller footprint:
Venice - 3 nights
Cinque Terre - 2 or 3
Florence - 4 nights
Tuscany - I think you have too much time here, especially with 2 day trips from Florence. I would at least do the 4 days in Florence if you’re heading out to Tuscany for 5 nights.
Skip Amalfi coast unless you have something specific you want to see there.
Rome - 4 nights - at least.

Posted by
1127 posts

Hello Tim L, and welcome to the Forum!

My first impression is that you are probably trying to do too many thing too far apart even for an "almost 3 week" trip. Going from Venice to CT is crossing Italy at nearly it's widest point and I would expect 8+ hours door to door to accomplish this. Anywhere in Tuscany to the Amalfi Coast is probably close to the same amount of time. Travel to AC is logistically difficult and full of potential delays. Also keep in mind that 2 nights is only 1 full day somewhere with days full of packing, lodging and travel on either side. So you'll have one full day in Venice, travel nearly all day to get to CT, have an evening, one full day and then maybe a morning there followed by 3+ hours to Florence getting out of your hotel probably late afternoon at best.

I know there is an urge to go everywhere and see everything but you also need to account for the realities on the ground of doing the country both east/west and north/south all in the same trip. This is especially true when you are including areas with difficult travel logistics.

Dropping CT would allow you to add a day to Venice and a day to Rome (both really deserve it) and eliminate a full day of travel which is almost getting a day back for the effort. My suggestion would be to drop the Amalfi coast, add a night to each Venice, CT and Rome. Venice and Rome both deserve more time and CT deserves at least another day to justify the full day of travel to get there. I think one of the two coastal areas is the outlier but which one is more important is up to you.

If you're determined to do all of this I would look at replacing the Amalfi coast with Sorrento since it is easier to get to and you can do both the AC and Capri as day trips from there. But as I said I think instead you should aim to do less overall. Part of Italian experience - especially in rural Tuscany - to slow down and really start to feel the slower pace of life and the difference in priorities. Planning always means making the hard decisions about what to leave in and what to leave out, but it will ultimately lead to a better vacation if you give yourself time to experience these places.

Hope that helps, have a great trip,
=Tod

Posted by
7982 posts

If anyone is considering omitting the Cinque Terre from their itinerary, I would say that’s smart. Years ago, it was a magical visit. On our last trip, it was so overcrowded that it was no longer wonderful. Based on my latest experience, and backed up by reports and opinions of others on this Forum, your two days would be better spent elsewhere than the C.T.

Posted by
5221 posts

I'm wondering if we should eliminate Cinque Terre...

Yes, and eliminate the Amaifi Coast also. Too much time will be lost just getting there. Plus you will lose at least 1/2 to 3/4 of a day each of the others times you relocate.

With the five nights, assign three to Venice and two to Rome. And the trip will look like this.

Venice: 5 nights

Florence: 4 nights (with two day trips to Lucca and another place)

Tuscany: 5 nights (rent a car, explore the area, drink wine and eat pasta)

Rome: 5 nights

Just something to consider.

Posted by
11912 posts

I'm wondering if we should eliminate Cinque Terre and add another night each to Amalfi Coast and Rome. We would take trains to get from one area to another.

I think 2 'coastal' stops in the time you have is one too many.

Amalfi coast is the geographical outlier, so that would be the logical one to eliminate.

Agree with others that Venice could use at least one more night.

Unless you have been to Rome before, it also could use more time.

Happy travels

Posted by
2 posts

Thanks so much for the great information. We will definitely be adjusting our itinerary.

Posted by
11788 posts

Our first trip was a bit like yours: Venice (4N), Cinque Terre (3N), Siena (3), Montalcino (3), Orvieto (2), Rome (5), Milan 1 before flight home. On reflection it was all too fast. Only in Rome did we feel,we’d done justice to the place and weren't too rushed.

TC, Joe, Valerie, Hiredman are all correct: you’ll enjoy more if you go fewer places. Save the Amalfi Coast, especially, for the future. It’s a pain to get to. So is the Cinque Terre for only 2 nights.

You will be back! In fact, you will probably be planning your next trip on the flight home.

Posted by
167 posts

Overall, it looks great to me, especially the "drink wine and eat pasta"!! But as was suggested, I'd eliminate Cinque Terre and add one night to Venice and one to either the Amalfi Coast or Rome, depending on your interests. From Tuscany, you could go to Amalfi. We did something like this and it was easy. We trained from Florence to Naples, and then on to Sorrento, which makes a great base for Amalfi. Depending on where you are staying in Tuscany, it should be easy to get down to Amalfi for three or four nights, then head up to Rome for the last three or four! Sounds like an excellent adventure to me!

Posted by
167 posts

"Years ago, it was a magical visit. On our last trip, it was so overcrowded that it was no longer wonderful."

I have to agree. CT is no longer magical, and sadly I won't be returning there. But in my opinion, the Amalfi Coast is very doable and so amazing. If it were me, I would definitely include it in a three week itinerary.

Posted by
11788 posts

Oh, gosh, no way would I spend five days in Venice

There is time to savor the place, get away from museums and crowds, get to know your way around without a map. We’ve been in the city 14 times for 1 to 7 nights. I’d go back in a heartbeat.