Luxury Tuscany Holidays

Tuscany has been dubbed the most beautiful region of Italy and it’s easy to see why with its rolling hills and mediaeval castles. Get lost in its beauty with a tailor-made tour…

Curated collection of luxury properties
Tailor-made holidays just for you
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Unique exclusive experiences

Scattered with villas, farmhouses and castles nestled deep in the heart of the rural countryside, Tuscany is a sight of awe with its olive groves, vineyards and rolling hills. Alongside the scenery, it has one of the most famous repositories of art in the world, with famous Renaissance paintings, sculptures, frescoes and architecture.

Tuscany covers a large area of 8,900 sqm and borders the regions of Liguria to the northwest, Emilia-Romagna to the north and east, Umbria to the east, and Lazio to the southeast. Tuscany's capital, Florence, along with Pisa and Empoli, sit on the river Arno which snakes its way through the region. As well as the typical hilltop towns, large parts are densely forested, and the Apennine Mountains are situated to the northeast of the region.

If you’re a traveller in search of art, history, wildlife, fine wine and cuisine, then a luxury Tuscany holiday is for you. Enquire today and see what your tailor-made tour could look like with Scott Dunn.

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Luxury Tours & Hotels in Tuscany

At Scott Dunn, we specialise in curating a collection of handpicked luxury villa-styled stays and boutique hotels in Tuscany that embody the essence of this enchanting region. Our unique stays range from charming farmhouses to historical estates, each with its own story to tell. Stay in a traditional Tuscan farmhouse surrounded by vineyards, or enjoy the grandeur of a centuries-old estate with breathtaking gardens. These unique accommodations allow you to immerse yourself in the culture and history of Tuscany, making your Tuscan holidays an unforgettable experience. Featured on our sample tailor-made itineraries, be inspired by Tuscany’s hotels, paired with exclusive experiences and stress-free travel, are woven together for the ideal bespoke holiday.

Properties
Itineraries

COMO Castello Del Nero

Tuscany, Italy

The beautifully converted 12th century COMO Castello del Nero is nestled in the undulating hills of the Chianti region of Tuscany. Siena, Florence and Pisa are just a stone's throw away and you can take your pick from superb local Chianti wineries.

Borgo San Felice Resort

Tuscany, Italy

Sink into an oasis of rural luxury in the heart of Tuscany, immersed in vineyards, with an abundance of facilities this is paradise found. This former hamlet has been transformed into a luxury hotel estate, nestled in the beautiful Chianti region.

Borgo Santo Pietro

Tuscany, Italy

This stunning boutique hotel located in the heart of the Tuscan countryside exudes charm and history. The lovingly converted 13th century villa, the centre of Borgo Santo Pietro, offers guests a luxurious haven in which to relax and unwind.

Castiglion del Bosco, A Rosewood Hotel

Tuscany, Italy

Rosewood Castiglion del Bosco in Tuscany is an exclusive country estate offering luxurious suites and villas with private heated pools, exceptional cuisine and great outdoor activities, set against the magnificent backdrop of the Val d'Orcia.

Castello di Casole

Tuscany, Italy

Belmond Castello di Casole commands a prominent hilltop position, offering magical views of the Tuscan countryside, combining Old World Tuscan charm with modern boutique luxury, elegance and sophistication.

Hotel Castello di Reschio

Umbria, Italy

Located just within the Umbrian border, Castello di Reschio, a recently-renovated grand estate, offers guests a slice of timeless Italy. Find yourself in the Tuscan hills by Andalusian horseback, indulge in homemade produce, or simply unwind by the pool.

Castel Monastero

Chianti, Tuscany, Italy

Castel Monastero is a beautiful and unique hotel housed entirely in a perfectly restored medieval hilltop village. With a fantastic spa and stunning menus overseen by Gordon Ramsay, Castel Monastero is a must for any Tuscan adventure.

Monteverdi Tuscany

Tuscany, Italy

An exclusive boutique retreat in a restored medieval village above the Val d’Orcia. Monteverdi blends 31 bespoke rooms, three private villas, a world-class spa, fine-dining, culinary academy, art, music and immersive Tuscan experiences.

Borgo Pignano

Volterra, Tuscany, Italy

Cocooned in 750 acres of organic farmlands, landscaped gardens and rolling Tuscan countryside, Borgo Pignano is housed in an 18th century villa, cottages and farmhouses with exceptional views and one of the most picturesque pools imaginable.

