48 hours in . . . Tuscany, an insider guide to Italy’s most seductive setting

Slow food, spas and spectacular hill towns

Cities bursting with priceless art? Florence, Lucca, and Siena fit the bill. Spectacular hill towns with gentle rhythms and sweet piazzas? Bagno Vignoni, Monteriggioni and Massa Marittima are only the start of a list of villages that will steal your heart. Add in top notch-spas focusing on local treatments alongside natural thermal waters, outdoor pursuits from trekking to mountain biking, and tucked away beaches for gentle swims to see why healthy types love the region.

Restaurants exemplify the Italian-invented slow food movement, and eating a bistecca alla Fiorentina or pici with truffles, alongside a Brunello or Super Tuscan wine is a wonderful education in the ingredients of this fertile area. For sybarites, sexy, one-of-a-kind hotels draw fans with infinity pools, custom beds, and wicked views over the unspoiled landscape. The mix of natural beauty and manmade pleasures makes it clear why Tuscany is arguably Italy’s most compelling destination – and a repeat visitor’s dream.

Ondine Cohane, our destination expert, offers her top tips on the hottest things to do and places to eat and drink this season. 

Eat

The best of Italy’s beach clubs include a great bar and restaurant, their own patch of lovely beach and sea, comfy sea loungers, and ooze style to boot. Rosso e Vino alla Doganae (Via Graticciaia, Chiarone Scalo; 00 39 0564 890344) gets top marks for all of the above, and its spaghetti alle vongole draws locals and insiders.

• The best restaurants in Tuscany

Drink

Poggio ai Santi, close to San Vincenzo, and not far from Bolgheri (one of my favorite wine towns), gets my vote for their pretty rooms, excellent restaurant, and jaw-dropping views. Now the owners have also added an aperitivo bar, Il Sale (Via San Bartolo, 100; 00 39 0565 798032), to add more sex appeal. Pick classics such as a Negroni, or choose an experimental cocktail concocted from the estate’s foraged herbs. While you sip take in that vast panoramic view stretching to the sea.

• The best hotels in Tuscany

Do

Make tracks for Maremma’s Regional Park (Via del Bersagliere, 7/9; 00 39 0564 393238). Formerly the playground of Tuscany’s Grand Duke, nowadays insiders can find stretches of pristine beach dotted with majestic pine trees and trails where the only companions are an occasional boar or deer. Best of all? The number of visitors is limited so it never gets too busy.

• The best attractions in Tuscany

Day one

MORNING

Breakfast in Italy usually involves just an espresso and cornetto but at Siena’s Bar Pasticerria Nannini (Via Banchi di Sopra, 24; 00 39 0577 236 009), both are done with aplomb. Join locals at the marble bar and sample their ricarelli (almond biscuits), a city specialty done particularly well here. Afterwards browse shops such as Dolci Trame (Via Pantaneto, 27; 00 39 0577 550 763) with its wonderful selection of Italian and international designers, and pick up local cheese or salami at Antica Pizzicheria, also known as De Miccoli (Via della Citta, 95; 00 39 0577 289 164).

Even without the Palio, the city’s twice a summer bareback horse race, Siena’s main square, the Piazza del Campo, is one of the most beautiful in Italy. Surrounded by cafés and restaurants, have a midmorning coffee at spots like Bar Il Palio (Piazza Il Campo, 47; 00 39 0577 282055), and take in the tableau of children, dogs and other tourists exploring the wide piazza in front.

Rather like a Medieval Stairmaster, the Torre del Mangia has hundreds of steps, but it’s worth the climb for its panoramic vistas over the city and the surrounding countryside. Lunch will be at Osteria Le Logge (Via del Porrione, 33; 00 39 0577 480 13) right off the Campo. It’s a legend for good reason: housed in a former pharmacy, it’s one of the best restaurants in town and has an encyclopedic wine list. Pick a seasonal special such as ravioli with pumpkin and be sure to ask for a table downstairs when you book — the dining room upstairs feels like an afterthought.

