Live like a local in Italy for a month

Start by seeing what your flight options are. It may work better to bookend flights to Sicily with Venice and Florence or Pisa (or even Rome) for Tuscany. That way you can take advantage of better prices and schedules for your inbound and outbound flights, and take cheaper in-country flights to Sicily (perhaps into Palermo and out of Catania or vice versa). A very rough sketch would be up to a week in Venice, two weeks+ in Sicily, and around two weeks in Tuscany--all tailored to your interests of course.
I don't buy general country books, instead I look for region/city specific guides. Peruse them at a library or bookstore to see which ones appeal to you. Blue Guides offer in-depth cultural and historical info--that is one I find pretty vital.

Thank you, Vital!
We will start with your advice.
Carlos

Carlos,

is it 10 days, 10 days, 10 days?

Will you have a car until you get to Venice?

What is "live like a local" to you? It won't be work all day, cook, clean up and watch the local news followed by a couple of shows, I don't expect.

But do you intend to work from your temporary home, remote working?

Have you been to Italy before?

I'd recommend more time in Sicily than in Tuscany and Venice. You really need at least 2 weeks in Sicily--and that's if you'll have a rental car for a good chunk of the time. Without a car, Sicily calls for longer than that. Add time if you want to go to the Aeolians.

Hi Nigel, great questions!
Our thoughts were to "live like a local who is retired" One of us is retired and the other one can take a 30 day sabbatical from the business.
We are thinking of breaking up our trip into 3 parts, Sicily, Tuscany, and Venice.
We are not sure of how much time we should allow in each region.
W have been to Italy once, we took a 14-day "bus tour that started in Rome went all the way to Venice and finished back in Rome, at the end of our stay in Rome we spent 5 days on our own.
We would LOVE any suggestions and recommendations that you may have.
We have driven UK and Portugal, is it much different in Italy?
Thank you for your post.

For your possible 10 days in Tuscany, I've always thought staying in or somewhere close to Poggibonsi would be the most ideal location. Really easy to day trip to Florence, Siena, the hill towns, and the Chianti wine region - in other words, never a dull day. A car would be needed.

Living like a local.
What does that mean?
This is what I have found often times about locals. They have not been to most of the museums in their town. They have not been many of the restaurants. They have not been to other sites that tourists may want to see.
Ask yourself. How many of the above have you been to in your own home area?
So maybe living like a local is just some sort of pie in the sky scheme to make you think you are into the scene and thus a step above the proletariat tourist.

"Living like a local. What does that mean"

I've always thought that staying somewhere for longer than 1 night, while travelling, was "living like a local."

Have you read Rick's "Europe Through the Back Door"? It sounds like you would get a lot out of it. It's about travelling as if you were a local.

I have three full shelves of travel guide books at home and I find Rick's is the best for first time visitors (or second or third time). We're using his "Italy" and "Rome" books at the moment.

Rick also has a great free app called Audio Europe with narrated walks around cities and museums that you can download in advance on wi-fi. There are 10 in Rome.

What has surprised us, since we arrived in mid-April, is how chilly it has been! The mandatory requirement to use winter snow tires on many roads (even in Tuscany) ends April 15 each year.

Carlos, it is great that you are already beginning the planning for your trip. My husband and I spend 2-3 months in Italy each year. I understand your desire to "live like a local". I have used that phrase many times myself. It may be more accurate to say you want to live as you would if you were a resident. Here is what it means to my husband and I.
1. We stay in apartments, not hotels.
2. We do grocery shopping at the local markets.
3. We do not have a car - we use public transportation.
4. We eat most of our meals at home.
5. We go to the same coffee shop (or ice cream shop, or bread store, etc.) and get to know the people who work there by name.
6. We speak Italian - even though not perfectly - we try. We laugh at our mistakes and enjoy when the locals correct us.
7. We visit "tourist" places but not daily and we hop on local buses to visit small villages in the surrounding area.

Have fun planning and anticipating your trip. It is half the pleasure of travel.

Book apartments or homes on VRBO or AirBnB - this is your best start to feel more local than tourist. Also, look for areas/neighborhoods that are off the beaten path a bit.
Shop local. Find out if there is a daily market in town and shop there for groceries. Cook meals at home.
Ask your apartment hosts for local restaurant recommendations that are less tourist haunts.
Research local transportation options. Many tourists avoid or forget buses. Taking the bus out to the countryside and visiting smaller towns can be quite fun.

Good luck in your quest!

