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A villa at dawn in the beautiful landscape of Tuscany, Italy.

Tuscany Holidays


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Tuscany holidays invite visitors to discover one of Italy’s most delightful regions. Explore the area while admiring the fairytale countryside of rural Tuscany, alongside mouthwatering cuisine.

With graceful rolling hills, historic towns like Siena and San Gimignano, lush vineyards and fertile olive groves, Tuscany’s lyrical beauty is renowned. It is also home to some of the finest wineries in the world, including the famous Chianti region.

Whether you're sipping a glass of delicious local wine, wandering through the ancient streets, or soaking up the warm Tuscan sun, every moment on a holiday in Tuscany feels like a dream.

Trailfinders offers a range of Tuscany holidays and our expert travel consultants are a mine of information about what to do here, often with first-hand travel experience. Whether you are looking to drive through the beguiling Tuscan countryside or simply relax in a luxurious villa – they are the perfect people to ask.
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OUR HOLIDAYS TO TUSCANY

Here’s a snapshot of some of our most popular Tuscany holidays. If you don’t see what you’re looking for, click on the link below them to see our complete range of holidays and tours in the destination.
Tuscany & Umbria Adventure
Tuscany & Umbria Adventure
Fly Drive Holiday
14 days / 13 nights

From legendary historic landmarks to rolling hills of lush vineyards and freshly made pasta, explore the best of Italian culture, countryside and cuisine on this incredible fly drive holiday.

Guide Price: €3,099 £Please contact us pp

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Walking in Tuscany
Walking in Tuscany
Guided Small Group Walking Tour
8 days / 7 nights

This lesser known corner of Tuscany is an excellent area for walking.

Guide Price: €2,349 £1,849 pp

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Discover Charming Lucca
Discover Charming Lucca
City Break
4 days / 3 nights

Showcasing its ancient Roman history, fairytale-like Lucca is one of the many treasures of Tuscany with towering Renaissance walls in the shadows of the Apuan Alps.

Guide Price: €799 £549 pp

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Tuscany Family Journey
Tuscany Family Journey
Family Holiday
12 days / 11 nights

Immerse your family in the culture and history of Florence before driving into the Tuscan countryside for a week in your luxurious villa.

Guide Price: €3,249 £Please contact us pp

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Best of Italy
Best of Italy
Guided Small Group Adventure Tour
14 days / 13 nights

The enduring phrase ‘la dolce vita’ (the good life) truly captures the essence of Italy.

Guide Price: €2554 £2255 pp

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Tuscany to the Amalfi Coast: Italy by Land & Sea
Tuscany to the Amalfi Coast: Italy by Land & Sea
Guided Small Group Adventure Tour
13 days / 12 nights

Italy’s greatest hits — and its best-kept secrets.

Guide Price: €3679 £3179 pp

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View all our holidays in Italy

WHERE TO GO IN TUSCANY

Each area of Tuscany boasts its own attractions and it is no exaggeration to say each merits a holiday in its own right.

Click on the tiles below for more details on each area of Tuscany. Alternatively, if you are looking for some inspiration, give us a call and speak to one of our expert travel consultants.
Florence
Florence
Explore the prestigious art history, incredible architecture and the gorgeous historic centre.
Lucca
Lucca
This picturesque city has a rich history exemplified by the well-preserved walls encircling the old town.
Pisa
Pisa
Aside from the Leaning Tower, Pisa has many other sites.
Rural Tuscany
Rural Tuscany
Rolling hills, castles, medieval villages and vineyards characterise this beautiful area. There is exquisite food, interesting history and wonderful scenery ready to be discovered.
Siena
Siena
Full of charm, Siena offers impressive medieval architecture, historic streets and excellent local cuisine.

OUR RECOMMENDED HOTELS IN TUSCANY

We feature a great range of accommodation across Tuscany, with something to suit all budgets. Stay in a beautifully restored boutique property with magnificent views or opt for a gorgeous property within a short drive of Florence.

What you won’t find here are thousands of Tuscany hotels to wade through. We have done the hard work for you and selected the best places to stay and our travel consultants are on hand to help, often with first-hand experience.
Castello di Casole, A Belmond Hotel
Castello di Casole, A Belmond Hotel
5 star

Tuscany

This lovingly restored 10th Century property sits at the end of a tree-lined driveway in the heart of Tuscany, where a tranquil oasis of manicured gardens, astonishing outdoor beauty and renowned Belmond service awaits.
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The Sense Experience Resort
The Sense Experience Resort
4 star

Tuscany

Nestled between a verdant pine forest and gorgeous crystal clear waters in the heart of the Tuscan Maremma, this property is a wonderful place to unwind.
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Anglo American Hotel, Curio Collection by Hilton
Anglo American Hotel, Curio Collection by Hilton
5 star

Florence

This historic hotel is conveniently located just a short walk from the train station and major attractions.
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Palazzo Feroci
Palazzo Feroci
4 star

Pisa

Once an aristocratic palace belonging to the Medici family, Palazzo Feroci has been renovated with elegance and style and boasts a strategic location in the heart of the city.
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Hotel Ilaria
Hotel Ilaria
4 star

Lucca

Boasting an enviable location within the old Renaissance walls of Lucca, this charming hotel sets you just steps away from a labyrinth of cobblestone streets lined with squares, cafés and restaurants.
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Grand Hotel Continental, Siena
Grand Hotel Continental, Siena
5 star

Siena

Experience traditional luxury in this exquisitely renovated 17th Century palace in Siena.
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View all our hotels in Tuscany

WHAT TO DO IN TUSCANY

As well as some awe-inspiring sights, Tuscany is also home to unforgettable experiences. These provide a unique insight into the culture that sightseeing alone simply can’t replace.

Our collection of unmissable experiences will really help bring your Tuscany holiday to life.
Tuscan Wine and Cheese from Florence
Tuscan Wine and Cheese from Florence
9 hours
Departs: Florence

Feast your eyes and your tastebuds on the joys of Tuscany! Head off-road on a 4WD journey through ...

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Brunello di Montalcino Wine Tasting Tour
Brunello di Montalcino Wine Tasting Tour
9 hours
Departs: Siena

What could be better than a day spent sipping some of Italy’s finest wines? Your expert guide will ...

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Siena Duomo Skip the Line & City Walking Tour
Siena Duomo Skip the Line & City Walking Tour
2 hours
Departs: Tuscany

The historic centre of Siena, a UNESCO World Heritage Site is a delight to explore on foot with its ...

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Tuscany Top Tips From Our Travel Experts

Faye O'Neill - expert
Faye O'Neill

I would highly recommend Fiesole as a wonderful twin centre holiday paired with Florence for those who don't have time for a big Tuscan villa holiday, as it is only 20 minutes outside of Florence, in a secluded and peaceful hill-top location.


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