AFTERNOON

Siena has many charming cities in its periphery but Monteriggioni is one of its true gems. Still surrounded by intact watch towers the small, wall-enclosed village gives one a quick education in the legacy of fortified hill towns. Alternatively, the Abbey of Galgano (Strada Comunale di S. Galgano; 00 39 0577 756738) is one of Italy’s most spectacular; the building no longer has a roof and the view up to the sky is, well, a spiritual experience. The site is also the setting for a series of outdoor summer opera. 

Winding north your next step should be a dip into one of Tuscany’s natural thermal baths. Try one out in Bagno Vignoni where you can also get a massage at the Adler Thermae (Strada di Bagno Vignoni, 1; 00 39 0577 889 001), or in one of the free options right outside the historic centre. Afterwards grab an Aperol spritz in the main piazza at Albergo Le Therme (Piazza delle Sorgenti; 00 39 0577 887 150); you can also while away a few hours in its private pools pre-cocktail.

LATE

Unesco-protected Pienza is still considered ‘the Ideal City,’ a moniker it won after architect il Rossellino conceived its Renaissance main square under the patronage of the then pope Pio II (he was from the small town). After exploring the main square take in the views at Bar Il Casello (Via del Casello, 3: 00 39 0578 749 105) with epic sunset views onto the Val d’Orcia and the now dormant volcano of Mount Amiata. 

You might not expect to find one of the best cocktail bars in Tuscany in a town of about a thousand residents but the population was in luck when Idyllium (Via Gozzante, 67; 00 39 0578 748 176) opened in Pienza, a hot spot for artisanal cocktails, excellent tunes, and hours that go well past midnight, especially on the weekend.

• The best restaurants in Tuscany

Day two

MORNING

Today you are going to be wine tasting, so start the morning with a less decadent pursuit. The Via Francigena is a 1,100-mile former pilgrim route that wound to France through Italy. Nowadays walkers, bikers and drivers can use both the asphalt and unpaved roads to see some of Tuscany’s most beautiful landscapes. Cyclists should book a tour with Cicloposso, a biking outfitter that creates custom itineraries, while ramblers will find well marked trails with towns and distances displayed on discreet signs.

• The best beaches in Tuscany

AFTERNOON

Decisions, decisions, decisions. Some of the best wines in all of Italy are made in Tuscany. You just have to choose what your palate is in the mood for: Brunello is one of the region’s highlights, a wonderful vintage made out of only Sangiovese and grown and bottled in the vineyards around Montalcino. Choose just one producer to taste or try many at the town’s Enoteca La Fortezza (Piazzale Fortezza, 9; 00 39 0577 849 211), which offers tastings from almost all of the local estates.

Chianti lovers, on the other hand, will want to head to the area of the same name. Try a few at Greve in Chianti’s Enoteca Falorini (Piazza delle Cantine, 6; 00 39 055 854 6404) — they have enomatic machines so you can try a glass of something usually only available by the bottle. And if you are on the coast, your wine tastings should include a stint around Bolgheri, home of the ‘Super Tuscans,’ a moniker designated to give winemakers the chance to experiment with blends to great effect.

LATE

You spent at least a day in Southern Tuscany (you would do well to stay a week) but now it’s time to think of northern pleasures. Volterra doesn’t get the attention it deserves, but that’s good news for travellers who want to avoid crowded places such as San Gimignano. In Volterra highlights include the 13th-century Piazzi dei Priori and the city’s Cathedral, with its perfect mix of Romanesque and Renaissance architecture. Restaurant-wise, choose La Carabaccia (Piazza XX Settembre,5; 00 39 0588 862 239), where the menu changes daily based on local and seasonal ingredients. 

Luxury Living

Castiglion del Bosco is a huge working wine estate with an impeccably manicured luxury resort and spa. Expect comfortable country interiors, and spacious rooms the size of many Italian city apartments. For dinner, choose between the more upscale Ristorante Campo del Drago (perfect for a romantic evening) and the cosy rustic-chic Osteria Canonica, both presided over by a talented and personable southern Italian chef. From the chef’s kitchen garden to the grape-must treatments available in the Daniela Steiner Spa, this place really puts its heart into living the Tuscan dolce vita.

