Are you dreaming of a Tuscany road trip but don’t know where to start? Here’s my Tuscany itinerary for one week covering beautiful landscape spotting, the best places to visit in Tuscany, wine, lovely food and pure Tuscan atmosphere. Sounds like your kind of fun?
Follow my one week in Tuscany itinerary and you will get all of that. To me, the amazing landscape was my number one motivation to go. The rolling hills with the cypresses just got me. I wanted to have a good mix of little Tuscan hill towns, some adventure, good food & wine and the typical landscape of Tuscany.
The Mediterranean climate invites you to visit Tuscany nearly all year long, but the most beautiful periods are most definitely spring and fall. I’ve chosen early September for my 1 week trip, which is quite a good period. However, fall is moving in the country and the very dry summer with no rain for three months left its traces and the rolling hills were not a saturated green, but brownish. Although this is not the scenery you see from the beautiful Tuscany galleries, the dry meadows do have its own dramatic look.
Tuscany is a huge region and you would need weeks and months to see all of it. After intense research based on my priorities I came up with this Tuscany trip itinerary for one week flying in and out Pisa covering the best things to do and to photograph:
Lucca – 2 nights
Massa Marittima – 1 night
Val d’Orcia – 2 nights
Chianti region – 2 nights
Lucca – 2 nights
This little medieval city close to Pisa is an absolute must for Tuscany visitors and to me, much more appealing than Pisa. A fortress wall is encircling Lucca which you can enter through four gates. Lucca is also called the city of 99 churches. I stayed in B&B Dolce Sosta in Capannori, a very nice little Bed and Breakfast with private parking, a beautiful garden and bikes to rent. It takes you a 10-minute drive by car to one of the gates of Lucca. Two nights in Lucca give you enough time to explore the town and the surroundings of Lucca. Find my comprehensive guide to Lucca here.


Massa Marittima – 1 night
From Lucca, I left to Massa Marittima. I took the route along the seaside passing beautiful Castiglioncello where I stopped for a coffee towards Massa Marittima. The Tuscan hill town is really small with less than 10k inhabitants, but it is a lovely place and just perfect for a stroll through the picturesque alleys. You have seen pretty much everything within one day. I booked a room in Residence Massa Alta, a charming Bed and Breakfast on top of the hill with private parking. Here’s what you can do in Massa Marittima.
Val d’Orcia – 2 nights
I do not have any words to describe the beauty of this valley. If the road would have allowed, I would have stopped every 2 minutes to capture the landscape and indulge the breathtaking views. Even though the meadows were brown and very dry due to the heat of the last months and lack of rain, the unique scenery is absolutely stunning. My base was the adorable B&B Antico Borgo in Seggiano, a town with less than 1000 inhabitants. Seggiano is located on a hill with steep, very narrow roads and a challenging parking situation. San Quirico, the heart of Val d’Orcia can be reached in half an hour by car. I didn’t mind the driving and really enjoyed the hospitality of the Antico Borgo staff and the local people meeting up in the Osteria of the B&B. Val d’Orcia has a lot of beautiful photo spots and charming little cities to visit and you should definitely drive through this valley during your week in Tuscany. It surely belongs to the best places to visit in Tuscany – make sure to add Val d’Orcia on your tour.


Chianti region – 2 nights
The landscape from Val d’Orcia to the Chianti region changes. From brownish meadows and beautifully arranged cypress roads, you reach a green landscape surrounded by vineyards. The „Strada del Vino e dell’Olio“ or also called the Chianti Classico road is full of vineyards, olive groves and small towns. If you’re into wine tasting, this is your place to be. I stayed in Villa Vittoria in the small town of Gaiole in Chianti. The Bed & Breakfast belongs to Lorenzo, the local butcher with a tradition since 1682. Gaiole is the perfect place to start your Chianti exploration tour. If you’re a solo traveler, you are warmly greeted and welcomed in Gaiole.
If you have some time left you can head to Siena or San Gimignano on your way back to the airport. If you’re still not sure whether you should go to Florence, you might get inspired by these photos.
Some essential Tuscany travel tips for you:
The best way to see Tuscany:
I do a lot of research prior to a trip, however, you can’t plan a vacation in every detail in advance. You need to have some flexibility to explore places that come up when you talk to locals. Often these places are very hard to reach by public transportation. That’s why I prefer to choose a rental car for most of my trips. Rental cars in Italy are quite affordable. I paid 70 Euro for a Fiat 500 for one week including all insurances. That’s a good deal, right? I strongly recommend you to discover the towns in Tuscany by car in order to see the immense variety and beauty of the region. I avoided highways in order to see as much as possible when driving from one spot to the other.
