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Ambitious itinerary

My husband and I are traveling to Italy from Sept 3-22. As the trip becomes a reality, I am getting more and more nervous about our itinerary. This is what we have planned:
Sept 3- Depart
Sept 4- Arrive in Milan. Spend day in Milan
Sept 5/6- Cinque Terre
Sept 7- Stop in Pisa/Lucca/ sleep in Siena
Sept 8/9/10 - Rome
Sept 11 - Visit Pompeii during the day /sleep in Sorrento
Sept 12 - Capri all day/go back to sleep in Sorrento
Sept 13- Positano all day/go back to sleep in Sorrento
Sept 14- Stop in Assisi/sleep in Florence
Sept 15/16/17- Florence
Sept 19/20 - Stop in Bologna/sleep in Venice
Sept 21 - Stop in Verona/sleep in Milan
Sept 22 - Depart
We plan on booking hotels/B&B ahead of time and travel by train and bus.
This is our first time in Italy, but we have heard it is relatively easy to take trains and busses.
If you are an experienced traveler or if you have been to Italy before, I would appreciate any advice/suggestion/ideas.
Thank you so much!!!!!

Posted by
11613 posts

I appreciate your wanting to squeeze in a lot, I still do after many trips to Italy. It is ambitious but if you want this quick pace, it's mostly doable. Without a car, I think your number of stops (I assume you mean on the way to your sleep destination) may be challenging, because of the time it would take to leave your luggage and retrieve it. I would skip the night in Siena and add it to Florence, plus one more night in Florence and do Pisa and Lucca as one daytrip and Siena as another. I would rearrange it as follows, with only one "stop" and a night in Assisi (even though it's only one night, you will see more of Assisi this way than on a daytrip from Siena or Florence):

4- Arrive in Milano, train to Venice
5- Venice
6- Venice (daytrip to Verona)
7- Stop in Bologna on the way to Florence
8- Florence
9- Florence (daytrip to Pisa/Lucca)
10- Florence (daytrip to Siena)
11- Cinque Terre
12- Cinque Terre
13- Assisi
14- Spare day/night somewhere (I would add it to Rome and take a daytrip to Orvieto)
15- Sorrento
16- Sorrento (daytrip to Pompeii in the morning)
17- Sorrento (Positano and the Amalfi Coast
18- Rome
19- Rome
20- Rome
21- Milano
22- Depart from Milano

Posted by
926 posts

I think it is way too much. Our first Europe trip, we had maybe a week in Italy? Can't quite remember, but we did what you are thinking, stop here, stop here, sleep here, stop here, sleep here.... Well I pretty much came out of it hating Italy. So much so, that when we just went back last summer and took our kids (14 years later) I almost didn't plan any Italy at all. I cannot honestly remember the difference in Siena, Orvieto, Assisi,....

But we decided to give it another go, and we slowed down, spent 3 nights in Rome, then 2 in Lucca (with a day trip to Pisa one day), then 3 nights in Venice. SO much better! I love Italy!

I wish on that first trip we would have made at least 2 nights stops, instead of these, "stop here, sleep here" things. I probably would have loved Siena, but we were hardly there, just to barely check in, sleep and leave. What's the point?

I think the CT/Pisa/Lucca/Siena leg is insane. I think you would be much happier with only 3 nights, just staying in one place (maybe Lucca, it is so cute!) - plus you will be tired in the first days - that is a brutal schedule. I would pick CT OR the other stuff (base somewhere 3 nights). Or just got to CT and then straight to Rome (stop for the afternoon somewhere if you must, but get to Rome to sleep).


Posted by
20729 posts

I like Zoe's schedule better. But I also think this schedule screams -- "Open Jaw Ticket" Into Milan and home from Rome. In total it will be cheaper, more convenient, and give you an extra day. Still a very packed schedule with lots of travel time.

Posted by
3475 posts

Zoe has given you the most appropriate schedule for what you want to see. While many would
find it too fast it is certainly doable.

Posted by
651 posts

You really must cut down on the number of places you plan to visit! It's too much too fast! Why go all the way to Venice to sleep there, without giving yourself any time to visit? Yes, transportation is good, but it's not going to get you there instantly. The train from Sorrento to Naples will take 70 minutes, then you need to take another train to Assisi (via Rome) which will take 3-4 hours, then a regular bus into town. And then you have to take the bus back to the train station for another 2.5 hour train ride to Florence.

Reality check. You have 18 nights in Italy, correct? Pick either Cinque Terre OR Sorrento. If you choose CT, and you MUST see Pompeii, you can do it as a day trip from Rome. All major cities need a minimum of 3 nights, plus more if you plan day trips from there. Smaller towns and cities you should plan for 2 nights. Drop Bologna, few people go there on a first trip. Drop Your first night in Milan, instead head straight to Verona as it is a quick train ride of about 1.5-2 hours. Buy the ticket as soon as you reach Milano centrale, do not purchase in advance as there might be travel delays.

