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Italy - 3 months - 3 Stops


I posted a question earlier in this forum but wanted to reframe it so I am starting over. Thank you in advance to all that participate!

My wife and I (late 30’s no kids) are planning to take a short leave next year. Working timeline is from week of April 17th 2023 through to the 90 day mark before we cross into Croatia for appx 2 weeks to cap of our trip.

She is studying and will spend the better part of her days doing school work. I am free to roam with maybe some self guided learning to fill my time.

My ask-we want to split our time up into 3 separate locations and would like to be somewhat diverse in how we chose our bases. It would be important that there is enough in the town/area to keep us interested for 4 weeks. We don’t plan on having a car but will rent one if necessary. Open to all combinations, recommendations and opinions. One important thing would be that there’s some form of evening culture/entrainment.

Working ideas are currently some combination of the following….

Lecce or Trani
Florence or Lucca

Mantova or Bologna
Aosta Valley
Sicily (however trying to avoid additional flying)

Open to all alternatives in all regions!

Quickly about us.

We spent 3 weeks in Italy in 2016 and hit most of the highlights. Venice, Ortesie in the Dolomites, CT, Florence, Tuscany (agritourismo) and Rome. Florence and would only be interested in spending a bit more time in Florence.

Lovers of culture. I will be working on learning the language. Lovers of history and museums. I am a chef by trade so of course food is of importance. But more so from a regionality stand point than just fancy restaurants. Love to hike and be in nature but could also very easily spend an afternoon in a piazza ppl watching.

Thank you so much!

Posted by
21995 posts

Let's take care of the gorilla in the room. The Schengen zone, 90 day rule. It is not smart to run it out to the 90th day since anything could cause a day or day delay in departing. The immigrant people can be and often are very strict on the 90 days. I would give yourself a margin of at least five days and maybe ten just in case something delays your departure. Both your arrival day and departure days count towards the 90. Twelve weeks is a much better way to look at and plan.

Posted by
4762 posts

Hi, I think I commented on your previous post so hope this is helpful. For your age, I would look for places that have a university in the city to increase the chance that you like the evening entertainment options. Other options I would consider because of that criteria are Arezzo & Perugia.

I would also check what the typical weather is for the locations you are considering & the months you are planning. If you like to bike, Mantova would be excellent, and they had great piazzas with a lot of locals gathering there.

I am glad to see Bergamo on your list. I would love to return and spend more time there.

Posted by
1084 posts

You can spend a week in Venice, and think you’ve “done” Venice.
You can spend a month there, and realise that you have barely scratched the surface.

Posted by
935 posts

You don’t mention art and your not wanting to spend more weeks in Florence leads me to think that art is not what draws you to Italy. So, I am basing my recommendations on language-learning, museums, food, and public transportation. Also, here’s a little bit of heresy: the food in Tuscany, while excellent, does not seem as varied as other regions. We are in Tuscany right now (for a bunch of art I needed to see) and having previously spent maybe two months in Tuscany we are getting a bit tired of seeing very similar menus everywhere we go. Eager to move on to the hinterlands of Liguria (ie not the coast).

OK, your first town is easy: Lecce before it gets hot in Puglia.

Second place: Bologna

Third: Padua. If I couldn’t live in Florence, I would live in Padua. You would love the markets and the piazze large and small, and it is well connected by train to Verona and many other great towns.

Fourth (you wanted three, but three weeks in four places is what I’d want if I were you and your wife): Torino or Alba. Partly because Torino has two of the best museums I’ve ever been to, but actually more because I want you to explore the different very local cuisines of neighboring Liguria without basing you in Genoa. My husband and I loved Genoa and will be there for the second time in a couple weeks, but it’s not real lovable. However, from Torino or Alba you can reach, say, Pieve di Teco in western Liguria in two hours by car and eat the Cucina Bianca of that area.

Hope this helps you with narrowing down —- it’s always a challenge!

Posted by
21470 posts

For me four weeks would be too long to spend in a small town that isn't virtually a suburb of a sight-rich city, but I'd add Padua to the list because of its proximity to so many great destinations accessible by public transportation. It's a university city, plus it's only 30 minutes from Venice.

I'd definitely want to include Sicily, especially since you're a chef.

Posted by
22 posts

I would second Turin (Torino). Outstanding museums (agree with nancys8 about some of the best we've been to), food, history, and architecture with amazing natural beauty right on the doorstep. Milan is about an hour away by train for even more options, but I like the size and feel of Turin. Plus I think you'll appreciate the regional contrasts with your other two stops, which presumably would be further south.

Posted by
5806 posts

You only had one city in Umbria, Orvieto. That is a great pick, but also consider Perugia.

Lucca is worth a day, I would go with Florence.

Also, ok you did Rome before, but how long did you stay there. I have been there twice, spending a total of 10 days and still haven't seen what I wanted to see, so I am going back in May.

Posted by
12 posts


Thank you for your response! Yes we are aware of the 90 day limit for Schengen zone and will be giving ourselves a grace period before we we move out side of the zone to finish our trip. In reality we are looking at 84 days total. So a bit of wiggle room.

However, I was not aware that Croatia was potentially joining the list Schengen countries next year so that throws a bit a wrench!

Posted by
12 posts


Yes, I think you did as well so I appreciate you offering some more insight on this post! Perugia has come up a few times now, so it is definitely becoming a contender. I really like your idea of the university town offering a bit more in terms of nightly entertainment. Don't know much about Arezzo but will continue to read up! Bergamo would be a great base but I think we are leaning towards Turin/Alba for that leg of the trip. However could be convinced otherwise as I continue my research. The hunt for the perfect medium size town is a struggle because of the many many options!