- Rent a small car. The roads in the cities and towns are narrow and parking might be tricky with a huge SUV.
- Make sure you’ve got an all-inclusive insurance package. Italians park like crazy and it is very probable that your car ends up with small damage. No one cares and you won’t find a piece of paper with the contact details behind the windscreen wiper. I speak from experience 😉
Parking
I had a Fiat 500, the smallest available car and I was so glad I had it. In some areas, parking is easy to find and easy to manage. In others, I had my challenges even with the 500. The white lines indicate free parking, the blue lines mean you have to pay. Always carry enough coins with you. The parking machines only take coins, no paper, no cards.
Google maps…
…is my best friend on the road. Even if I didn’t always have a plan where I’m going, I absolutely needed Google maps to find my way back to my base. And you can save your favorite spots to look them up later. Make sure to have access to Google maps during your Tuscany road trip.
What to pack for a week in Tuscany?
Let’s assume you do your trip in spring or fall, these are your ultimate must-pack items:
- Even with minus degrees in Winter, I usually keep my bedroom window open and I never get cold. However, the bedsheets in Tuscany are very thin and it really happened that I was freezing at night. Pack something to wear at night in case the sheets don’t do their job.
- Talking about getting cold. Bring a pair of warm socks. There’s nothing worse than having cold feet.
- You’re never wrong with a wind and rain jacket. Especially in the morning and evening it might get a bit chilly or you’re facing a rainy day – you’ll be happy to find it in your suitcase.
- Earplugs! All the B&Bs I stayed in were lovely and charming, however, I suffered a bit from the noise from other guests or residents. There are always people who come back late and are not considerate of other guests or children screaming or there’s music playing somewhere.
Enjoy this stunning part of lovely Italy and leave some room for improvisation and flexibility.

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Oh, excellent, I saw that you were close! I returned home (in southern Tuscany, Capalbio) in the end of August and suffered observing how nothing was green yet. The yellows and browns are quite depressing after green Slovenia. Still, home is home and I know it will get greener soon, at the latest by November 1st when mould and mushrooms come together with seasonal humidity.
I see that you made yourself quite a plan! Sounds and seems great. I bet one week was short but sweet. Now imagine returning in luscious April (I know you do already). 🙂
I have not visited all places you mention but my to-visit list is pages and pages long and new towns are added regularly. I agree about Lucca and have enjoyed Castiglioncello as well as nearby Volterra. As it is, I’m more often to be found in the south of Tuscany with Umbria and Lazio. I have not yet visited Massa Maritima though, no matter how close I am. Will do sooner or later. Also I have learned from your post that Leghorn is the English word for Livorno. 😮 Have you heard about the recent floods with casualties? Terrible!
Anyway, I’d be happy if you tell me when you’re coming near here again. You never know…
I’m sure people will appreciate your way of doing Tuscany. It’s a rewarding one. It might even improve with spring.
I was about to pass Capalbio, but then decided to go to Massa Marittima which was closer to my next stop Val d’Orcia. One week is nice, but just not enough. But then it was quite exhausting because I was rushing from one spot to the other, doing so research and kept shooting. I will definitely come back in Spring. Let’s stay connected. If I manage to come to your place, I’d be happy to meet up. Thanks so much for your comment.
Oh yes, let’s, I’ll be right here.
Tuscany is such a beautiful area in Italy. We did a road trip through Tuscany a few years ago and enjoyed it so much. We did not visit Lucca, it’s still a town I’d love to go back for. Your photos are really stunning!
Thank you so much, Sabine. You should definitely go for Lucca. It is so charming.
Thank you for this post, I am actually thinking to go for a road trip to Tuscany next year so I really appreciate that you shared with us this itinerary! Stunning photos 🙂
Thanks so much, Lanka. Oh yes – please do that. You will love Tuscany. I will share some more posts within the next weeks.
these little towns are so cute… I love visiting Italy but have never been to Tuscany, thank you for the inspiration. it is always so nice to get out of the major cities and explore the countryside!
I’m glad you got some inspiration. I prefer to visit smaller towns and city rather than the big, famous ones. I hope you’ll make it to Tuscany soon.
Ever since I watched the “Under the Tuscan sun” I’ve been meaning to do an epic Italian itinerary around Tuscany. Well, those views sure look lush and those villages are incredible. I’d love to visit!
