Experience Tuscany
with
iCastagni
PRE-PLANNED
VACATIONS
IN TUSCANY
CRAFTED BY US
FOR YOU
We love designing bespoke/tailored itineraries for our guests but we also like to offer our own specially crafted vacations too, bringing together the most magical experiences this beautiful area has to offer.
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We believe that quality and authenticity are key to creating unforgettable moments and memories in Tuscany, so each vacation 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 program to our site.
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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, or get in touch with us about designing a bespoke/tailored vacation itinerary just for you and your group.
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upcoming pre-designed vacations and events
14-20 JUNE
2025
The Real Tuscany
Dreaming of Tuscany but not sure where to go, what to see, or how to organise yourself, your budget, and your time? We live here all year round and know this pocket of paradise like a life-long friend. Let us guide you as you experience the 'real' Tuscany, not the one manufactured to give visitors an over-priced and
in-authentic experience. We will avoid all the tourist pitfalls so that you can see Tuscany for what it really is - one of the most magical places on the planet.
Scroll down to learn more.
31 AUGUST TO 6 SEPTEMBER 2025
My Old Tuscany Home
DETAILS COMING SOON
DATES COMING SOON
2026
the food, the wine, the people,
the history, the art, the architecture...
The Real Tuscany Week
31 August-6 September 2025
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The Real Tuscany ​
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 will taste wines from the area paired alongside delicious, locally-sourced food made daily in family-run restaurants . You will meet local Italians as they live a life underpinned by friends, family, and food. You will visit a beautifully-positioned vineyard to experience the ancient art of winemaking; visit some of Tuscany's most-famous towns, Siena, Montepulciano, and Pienza with a relaxed and knowledgeable guide who will bring these towns alive for you. 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.
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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.
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Scroll down to see an outline programme; for more detailed information or to discuss details, please contact us by clicking the button below.
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)
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iCastagni is delighted to invite you to
The Real Tuscany
OUTLINE PROGRAM
SUNDAY - ARRIVAL
Settle into your home for the week; a beautifully-preserved medieval Tuscan village with real Italian life and a real Italian community as its beating heart. We will start the week by enjoying dinner together in a family-run village restaurant where all dishes are home-made in a tiny kitchen.
Welcome to Tuscan living.
TUESDAY
After wine, it has to be food. We will experience the joy of eating locally-produced foods which have accumulated zero air-miles as we visit neighbouring Montepulciano, a town which embodies much of classic Tuscany; magnificent historic buildings, winding narrow streets, and views across a countryside landscape full of olive groves, farmhouses, and lines of cypress trees.
THURSDAY
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 before enjoying the fruits of our labours for lunch; in the afternoon 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, mouth-watering pizza made for us by an Italian chef.
MONDAY
Let's start with one of the area's greatest products; wine. We will visit at a beautifully-positioned local vineyard, where we will be be welcomed by the owner and shown around her glorious winery. We will taste her fantastic wines and enjoy them over lunch in her home. An easy afternoon will be followed by a typical Italian aperitivo (evening drink and snack) at the hotel before a short wander for dinner in another family-run restaurant.
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WEDNESDAY
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 as we visit Siena, home of the world-famous Palio horserace and guardian of some of Tuscany's greatest artistic treasures. Spend a day wandering ancient streets and marvelling at the majestic beauty of this vibrant yet warm and friendly city.
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FRIDAY
Today we will visit the glorious Val d'Orcia (above) to immerse ourselves in the typical Tuscan landscape of rolling hills and lanes dotted with cypress trees waving gently in the breeze. A lazy lunch will be followed by Italian gelato - this will be the real thing, not one produced on an industrial scale miles away. A relaxing afternoon will then lead into clinking wine glasses full of Brunello wine with a sumptuous final dinner.
SATURDAY
this vacation doesn't end on Friday night. On Saturday morning we will have breakfast 'Italian style' at the village cafe where the entire community comes together to enjoy hot coffee and warm pastries. A great opportunity to experience being part of a truly authentic Italian community.
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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. You can then relax in the knowledge that everything is covered, apart from your private purchases.
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 arranging private driver transfers to/from iCastagni, please ask.
to keep this event small and special, the total number of spaces available is capped at twelve
you may book as few or as many of the twelve spaces as you would like (subject to availability)