Luxury Tuscany Vacations

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

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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 square miles, roughly the same size as the state of New Jersey. A region in central Italy, Tuscany borders Liguria 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 traveler in search of art, history, wildlife, fine wine and cuisine, then a luxury Tuscany tour is for you. Enquire today and see what your custom-made trip could look like with Scott Dunn.

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Things to Do in Tuscany

Tuscany vacations are a treasure trove of cultural and historical attractions, making it an ideal destination for those seeking an enriching 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 personalized culinary experiences allow you to savor the authentic flavors of Tuscany while learning about the region's gastronomic traditions, all customized to your preferences.
Exclusive Wine Tastings

Tuscan wine is world-renowned, with many villages offering their own personalized 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 medieval 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 vacation 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 medieval villages while you take in the surrounding landscapes.

Countryside Cooking Classes
Exclusive Wine Tastings
Village Hop
Explore the outdoors

Meet Our Specialists

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Our team of specialists are waiting to help you book your next adventure. Contact us today to start planning your personalized 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 traveling 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.