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Best things to do & places to stay:

Last updated: 14 December, 2022
Expert travel writer: Nicky Swallow

It’s not difficult to see why Tuscany is one of Italy’s (indeed, Europe’s) most popular holiday destinations. The region has it all: treasure-filled art cities and postcard-pretty hill towns, a long sandy coastline, high mountains and gently rolling hills plus superb food and wine with a thriving restaurant scene.

Even leaving aside Florence, there’s enough art to keep culture vultures busy for weeks, while outdoors-y types can dive into a whole range of activities.

Add a plethora of fabulous hotels (from agrotourism stays to boutique heritage boltholes and five-star grand dames set in converted castles), and you have all the ingredients of an unforgettable, soul-enriching holiday.

Orientation

Tuscany has extraordinary geographical variety within the region; high mountains (the marble-rich Apuan Alps), a long, sandy coastline, thickly-wooded and vine-striped hills, wide river valleys, fertile farmland, and an archipelago of seven islands.

Pisa (about 90 minutes’ drive north-west of Florence) is, of course, home to the leaning tower. Siena, Tuscany’s second-biggest town is 85kms (about 1 hours’ drive) south of Florence. Between the two lies the world-renowned wine region of Chianti.

The Val D’Orcia, peppered with Tuscany’s famous hill towns, is far to the south.

The bucket list experiences our writer says you must do in this destination

Leaning Tower of Pisa

Pisa, Tuscany, Italy

One of Italy’s most popular sights, an astonishingly beautiful but leaning belltower dating back to 1173, doomed from the outset having been built on unstable sand and clay. The still-famously titling tower still attracts millions of visitors a year, for the unnerving climb up its 293 steps.

Best for ages: 10+ | £15

Palio di Siena

Siena, Tuscany, Italy

The most famous bareback horserace in the world, Il Palio is an extraordinary spectacle that sees horses and riders gallop three times round Siena’s glorious, medieval Piazza del Campo. A centuries-old means of settling of neighbourhood scores, it defines the social, cultural and political fabric of the city each year.

Best for ages: 13+ | Free | 3 hours

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Chianti Wine Region

Chianti, Tuscany, Italy

Home to some of Italy’s best wines, the DOCG Chianti Classico stretches across 177,500 acres of undulating, vine-striped land between Florence and Siena.

Best for ages: 18+ | Free

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Walk from Montalcino to Sant Antimo

Montalcino, Tuscany, Italy

A beautiful 3-hour walk (just over 8 miles) that takes you through farmland and Brunello wine country, passing old farmhouses and tiny stone hamlets that have remained unchanged for centuries.

Best for ages: 13+ | Free | 3 hours

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Other worthwhile experiences in this destination if you have the time or the interest

Abbey of Sant’Antimo
Experience

Abbey of Sant’Antimo

Castelnuovo dell'Abate, Tuscany, Italy

The beautiful Benedictine abbey of Sant’Antimo lies in open countryside close to Montalcino and dates from the 8th century; the resident monks sing Gregorian chants each evening.

Best for ages: 18+ | Free

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Arezzo Antique Market
Experience

Arezzo Antique Market

Arezzo, Tuscany, Italy

Held on the first weekend of each month, this huge market with stalls selling everything from vintage postcards to Renaissance paintings is laid out in and around Piazza Grande, attracting vendors and buyers from all over Italy.

Best for ages: 8+ | Free

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Bolgheri Wine Region
Experience

Bolgheri Wine Region

Bolgheri, Tuscany, Italy

The Bolgheri region was where the first so-called ‘Super-Tuscan’ wine was made in the 1980s, and it continues to be exported around the world. The village of Bolgheri is postcard pretty; wine estates to visit include Ornellaia (book well ahead), Podere Sapaio and Le Macchiole.

Best for ages: 18+ | Free

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Civic Museum of Sansepolcro
Experience

Civic Museum of Sansepolcro

Sansepolcro, Tuscany, Italy

Sansepolcro’s unassuming town museum houses two of the most celebrated works by Piero della Francesca who was born in the town sometime between 1410 and 1420; his Resurrection and Maddona della Misericordia. A must-see for devotees of the artist.

Best for ages: 18+ | £8

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Our selection of the best Viator tours of this destination, plus helpful tickets and transfers

 Walking Tour of Siena with food & Chianti wine

Walking Tour of Siena with food & Chianti wine

Siena

Welcome to the Gem of Tuscany, Siena. I will take you for a wonderful walk and show you the gems that this city has to offer. We will see &...

