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
31 MAY-6 JUNE
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5/31 to 6/6
21-27 JUNE
2026
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6/21 to 6/27
30 AUGUST-
5 SEPTEMBER
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8/30 to 9/5
4-10 OCTOBER
2026
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10/4 to 10/10
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.
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Scroll down to learn more.
The cost of this vacation is Euros 5,975 per person and includes your accommodation at iCastagni AND all elements on the itinerary - all lunches, dinners, breakfasts, aperitivi and drinks, all transport during the program, all entry tickets, tours, tastings, and tolls. Once you have paid for your vacation you can relax in the knowledge that you only need funds for your personal purchases. ​ The cost does not include any transport outside the itinerary (such as your transport from your point of departure and your arrival at iCastagni, nor any onward journeys at the end of the program). We can help with bookings for private transfers once you have arrived in Italy; please ask for details.
​to keep this trip special, the group size is capped at ten. You may book as many or as few of the slots as you would like, subject to availability.
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Do you have a larger group? Please contact us for details of 'The Real Tuscany' exclusively tailored to you and your group.​
31 MAY-6 JUNE
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5/31 to 6/6
Wines and a Side
Ready for a deep dive into Tuscan wines with a side program for fellow travellers where desired?
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Welcome to an exceptional experience for wine enthusiasts. Our 'Wines and a Side' vacation offers you the opportunity to really engage with wine as you visit and meet dedicated individuals creating some of the world's best bottles. Fully connect with wine by walking among the vines, speaking to the owners and winemakers, and of course by engaging in the art of tasting. Selections will be enjoyed alongside fine cuisine on a truly refined journey through the world of Tuscan wine.
A parallel side program will allow you, or your less-wine-focused-fellow traveller, to take a pause to enjoy some of southern Tuscany's other delights when preferred. ​​​​​
The cost of this vacation is Euros 6,100 per person and includes your accommodation at iCastagni AND all elements on the itinerary - all lunches, dinners, breakfasts, aperitivi and drinks, all transport during the program, all entry tickets, tours, tastings, and tolls. Once you have paid for your vacation you can relax in the knowledge that you only need funds for your personal purchases. The cost does not include any transport outside the itinerary (such as your transport from your point of departure and your arrival at iCastagni, nor any onward journeys at the end of the program). We can help with bookings for private transfers once you have arrived in Italy; please ask for details.
​to keep this trip special, the group size is capped at ten. You may book as many or as few of the slots as you would like, subject to availability.
​​​​
Do you have a larger group? Please contact us for details of 'Wines and a Side'' exclusively tailored to you and your group.​
21-27 JUNE
2026
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6/21 to 6/27
Love at First Bite
Experience the Unbeatable Taste of Italy
​Welcome to a vacation dedicated to the wonder and joy of Italian cuisine.
Italian food is famous for being simple but exceptional and the recipes from Tuscany showcase this in a magical, mouth-watering way.
UNESCO, the part of the United Nations which promotes standards in educational and cultural issues, awarded Italian cuisine formal recognition in late 2025. This news encouraged us to develop a vacation we had been pondering for a while; a vacation with Italian cuisine at its heart.
Enjoy a week dedicated to authentic flavourful food, culinary excellence, and dishes rooted in cherished recipes shared through generations. Experience the joy of eating local foods nurtured by Tuscan sunshine as you travel from one beautiful hilltop town to the next. This is food as it should be - local, freshly-prepared, and with no need for preservatives, chemicals, E-numbers and unpronounceable additives.
Experience the timeless taste of Italy - unchanged and simply unbeatable.​​
The cost of this vacation is Euros 5,975 per person and includes your accommodation at iCastagni AND all elements on the itinerary - all lunches, dinners, breakfasts, aperitivi and drinks, all transport during the program, all entry tickets, tours, tastings, and tolls. Once you have paid for your vacation you can relax in the knowledge that you only need funds for your personal purchases. ​ The cost does not include any transport outside the itinerary (such as your transport from your point of departure and your arrival at iCastagni, nor any onward journeys at the end of the program). We can help with bookings for private transfers once you have arrived in Italy; please ask for details.
This is not a cooking vacation - it is a vacation for those who enjoy quality, 'real' food and the joy of eating and living well. The itinerary will involve some cooking alongside our private chef; visits to vineyards and specialist food producers; eating out in a variety of venues from a villager's home, through local fun-packed small restaurants where each dish is made to order in a tiny kitchen, to going behind the scenes of a Michelin-star restaurant.  A vacation for food-lovers
​to keep this trip special, the group size is capped at ten. You may book as many or as few of the slots as you would like, subject to availability.
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Do you have a larger group? Please contact us for details of 'Love at First Bite'' exclusively tailored to you and your group.​
30 AUGUST-
5 SEPTEMBER
​
8/30 to 9/5
Wines and a Side
Another Bottle?
Ready for a deep dive into Tuscan wines with a side program for fellow travellers where desired?
​
Welcome to an exceptional experience for wine enthusiasts. Our 'Wines and a Side' vacation offers you the opportunity to really engage with wine as you visit and meet dedicated individuals creating some of the world's best bottles. Fully connect with wine by walking among the vines, speaking to the owners and winemakers, and of course by engaging in the art of tasting. Selections will be enjoyed alongside fine cuisine on a truly refined journey through the world of Tuscan wine. An added bonus is the possibility that, depending on wine-makers' decisions, this program might neatly coincide with the 2026 harvest.
A wonderful and special added element.
A parallel side program will allow you, or your less-wine-focused-fellow traveller, to take a pause to enjoy some of southern Tuscany's other delights when preferred. ​​​​​
The cost of this vacation is Euros 6,100 per person and includes your accommodation at iCastagni AND all elements on the itinerary - all lunches, dinners, breakfasts, aperitivi and drinks, all transport during the program, all entry tickets, tours, tastings, and tolls. Once you have paid for your vacation you can relax in the knowledge that you only need funds for your personal purchases. ​ The cost does not include any transport outside the itinerary (such as your transport from your point of departure and your arrival at iCastagni, nor any onward journeys at the end of the program). We can help with bookings for private transfers once you have arrived in Italy; please ask for details.
​to keep this trip special, the group size is capped at ten. You may book as many or as few of the slots as you would like, subject to availability.
​​​​
Do you have a larger group? Please contact us for details of 'Wines and a Side'' exclusively tailored to you and your group.​
4-10 OCTOBER
2026
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10/4 to 10/10
the food, the wine, the people,
the history, the art, the architecture...
The Real Tuscany Week
our 2025 Real Tuscany vacation was magical
so we've decided to offer it again in 2026
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The Real Tuscany ​
June 21-June 27 2026
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 beautifully-positioned vineyards and 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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For further information or to discuss details please contact us by clicking the button below.
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to keep this event small and special, the maximum number of participants is capped at ten
you may book as few or as many of the ten places as you would like
(subject to availability)
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The cost of this vacation is Euros 5975 per person and includes your accommodation at iCastagni AND all elements on the itinerary - all lunches, dinners, breakfasts, aperitivi and drinks, all transport during the program, all entry tickets, tours, tastings, and tolls.
​
Once you have paid for your vacation you can relax in the knowledge that you only need funds for your personal purchases.
​
The cost does not include any transport outside the itinerary (such as your transport from your point of departure and your arrival at iCastagni, nor any onward journeys at the end of the program.
We can help with bookings for private transfers once you have arrived in Italy; please ask for details.
