I am headed to Italy for the first time in May. I need help finishing my itinerary. (I know it’s late planning, but everywhere I’ve looked has plenty of highly rated lodging left so I am not worried about that part. In fact, I gave a lot of thought to going without reservations, but I have come to my senses, I guess. )
I am traveling by myself (I ALWAYS travel with friends or family-this is an indulgent bucket list thing for me) after 12 days with my DD in Croatia and Greece.
I have 5 nights planned (and reserved) in Florence so far (may add one more night to accommodate some day trips). I will spend my last 2 or 3 nights in Rome.
I would like 4 or 5 nights each in two other locations. Advice? I care about charming old town streets to stroll (the older, the better), easy day trips, and history museums/sites. Food and art are appreciated but secondary criteria for me. Bonus if there is a scenic train trip from Florence OR back to Rome involved.
Venice? Verona? Sorrento?
(For this trip, I am not interested in Milan, or Lake Como area.)
I loved Siena and Bologna. Or if you want to try something smaller and rural, in contrast with the cities you’ll visit, try Montepulciano and Montalcino, San Gimignano, or Pienza.
Another option you might consider is using AI tools like ChatGPT or Claude to help draft an itinerary. We’ve done that for a few trips (including an upcoming one to Portugal), and it’s been really helpful. You can refine the plan as much as you want with follow-up prompts.
That, coupled with suggestions and feedback from experienced posters here, will help create a great itinerary.
If you aren’t familiar with the AI tools, you can just access them on their website and enter your whole first post in the prompt. No technical expertise needed!
Yes, Cinque Terre is lovely! Especially in the evening. We stayed in Vernazza and hiked to all the villages. It was fairly challenging. Also went up to Portofino for a day.
Venice . . . We spent a week there 2 years ago. My favorite place in Italy is the Amalfi coast. I especially liked Capri. And what about visiting Pompeii?
Also a Venice vote. It’s magical (to my great surprise). I personally would find 5 days in Florence too much though it sounds like you’re doing some day trips. Rome is great.
My husband LOVED Venice and would go back in a minute. I really want to go to Cinque Terra and the Amalfi coast at some point. We are going to Tuscany this year, on a cycling trip.
Thank you everyone for the suggestions. I have some follow-up questions:
This is such different traveling than I am used to so I am having trouble deciding how long to stay in each possible locale. ( I generally like to stay in one place-sometimes for several weeks and satellite out from there) In addition to my 2 nights in Rome (probably not enough but I originally wasn’t going to go there at all. Big cities are not my thing), I have 13 nights to play with.
I will definitely go to Florence, Venice and Siena. How much time do I need in each city?
What about the Cinque Terra? I was originally planning on a day trip there from Florence, but now I’m leaning toward at least one night and walking to each of the villages. Is one night enough?
Sorrento/Amalfi coast is also on the short list but I am not sure I can squeeze it all in. I will have had almost two weeks in seaside areas in Croatia and Greece so this may be the area that gets cut. Is that a mistake?
Anyone want to recommend a historical fiction novel set in Florence, Venice, Cinque Terra or Sienna area?
If you haven’t been to Rome before add another day at least. It is so rich in history and fascinating things to see and experience. Take tours of the main sites.
It’s sounds like you’re doing this by train. Without a car I would say much of Tuscany and Umbria is going to be inaccessible to you. However there are a few towns that are on train lines that you can get to such as Perugia, Assisi, or Orvieto. You take a bus or tram up from the station to the hilltown.
I would skip Sorrento, it will take too much time to get that far south IMO. The Cinque Terre is a possibility if you’re a coastal fan but stay in Levanto instead of one of the CT towns (which are a 5-10 minute train ride away). It’s where the Rick Steves tours stay these days.
Since food is secondary my top suggestion Bologna is a bit less compelling since it’s in the Emilia-Romagna region (Parma ham, Parmigiano-Reggiano, Modena vinegar, etc). However it is still an attractive older town with miles of covered porticos and several museums. The smaller towns of Parma and Modena are among those that make great daytrips. And the University of Bologna is the oldest university in the entire Western world. Bologna is popular for conventions which at times makes hotel rooms scarce.
For train travel be sure to put the Trenitalia app on your phone if you have data coverage in Italy. Instead of standing in lines for ticket machines or agents you simply buy on your phone and show the conductor your screen. It’s also handy for looking up schedules on daytrips; I like to go somewhere and not buy the return ticket ahead so I can leave when I want.
Honestly the problem with Italy is there are too many interesting places to visit! On any one trip great places need to be cut. One last suggestion is to spend some time on YouTube when you’ve picked a set of candidate towns; these days lots of people have put up walking tour videos and you can get a sense of what you’ll see.
with Siena