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.
 
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!
 
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:)
 
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.
 
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.
 
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!
 
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.
 
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!
 
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.
 
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.
 
Hello Lourdes,

We also have a 3 week stay in Italy planned this coming August. We are landing in Rome and are looking at Tuscany. But we don't want to relocate every few days. But would rather have 1 main Homebase and drive and visit. We have 2 young kids so would rather spend time enjoying everything possible while not moving too often not too far away. We are ok driving for an hour in each direction... Your perspective would be greatly appreciated. Thank you
 
Ciao Debren and welcome to our forum!

3 weeks in August will be fabulous, and with small kids, I also recommend finding one place as your base and then driving around.
Is this your first time in Italy? What are your must places to see while here? Just trying to figure out whether you want to spend the entire 3 weeks in one place in Tuscany or thinking of also spending some time elsewhere.

First suggestion would be to stay in southern Tuscany as a great solution for your family if you're planning on also exploring Rome and Umbria while here... but staying closer to Florence would be better to explore Pisa, Lucca and the northern Tuscan coast. Tuscany in the end is pretty big and whether you stay north or south would impact what you do.
Do you want to stay close to the coast to spend some days at the beach? Most places have pools, so you don't have to stay along the coast at all, but your base will have to at least be within an hour drive if you do decide you want to do day trips to beach.

One possibility I recommend if you want to explore Tuscany and Umbria, as well as Rome, is Camporsevoli. It is a small village completely turned into resort with apartments that is pretty close to the Tuscany/Umbria border and close enough to the A1 that makes moving around for day trips easy. It is also its own oasis where you can stay put by the pool and enjoy nature and time together away from crowds (it being August, most crowds will be at the sea and beaches). It isn't that close to the coast but it will be perfect for exploring the hot springs in the Val d'Orcia (like the Bagni di San Filippo and Bagno Vignoni, all less than an hour away) and the wonderful landscapes of the Val d'Orcia as well as Perugia and Assisi and Lago Trasimeno, all in Umbria.

I'll leave you with that one suggestion for now, I'd like to hear whether you already have a list of places you'd like to visit during your time here so that I can give more suggestions on a home-base in Tuscany based on what you'd like to see/visit while here, over the 3 weeks in Italy.

- Lourdes
 
Ciao Lourdes

Greatly appreciate your input.
We have been to Italy a few times but never truly explored Tuscany.

We would definitely like to visit Florence, Pisa, Livorno, Montepulciano then wine and cheese exploring, shopping... And beaches! As many as we can squeeze in.
Your recommendation sounds great

Having a pool is a must

Some of our family still lives in Italy which means we will be visiting them near Civitavecchia.

Our thought was to spend the first portion of the trip near Florence or Pisa, then relocate near Umbria border before a final 2 or 3 day stay in Rome to visit family.
 
I would give Camporsevoli a chance to see what they have open for August, from there you can make it to Umbria and all of southern Tuscany, including Montepulciano and Arezzo and Cortona, the natural hot springs at Bagni San Filippo for the kids especially!
For beaches, I would recommend breaking up the weeks and looking at someplace closer to the coast, because there are hills and Mt Amiata in southern Tuscany which makes for longer drives to the coast, not really a day trip I would recommend. So how about
Casa Campi di Sotto - https://www.tuscanyaccommodation.com/casa-conti-di-sotto.html or Club Le Cannelle - https://www.tuscanyaccommodation.com/club-le-cannelle.html ? I think both would be great options for the coast, both for beaches and exploring the Maremma area. If you want to stay directly in a small coastal town, you can look at Casa Laura - https://www.tuscanyaccommodation.com/casa-laura-follonica.html
We personally go with our 3 kids to Poggio all'Agnello a further up north - https://www.tuscanyaccommodation.com/poggio-all-agnello.html so we can do both beaches and time by the pool, but then we don't do much else, just relax. If you wish to include that, take a look! You can most definitely do day trips along the coast from here, to Livorno and even to Pisa, but it also would be nice to explore the smaller towns along the coast.
 
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