Rooms from £2,358. Località Castiglion del Bosco; 00 39 0577 1913001

Boutique Bolthole

An American lawyer falls in love with Tuscany, buys up most of a small village, and turns it into a rural idyll. Luckily for his intended audience, his vision was spot on, and Monteverdi Resort and Spa is an elegant, sprawling hotel, in keeping with the area’s original architecture. Custom beds, standalone tubs and rain showers, iron-wrought lanterns and mirrors, and local stone floors have set a new standard for chic in the valley. The terraced gardens are just as charming: a lap pool is bordered by lavender bushes. Don’t miss the destination restaurant, Oreade, which focuses on local and seasonal ingredients.

Double rooms from €590 (£512). Via di Mezzo, 53047 Castiglioncello del Trinoro; 00 39 0578 268146

Budget Beauty

For those looking for a taste of true Tuscany, with a family atmosphere and gorgeous landscapes right outside the door, there are few more intimate or welcoming spots than Follonico. The restored 200-year-old farmhouse is a labour of love, surrounded by well-tended organic gardens, the family’s animals and olive groves. Each guest unit has its draws: an open fireplace; beautiful sunset views; or terraces and hot tubs. Guests are invited to become part of the farm’s rituals, tending the garden or learning about olives, a 101 to Tuscan farm life.

Double rooms from €180 (£154). Località Casale 2, 53049 Montefollonico; 00 39 0577 669773

• A complete guide to the best hotels in Tuscany

Make tracks to Pienza’s Officine 904 (Via Dogali, 16; 00 39 0578 190 817), where you’ll find chic leather bags in clean shapes and vibrant colours. 

You never know what you’ll find when you venture to luxury outlets like The Mall (Via Europa, 8, Leccio Reggello; 00 39 055 865 7775) near Florence. Supply and sizes vary but for basics such as handbags and sunglasses it is always worth a trip.

Tuscany is one of those places that really does offer four seasons. Expect lush wildflower-dotted landscapes in spring, hot summers perfect for swimming, autumns with beautifully coloured forest, and winter for cold but often blue-skied days and less crowds.

Spring and autumn are my favorite months to visit, with a plethora of seasonal and local produce, sunny days that aren’t too boiling for sightseeing, and hotel prices that are lower than high season. Throughout the year, keep an eye out for local festas — they are one of Tuscany’s most authentic offerings.

Essential Information

British Embassy/Consulate:(00 39 055 284 133; gov.uk). Approximately 3 million British nationals visit Italy a year so the website is up to date with information on events like heatwaves or volcanic eruptions, airport renovations, and any security issues. Check out the ‘Living in Italy’ entry too.

Tourist offices: There are tourism offices all over the region. Check out italia.it to find the one closest to you. 

Ambulance: dial 118

Police: dial 112

Fire: dial 115
 

The basics

Currency: Euro

Telephone code: from abroad, dial 00 39, and then a zero at the start of the landline number; mobile numbers don’t need a 0. 

Time difference: +1 hour

Travelling times: Flights from London to Florence take about two hours and ten minutes. Pisa is another option with same flight time.

Local laws and etiquette

When greeting people, use the more formal expressions, “Buon giorno” or “Buona sera” instead of “ciao.” 

When visiting churches and abbeys do bring something to cover your shoulders and when visiting during mass, be sure to be quiet and respectful. Dressing up for meals in nicer restaurants usually results in better service.

Beware the many speed cameras dotting Tuscany’s back roads by respecting the limits. When parking watch for the coloured lines — in general white are free, blue paid parking, and yellow for residents. Do not enter ZTL, zona traffica limita.

Author bio

Ondine Cohane moved to the Unesco-protected town of Pienza 13 years ago in pursuit of a la dolce vita lifestyle and to open two boutique hotels. Close to home and further afield, Ondine is constantly seeking out the country’s latest openings, as well as appreciating the classics. 

Telegraph Travel’s best hotels, tours and holidays in Tuscany, tried, tested and recommended by our Tuscany experts.