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Castiglion Del Bosco, Montalcino, Tuscany, Italy

Rosewood Castiglion Del Bosco

Boutique
Tuscany, Italy

Set in an 800-year-old estate within the beautiful Val d’Orcia region in Tuscany, the restored 17th and 18th Century farmhouses have been converted into luxury villas and suites. This spectacular hotel offers an idyllic base to become immersed within the Tuscan way of life.

The 10 immaculate villas and 23 suites have all been carefully designed to incorporate the old with the new. The villas feature lavish bedrooms, private pools and bespoke furniture, with a personal chef to conjure up culinary delights. The suites offer privacy with spacious bedrooms and airy living rooms.

During your stay, participate in cooking classes with ingredients taken from the organic kitchen garden, dine at the rustic restaurant that overlooks green hills and sweeping vineyards or take to a bike to discover the grounds.

Why we like Rosewood Castiglion Del Bosco

With a wide range of activities from golf to truffle hunting with dogs, this hotel is the essence of a simplistic Tuscan experience, all set within 5,000 acres of magnificent countryside.

Rosewood Castiglion Del Bosco, Montalcino, Italy

Rosewood Castiglion Del Bosco, Montalcino, Italy

Rosewood Castiglion Del Bosco, Montalcino, Italy

Idea

Rome, Abruzzo and Puglia

A wonderful off-the-beaten-track journey through the heritage, gastronomy and agriculture of the southern regions of Abruzzo and Puglia. This trip is jam-packed with experiences and activities that make a positive impact through your connection with the…

15 days from £5,395pp

St Peter's Basilica, Rome, Italy

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Idea

Winter Wolf Tracking – The Apennines

This seven-day winter itinerary to Italy explores the extraordinary social life of wolves, along the paths and valleys of national parks. Against a backdrop of remarkable mountain scenery, gain an understanding of the complex coexistence of…

7 days from £2,250pp

Three wolves walking up snow covered, rocky mountainside.

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Idea

Wildlife Tracking in the Apennines

Join expert nature guides to explore the rugged wilderness of Italy’s central Apennine mountains. Set camera traps, follow bear and wolf tracks and learn about conservation efforts to protect the wildlife. Stay in picturesque villages, home…

8 days from £2,345pp

Mountain goat (chamois) sat on cliffs edge with rolling green mountainsides in background.

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Italy – Combine Rome with Almafi Coast

Get your fix of city and sea with this week-long holiday suggestion to Italy, combining ancient Rome with the beautiful Amalfi coast.

7 days from £1,950pp

South Coast, Capri Island, Italy

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Italy – The Northern Lakes

Combine the pretty towns, palaces and gardens of the stunning Italian Lakes with historic Italian cities of Verona and cosmopolitan Milan.

7 days from £2,050pp

Villa in Lake Como, Italy, Europe

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Self Drive Italy – Discover Authentic Sicily

Sicily, the largest island in the Med with Mount Etna dominating much of its skyline, is an incredibly beautiful and alluring destination. Discover the highlights at your own pace with a self-drive holiday to Italy.

9 days from £1,600pp

Greek Roman Theater with Etna erupting, Taormina, Sicily, Italy

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Italy – Sorrento, Capri and Pretty Puglia

Full of southern soul, beautifully sun-bleached, weathered and worn, this is Italy as its most ancient. Rugged mountains, fiery volcanoes and glittering coastal grottoes wait to be explored.

9 days from £2,200pp

Martina Franca, Puglia, Italy

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Idea

Pizza Making and Gladiators in Italy – Family Holiday

Visit two highlights of Italy, Rome and Sorrento, on the Amalfi Coast, explored from a family-friendly angle of ancient gladiators, pizza making and uncovering the history of Pompeii.

7 days from £1,300pp

Ice cream, Italy

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Idea

Italy – The Cultural Highlights

This holiday to Italy is an excellent first visit option that covers good ground including the main highlights of Florence, Venice, Padua, Rome and Milan. Visit these well-known cities and enjoy their art, architecture and history.