I think I’ve not watched “Under the Tuscan sun”…, I will check it out. If you’ve got the chance to visit, you should do it. Spring and fall are perfect.
Those of us who live in Tuscany kind of make fun of that movie… it’s a fun “romp” but… gives some unrealistic impressions. I was living in Florence when it came out, and back then a lot of expats who were negative about it were also I think experiencing some jealousy about how successful Mayes’ books were. Now 13 years later I’ve moved back to Tuscany, this time Lucca, and I still hear expats taking the piss out of that movie. LOL, but Hollywood is Hollywood.
haha – I need to watch it 😉
Ciao, from what spot did you take the photo of the Belvedere house in the Val d’Orcia?
I live outside Lucca (moved 4 months ago) and would be interested to see the Lucca guide you’re putting together. Let me know when it’s ready! (chandi at paradise of exiles dot com)
Hi. I will post the Lucca guide on Tuesday. You can find the viewing spot of the Belvedere house on google maps. I will be posting an article about all viewing points soon
I am going to Tuscany for a month and your post recommended some really great areas to explore! I will definitely go to Chianti and to Lucca. The scenery from Val D’Orcia is so beautiful, I will have to go there as well. I will be having a motorbike to go around as I don’t have a driving license so I will be able to explore all the slow roads through the countryside 🙂
That’s amazing. With motorbikes it’s even easier because you can literally stop everywhere. Val D’Orcia is a must. The landscape is just amazing. I will be posting a few more in-depth articles in the next weeks. Enjoy your trip! 🙂
I love your guide. I had no idea Tuscany was so good. Including parking tips is just so helpful. We had so much trouble navigating those narrow roads in France. Finding parking was a whole different ball game!
Thank you so much. I’m glad it is helpful. That’s why I took the smallest car available and even then I had beads of perspiration on my forehead from time to time 😉
Just forwarded this post to my best friend who is now studying in Italy. Your photos are awesome!
Thank you so much!
My friend is from Tuscany and she kept telling me how beautiful it is… but your pictures really says it all! Amazing! I will use your article as my travel guide when I go there!! 🙂
Perfect – I hope you’ll make it there soon 🙂
Omg, love this post so much! As many times as I’ve been to Italy, I have yet to make it to Tuscany. And Tuscany is high on my bucket list! I dream of wine hopping through the region. Your post is full of great details that I’ll for sure will refer back to it!
I’m so glad you like it and find it useful. I like your wine hopping idea 😉
Wow! Val d’Orcia looks absolutely breathtaking! I hope to make it to Tuscany one day.
So gorgeous! I feel like I can smell the grapes from here! Something out of a movie!!
Thank you very much!
OMG this post is everything. I’ve never been to Tuscany but I’ve been to other spots in Italy and if this region is anything like people say it is, man do I need to get myself out there!
Haha…yes, get yourself out there 😉
Nicola, planning a Tuscany tip next October. Looking at a hotel in Montalcino and one in Val D’Orcia. Which location would you recommend? Thanks!
Hi James, both locations are great and with a car you can explore the whole region. I sent you an email.
Hi Nicola,
Wow thanks for this post and the other one on the photography spots in Val D’Orcia. I’m heading there this May and it will be very helpful. Is it safe to just stop by the road to take those photos? Some I know you have mentioned that there is a small parking area. And also, where did you get a rental car for 70 euro per week? I’ve been searching and its more like 70 euro per day!
Hi Mike, thanks for your comment. I’m glad my posts are helpful. You will find spots where you can pull over the car and stop. Italy is quite easy on that. I think I booked my rental car with billiger-mietwagen where I found this offer. 70 is very low, but you might get one for 150 a week. Let me know if you’ve any questions. Have a great trip!
Thanks for the reply, Nicola. I checked out that website, and it seems to be all in German, so I might need to look around more. I’ve heard horror stories of the Autoeurope consolidator, where they somehow find ways to make you pay for damages etc.
Is it safe to go into the fields by these places? Some photos I see people actually venturing into the fields. I wouldn’t want to encounter any snakes, or the owners of these places coming after me.
Before you leave, check the car closely. If you find even little damages, make them mark them on the contract. And also make sure to have an insurance which covers any damages. I had a scratch on the bumper (parking in Italy can be crazy and no one cares) and had to pay for the damage, but received the money back from the insurance.
I walked into fields, but didn’t cross private properties without asking. I didn’t think of snakes actually -)
Thanks for the tips Nicola! Shall keep them in mind when I am renting. The flights have been booked. Now to choose a good agriturismo amongst the many in the Val D’Orcia region.