3 weeks in Italy

Leighsouth

Member
We will have 3 weeks in Sept. 2023 and are looking for small villages, interested in wineries & delicious food and love the sea. We had thought we would spend 3/4 days in each village, but are open. Looking at primarily Tuscany and area. We were thinking of renting a car, although would plan on transit and tours for Florence. Any suggestions for must see/stay areas would be appreciated. We are starting to plan... Thank-you for the information in your threads! I have started to read through those.
 

Lourdes

The Tuscan Expert ;-)
Staff member
Welcome to our forum! That sounds like a marvelous plan! 3 weeks will give you a good chance to discover the small villages off most people's radar and areas that are cool to explore. If you will have a car, it will make it much easier to move around and spend your time wisely, including moving to a different area every 4 days. You will have to see and

Look into staying in Maremma, in the southern part of Tuscany. The small villages of Pitigliano, Sorano and Sovana, Saturnia... then along the coast Capalbio, Orbetello and Talamone. Wine country around Scansano, and a bit north Montecucco.

Another area: Valdorcia. Towns of San Quirico, Montalcino, Pienza, Montepulciano, Buonconvento. Wine areas of Brunello and Rossi di Montepulciano, as well as Valdorcia.

Move on to Arezzo and explore Cortona and Sansepolcro, Anghiari.

Move on to Chianti to explore Castellina in Chianti, Radda, Gaiole, Panzano, San Donato in Poggio, Greve. Make sure to visit Siena either while here or in Valdorcia.

Then there is Florence. I would say a minimum of 3 days.

Last, you could head back toward the coast between Pisa and Lucca. There is a small hill range called Monte Pisano in the middle that is off the radar of most people but has neat villages: Vicopisano, the Certosa Abbey, the spa town of San Giuliano Terme, the Pieve di Compito and nearby camellia garden. This is lovely for people who love the outdoors, as there is chance to do hiking here too. From here you could head to the beach: either to Tirrenia to be close to Pisa or further north toward Viareggio. Make sure to include Pisa and Lucca, at the very least half a day for Pisa and a day for Lucca.

I think I've given you lots of areas to consider -- now there is wine tasting in all of these areas, so with sightseeing, drinking and eating, I think you will easily fill up those 21 days! Plan to have Florence either at the very start or end so that you can use the car the rest of the time.

Take a look at the entire site - here is just an article for Pitigliano: https://www.discovertuscany.com/maremma/pitigliano-highlights.html
There are similar articles for most of all the places I've mentioned above. So get in, get lost and make notes. Let me know if you need more info or ideas as you make your plans and have fun!
 

Leighsouth

Member
Welcome to our forum! That sounds like a marvelous plan! 3 weeks will give you a good chance to discover the small villages off most people's radar and areas that are cool to explore. If you will have a car, it will make it much easier to move around and spend your time wisely, including moving to a different area every 4 days. You will have to see and

Look into staying in Maremma, in the southern part of Tuscany. The small villages of Pitigliano, Sorano and Sovana, Saturnia... then along the coast Capalbio, Orbetello and Talamone. Wine country around Scansano, and a bit north Montecucco.

Another area: Valdorcia. Towns of San Quirico, Montalcino, Pienza, Montepulciano, Buonconvento. Wine areas of Brunello and Rossi di Montepulciano, as well as Valdorcia.

Move on to Arezzo and explore Cortona and Sansepolcro, Anghiari.

Move on to Chianti to explore Castellina in Chianti, Radda, Gaiole, Panzano, San Donato in Poggio, Greve. Make sure to visit Siena either while here or in Valdorcia.

Then there is Florence. I would say a minimum of 3 days.

Last, you could head back toward the coast between Pisa and Lucca. There is a small hill range called Monte Pisano in the middle that is off the radar of most people but has neat villages: Vicopisano, the Certosa Abbey, the spa town of San Giuliano Terme, the Pieve di Compito and nearby camellia garden. This is lovely for people who love the outdoors, as there is chance to do hiking here too. From here you could head to the beach: either to Tirrenia to be close to Pisa or further north toward Viareggio. Make sure to include Pisa and Lucca, at the very least half a day for Pisa and a day for Lucca.

I think I've given you lots of areas to consider -- now there is wine tasting in all of these areas, so with sightseeing, drinking and eating, I think you will easily fill up those 21 days! Plan to have Florence either at the very start or end so that you can use the car the rest of the time.