Thank you so much to everyone for their suggestions and recommendations.

Periscope, thank you for your suggestion of staying longer in Sicily, my wife's ancestors are from the island and we may just stay here longer.

Markwilson, we have not heard of Rick Steves's book of "Europe Through the Back Door" and will look at his app and thank you for the heads up on preparing for the weather.

Treemoss2, we live in the Boston area and do the tourist track through our city often, when family are visiting our area and request the museums and restaurants often

Charylm, we LOVE your suggestions of we want to live as you would if you were a resident!
When you stay for 2 to 3 months, do you stay in a specific region or do you move around during your stay?

Marc, we are airbnb users when we travel, and both love cooking and trying new dishes, and thank you for taking busses, we are public transportation riders in the Boston area.

<3

Our thoughts now are to take it slowly. A few years ago we flew into Turin and did Aostra (and Monte Bianco on a blue sky day), Cinque Terra and Lucca over almost 2 weeks using trains and buses and then took the train to Sienna to pick up a car for Tuscany as buses would be difficult. We were staying most places for 2 nights as it gives a different feeling than day trips. We did an agrotourismo near Volterra, generally B&Bs in San Gimignano, Montapulciano, Montalcino and returned the car to Sienna and spent a couple of nights there before catching a train to Florence. We spent a few nights before catching a train to Turino to overnight before catching our flight.
We’ve booked our October trip to Rome, Umbria, Lake Como, Lake Maggiore and Dolomites returning to Rome to fly home, spending 3 nights at each place and travelling between them by train. A couple of days will involve long train trips but I don’t have to drive nor go through the hassle of flights.
It isn’t quite living like a local but leisurely sitting at a local cafe for lunch &/or a pre-dinner drink feels a bit like a local rather than the bus loads of tourists who have less than 2 hours in each town and can visit 3 or more in one day. There was enough stress in my working life so now I take it a little easier. We’re celebrating our 35th anniversary during this trip and I’m lining up what I hope will be a good meal in Orvieto.
I’m using Rick Steves ‘Italy’ but also checking the local area tourist web pages and various travel e-magazines.

We sort of lived like locals in Venice. “Sort of” in that we did not work, never needed a dentist, so did not do those things which locals have to do. We stayed for two months. I wrote a bit.

https://www.fodors.com/community/europe/venice-a-sort-of-trip-report-867683/

Carlos:
You asked if we stay in one area or move around. Usually we stay for 6-8 weeks in Siena. We have come to think of the city as our second home. (In fact that is where I am right now.) But during each trip, for two weeks, we visit some region of Italy or some other country that we have never been to. That way we satisfy our desire to see and experience the new while enjoying the familiar.

Agree with Charylm....I have had many long term stays in Italy to melt into the culture. I also rent apartments...more reasonable than a hotel for long stay. 2019 I was in Florence for 6 months (I have citizenship) and made side trips from there rather than relocate too much. This year, I'm splitting my 6 month stay into 3 places...Florence rents have moved out of my budget range. I will stay for three months in a small town close to Florence so I can day trip into the city to visit friends and favorite places etc. Then Genoa for a month then last two months in another town on the Ligurean sea.

With a long visit, it is wonderful to not feel obligated to "do" something every day...as Charylm stated...go to local market (which are the BEST) and cook most of your meals at home. Living like a local also means taking time to do laundry and time for it to dry (I have never had a dryer in any apartment...so line dry overnight). You can take your laundry to the lavandaria but that is still an hour or so of your day to sit while you wash & dry. Florence had several heat waves when I was there so I would visit the market early and stay inside to read etc. and not worry I wasn't out and about as I have lots of time. With the one month, you may want to make the most of every day but take time to sit still and enjoy a gelato or a beverage while people watching on a piazza.

I'm sure you will have a wonderful time....relax, enjoy and make memories!

Thank you everyone for your advice!
We have decided to stay 6 weeks in May of 2023 and will be spending 2 weeks at three different locations, of which we have not narrowed down which ones as of yet.
We have ordered Rick Steve's Europe through the back door and his Italian books.
Would love to know any additional suggestions should anyone else come across this forum, and we will keep an eye out for other forums on Italy.
<3

I think that's a good middle-ground. Most of us do want to see a lot of places (and are constrained by the 90-day Schengen limit even if we are retired), so a very long stay in one city may not be ideal. But it's wonderful to really stay put for a while. It's very relaxing to know you don't have to pack up and move on for two weeks.