Here is my suggestion:

2 nights Verona
3 nights Venice
4 nights Florence (day trip to Siena)
2 nights Assisi
4 nights Rome (day trip to Pompeii)
2-3 nights Cinque Terre
1-2 nights Milan

Posted by
11 posts

Thank you so much to all of you who are giving suggestions. I really appreciate it. We bought our tickets last night, so I dont know if we want to exchange them and try the open jaw. We thought about that in th beginning, but decided to arrive and depart from Milan. I am thinkning about the itineraries you all posted. I might reduce the places we want to visit and spend more nights in less cities. Thank you all. If you have more suggestions, they are welcomed.

Posted by
31073 posts


I agree with the others that your initial itinerary was too ambitious and you'd spend a lot of time in transit rather than enjoying the places you've come to see. The alternative suggested by Zoe would be a good one to consider.

"This is our first time in Italy, but we have heard it is relatively easy to take trains and busses."

Travel by train and bus in Italy is relatively easy, but there are some potentially expensive "caveats" to be aware of. If you need further information, post another note.

Posted by
11 posts

Thank you, Ken and everyone else. I am discussing with my husband tonight. I appreciate all your comments and suggestions.

Posted by
506 posts

I know Zoe seems to know so much about Italy, I just wonder why stay so many days in Florence which after I just booked part of our trip there, seems to be such an expensive city to do all these day trips out of. I am not sure what the alternative would be to that but I feel like the Florence part of our trip is the most expensive and to really not spend much time in Florence it doesn't make sense to me.

Posted by
11613 posts

Judy, I recommended four nights in Florence because of its good transportation connections (the OP will not have a car) for the desired destinations while minimizing hotel changes. There is plenty to do in Florence for four nights, even without daytrips. Also, a good range of options for food/lodging in all price categories.

Posted by
9454 posts

Zoe nailed it! It is an ambitious itinerary, but by using bases and day trips, you won't be quite so exhausted as you would with all the packing/unpacking/relocating.

I do not find Firenze particularly expensive. It is certainly less expensive than Venice or Rome. One can find good rooms/apartments at about €100 per night for two. It is a charming and easy to navigatge place to come "home" to after a day trip and train connections are terrific!

Posted by
14036 posts

Another reason why Zoe's suggestion of Florence as a base is that the historic center is compact and the train station is on the edge of it, so it's a short walk to/from the train and to/from the hotel. After a tiring day trip, it's easy to go back to the hotel for a rest and change of clothes before going out to dinner. Or if the day trip includes a late dinner, a short walk home to bed. No waiting for buses or trams, no taxi fares.

Posted by
11613 posts

Thanks, Chani, also, Firenze is a great city at night, after daytripping.

Posted by
11 posts

Thank you Zoe and every one else for your suggestions. Your itinerary as well as Angela's definitely opened my eyes to rethink ours. I agree, although expensive, making the big cities our base will be, in the long run, better for us for all the reasons explained before. I am ok with sacrificing money in order to make our trip more enjoyable and a worry free. I look at it as 'investing' our money :) and believe me, we can use every penny. We bought Rick Steve's book on Italy and have been watching his YouTube videos. After watching the Florence video, I knew that was a city I definitely wanted to extend our stay. I am still working on our itinerary and know I need to act fats because our nest step is booking the hotels. Thank you all.

Posted by
96 posts

There are 2 ways to "do" Italy. One is to "see" Italy. The other is to go a little slower and "be in Italy". Several years ago I traveled down the boot with my granddaughter. We "were" in Italy, we didn't rush, we talked to people. ate at little bars and cafes, and walked at night, sat on the beach. We saw the Duomo, the Vatican, Venice, Florence, Rome. but leisurely.

I put her on the plane to go home and met a friend who was just coming in, We went up the boot and "saw" Italy. All the gorgeous art, cathedrals, the Vatican.

Both were great experiences, but I really liked the slower pace. We realy felt like we were in Italy instead of viewing it thru a window.

Posted by
11 posts

Ok friends, I promise this is the last time I bother you :)
What about this itinerary for September:
2 nights Milan

2 nights Venice
4 nights Florence (day trip to Pisa/Lucca)
2 nights Siena (day trip to Assisi)
2 nights Rome

2 nights Sorrento (day trip to Pompeii) (day trip to Positano)
1 full day back to Rome - taking the overnight train to La Spezia
2 night CT
1 day Milan

I also thought about going to Pompeii straight from Rome and then to Sorrento, but I’m not sure.
Does this look better?

Posted by
1804 posts

I would skip those first two nights in Milan and head right to Venice. And I don't like stopping twice in Rome. How about something like:

  • Venice -- 3 nights
  • Florence -- 4 nights, with day trips (Pisa, Siena)
  • Assisi -- 1 night
  • Sorrento -- 4 nights, with day trips (Positano, Pompeii)
  • Rome -- 3 nights
  • CT -- 2 nights
  • Milan -- 1 night
Posted by
651 posts

2 nights in Sorrento is not nearly enough! 3 should be the minimum stay. I was there for 4 nights, and that seemed just about perfect.