10 days from £3,700pp

Florence Dome Covered in Snow

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Amalfi Coast Private Yacht Charter

Cruise the stunning Amalfi Coastline on board your private catamaran, exploring dramatic hillside villages, secluded bays and idyllic islands all the while receiving a first-class sailing experience.

8 days from £4,050pp

Need Inspiration?
Browse our Italy holiday ideas.

We know a thing or two about bespoke holidays – we’ve been creating them since 1989. Take a trip through the Italy holidays that we love today.

Idea

Rome, Abruzzo and Puglia

A wonderful off-the-beaten-track journey through the heritage, gastronomy and agriculture of the southern regions of Abruzzo…

15 days from £5,395pp

St Peter's Basilica, Rome, Italy

View Holiday Idea

Idea

Winter Wolf Tracking – The Apennines

This seven-day winter itinerary to Italy explores the extraordinary social life of wolves, along the paths…

7 days from £2,250pp

Three wolves walking up snow covered, rocky mountainside.

View Holiday Idea

Idea

Wildlife Tracking in the Apennines

Join expert nature guides to explore the rugged wilderness of Italy’s central Apennine mountains. Set camera…

8 days from £2,345pp

Mountain goat (chamois) sat on cliffs edge with rolling green mountainsides in background.

View Holiday Idea

Idea

Italy – Combine Rome with Almafi Coast

Get your fix of city and sea with this week-long holiday suggestion to Italy, combining ancient…

7 days from £1,950pp

South Coast, Capri Island, Italy

View Holiday Idea

Idea

Italy – The Northern Lakes

Combine the pretty towns, palaces and gardens of the stunning Italian Lakes with historic Italian cities…

7 days from £2,050pp

Villa in Lake Como, Italy, Europe

View Holiday Idea

Idea

Self Drive Italy – Discover Authentic Sicily

Sicily, the largest island in the Med with Mount Etna dominating much of its skyline, is…

9 days from £1,600pp

Greek Roman Theater with Etna erupting, Taormina, Sicily, Italy

View Holiday Idea

Idea

Italy – Sorrento, Capri and Pretty Puglia

Full of southern soul, beautifully sun-bleached, weathered and worn, this is Italy as its most ancient.…

9 days from £2,200pp

Martina Franca, Puglia, Italy

View Holiday Idea

Idea

Pizza Making and Gladiators in Italy – Family Holiday

Visit two highlights of Italy, Rome and Sorrento, on the Amalfi Coast, explored from a family-friendly…

7 days from £1,300pp

Ice cream, Italy

View Holiday Idea

Idea

Italy – The Cultural Highlights

This holiday to Italy is an excellent first visit option that covers good ground including the…

10 days from £3,700pp

Florence Dome Covered in Snow

View Holiday Idea

Idea

Amalfi Coast Private Yacht Charter

Cruise the stunning Amalfi Coastline on board your private catamaran, exploring dramatic hillside villages, secluded bays…

8 days from £4,050pp

View all holiday ideas View all cruises

Where to stay in Italy

Our team has handpicked this collection of properties to give you luxury options in styles to suit any journey.

More luxury accommodation

Tenuta di Murlo

Villas / Exclusive use
£££££

Hidden amongst the Umbrian hills, tucked away on…

Forestis

Wilderness
£££££

Forestis is a five-star mountain retreat and spa…

Forestis, Restaurant, Dolomites, Italy

Castello di Ugento

Boutique
£££££

Protecting and standing tall over the town of…

Aman Venice

City
£££££

As sumptuous and romantic as the city itself…

Roof Terrace, Aman Venice, Venice, Italy

Siena House

Villas / Exclusive use
£££££

Siena House is much more than just a…

Room, Siena House, Tuscany, Italy

COMO Castello del Nero

Boutique
£££££

Situated in the town of Tavarnelle Val di…

Why Choose Steppes?

Our knowledge and expertise set us apart. So too our curiosity. It is this that drives us to create a journey that is really bespoke to you, all the while ensuring we travel and operate sustainably.

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