We may spend a shorter amount of time in the Montova/Verona/Bologna area just because it doesn't feel right missing it!

Posted by
12 posts


I don't disagree with you. However Venice likely wont make it this time around.

Posted by
12 posts


Florence is very likely going to end up on our itinerary. As it is my wife's first choice :). What I am struggling with is that it is costly and am having a difficult time finding a decent apartment for our budget (which is modest) that we would find ourselves comfortable in. I also know the crowds you deal with year round can be a bit of a struggle. DO you have any recommendations where to search for Florence accommodations outside of the usual Air BnB/Booking etc.

Bologna is very appealing and it aligns with the university town thought from a previous recommendation...however it would have to be between Florence & Bologna or Turin and Bologna. or completely cut out the Sourthern portion of the trip. Hard call.

We will likely end up in either Lecce or Sicily. TBD. Another tough call.

My wife wants to limit the transitioning so she doesn't get to distracted from school but the more I discuss this the more likely we will end up with 4 stops instead of 3.

thank you so much for your insights!

Posted by
4484 posts

Croatia won't work if it does join Schengen as planned, but Montenegro will, and there's plenty to do for 10-15 days there.

Posted by
12 posts


Thank you for sharing this. I was not aware. Definitely throws a bit of a wrench in things. I will have to keep an eye on this.

Posted by
12 posts


Lucca is worth a day? How about the region in general? Worth a few weeks? It would not feel right not spending any time on the water during our stay!

Puglia vs Sicily...any thoughts?

We will likely start our trip in Rome. Just a few days to acclimate then move on.

Posted by
12 posts


Thank you for your response! Turin! This excites me. Any recommendations on areas of the city to stay?

Posted by
22 posts

One of your responses suggested a choice between Turin and Bergamo. We really enjoyed Bergamo and we loved the architecture and history, but I would still pick Turin. Then another of your posts suggested a choice between Turin and Bologna. (Are you getting a Sweet 16 bracket vibe too??!) And honestly, that would be a tougher one. I might still give it to Turin by a hair, but gosh Bologna would be great too. Keep us posted...

ANYWAY, you asked about Turin. Last time we were there we stayed in the Lingotto neighborhood. It is quieter and definitely not as picturesque, but we liked it. Don't roll your eyes, but the Eatily there (the first and original) is fantastic, and not (completely) a tourist destination. It is also close to the Museo Nazionale dell'Automobile, one of the two museums I mentioned as among the best I've ever seen, as well as the famous Fiat factory. We are returning to Turin in May and this time we're looking a smidge closer to the center at the San Salvario neighborhood. Mostly it is just better Airbnb stock and nothing to do with Lingotto (we stayed at a hotel last time), and honestly, I don't think you can go wrong with either. Both are on the Turin Metro Line, which I think you'll find useful. I do think for month-long stays there's something to be said for not being right in the thick of things...

Hope this helps. I'm following this thread. I love the idea of three one-month(ish) stays, and am eager to find out which three you pick.

Posted by
10259 posts

As to lodging, have a look at Sabbatical Homes. Sometimes far cheaper than the major platforms and quite the cultural experience. We spent 18 months in one in Rome.

Posted by
935 posts

In Torino, we stayed about three blocks away from the Egyptian museum, near Piazza Carlo Emanuele II and could walk everywhere except to the car museum.
$59 a night

Given your interests, I would have said Sicily for sure except it’s more of a hassle to get there and to get all over the island without a car from one base. We had a car there and two weeks and still needed three bases.

Posted by
1947 posts

In the Lecce vs Sicily debate, I would strongly urge Sicily, and in particular Ortigia. We spent about a week in Lecce one October, without a car, and it was one of the longest weeks in our 20 years of travel. Public transportation was difficult. And the long daily siesta made us crazy. Lecce literally turns into a ghost town between about 2 and 6 pm. No shops or restaurants are open — in fact restaurants don’t reopen (even for pizza) until 8 pm. We did take day trips to Gallipoli and Otranto, and did a winery tour, but overall it was a disappointment.

Ortigia, by contrast, is vibrant and gorgeous. Lots to see and do all hours of the day. Very walkable. Lots of public transportation to nearby towns. We were there for a week too and hated to leave.

Posted by
939 posts

Don’t let anyone talk you out of Turin! It’s my favourite bigger city in Italy. And day trips into the surrounding mountains or wine country are so easy. And yes, as a previous poster said, you can drop into Liguria.

Padua would definitely make my list too, for liveliness, beauty, things to do. But…how are you with heat? If it is the 2nd or 3rd stay on your trip, it will be hot. This past year it was HOT. And dry. The Po valley had a desperate year, including water rationing. Bologna also sits in a bowl that gets brutal in summers. Well worth a visit, but I wouldn’t stay a month in the summer.

Puglia…Bari and surrounds (Monopoli, etc.) would be more hopping than Lecce. Same problem with heat and dryness in the summer, but it’s better along the coast, so I might keep that in.

I have not been to Sicily, hoping for 2023. A poster above recommended Ortigia, sounds like a great choice. a wild card…Imperia along the Italian Riviera, quite near France. It’s a biggish town, lots going on, great food, lots of hikes and fun trips inland.

What about Sulmona? Less than two hours from Rome, a town that’s been lively since before the Romans. A fabulous farmers’ market 2x/week. In Abruzzo, “si mangia bene” - one eats very well. Easy to visit Tivoli and other towns the popes made wealthy, or to go further into the Abruzzo national parks for some hiking time.

Posted by
1907 posts

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