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Bucket list destination:

Last updated: 29 June, 2023
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.

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

Pisa and Lucca Day Trip from Florence

Florence

Pisa and Lucca Day Trip from Florence
Discover the elegant cities of Pisa and Lucca, on a Tuscany day trip from Florence! With an expert tour leader, explore the Pisa square of Piazza dei Miracoli to see Pisa Baptistry and the legendary Leaning Tower of Pisa, a UNESCO World Heritage site. Visit Pisa Duomo to learn about its history, and then spend the afternoon in nearby Lucca, one of Tuscany’s lesser-known gems. Enjoy a walking tour, seeing Piazza dell 'Anfiteatro, Lucca Cathedral and more, and finish with a slice of 'buccellato,' Lucca’s signature cake.

Price: €52

Min age: 0

Rating 4.05 / 5 [198 ratings]

Tour supplied by:

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Siena San Gimignano Chianti Pisa and Lunch with Wine Tasting

Florence

Siena San Gimignano Chianti Pisa and Lunch with Wine Tasting
Your Highlights of Tuscany discovery begins with Pisa. Where we reach Piazza Miracoli, dominated by the Cathedral, the Baptistery and the Leaning Tower. From Pisa, we drive over the countryside up to San Gimignano, where a traditional Tuscan lunch with the tasting of four different wines, will be served in a characteristic Restaurant, located along the famous "Via Francigena". After lunch time, your visit continues to the discovery of a Tuscan medieval pearl, the stunning village of San Gimignano, Unesco world heritage, known for the ancient town planning still intact. Our last stop is Siena, where our local guide will take you on a guided walking tour along the small medieval streets and squares, passing the oldest bank in the world "Monte dei Paschi", the Piazza del Campo where the famous "Palio" horses race takes place twice a year, to the spectacular Cathedral. Then you have free time to visit the historic center as you like. Please note that the order of the visits may change

Price: €59

Min age: 0

Rating 4.46 / 5 [324 ratings]

Tour supplied by:

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San Gimignano, Siena, Monteriggioni: Fully Escorted Tour, Lunch & Wine Tasting

Florence

San Gimignano, Siena, Monteriggioni: Fully Escorted Tour, Lunch & Wine Tasting
Discover the easiest way to visit Siena, San Gimignano, Monteriggioni* and Chianti at a smart price. Escorted Day Trip with licensed Tour Escort on board. 3 course typical Tuscan lunch in a Chianti Winery, Wine Tasting with three different Chianti Wines, extra virgin olive oil, balsamic vinegar and “vin santo”. Free time to visit Siena, San Gimignano and Monteriggioni. Make the most of the commentary on the bus about the history, art and landscape and visit at your leisure the most famous and charming cities in Tuscany. (*) From November to March, the itinerary does not include the stop at Monteriggioni and the return to Florence is approx 30 minutes earlier     

Price: €67

Min age: 0

Rating 4.55 / 5 [95 ratings]

Tour supplied by:

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Pisa, Siena and San Gimignano Day Trip with Lunch & Wine Pairing

Florence

Pisa, Siena and San Gimignano Day Trip with Lunch & Wine Pairing
There’s more to Tuscany than Florence. Leave the city behind and discover three other enchanting Tuscan destinations on this day trip to Siena, San Gimignano and Pisa. Take a guided tour of beautiful Siena, famous for its bareback horse race and the Gothic Siena Cathedral, and taste typical Tuscan food and wine during a 3-course lunch in a local winery or restaurant surrounded by picture-postcard Tuscan landscapes, where vineyards, rolling hills and olive groves will be your travel companions. Then, enjoy free time to explore San Gimignano, a picturesque medieval village, and Pisa, home to the UNESCO-listed Leaning Tower of Pisa.

Price: €79

Min age: 0

Rating 4.37 / 5 [2824 ratings]

Tour supplied by:

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Tuscany Day Trip from Florence: Siena, San Gimignano, Pisa and Lunch at a Winery

Florence

Tuscany Day Trip from Florence: Siena, San Gimignano, Pisa and Lunch at a Winery
Famous for a wealth of art, history, striking landscapes and outstanding produce, Tuscany really does have the best of all worlds! With only a day to spare, see the best Tuscany has to offer on this full-day guided coach trip from Florence.

Price: €85

Min age: 0

Rating 4.83 / 5 [12817 ratings]

Tour supplied by:

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Private Tuscany Tour: Siena, Pisa and San Gimignano from Florence

Florence

Private Tuscany Tour: Siena, Pisa and San Gimignano from Florence
Experience a full-day, private tour of the Tuscan gems, Pisa, Siena, and San Gimignano. Let your private driver do all the paperwork and explore Siena, Pisa and San Gimignano at your own pace. With hotel pickup and drop-off from Florence, you will be able to sit back and enjoy the picture postcard Tuscan countryside surrounding you and your travel companions. Make the most out of this private experience with a private and knowledgeable driver at your full disposal. Design with him the itinerary of your dreams!

Price: €474

Min age: 0

Rating 4.84 / 5 [99 ratings]

Tour supplied by:

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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.

Other guides relevant to this destination

Florence

Tuscany, Italy

Florence

A heady mix of incomparable Renaissance art, gorgeous palazzos, Tuscan cuisine and home-grown haute couture.

Siena

Tuscany, Italy

Beautiful view of Dome and campanile of Siena Cathedral, Duomo di Siena, and Old Town of medieval city of Siena in the sunny day, Tuscany, Italy

Arguably the most perfect medieval city in the world, Siena is a glorious ensemble of red brick buildings and exquisite monuments, famous for its fan-shaped Campo and Il Palio horse race.