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Tuscany Holidays

In Tuscany holidays are the perfect balance of country and city; day trips to Florence or Pisa coupled with lounging poolside at your villa with a view. This is quintessential Italy with feasts for both eyes and palate.

Find your perfect Tuscany holiday

Tuscany holidays are about a regional lifestyle and is arguably the greatest lure for travellers seeking holidays in this fabulous region with villa-living being the ideal. The Tuscans seem to have found a perfect balance between country and city living. As well as pampering in olive oil treatments and wallowing in hot springs, you can enjoy pasta feasts, and the views of the gorgeous rolling countryside of Tuscany. Holidays to the region should include visits to the notable cities of art, such as Florence, Siena, Lucca, Pisa and Arezzo and the Etruscan sites around Volterra, Chiusi and Pitigliano.


Tuscany holidays must include a visit to Florence, one of Italy’s top three destinations. It’s a remarkable city with a celebrated past that lives on in this well preserved city. A Renaissance Florentine standing in Piazza della Signoria would know exactly where he was, even today. Many of the buildings are either unchanged or echo those of the Renaissance city, despite today’s designer-clad Florentines sipping aperitivi at Rivoire.

Nearby, the Palazzo Vecchio has been the emblem of Florentine power since the 14th century. The square is adorned with a statue of Michelangelo’s David, but be sure to visit the original in the Accademia gallery. Walk up to Piazzale Michelangelo for yet another copy of David, and the finest sunset views. Apart from the great art treasures on show in the Uffizi Gallery and the Pitti Palace, Florence province offers peace and quiet in Fiesole, or in vine-clad Chianti country.


Siena, which is the counterpoint to Florence, is as medieval as Florence is Renaissance. This compact, pink-tinged city is a delight to explore, from the shell-shaped Campo to the galleries full of soft-eyed Sienese Madonna’s. Holidays in Tuscany are inevitably filled with views of gardens and natural areas that have been landscaped since time immemorial, with the Val d’Orcia, south of Siena, representing quintessential Tuscany. The harmonious landscape reveals clusters of cypresses, ribbons of plane trees, vineyards on the slopes and lone farms perched on limestone ridges. This is the landscape of the Tuscany holidays we all dream of.

The Tuscan city of Lucca

The Tuscan city of Lucca

Rugged Terrain

Closer towards the Emilian border the Tuscan terrain becomes more rugged, made even more dramatic by deep green forests. Michelangelo’s marble quarries of Carrara which make a fascinating half day visit,and the Apuan Alps around Garfagnana will easily claim the second half of a day. Towards Umbria, Tuscany’s drama melds into landscapes of hazy green hills.


The wide sandy beaches of Tuscany make for excellent very Italian beach holidays with well organised lido’s with lines of loungers and parasols. Tuscany’s coast, the beaches surpass those on the Adriatic coast, whether in the resort of Viareggio, Forte dei Marmi or in the wilder Maremma, south of Pisa, bordering Lazio.  If Forte dei Marmi is for socialising and being seen, the Maremma is for nature-lovers and families.

There are many beautiful areas with beach and swimming opportunities in Tuscany. Holidays located near beach resorts offer an extremely varied experience. Choose from the wild Maremma, or the lively island of Elba, chic Punta Ala and Porto Santo Stefano, or glamorous Forte dei Marmi, where Florentines retreat for designer shopping and smart seafood restaurants.


Of course, you’ll visit Pisa! The city celebrated for its Leaning Tower (which British engineers have helped stabilise!) but the whole Campo dei Miracoli area around the Tower deserves attention for its Pisan-Romanesque architecture. Out of town, Bagni di Pisa is a romantic 18th-century spa resort with a view of the Leaning Tower. Tuscan spas are among Italy’s finest and may date 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. The Florentine fashion industry predates the Renaissance. What’s more, Gucci, Pucci and Ferragamo launched their empires from here. If you tire of art and fashion, plunge into San Lorenzo market for leather, silk scarves and ‘marbled’ paper. Or cross the river to the Oltrarno district, where the crafts tradition is still thriving, The Florentines have been goldsmiths since the Middle Ages and the remaining workshops line the quaint Ponte Vecchio.

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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