top of page





We love designing bespoke itineraries for our guests but every now and again we like to offer our own specially crafted experiences. We believe that quality and authenticity are key to creating unforgettable moments and memories in Tuscany, so each experience is meticulously tested by us to ensure that every detail has been fine-tuned and every element runs smoothly. When we are satisfied that everything is perfect, we add the programme to our site.  

If you see an experience advertised, read on in order to book your place(s). If you don't see anything at the moment, it's because we are still planning, trialling, editing and finessing.  But please come back soon to read all about it.


a week-long programme 

which guarantees you will experience Italy as the Italians do


NO tourist traps


NO elements created 'especially for tourists', which provide an inauthentic and overpriced experience

NO visits to places where there is one price for visitors and another for locals


The Real Tuscany Week
the food, the wine, the people,
the history, the art, the architecture, the...

Real Tuscany

1-7 September 2024
31 August-6 September 2025


The Real Tuscany Week

the food, the wine, the people,the history, the art, the architecture, the...

Real Tuscany


1-7 September 2024

31 August-6 September 2025

If you’re looking for an authentic Tuscan experience, 'The Real Tuscany' will suit you perfectly.  Let the natural beauty of the surrounding landscape envelop you as you immerse yourself in Italian life.  


Allow us to take you on a journey through stunning hilltop villages and ancient towns, where you’ll taste wines from the area paired with delicious, locally-sourced food. You will meet locals as they live a life underpinned by friends, family, and food.  A visit to a beautifully-positioned local vineyard will allow you to experience the ancient art of winemaking; walk among the vines and and see the magic of the process as the grapes transfer from sun-drenched jewels on the vine into delicious wines.  You will visit some of Tuscany's most-famous towns, Siena, Montepulciano, and Pienza, and wonder at their glorious buildings and vast collections of art. There will be ample opportunity to shop, wander, drink rich thick espresso, enjoy glasses of chilled-white, or robust-red, wine, and relax into the Tuscan way of living.

We live in this beautiful part of Italy all year round and know it like a life-long friend. We know the places to go and the ones to avoid and will be by your side throughout as you slow down, experience, and find yourself getting in step with the innate Italian talent for enjoying life.


Join us for a week which is sure to please the senses and enrich the mind.

For more information, please contact us using the form below or scroll down to take a look at the outline programme.

to keep this event small and special, the maximum number of participants is capped at twelve you may book as few or as many of the twelve places as you would like

 (subject to availability)



Dreaming of Tuscany but not sure where to go, what to see, or how to organise yourself, your budget, and your time?  Been to Tuscany before but now want to delve a bit deeper into this wonderful country?


iCastagni is delighted to invite you to

The Real Tuscany 

s a m p l e   i t i n e r a r y



Settle into your home for the week; a medieval Tuscan village with real Italian life and a real Italian community as its beating heart.  Welcome to Tuscan living.



After wine, it has to be food. How do Italians eat carbs and remain so fit, slim, and healthy? We will experience the joy of eating locally-produced foods which have accumulated zero air-miles and zero additives as we visit the neighbouring town of Montepulciano. Montepulciano embodies much of classic Tuscany; magnificent historic buildings, winding narrow streets, and views across a countryside landscape full of olive groves, farmhouses, and elegant cypress trees waving in the gentle breeze.  In the evening we will visit a tiny village where nothing really happens, until a restaurant opens its doors... 


Pepperoni Pizza

Pasta, Pienza, and Pizza.  The first topic around a Italian family breakfast table?  What shall we eat tonight? We will start the day learning how to make our own pasta with only 3 ingredients and a bit of elbow grease; we will visit the Renaissance jewel of nearby Pienza to explore its stunning architecture and unique history, its quality shopping, and quintessentially-Italian atmosphere.  We end the day biting into fresh-from-the-woodburning-oven, crispy, mouth-watering pizza made for us by an Italian chef in his own home. 



Let's dip into one of the area's greatest products; wine. We will be focusing on the wines produced in the spectacular countryside around us and will be welcomed at a beautifully-positioned local vineyard by the owner to taste her fantastic wines, and enjoy them over lunch. We end our wine day at home with a magical aperitivo, followed by Tuscan home-cooking in a village restaurant.


Siena High Res Shutterstock_221007010.jpg

Yes, Italians sightsee and shop, but they know how to do it in a way which keeps them cool, comfortable, and crowd-free. We will share their secrets with you in our regional capital, Siena, home of the world-famous Palio horserace and guardian of some of Tuscany's greatest artistic treasures.


Dinner Party

We will treat ourselves today and roll all the best elements of the week into our last day.  A true Tuscan combination of wine, food, stunning scenery, laughter and a traditional Italian Friday evening



One last coffee and pastry at the village cafe to say goodbye to your new local friends, then a leisurely departure and a chance to wave goodbye - until next year.

Cost: The cost per person for the week is Euros 5975 (or USD 5975 if you would prefer to pay in dollars). Guests will be accommodated at iCastagni Private Hotel. The cost includes your accommodation at iCastagni plus all items listed on the itinerary - all lunches, dinners, drinks, breakfasts, transport during the itinerary, tickets, tastings, tours and tolls. The cost does not include your transport to/from Italy or your transfer to/from your point of arrival/departure in Italy and iCastagni. If you would like our help with private driver transfers to/from iCastagni, please ask.   

you may book as few or as many of the twelve available spaces as you would like, subject to availability

Friends Talking

Coming soon....

a small-group (maximum 10 participants) 'learn and speak Italian in Italy' for beginners. 

bottom of page