Tuscany 10-day Itinerary
Italy
Where to go and what to see in Tuscany to get the most from your trip – a 10-day itinerary from destination expert and leading travel writer Nicky Swallow.
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Overview >Bucket list experience:
A day in San Gimignano
San Gimignano, Tuscany, Italy
Last updated: 08 November, 2022
Sometimes dubbed the medieval Manhattan for its clutch of slim towers (visible for miles around), iconic San Gimignano is Tuscany’s most famous (and most visited) hill town. Arguably over-restored, it is nonetheless achingly pretty, a set piece of medieval palazzi, graceful piazze, narrow streets and the aforementioned towers – of which only 14 survive of an original 72.
A good way to start a visit is by climbing the 218 steps of the Torre Grossa for an overview of the town and its jumble of red rooftops. Then wander the Piazza della Cisterna (containing the town’s old well) and Piazza del Duomo – both are lovely, the latter lined with impressive palazzi.
While you’re there
Art lovers should stop by the Pinacoteca, housing a collection of 12th- and 15th-century paintings from Florence and Siena while the 12th-century Collegiata church has superb frescoes and a chapel decorated by Ghirlandaio. It’s also worth wandering into the quieter northern reaches of the town to see the frescoes by Benozzo Gozzoli in the church of Sant’Agostino.
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Price: Free
Minimum age: Any
Age suitable: 18+
When: All year around
Getting there & doing it
San Gimignano is easy to visit independently, and that way you stand a better chance of dodging the tourists.
It lies about halfway between Florence and Siena, off the superstrada that runs between the two. There is a good bus service from both places; the bus stops right at Porta San Giovanni, the main entrance to the town. The journey by car is around 40 mins from Florence and 30 mins from Siena. Note that parking within the old town is impossible; there are four car parks outside the old town walls – all are just a short walk from the centre.
The tourist office is in Piazza del Duomo and carries information about a series of guided tours of the city centre and walking tours in the nearby hills, as well as details of the combined entrance tickets for the main museums.
When to do it
There is little hope of avoiding the tour groups and crowds of day-trippers if you visit in summer, especially July and August. Staying the night is one solution (most leave at the end of the day) or visit very early in the morning. Winter is the ideal season for doing the museums, but weekends should be avoided if possible.
Experience
Civic Museum of San Gimignano
San Gimignano, Tuscany, Italy
The picture gallery houses a collection of 12th- and 15th-century paintings from Florence and Siena. Look out for a 13th-century painted crucifix by Coppo di Marcovaldo, and paintings by Benozzo Gozzoli and Filippino Lippi.
Best for ages: 18+ | Free
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Experience
Collegiata di Santa Maria Assunta
San Gimignano, Tuscany, Italy
The 12th-century Collegiata church has superb frescoes and a glittering interior, its vaults decorated with golden stars. The Santa Fina chapel is painted by Domenico Ghirlandaio.
Best for ages: 18+ | Free
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Experience
Gelateria Dondoli
San Gimignano, Tuscany, Italy
Dondoli has earned world-wide acclaim for the quality of its gelato, made from seasonal ingredients and the best local eggs, milk and cream. High season queues are insane, but it’s worth persisting to try unusual flavours such as Santa Fina (saffron and pine nuts) and Champelmo (pink grapefruit and champagne).
Best for ages: 4+ | Free
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Our selection of the best Viator tours of this attraction or activity
Gourmet Wine Tour San Gimignano Wine Tasting - San Quirico Winery
San Gimignano
Enyoy a Gourmet Wine Tour in Tuscany!
San Quirico Winery in San Gimignano invite you for guided Winetasting and Visit of Wine Cellar! ...
€20 | Rating 4.66 / 5 [15 ratings]
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Private Wine and Extra Virgin Olive Oil Tasting
San Gimignano
Take a break on a family farm surrounded by the flavors of Tuscan products. The experience will start with a detailed introduction to the ag...
€25 | Rating 4.91 / 5 [12 ratings]
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Essence of Tuscany - Wine & Evo oil Tasting
San Gimignano
This experience is a full immersion in the wine and Evo oil world, the focus is not the food but what we produce with so much passion.
Rela...
€25 | Rating 4.63 / 5 [19 ratings]
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Montepulciano area: Exclusive Winery Tour & Tasting Experience
Montepulciano
Enjoy an exclusive wine-tasting experience in a unique cellar in Montepulciano, very close to Umbria.
Discover an exclusive winery, a few k...
€30 | Rating 4.66 / 5 [6 ratings]
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Our writer’s picks of the best places to stay near this experience, closest first
Borgo Pignano
Pignano, Tuscany, Italy[8.6 miles]
A beautifully-renovated 18th-century villa and its surrounding hamlet, set on a 750-acre estate in the middle of rural Tuscany.
Official star rating:
Como Castello del Nero
Tavernelle, Tuscany, Italy[15 miles]
A converted 12th century castle, with superb spa and restaurant. A perfect Tuscan countryside retreat, but close enough to the attractions of Florence, Siena and the Chianti Wine Region.
Official star rating:
Belmond Castello di Casole
Casole D'Elsa SI, Tuscany, Italy[16.5 miles]
A luxurious country estate, complete with 10th-century castle, set in 4,200 acres of unspoilt Tuscan countryside and home to a world-class spa and fine dining restaurant.
Official star rating:
Destination guides including or relevant to this experience
Tuscany
Tuscany, Italy
The astonishingly beautiful region of Tuscany has it all: art cities and ancient hill towns, high mountains and long sandy beaches, alongside luxurious hotels and some of Italy’s best food and wine.
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Overview >Our writer’s recommendations of other bucket list experiences our writer says you must do in this destination, closest first
Chianti Wine Region
Chianti, Tuscany, Italy[15.5 miles]
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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A day in Volterra
Volterra, Tuscany, Italy[16.4 miles]
Steeped in history, the fortified hilltop town of Volterra offers glimpses of Etruscan and Roman life, among streets dating back to the 12th and 13th centuries.
Best for ages: 18+ | Free
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Overview >Other worthwhile experiences near this experience if you have time or interest..
Experience
Cucina Giuseppina Cooking School
Certaldo, Tuscany, Italy[8.8 miles]
An excellent cooking school based in Certaldo (southwest of Florence) offering truffle-hunting experiences in the Chianti woods, followed by a truffle-based lunch or cooking lessons with truffles.
Best for ages: 13+ | £120 | 3-4 hours
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Experience
Cooking classes at Jul’s Kitchen
Colle di Val D'Elsa, Tuscany, Italy[11.6 miles]
Colle Val d’Elsa Food writer/blogger and photographer Giulia Scarpaleggia and her husband run the excellent ‘Jul’s Kitchen’ offering a range of hands-on cooking classes alongside courses in food writing and photography. Classes are held in their house in the countryside between Siena and Florence.
Best for ages: 13+ | £70 | 3 hours
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