Where would YOU go if you had a month to relax in a sleepy little town in in Italy?

I would be looking at towns on Lake Maggiore. We spent a couple days in Stresa, which is probably busier than you might like, but it was stunning. When we win the lottery, one of our homes will be there.

I want to return to Bassano del Grappa over and over. It is charming, features water and mountains, has an Alpine feel and is a short train ride from Venice.

Careful what you ask for. Sleepy may mean no public transport and isolation.

Back before everyone was going to Lucca, I spent a week there and loved it. Train to Florence in an hour, several buses or trains to other locations including the coast. Found my favorite bar for coffee every morning.

Wherever you choose, make sure there is frequent transportation to other places that does not rely on school bus routes.

Most Italians vacation the month of August and they go to the beaches and lakes. So this wouldn’t be the ideal time to look for somewhere quiet and remote in those areas. Many businesses are also closed, especially the non touristy areas while they are on vacation.

One of my favorites among many is Spello. Read “Il Bel Centro” for inspiration. But, Michelle does mention that when it’s hot outside, locals aren’t out until the evening to socialize. So, I’m not sure it’s a good one for August.

Farther north, Cremona, Mantova were both less expensive and atmospheric, but this isn’t rolling hills. Not sure if Ferrara is too busy for you.

If you’re in the small Tuscan or Umbrian towns, you’re going to need a vehicle which then doesn’t make it inexpensive. Arezzo could give you the bus or train day trips into Tuscany and Umbria. You’re describing something small, but I also think Perugia with the views overlooking the beautiful rolling hills could be a viable option if you found a little place with some charm. It’s on a good train line for exploration.

Just a touch of reality - can you speak Italian? The conversations you’re imagining in the smaller towns will be very limited if it’s depending on English being spoken. On the other hand, Perugia has an international college, so an experience you’re dreaming of might be possible.

Here’s my two solo.trips that mention those cities. I do like the smaller quaint ones!

https://community.ricksteves.com/travel-forum/trip-reports/trip-report-please-do-not-comment-until-i-change-the-title-filling-in-the-report-thanks

https://community.ricksteves.com/travel-forum/trip-reports/solo-trip-to-italy-2018

Do you plan to rent a car or rely on public transportation alone?
August is busy with vacationers, but knowing if you rent a car or not helps making suggestions

South end of Sardinia.

Honestly? I'd go to Venice. At first, you wouldn't think of it as a sleepy town, but if you're not where all the tourists are, then it is a sleepy town.

But my choice of island probably fits better with what you're looking for :-) Capri is a dream once the day-trippers have left. The Aeolian Islands would also be at the top of my list.

I have stayed in an Italian town for a month and it was a great experience but here are my cautions and thoughts:

"Sleepy" towns are either untouristed or off-season for tourists. As others have mentioned this means reduced transportation options and opportunities. Off season can also mean closed restaurants and attractions as Italians take their vacations like any place with a strong season. This also means how much Italian you speak becomes important because while English is pretty common in touristy places and hospitality it fades pretty quickly in the country and with older Italians.

The limitations on your Italian will also limit how well you can get to know the people. Italian love to talk but you can exhaust basic language skills pretty quickly. And not being able to follow the tales of their children and cousins limits how much you can talk about the the things they want to share with you. And especially if you are traveling alone this can isolating. As much as everyone hates to think of themselves as even temporary ex-pats an ex-pat community can really help you discover a place.

Italian towns also often have festivals and events and these can be great to be present for, but trying to book a place for a month can often overlap with a really booked up week or weekend that can ruin your plans. Or make them much more expensive than it would otherwise be. In late October/early November Lucca hosts a comic-con that brings 8x the normal population to the old town and the availability and the prices for that weekend are crazy.

Sleepy can also mean fewer places to choose from to stay but hopefully also lower prices.

My advice is to find the cuisine/culture than most interests you in Italy and start there. Regions heavily dictate cuisine in Italy and you're not a big fish eater booking a place by the coast will probably disappoint you with the choices. After that balance size with "enough" connections to the outside world and restaurant and attraction options with the small enough to "get to know it" town. You need enough restaurants to sample from while you're there to really discover new things.

Once you shed your tourist mode and downshift it is shockingly to fall into the gathering water, bread, a few vegetables daily routine to cook and just explore. I did one of the eight potential side trips I had possibly planned and the time passed amazingly quickly. I completely recommend it but it is not without its pitfalls.

Best of luck finding what you're looking for,
=Tod

Re. Mignon's comment. I think there are many sleepy towns throughout Italy, but agree on Venice. I felt like 80%of the island was "sleepy"

We just did a great 12 day tour of Tuscany and Umbria with Road Scholar.
We fell in love with Siena, Assisi, Spoleto and Orvieto.

Pisciotta in the Cilento.
But August is not the best month for any of these.

Look up Pisciotta. Hill town close to good beaches. Local flavor.

The problem is that August is often very hot in most of Italy and it's the big holiday month for Italians who escape from the big cities. Many go to the sea, so forget the deserted beaches because in August in Italy there aren't any. Many others, who maybe still have a small apartment in the hills/mountains/middle of nowhere because their grandparents or even great grandparents were from there, return to that sleepy unspoilt village/town you are thinking of. (I live in one and August is stressful even here!)
So quiet in August...?
Milan (yes, really, it's the only time I visit because yes there are some tourists but there's a lot of space and the locals have mostly left and other big cities like Turin, but that's not what you're looking for.
Lake Iseo is quieter than other places in August
https://slowtravelitalyspain.blogspot.com/2023/04/10-tips-and-advice-for-visiting-lake.html
Maybe towns like Novara or Vercelli - which will be partially empty for August?
Perugia mentioned above is a good idea

Well I hate to be a one-trick pony but...Abruzzo has everything you asked for, as long as you stay away from the beaches in August. The mountain towns in the national parks are wonderful in August, lively with festivals and concerts, restaurants and shops are open. But you would either need a car or really mean it when you said a sleepy little town. ONE town, as transit is limited. From my town, there are several daily buses to Pescara so it's possible to get out (except Sundays), and other towns have regional train stations. We also have an expat community. It can be hot but the nights generally cool down.

You can look up some of my other posts for suggestions of small towns to visit. Or check out Abruzzissimo e-zine and Abruzzo Expat Community Facebook group if you're curious. Caramanico Terme, Tagliacozzo, Atri...it's a long list of possibilities.

Dunno....an endless list really:
Pitigliano, Scilla, Bevagna, Trevi, Gallipoli, Urbino, Trani...
-for something completely different: maybe check out the quasi-ghost town of Pentedatillo, a sort of Calabrian Matera just now opening up with a couple lodgings. Located in the remote Aspromonte Park.

Good luck.
I am done. the end

Sienna and Orvieto hold a very special place in my heart!

I love your question because I have the same situation. I am in the Chianti area for my daughter's wedding and have about 10 days on my own before I fly home. It will be August. I know hot and Italians vacation during this time but it is the time I have to fill. I spent a couple of days in Orvieto, Sienna and Lucca several years ago and absolutely loved it. Is there a place similar. Great size, good food, rich history and quaint charm? I like the small family accommodations as well.

I would consider Regio Emilia. It is a charming city with goid train access to Parma, Modena and Bologna. It has several squares that come alive at night with outdoor dinning and drinking opportunities.

I recommended Pisciotta, above; here is more information:

https://www.visititaly.eu/places-and-tours/pisciotta-a-small-paradise-on-the-cilento-coast

I also love Nelly's idea of Abruzzo!! We spent a few weeks in that area a few years back and I am longing to return!!