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Bucket list destination:

Tuscany

  • Tuscany, Italy

Last updated: 24 November, 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.

Tours, tickets & transfers

9

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

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

Viator

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 4.82 / 5 [14143 ratings]

Tour supplied by:

Viator Logo
Website >

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

  • Florence

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

Viator

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 €65

Min age 0

Rating 4.36 / 5 [3144 ratings]

Tour supplied by:

Viator Logo
Website >

Siena and San Gimignano: Small-Group Tour with Lunch from Florence

  • Florence

Siena and San Gimignano: Small-Group Tour with Lunch from Florence

Viator

Enjoy the high quality of this small-group tour - the perfect experience in order to discover art, history, landscapes, food and wine in a comfortable and relaxed way with more personalized attention of a small group. Depart from Florence, see the highlights of Siena through the eyes of a licensed guide, admire the marvelous Tuscan landscape, taste genuine Tuscan food paired with great wines, and finish your day relaxing in the hill top village of San Gimignano.

Price €149

Min age 4

Rating 4.91 / 5 [1011 ratings]

Tour supplied by:

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Website >

Tuscany: Day Trip to Pisa, Siena, San Gimignano, and Chianti

  • Florence

Tuscany: Day Trip to Pisa, Siena, San Gimignano, and Chianti

Viator

Spend the day discovering the highlights of the Tuscan countryside on this guided tour, together with its amazing art cities and tasting food & wine. Make your way through the rolling hills as you discover the charm of Pisa, San Gimignano, and Siena. Your first stop will be Pisa. See the cathedral, baptistery, and, of course, the famous Leaning Tower, one of the most iconic buildings in the world. From Pisa, drive past hilltop hamlets scattered across some of the most enchanting areas of the countryside. Arrive at San Gimignano where a Tuscan lunch with wine tasting will be served. Continue to the medieval village of San Gimignano, UNESCO World Heritage site often nicknamed the “Manhattan of the Middle Ages” because of its famous towers. End the tour in Siena. Stroll the pedestrian historical center and visit the beautiful cathedral. Take a walking tour along the medieval streets and squares, passing the oldest bank in the world, and the Piazza del Campo.

Price €65

Min age 0

Rating 4.66 / 5 [639 ratings]

Tour supplied by:

Viator Logo
Website >

Self-Drive Vintage Fiat 500 Tour from Florence: Tuscan Hills and Italian Cuisine

  • Florence

Self-Drive Vintage Fiat 500 Tour from Florence: Tuscan Hills and Italian Cuisine

Viator

Step back to 1960s Italy as you drive an eye-catching vintage Fiat 500 car through Tuscany! Following a guide out of Florence, drive into the lush Tuscan hills, passing through picturesque villages and attracting nostalgic glances from admiring passersby. Your 4-hour tour ends in the best possible way – with a relaxing meal on a private terrace. This unique Florence tour is limited to five cars (with 15 people total), ensuring you'll enjoy a small-group experience.

Price €130

Min age 8

Rating 4.85 / 5 [565 ratings]

Tour supplied by:

Viator Logo
Website >

Travel advice

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.

Destination guides

6

Other guides relevant to this destination

San Gimignano

  • San Gimignano, Tuscany, Italy

San Gimignano

Destination guide

Sometimes dubbed ‘Tuscany’s Manhattan’ for its clutch of slim medieval towers (visible for miles around), iconic San Gimignano is the region’s most famous (and most visited) hill town.

Florence

  • Florence, Tuscany, Italy

Florence

Destination guide

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

Volterra

  • Volterra, Tuscany, Italy

Volterra

Destination guide

Volterra, a picturesque hilltop town in Tuscany, Italy, is steeped in history and charm. Known for its well-preserved Etruscan walls and Roman amphitheatre, Volterra offers a glimpse into ancient civilizations. The town is also famous for its alabaster craftsmanship and medieval architecture, attracting visitors with its unique character and stunning views of the surrounding countryside.

Siena

  • 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

Destination guide

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.

Lucca

  • Lucca, Tuscany, Italy

Lucca

Destination guide

A picturesque mix of Medieval and Renaissance buildings, Lucca is a gem of a town that never gets over-run with tourists, giving it a delightfully authentic feel.

Pisa

  • Pisa, Tuscany, Italy

Pisa

Destination guide

Pisa, a city in Tuscany, Italy, is globally renowned for its iconic Leaning Tower. The beautiful Piazza dei Miracoli is a UNESCO World Heritage site, featuring the Cathedral and Baptistery. Pisa also offers a rich history, charming narrow streets, and vibrant squares. It is a captivating destination for history enthusiasts and art lovers alike.