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
- 24/7 seamless support
- 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.
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.
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Little Adventurers in Italy
Rome, Florence, Tuscany, Lake Garda, Venice
Experience Italy’s highlights as a family, from Rome’s wonders and Florence’s art to Tuscany’s countryside and Lake Garda’s fun—ending in magical Venice, with family-friendly hotels and engaging activities delivering memorable moments for all ages.
SGD $14,400 pp
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Best of Italy
Rome, Tuscany, Florence
Experience the very best of central Italy on this immersive journey through Rome, Tuscany, and Florence. From the grandeur of ancient Rome and the treasures of the Vatican to the rolling hills and culinary delights of Tuscany, and finally the Renaissance splendour of Florence, this itinerary blends cultural exploration, authentic local experiences, and luxurious comfort.
SGD $17,600 pp
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Wild Encounters: Italy
Volterra, Porto Ercole, Rome, Sorrento
Experience Italy like never before with this 12-day journey through its most enchanting natural landscapes, from the rolling Tuscan hills to the sparkling waters of the Amalfi Coast. This itinerary has been crafted for travellers seeking an immersive connection with wildlife, flora, and the environment, alongside luxurious accommodations and curated cultural encounters.
SGD $23,900 pp
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The Flavour Trail: Emilia Romagna & Tuscany
Emilia Romagna, Tuscany, Italy
Discover Italy’s culinary and cultural gems from Milan to Tuscany. Stay in elegant retreats, enjoy exclusive tastings of Parmigiano, balsamic, and Chianti Classico wines, experience Ferrari thrills, and savour Michelin-starred dining. An intimate journey crafted for gastronomes and culture lovers.
SGD $13,600 pp
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Ultimate French & Italian Riviera Road Trip
Cannes, Côte D'Azur, Monaco, Cap-Martin, Portofino, Lake Como, France, Italy
Embark on the Ultimate French & Italian Riviera Road Trip, a bespoke self-drive itinerary that takes you on a journey through the most glamorous destinations of the Riviera. Over the course of 12 nights, you'll experience the iconic charm of Cannes, the elegance of Monaco, the beauty of Portofino, and the serenity of Lake Como.
SGD $17,400 pp
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Perfect Pairings: Rome & Umbria
Italy
Lose yourself in the artistic secrets of Rome and Umbria on this dual Italy tour. Skip the crowds in Rome to soak up the wonder of the Vatican Museums and the hidden secrets of the Baroque centre. Submerge yourself in the beauty of the Umbrian countryside, take in the wonder of Assisi and meet expert artisan crafters.
SGD $17,200 pp
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Perfect Pairings: Florence & Rural Tuscany
Italy
Bespoke private experiences and sublime boutique retreats showcase Italy's beauty on this indulgent tour. Revel in the glorious beauty and culinary delights of Florence with your personal Michelin-starred chef cooking session. Immerse yourself in the idyllic Tuscan countryside with exclusive vintage wine tastings and truffle hunting.
SGD $15,900 pp
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.
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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.
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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.
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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.
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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
FAQs about Tuscany Holidays
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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.
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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.
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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.
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