Tuscany Holidays
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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.
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 – 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.
A Taste of Tuscany
Italy
Fly Drive Holiday
6 days / 5 nights
6 days / 5 nights
From the world-famous art and history of Renaissance Florence to the lyrical landscapes and exquisite wines of rural Tuscany, discover one of Italy’s most enchanting regions on this delightful short break.
The Best of Tuscany & Umbria
Italy
Fly Drive Holiday
13 days / 12 nights
13 days / 12 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.
From Florence to Fiesole
Italy
Multi Centre Holiday
8 days / 7 nights
8 days / 7 nights
Experience a marvellous combination of Tuscany’s cities and countryside on this memorable holiday.
Discover Charming Lucca
Italy
City Break
4 days / 3 nights
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.
Tuscan Family Adventure
Italy
Family Holiday
11 days / 10 nights
11 days / 10 nights
Immerse your family in the culture and history of Florence before driving into the Tuscan countryside for a week in your luxurious villa.
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. Alternatively, if you are looking for some inspiration, give us a call and speak to one of our expert travel consultants?
Click on the tiles below for more details on each area. Alternatively, if you are looking for some inspiration, give us a call and speak to one of our expert travel consultants?
Florence
Explore the prestigious art history, incredible architecture and the gorgeous historic centre.
Lucca
This picturesque city has a rich history exemplified by the well-preserved walls encircling the old town.
Pisa
Aside from the Leaning Tower, Pisa has many other sites.
Rural Tuscany
Rolling hills, castles, medieval villages and vineyards characterise this beautiful area.
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.
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
Tuscany
This lovingly restored 10th Century property sits at the end of a tree-lined driveway, where a tranquil oasis of manicured gardens and renowned Belmond service awaits.
Relais Villa Olmo Food & Wine Resort
Tuscany
Built on the foundations of a 16th Century hamlet, this Tuscan country mansion is nestled amongst undulating hills, fragrant olive groves and vineyards.
Anglo American Hotel, Curio Collection by Hilton
Florence
This historic hotel is only a 10 minute walk from the Firenze Santa Maria Novella train station and just a short distance from the city’s renowned cultural gems including the Ponte Vecchio, Il Duomo and the Uffizi Gallery.
COMO Castello Del Nero
Tuscany
Enveloped by verdant hills and lush vineyards, this sophisticated property is a luxurious sanctuary in the Tuscan countryside.
Hotel Ilaria
Tuscany
Boasting a brilliant location inside the old Renaissance walls of Lucca, Hotel Ilaria welcomes you warmly to this charming town.
Grand Hotel Continental, Siena
Tuscany
Experience traditional luxury in this exquisitely renovated 17th Century palace in the heart of Siena.
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.
Our collection of unmissable experiences will really help bring your Tuscany holiday to life.
Tuscan Wine and Cheese from Florence
9 hours
- Enjoy wine, extra-virgin olive oil and cheese tasting
- 9 samples of wine
- 3 course meal at a Tuscan winery restaurant
Brunello di Montalcino Wine Tasting Tour
9 hours
- Explore Brunello di Montalcino wine cellars
- Learn about the wine-making process from your expert guide
- Visit three wineries and enjoy a Brunello di Montalcino wine tasting at each one
- Enjoy a walk through Tuscany’s lovely town of Montalcino and the mystical abbey of Sant'Antimo
- Savor a delicious Tuscan lunch at a family-run winery
Siena Duomo Skip the Line & City Walking Tour
2 hours
- Visit Siena's UNESCO World Heritage-listed Old Town
- Discover top Siena attractions, such as the Basilica of San Domenico and Piazza del Campo
- Enjoy skip-the-line entrance to the Siena Duomo
Tales from the Trail
Top tips and travel inspiration from the Trailfinders team
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