La Bandita Townhouse

Pienza, Italy

Escape to Pienza, an idyllic medieval city that is small in size but grand in character. Tucked away amongst its golden-stoned buildings, La Bandita Townhouse is a hip oasis of modern design with exceptional cuisine and a laid back vibe.

Grand Sina Hotel

Siena, Tuscany, Italy

Set in the heart of Siena in a 16th-century palazzo, Grand Hotel Continental Siena offers a luxurious base from which to explore this historical city and the rolling hills of the Tuscan countryside beyond.

Hotel Il Pellicano

Tuscany, Italy

Il Pellicano offers timeless Italian elegance on the Argentario coast with stunning sea views, Michelin-star dining, a private beach, wellness spa, and individually styled rooms and suites for a serene luxury escape.

9 nights

Teens-First Adventures: Classic Italy

Venice, Florence, Tuscany, Rome

From Venice to Rome in ten days. Canals, quad bikes, gladiator VR.

Things to Do in Tuscany

Tuscany holidays are a treasure trove of cultural and historical attractions, making it an ideal destination for those seeking an enriching holiday experience. While everyone knows about exploring cities, like Florence and Pisa, here’s what we recommend for getting under the skin of the Tuscan hills.

Countryside Cooking Classes

Food and wine are integral to the Tuscan experience and indulging in wine and culinary tours is a must.

Explore the renowned Chianti region, where you can sample exquisite wines and enjoy traditional Tuscan dishes prepared by local chefs. Our bespoke culinary experiences allow you to savour the authentic flavours of Tuscany while learning about the region's gastronomic traditions, all tailored to your preferences.
Exclusive Wine Tastings

Tuscan wine is world-renowned, with many villages offering their own bespoke collection and even some luxury Tuscany hotels boasting historic onsite wineries.

The Rosewood Castiglion del Bosco is a 5000-acre estate, and while the list of incredible things here is endless, it’s the critically acclaimed winery that really makes this a staple of Val d’Orcia. Producing the famed Brunello di Montalcino, its wine tours and tastings are some of the best.

All along this region, you’ll find wineries eager to showcase their collection.
Village Hop

The mediaeval towns and villages that dot the Tuscan countryside are one of the main highlights of the region. Truly reminiscent of a time of warring elites and political intrigue, village-hopping and exploring the towns on your holiday in Tuscany is a must.

Montalcino and Montepulciano are quintessential visits in Val d’Orcia and icons of the vibrant wine scene in Tuscany. As well as seeing the towns, enjoy private wine tours of local family-run estates, where you’ll see the multi-generational farms and learn their stories over a glass of Brunello di Montalcino.

Pienza is another town we highly recommend. A UNESCO world heritage site, tour 8th-century abbeys, climb the Tower of Tentennano and wander the streets with a private guide who will teach you the secrets of their historic town.
Explore the outdoors

For those who crave the great outdoors, Tuscany offers a plethora of activities that highlight its stunning landscapes.

Hiking through the rolling hills of the Val d'Orcia or biking along the picturesque vineyards provides a unique perspective of the region's natural beauty. For a truly unforgettable experience, take an e-bike tour with a private guide, where you can witness breathtaking views that will leave you in awe. Visit the thermal baths of Bagno Vignoni and mediaeval villages while you take in the surrounding landscapes.

Countryside Cooking Classes
Exclusive Wine Tastings
Village Hop
Explore the outdoors

Meet Our Specialists

Meet our Italy Experts

Our team of specialists are waiting to help you book your next adventure. Contact us today to start planning your tailor-made trip.

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What is the best time to visit Tuscany?

The best time to visit Tuscany is during the spring (April to June) and autumn (September to October) when the weather is pleasant, and the landscapes are at their most vibrant. These seasons also coincide with fewer tourists, providing a more relaxed and enjoyable experience.

Learn more about the best time to visit Italy.
Are there family-friendly activities in Tuscany?

Yes, Tuscany offers a wide range of family-friendly activities, including visits to historic sites, cooking classes, and outdoor adventures. Our family-friendly accommodations ensure that everyone has a comfortable and enjoyable stay, with amenities such as private pools, interconnecting rooms and spacious outdoor areas.
What is the best area of Tuscany to stay?

When it comes to travelling Tuscany we recommend basing yourself in the countryside, with Val d’Orcia topping our list as well as one of the many Borgo properties, like the Borgo San Felice in the Chianti region, the Borgo Santo Pietro just outside Siena or the Borgo Pignano in Volterra. From here you can take day trips to the bigger cities, or end the trip with a night or two in the capital, Florence.