€49 | Rating 4.93 / 5 [29 ratings]

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Chianti Wine Tour with tuscan Lunch, Visit to S.Gimignano and Organic Wineries

Chianti Wine Tour with tuscan Lunch, Visit to S.Gimignano and Organic Wineries

Florence

Small Group/ Two wineries/ San Gimignano/ lunch/ guided wine tastings/ gelato world champion/ piazzale Michelangelo and more.. First we tour...

€190 | Rating 4.93 / 5 [497 ratings]

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Florence Half Day Tour with Uffizi, Michelangelo’s David and Accademia

Florence Half Day Tour with Uffizi, Michelangelo’s David and Accademia

Florence

Combine two best-selling Florence tours at a discounted price, and enjoy a half day of art and sightseeing in the city! This small-group Flo...

€89 | Rating 4.47 / 5 [1794 ratings]

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Livorno Shore Excursion: Pisa and Florence Private Day Trip

Livorno Shore Excursion: Pisa and Florence Private Day Trip

Florence

When your cruise ship docks in Livorno and you have only a single day to see the surrounding Italian towns of Pisa and Florence, you’ll need...

€330 | Rating 4.76 / 5 [168 ratings]

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Our writer’s picks of the best places to stay in this destination

Agriturismo Il Rigo

Casabianca, Tuscany, Italy

A long-established agriturismo located in a glorious setting just outside lovely old San Quirico in the Val d’Orica. A working organic farm run by the ninth generation of a family.

Official star rating:

Follonico Hotel

Torrita di Siena SI, Tuscany, Italy

A mellow old farmhouse set in beautiful countryside in the UNESCO-protected Val d’Orcia, restored by its owners into a laid-back, intimate agriturismo.

Official star rating:

AdAstra

Florence, Tuscany, Italy

An aristocratic mansion set in a magnificent private garden, AdAstra offers 16 beautiful rooms filled with antiques, up-cycled retro pieces and quirky design touches.

Official star rating:

Hotel Palazzo Guadagni

Florence, Tuscany, Italy

Set on lively Piazza Santo Spirito, this charming three-star hotel has bags of character in addition to modern facilities and services. The top-floor loggia is a magical spot for an aperitivo.

Official star rating:

When to go

Tuscany is a year-round destination, but peak season runs between and May and October, although at either end of this, there will be fewer tourists compared to high summer. July and August can be very hot and very crowded; spring and autumn are ideal times to visit.

Winters can be cold and wet, but visitor numbers fall sharply and you can play at being a local.

Getting there and away

Florence’s small airport is more central to the rest of Tuscany than Pisa’s. Both handle European and domestic flights.  Direct flights from the US arrive in Milan or Rome, and there are good connections onto Rome Termini and Milan Centrale stations, which then have excellent onward train connections to Tuscany’s main hubs.

From Florence airport, there’s a regular tram service into the city centre and Santa Maria Novella station. From here, there are frequent train connections to Siena, Arezzo, Pisa and Lucca. From Pisa airport, there is a train into Pisa Centrale, from where you can catch a train into Florence for connections to the rest of Tuscany.

Getting around

Both train and bus connections within Tuscany are excellent. A train service runs between the main towns and Florence, while smaller villages are often better connected by the excellent bus network. Trains are run by Trenitalia. Bus companies vary according to the area served.

Cycling is a good way to get around country areas, and cycling holidays are very popular. But try to avoid cycling during the hottest hours of the day in high summer. A Vespa or vintage Fiat 500 is a fun way of covering short distances, and there are various companies that hire both.

But the best way to tour Tuscany is by car; it allows you to be spontaneous and stop along the way for coffees and lunch, wine tastings, souvenir buying, sightseeing and selfies. All towns have car parks (often outside the old town walls), although these can get busy in high season.

Where to stay

Tuscany offers a huge variety of places to stay with many of the best hotels and villas lying outside the main towns.

Florence is the one exception to this rule. From fabulous five-star resorts with all the bells and whistles to much more low-key, boutique rural retreats and farmhouse-style agriturismo accommodation.

Tuscany is a large region, so if you want to see all Tuscany has to offer, it’s best to choose two or three bases, and spend three days in each. Stay in Pisa or Lucca to visit both these towns, either in Siena or in the countryside nearby for visiting Siena itself and the Chianti wine region, and near Montepulciano or Pienza for the Val d’Orcia.

Our writer’s recommended itineraries for this destination

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