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 with Scott Dunn.

Curated collection of luxury hotels and vineyard estates
Tailor-made holidays designed around you
Private countryside touring and local experiences
24/7 seamless support

Scattered with villas, farmhouses and historic estates, Tuscany is a sight of awe with its olive groves, cypress-lined roads, vineyards and rolling hills. Tuscany has one of the most famous repositories of art in the world, from the Renaissance art and architecture of Florence to centuries-old hilltop towns such as Siena and Pienza.

Beyond the scenery, Tuscany is a region to experience slowly. Visit Chianti wine estates, learn traditional Tuscan recipes with local cooks and discover artisan workshops before returning to the privacy of a countryside estate or vineyard retreat.

If you’re a traveller in search of art, history, wildlife, fine wine and cuisine, then a luxury Tuscany holiday is for you. Our specialists will match you with the right luxury countryside stay, arrange private-guided experiences and seamlessly combine Tuscany with Florence, Rome or other destinations across Italy.

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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020 8682 5040

Why Visit Tuscany?

Tuscany rewards travellers with rolling vineyards and hilltop towns where Renaissance art, centuries-old wine estates and family-run trattorias all sit within easy reach of one another. It's a region best explored unhurried, whether that means tracing Chianti's back roads by day or lingering over a long dinner of wild boar pappardelle by candlelight. Tuscany suits couples after a romantic escape, families wanting culture alongside countryside adventure, and food and wine lovers keen to learn from the people who grow, cook and pour it.

Tuscan Food & Wine Culture
Luxury Countryside Living
Hilltop Towns & Heritage

Tuscan Food & Wine Culture

Embark on your dream Tuscany wine holiday, from the vineyards of Chianti to homecooked meals from family recipes passed down through generations.

Tour Tuscany's wine estates – Travel through Chianti and visit historic cellars before visiting celebrated wine towns such as Montalcino and Montepulciano.
Take a Tuscan cooking class – Join a private class at a local farm and prepare regional dishes using traditional techniques and seasonal ingredients.
Behind-the-scenes on Tuscan ingredients – Forage for truffles in the countryside or visit a dairy farm in Val d'Orcia to learn how local cheeses are made.

Luxury Countryside Living

Experience the Tuscan countryside on your holiday, from exploring the region in depth to including it in a multi-centre journey through Italy.

Florence to Siena family holiday – Road trip from Florence into the Chianti Hills and onward to Siena on a multi-centre Tuscany holiday.
Milan to Tuscany food holiday – Taste your way south through Milan, Bologna and Florence before reaching Tuscany for Chianti Classico wines.
Stay in fully restored Tuscany estates – Relax among the Chianti vineyards at Borgo San Felice or stay in central Siena at Grand Hotel Continental for historic city-centre base.

Hilltop Towns & Heritage

Tuscany's hilltop towns let you access centuries of art, architecture and rural traditions in the heart of the countryside.

Follow the Val d’Orcia route – Take the scenic roads between Pienza and Montalcino, passing cypress-lined hills and historic villages along the way.
Guided tour of Renaissance towns – Explore Tuscany's small villages and explore their Renaissance architecture with a private guide.
Adventure on the Tuscan coast -  Ride on horseback through Maremma Regional Park or explore the waters around Monte Argentario by private boat.

Luxury Hotels & Tailor-made Itineraries for Tuscany

At Scott Dunn, we specialise in matching you with the right countryside hotel or wine estate for your holiday. Stay among the Chianti Classico vineyards at Borgo San Felice, where Scott Dunn guests can enjoy a complimentary vineyard experience, or settle into a private villa at Monteverdi Tuscany, set within a restored mediaeval village.

Where you stay in Tuscany just a part of your tailor-made journey through Italy. Our suggested itineraries below are for inspiration, with every detail customisable to how you like to travel.

Experiences
Properties
Itineraries

Conscious Cuisine: Wine Estate San Felice

Tuscany, Italy

An Exclusive experience at Borgo San Felice: A guided one-hour vineyard and wine-tasting experience showcasing the Sangiovese grape through three estate-produced wines, paired with chef-prepared canapés.

Wine tasting and lunch in Chianti

Tuscany, Italy

Journey through Chianti’s rolling hills to two renowned wineries. Enjoy guided tastings, a private cellar visit, and a relaxed wine-paired lunch—all set against the breathtaking backdrop of Tuscany’s vineyards and olive groves.

Golf & Wine Experience at Castiglion del Bosco

Tuscany, Italy

A refined golf and wine experience at Castiglion del Bosco, pairing Tom Weiskopf’s signature course with iconic wines, gourmet bites and sweeping Tuscan views.

Forest bathing in Castelvecchio Reserve

Tuscany, Italy

A slow, mindful walk through Castelvecchio Reserve with forest-bathing expert. Immerse in nature's sights and sounds. Afterwards journal, sketch, reflect deeply to connect with experience.

Quad bike across Tuscany

Tuscany, Italy

An adrenaline pumping adventure across rugged trails and rolling Tuscan hills. Navigate dirt paths through vineyards, olive groves, medieval villages. Stunning landscape from thrilling new perspective.

Meet with local pecorino cheese maker in Val d'Orcia

Tuscany, Italy

Soak up the wonderful atmosphere of daily family life on a this wonderful cheese farm, meet the animals, observe the production and taste a gourmet display of local cheeses.

Tuscan cooking class

Tuscany, Italy

Discover the art of Tuscan cuisine with a private cooking class at a local farm. Under the guidance of a local cook, you'll learn how to prepare traditional recipes and then enjoy your dishes for lunch.

