Two Weeks in Tuscany:Planning the Best Itinerary|TuscanyChic

Two weeks in Tuscany

Anonymous asked 3 years ago
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Two weeks in Tuscany

Hi, Elena!

I like a lot your blog, full not only with useful information, but also very helpful!
I hope you can help us as well with planning our two weeks trip and stay in Tuscany.

First of all – both me and my wife we love dearly Tuscany, each one for personal reasons.
Me – because in my frequent travels and crossing all over Europe as well as the rest of the world (only Australia excluded) I’ve never seen more beautiful areas than Tuscany and my home country Bulgaria (the latest by understandable reasons).
Her – because she has been deeply involved all her life in the Italian history, language, style of living, culture etc. (she is a professor of Italian language in Sofia University).
Both of us we love the simple, natural way of living, we enjoy the nature very much, therefor we would rather prefer to have as a base to stay more rural environment than big and noisy towns. Certainly, during our stay we would like to visit as much as possible attractive sites and places located around and that’s the purpose for coming with a car – to be flexible, independent and mobile.
We have visited Italy before in several occasions, but never stayed in Tuscany so for us that’s an unfulfilled dream so far.
Can you help us with suggesting suitable accommodating place to stay, satisfying the above conditions as well as an appropriate itinerary for the purpose of our tour?
Timing is not critical for us (we are old enough to be relatively free), but excessive heat season should be avoided. Most probably we’ll be traveling either two of us or accompanied by two family friends.

I took the liberty to write to you first and in English (my Italian is quite clumsy), but in case you decide to help us in that matter – it will be probably better to put you in touch directly with my wife for the sake of ease of conversation and understanding.
Nevertheless, I’ll be looking forward to your answer,
With my best regards,
I. Voykov

2 Answers
elena nacci Staff answered 3 years ago
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Thanks a lot for your nice message! so happy to hear you find my blog useful! It’s a pleasure to help you planning your trip!
Tuscany is so beautiful and you have even more reasons to come and visit it 🙂
In two weeks you will have a lot to see and do. As you’re staying 2 weeks my suggestion is you split your stay in 2 parts and stay in 2 different locations in Tuscany so to get the most out of of your vacation. But in case you’re not willing to change place, then you may well opt for a central destination in Tuscany, like Chianti, or also the Val d’Orcia.
My favorite rural areas of Tuscany are in fact Chianti and Val d’Orcia; I always suggest choosing among the 2, and when possible, as in your case, stay in both locations.
Chianti has high hills, castles, scenic landscape and small villages, while it’s renowned for its wines obviously. Val d’Orcia is quite different from it, having more soft hills, again castles and abbeys, and striking ancient villages like Pienza and Montalcino. Val d’Orcia is located south of the fantastic medieval town of Siena and is another famous wine producing area…Brunello di Montalcino is one of the best wines of Italy.
Take a look at this post where I actually speaks of both regions and explains their main differences, while also give a look at the links above for the single areas and see the images to have an idea of how each place looks like.
As far as accommodations, I’m suggesting some properties I love, but as you’re not specifying the type of place you’re looking for, just have a look and eventually get back to me for further options 🙂
In the heart of Chianti, I recommend:
Villa Bordoni, charming hotel offering beautiful rooms and suites enjoying great privacy in a stunning location in the countryside. The views are enchanting.
Villa Vignamaggio, a beautiful Renaissance Villa famous for being the birthplace of the Monna Lisa. You can choose between charming rooms or apartments. The landscape is again lovely, and you can taste their Chianti wines and live oil.
In Val d’Orcia, I recommend:
Relais la Saracina, a chic farmhouse near the stunning Pienza, the best place to be for breathtaking views and excellent food. La Saracina has beautiful rooms and apartments in country chic style.
Locanda del Loggiato, offers romantic rooms in Bagno Vignoni, one of my favorite places in Tuscany, a very suggestive place all to discover! You may enjoy its thermal waters while there. Still in Bagno Vignoni, I recommend Hotel le Terme, characterized by enchanting vistas over the ancient Renaissance pool and having 2 indoor thermal pools.
As for your itinerary, while in Chianti go visit San Gimignano, Lucca, Pisa, Florence, and Chianti itself, here is a full list of the day trips you can make from there.
While in Val d’Orcia explore the many treasures of the area itself, Cortona, Montepulciano, and a bit more south, the stunning “Città del Tufo”; Pitigliano, Sorano, and Sovana.
I remain at your complete disposal,
Enjoy your planning,

elena nacci Staff answered 3 years ago
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It’s me again:-) I missed to include the link to this useful article about spending two weeks in Tuscany. Take a look just to have an idea of all the fantastic sights you can cover during your stay.