Given a choice, I would day trip to Siena from Florence, and stay 2 nights in Assisi. The reason being that the sights in Siena are fairly close together, whereas in Assisi you'll be walking from one end of town to the other to see everything. Plus I LOVED the hotel I stayed at in Assisi, La Pallotta! Such a charming place, so friendly, lots of extras included such as afternoon tea, bottled water, and a charming tower room to relax in. They will even wash your clothes for free and hand them to you the next morning folded and still warm.

Yes, you can see Pompeii en route to Sorrento. I did that! They have baggage check for your luggage. Just keep in mind that there is more than one "Pompeii" stop, and you need to be on a train that goes to Pompeii Scavi and not the modern town of Pompeii which is a few miles away.

Posted by
11613 posts

The journey from Roma Termini to La Spezia Centrale is about 4 hours at the longest, Trenitalia does not show a night train.

Posted by
9454 posts

Zoe's original plan above was excellent. Charlene's latest idea also very good. With your own plan, you are trying to go to too many places for stays that are too short. Forget night trains. If they exist, they do you no good. Two nights in Rome is not worth doing. Better to have fewer QUALITY stops and enjoy.

You will not believe how much time you will spend getting oriented and figuring things out in each new place! If you stay 3, 4, 5 nights in a place, you develop a sense for it: where to get coffee in the morning, what bus stop works for you, where the panini look good. You'll have time to try the cute restaurant you saw but didn't know about, or just stop and sit over a glass of wine and realize how wonderful it is! Italy is not a race. You need TIME to live, to eat, to sleep -- even to do laundry! You can only see a couple of sites a day without going crazy. Have a back-pocket plan in case you have steam to go 12 hours a day every day, but I think you will collapse and not enjoy it as much!

Posted by
31073 posts


I agree with Charlene's suggestions. A few more thoughts.....

  • Definitely skip the two nights in Milan at the beginning, as your time would be better used elsewhere (IMO).
  • You don't need to spend a full day getting from Sorrento back to Rome. The Circumvesuviana from Sorrento to Naples is about an hour and the Freccia from Napoli Centrale to Roma Termini is about 1.5 hours.
  • As Zoe mentioned, no need to take a night train from Rome to the Cinque Terre as it's a very easy trip and best done during the day. There are a few direct trains from Roma Termini to La Spezia Centrale every day, and if you can connect with one of those the trip will be about 3H:45M. If coming from Sorrento, to most likely direct train you'll be able to connect with is a departure from Rome at 11:57, arriving Vernazza at 16:16 (time 4H:19M). You'll need to get a fairly early start from Sorrento though. There are numerous trains on that route, but others have more changes and take longer.

You didn't say which of the five C.T. towns you'd be staying in (or perhaps I missed it). I used Vernazza in calculating the rail trips, as that seems to be the usual favourite with many here (although not my favourite). In any case, it doesn't make much difference as the towns are only 5-10 minutes apart by local trains.

Are you using the Italy guidebook? You'll still need to do lots of "fine tuning" for things like getting from the station in Assisi to the town. If you need a hotel suggestion there, post another note.

Posted by
11 posts

Thank you all so much. We are staying in Milan the first day because we want to see the "Last Supper", "La Pieta" and Duomo. Our last day in Italy falls on a Monday and museums are closed in Milan.
We also decided we are not going to Assisi. Everyone is right. We tried to pack our itinerary with too many cities and we want to be able to enjoy Italy. Quality vs quantity :)
So here it is, one more time:
Milan 1
Venice 2
Florence 4 (day trip to Pisa) (day trip to Siena)
Sorrento 3 (day trip to Pompeii) (day trip to Positano)
Rome 4
CT 3
No overnight train. In CT we want to stay in Monterosso al Mare. We added 1 day in CT because I really want to relax and enjoy the the scenery. To be honest I feel a little overwhelmed with all the planning. Now we have to book hotels, and learn a little more about the trains. I will take advantage of this forum and post questions on how to get from city to city. I am using Rick's guide, but I find the forum extremely helpful. Everyone is no nice and willing to help. Thanks.

Posted by
11613 posts

I use to compare hotels. You can filter results by price, location, amenities, review ratings (only written by former guests), parking, breakfast included, wifi, and other criteria. You can use the map function to pinpoint locations.

Posted by
498 posts

I'm assuming you know you must book Last Supper tix well in advance and that there is almost no availability for tix?

Posted by
31073 posts


"In CT we want to stay in Monterosso al Mare."

Good choice but even for travel in September, I'd suggest getting a hotel booking there SOON! That's often a very busy time for tourism in the C.T.

Have you got the transportation details worked out for your day trips to Siena, Pompeii and Positano?

Posted by
11613 posts

It can be difficult to get tickets for Leonardo's Last Supper from the official website, but you may find them available from a broker (I use Select Italy, you can buy only Last Supper tickets or have them included in the city tour, I only buy the Last Supper tickets). AThis costs more than the face price of the ticket but less than tour prices that include the Last Supper.