Cooking classes at La Canonica

Tuscany, Italy

Learn how to make some of Tuscany's classic dishes at La Canonica cooking school at Castiglion del Bosco, alongside expert chefs who will guide you in the art of creating authentic Tuscan cuisine.

Truffle hunting at Borgo Pignano

Tuscany, Italy

Explore the forests of Borgo Pignano's estate with your experienced truffle hunter and their dog, searching for renowned Tuscan truffles, and discover the unique skills required to find these famous treasures.

Tuscan cookery lesson at Borgo Santo Pietro

Tuscany, Italy

Spend a fun and informative day learning about the regional specialities of Tuscany. Test your cooking skills and choose from a variety of classic Italian dishes to attempt for yourself under the tutelage of a skilful chef.

Wine Tours of Tuscany

Tuscany, Italy

Discover first hand the reason Italian wines have become some of the most well known and best loved wines in the world.

Wine Tasting at Borgo Pignano

Tuscany, Italy

Enjoy a wine tasting session in Borgo Pignano's medieval wine cellar, where you'll have the opportunity to taste a selection of local organic wines, as well as those produced on the estate.

Borgo San Felice

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 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.

The Sense Experience Resort

Tuscany, Italy

A refined eco-luxury retreat in Tuscany’s Maremma, The Sense Experience Resort blends beachfront living and gourmet dining with sustainable design, serene rooms, and immersive experiences in nature for a truly unforgettable coastal escape.

Castelfalfi

Tuscany, Italy

A beautifully restored Tuscan estate between Florence and Pisa, Castelfalfi combines a medieval borgo, 146 stylish rooms and suites, superb spa, golf and pools, plus outstanding Tuscan dining amid vineyards and olive groves.

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.

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.

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.

Rosewood Castiglion del Bosco

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.

Belmond 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.

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.

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.

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 San Felice Italy
Borgo Pignano Italy
The Sense Experience Resort Italy
Castelfalfi Italy
Borgo Santo Pietro Italy
Hotel Il Pellicano Italy
COMO Castello del Nero Italy
Rosewood Castiglion del Bosco Italy
Belmond Castello di Casole Italy
Castel Monastero Italy
Castello di Reschio Italy
Monteverdi Tuscany Italy

9 nights

Iconic 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.

From

£9,200 pp^*

13 nights

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.

From

£8,000 pp^*

11 nights

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.

From

£13,200 pp^*

8 nights

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.

From

£7,500 pp^*

5 nights

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.

From

£9,400 pp^*

9 nights

Teens-First Adventures: Classic Italy

Venice, Florence, Tuscany & Rome

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

5 nights

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.

From

£8,700 pp^*

Tuscany’s Most Beautiful Historic Towns

Explore the historic towns, cuisine, wine and landscapes that define the Tuscan countryside.

Siena

Set between the Val d'Elsa and Crete Senesi, Siena has preserved much of the mediaeval character that defined its 13th-century golden age. Spend time in Piazza del Campo, visit the art-filled Palazzo Pubblico and admire the intricate mosaic floor of Siena Cathedral, or come in July or August when the Palio horse race transforms the city. We can also take you into neighbouring Chianti for private wine tastings and time on historic estates.
San Gimignano

San Gimignano rises above the Elsa Valley with a skyline of mediaeval stone towers, 14 of the original 72 still standing today. Walk its historic streets and climb higher for views across the Tuscan countryside, then taste Vernaccia di San Gimignano, the local white wine known for its distinctive character. Scott Dunn can include the town as a private day trip between Florence and Siena or as part of a longer Tuscany journey.
Cortona

Rising above the countryside of eastern Tuscany, Cortona is a hilltop town of stone streets, Renaissance palaces and far-reaching views towards the Val di Chiana. Explore Piazza Signorelli and the MAEC museum, climb to the Medici-built Fortezza del Girifalco or settle in for a dinner of hearty Tuscan dishes such as pasta with wild boar. Scott Dunn can weave Cortona into a private journey through the quieter towns of eastern Tuscany.
Lucca

Encircled by remarkably intact 16th-century walls, Lucca offers a relaxed way to experience Tuscany's long history. Walk or cycle along the ramparts before visiting the Cathedral of San Martino, where works include Tintoretto's Last Supper, or discover the city's musical connection at the Puccini Museum. We can also combine Lucca with nearby Pietrasanta and the Tuscan coast for a Tuscany beach holiday.
Pienza & Volterra

Pienza sits among the rolling hills of Val d'Orcia and to many is one of the best Renaissance towns in Italy. We recommend having a private guide lead you through its Renaissance square and the gardens of Palazzo Piccolomini to drink in the history and beauty of this town. Further north, Volterra takes you back to Tuscany's Etruscan and Roman heritage where you can pass through its ancient theatre, Romanesque Volterra Cathedral and mediaeval Piazza dei Priori. Scott Dunn can bring both into a tailor-made Tuscany countryside holiday alongside private touring and boutique stays.

Siena
San Gimignano
Cortona
Lucca
Pienza & Volterra

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.
Is Tuscany good for families?

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 to stay in Tuscany?

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.
What are the best towns to visit in Tuscany?

Some of the best towns to visit in Tuscany include Siena, San Gimignano, Lucca, Cortona, Pienza and Volterra. Each town shows you a different side of Tuscany, from Siena's mediaeval piazzas and San Gimignano's towers to the Renaissance streets of Pienza and slower pace of Lucca.
Can Scott Dunn arrange private wine tours in Tuscany?

Scott Dunn can arrange private wine tours and holidays, including visits to estates in Chianti Classico, Montalcino and Montepulciano. We can build tastings, vineyard visits and time with local producers into a wider tailor-made Tuscany itinerary.