Take a look at the entire site - here is just an article for Pitigliano: https://www.discovertuscany.com/maremma/pitigliano-highlights.html
There are similar articles for most of all the places I've mentioned above. So get in, get lost and make notes. Let me know if you need more info or ideas as you make your plans and have fun!
Thank-you so much for these great ideas for our trip! I truly appreciate your time:)
 

Lourdes

The Tuscan Expert ;-)
Staff member
(y) :) glad to help, let me know once you have a chance to explore and take notes and see what you've come up with :D
 

Leighsouth

Member
Hi! I have been obsessed with trip planning:) So many options...I have booked one week in San Gimingnano as it seemed to be a good location to explore the area. I have given us about 4/5 days before we get to our Farmstay there. We are completely O.K. with driving. What I am wondering is, where to fly into. Have thought to fly into Rome, take a few days in Maremma towards San Gimingnano, and then make our way to Lucca area ( or in between), and then possibly toward Cinque Terra and around the other side? Or we could fly into Milan? What are your thoughts? We thought if we fly into Rome, we would take 3 days there before leaving, or completely miss Rome this time.
 

Lourdes

The Tuscan Expert ;-)
Staff member
Ciao! Sounds like you're enjoying and having fun with the planning. :)
Have you been to Rome before or to Milan? Either is good to fly into, especially in September where there aren't problems with fog in Milan. So I'd take a look, check rates and then decide which one to spend a few days in. I personally love Rome and a few days there always leads to exploring new areas and revisiting the main ones so I don't think it is a waste of time at all. Not sure where you're coming from but Bologna and Pisa are also other options for flying in.
 

Leighsouth

Member
Ciao! Sounds like you're enjoying and having fun with the planning. :)
Have you been to Rome before or to Milan? Either is good to fly into, especially in September where there aren't problems with fog in Milan. So I'd take a look, check rates and then decide which one to spend a few days in. I personally love Rome and a few days there always leads to exploring new areas and revisiting the main ones so I don't think it is a waste of time at all. Not sure where you're coming from but Bologna and Pisa are also other options for flying in.
Thanks so much. We are coming from Canada, and there are decent flights to Rome. That was my first thought, fly in, and then at the end of our trip, spend 3 nights before leaving. If we did this, would you suggest a car rental directly from there, or? Thanks for your help!
 

Lourdes

The Tuscan Expert ;-)
Staff member
Then it makes sense to fly into Rome and back out, you could definitely leave it to the end. I would suggest, considering you do arrive jet-legged, to not get the car right off in Rome. Take the train to Florence, there are many fast trains from Rome Termini station, then spend your first few days in Florence. Only once you're ready to leave Florence, rent the car and then head off to explore Tuscany. That gives you a few days of rest before driving here.
 

Leighsouth

Member
I have been looking at different routes and have booked one week in San Gimignano, as I thought it would be a good central location to explore. We are now thinking arriving and departing from Florence might be the way to go. There are direct flights from Canada. Thought we'd spend 3 nights in Florence, then head to S. Gimignano from the 12-19th, and then had considered heading to Viareggio, for 3 nights? Would like to see Cinque Terra. Thought that we would make our way towards Arezzo (Montepulciano etc. ) and then to Maremma (Pitigliano) or Grosseto and then back to Florence. Does this seem like an decent route? I know we will be back tracking, but by the looks of things there is a different route through some of the smaller areas. It's a little overwhelming planning without knowing any of the areas. If you have a more logical route, please let me know! Thanks so much, any help is appreciated!
 

Lourdes

The Tuscan Expert ;-)
Staff member
Yeah you might be backtracking but with 3 weeks and not being in a hurry, it should work out fine.
I would just say if you want to visit Cinque Terre, then head to CT and not Viareggio. It isn't the same thing and doesn't make sense to use that as a base for CT. La Spezia would be a better base, but you can just stay in Monterosso al Mare considering you will have the car. It's the easiest to drive to.
Maybe after CT I would head straight south to Maremma first, then head toward Arezzo, doing Monte Amiata drive along the way and drive through Val d'Orcia. You could stay in Montepulciano and use that as a base rather than Arezzo. Then head north to Florence.
 

Leighsouth

Member
Yeah you might be backtracking but with 3 weeks and not being in a hurry, it should work out fine.
I would just say if you want to visit Cinque Terre, then head to CT and not Viareggio. It isn't the same thing and doesn't make sense to use that as a base for CT. La Spezia would be a better base, but you can just stay in Monterosso al Mare considering you will have the car. It's the easiest to drive to.
Maybe after CT I would head straight south to Maremma first, then head toward Arezzo, doing Monte Amiata drive along the way and drive through Val d'Orcia. You could stay in Montepulciano and use that as a base rather than Arezzo. Then head north to Florence.
Thank-you!!! That makes much more sense and I looked at Monterosso al Mare so will go that route. You have been so helpful Lourdes! So appreciated!! Again, many thanks.
 
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