very occasionally we offer
pre-designed-by-us small group vacations
for single travelers and couples
upcoming pre-designed journeys
31 MAY-6 JUNE
2026
5/31 to 6/6
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.
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.
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
2026
5/31 to 6/6
21-27 JUNE
2026
6/21 to 6/27
Wines and a Side
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.
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
6/21 to 6/27
30 AUGUST-
5 SEPTEMBER
2026
8/30 to 9/5
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.
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
2026
8/30 to 9/5
4-10 OCTOBER
2026
10/4 to 10/10
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
10/4 to 10/10