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Tuscany Holidays

In Tuscany, holidays are the perfect balance of country and city; day trips to Florence or Pisa and lounging poolside at your villa with jaw-dropping views of vineyards and rolling hillsides. This is quintessential Italy with a feast for both eyes and palate.

Find your perfect Tuscany holiday

Florence – Tuscany holidays must include a visit to Florence, one of Italy’s top three destinations. It’s a remarkable city with a celebrated past. Many of the buildings maintain their Renaissance charm, though the city has also become very cosmopolitan. Visitors come to Florence for its incredible fashion and art – from the iconic statue of Michelangelo’s David just outside the Palazzo Vecchio, to the great treasures on show in the Uffizi Gallery.

Pisa – Of course, you’ll visit Pisa! The city celebrated for its Leaning Tower. The Campo dei Miracoli area around the Tower has dramatic Pisan-Romanesque architecture. Stay at the Bagni di Pisa, a romantic 18th-century spa resort with a view of the Leaning Tower.

The leaning tower of Pisa in Tuscany, Italy

The leaning tower of Pisa in Tuscany, Italy

Siena – Siena is as medieval as Florence is Renaissance. It is a delight to explore, from the main square to the galleries full of masterpieces. The Val d’Orcia, south of Siena, represents quintessential Tuscany, with clusters of cypresses and sloping vineyards. Towards Umbria, Tuscany’s dramatic hillsides meld into hazy green hills. This is the Tuscany landscape we all dream of.

Beaches – The wide sandy beaches of Tuscany make for excellent Italian beach holidays.  On Tuscany’s coast, the beaches surpass those on the Adriatic coast. Choose from the lively island of Elba, chic Punta Ala and Porto Santo Stefano, or glamorous Forte dei Marmi, where Florentines retreat for designer shopping and lovely seafood restaurants.

Tuscan Spas – Tuscan spas are among Italy’s finest, dating back to Etruscan or Roman times. Spas such as Grotta Giusti, in Monsummano Terme, combine gracious 19th-century living with thermal pools and steamy grottoes dubbed ‘the eighth wonder of the world’ by Giuseppe Verdi.

Holidays in Tuscany are among Italy’s most appealing and popular. The region’s mix of shopping and sightseeing make days pass by too fast.

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Top Tips


The Avignonesi estate near Cortona has the best Vino Nobile da Montepulciano - you can also tour the estate.
Tip from Italian Country Cottages

For the best small producer of wine and olive oil in the Chianti, try Casanuova di Ama just 10 minutes by road from Radda in Chianti. Run by the Bencini family, they produce 4 different red wine varieties (including Chianti Classico), a white wine variety and the dessert wine Vin Santo. Wine tasting during your Tuscany holidays is a very unique and authentic experience. Just turn up, the owners will be delighted to see you.

Where to eat

To sample the true 'Tagliata' go to “Il gatto e la volpe” in the centre of Grosseto. Very reasonable prices too. Visit the butcher shop/restaurant of Dario Cecchini: The Singing Butcher of Panzano in Chianti who pays homage to all things beef.
Tip from Headwater Holidays

The best place in the world (allegedly) to buy cantuccini biscuits has to be the Biscottificio Antonio Mattei in Prato town centre, via Ricasoli 20. An absolutely wonderful selection of sweets traditionally crafted, including the famous almond cantuccini should be sampled during your holidays in Tuscany.

What to see

Visit the Tuscany gardens of the Villa Medici (Florence) and then visit the Villa San Michele. Sip a glass of prosecco from the terrace, the cost of which will be almost as breathtaking as the setting, (it's a five-star hotel in a palazzo designed by Michelangelo), but together they're worth every centessimo.
Tip from Tuscany Now

There are eleven villages or towns named San Casciano in Italy, (three are in Tuscany alone). Fortunately most of them have a descriptive snippet tacked on. San Casciano in Val di Pesa is the one in the Pesa Valley, San Casciano di Bagni is known for its thermal baths. In every region there is Castiglione del Lago a village that grew up around a castle on a lake.
Tip from Tuscany Now

Visit La Foce on Wednesday mornings in Chiangiano Terme. Designed by Cecil Pinsent it is one of Tuscany's great gardens made for Iris Origo, author of 'The Merchant of Prato.
Tip from Italian Country Cottages

Great views can be enjoyed during your Tuscany holidays from the terrace of Fellini's favourite drinking hole at Poliziano's in Montepulciano.
Tip from Italian Country Cottages

The upper nave of Siena Cathedral can now be visited. Check the great views of the peppermint-like interior.
Tip from Italian Country Cottages

Visit the Vasarian Corridor in Florence (Corridoio Vasariano) – it's the 1km long corridor the Medici used to go from the Palazzo Vecchio to the Uffizi and the Palazzo Pitti.
Tip from Headwater Holidays.

Visit Il Giardino dei Tarocchi near Capalbio in the South. The 'Tarot Garden' may be loosely described as a gigantic art installation but it is rather unique. French artist Niki de Saint-Phalle took 17 years to build this collection of towering Tarot figures that you can walk through, on and around.

There are many activities available to amuse the kids during your holidays. In Tuscany, be sure to visit Parco Arcominerario di San Silvestro near Campiglia Marittima. This unusual attraction offers a funny, interesting and unique exploration of a Tuscan mine. The tour also includes explanations of the mining and metallurgical cycle, the mining tunnels, a walk into a medieval village of miners and a trip on the underground train too.
Tips from Tuscany Now

Shopping in Florence

Holidays in Tuscany would not be complete without at least one shopping excursion so follow your nose to the Officina Santa Maria Novella, on Via della Scala, where the Dominicans created an apothecary shop in 1221. In time, this frescoed gem has become an artisanal perfumery, the place for sultry scents and potions that will linger in your memory long after you leave Florence.

Visit the Salvatore Ferragamo Shoe Museum in Florence. Salvatore Ferragamo, the shoemaking founder of the Ferragamo fashion dynasty was the first celebrity shoemaker, making shoes for film stars and royalty, as well as for the mistresses of Hitler and Mussolini. The Ferragamo's palace can be found in Via Tornabuoni.

The Florence Card

The Florence Card (50 euros) may not save much money but it saves you the hassle of making reservations for the top sights (Uffizi and Accademia galleries), and allows you to bypass the long lines during your holidays. In Tuscany the card covers most sights, and free use of city buses for 72 hours.

Sat Navs can be a tremendous help in Tuscany. Holidays that include a car rental allows you to see much more of the countryside and many rentals have Sat Nav on board. A key shortcoming of navigators is that they may overlook the restricted traffic areas within the medieval towns, called ZT L or Zona Traffico Limitato. They're clearly marked and rigorously monitored by cameras. Ignore the signs and your car hire company will eventually send you a ticket for 200 Euros or more.
Tip from Tuscany Now