No other regions – and not many countries – have Tuscany’s immeasurably rich combination of culture, food, wine, medieval villages, historic towns, art-filled cities and sublime pastoral countryside. Ten days, of course, are not enough to do it justice.

But they’ll suffice for the highlights, as well as for some hidden corners. And they’ll almost certainly be enough to inspire a return visit.

Florence, our starting point, might seem all about art, with its world-class museums and galleries – not least the Uffizi – fresco-filled churches and masterpieces by Michelangelo, Donatello and countless others. But it’s also a city of timeless medieval streets, peerless views, great cafés and restaurants, and plenty of excellent shopping.

The rest of Tuscany, too, defies expectations. It offers not just varied and lovely landscapes – vineyards, mountains, cypress-topped hills – but also numerous sleepy villages, ancient monasteries, scenic backroads and medieval towns such as Lucca and Siena that are the equal of any in Europe.

Our itinerary can easily be extended, perhaps by adding a day or two in Siena, a detour to see Sovana and Pitigliano, a drive to the region’s often overlooked coast or to the mountains of the Garfagnana, above Lucca. But if ten days is all you have, console yourself with a simple thought – you’ll be back for more. 

Cradle of the Renaissance

Prompt arrival in Pisa or Florence should leave you an afternoon to start sightseeing in Piazza del Duomo, Florence’s medieval and religious heart, dominated by the Duomo, or cathedral, topped by Brunelleschi’s famous dome. Skip the interior, which is disappointing – with long queues – and rather than the dome, climb the adjacent Campanile (belltower), which has better views.

Definitely see the interior of the Baptistery, and its 13th-century mosaics, and – if not now, then at some point – the Museo dell’ Opera, a superb museum devoted to the art of the Duomo over the centuries.

Now walk down Via de’ Calzaiuoli, Florence’s principal axis, which links Piazza del Duomo to the city’s civic focus, Piazza della Signoria. Enroute pause at the church of Orsanmichele, admiring the ground-breaking Renaissance sculpture on its exterior and its lovely, fresco-covered interior (reopens in September 2023).

In Piazza della Signoria, wander the sculptures dotted around the square, especially those of the Loggia della Signoria, where Cellini’s Perseus is the star turn. If time allows, admire the astonishing interior of the Palazzo Vecchio, Florence’s town hall for some seven centuries. At the very least, step into its beautiful frescoed courtyard.

Now, or later in the evening, walk from the square for views of the Arno and the celebrated Ponte Vecchio. 

For accommodation, you’re spoilt for choice. The Telegraph’s guide to the best hotels in Florence has options for every budget. 

Churches and canvas

Start your second day east of Via de’ Calzaiuoli, picking a route past the little churches of Santa Margherita, San Martino del Vescovo and the Badia Fiorentina en route for Santa Croce. This is one of Italy’s great churches, filled with frescoes by Giotto and the tombs of Michelangelo, Galileo and others, with the Cappella dei Pazzi, one of Brunelleschi’s most intimate masterpieces, alongside.

Before lunch, visit the Bargello, filled with the finest sculptures, paintings and decorative arts, and perhaps the excellent Museo Galileo, devoted to the history of science and too often overlooked.

Vini e Vecchi Sapori (0039 055 293045) is great little spot for lunch, just off Piazza della Signora, but be sure to book. Or join the locals for street food at the kiosk at the intersection of Via de’ Cerchi and Via dei Tavolini.

This afternoon, visit the Uffizi, Europe’s greatest gallery of medieval and Renaissance art, which you should have booked (see “Insider Tips” below). Spend most time with the many famous paintings in the first 10 rooms.

Devote late afternoon to the atmospheric streets west of Piazza della Signoria, taking Borgo Santi Apostoli via the churches of Santi Apostoli and Santo Stefano to Santa Trinita, home to frescoes and a sumptuous altarpiece by Ghirlandaio. Then walk west on Via del Parione and loop back on Via della Vigna Nuova and Via del Purgatorio. 

Street food and gardens

Make your final morning in Florence about Michelangelo, with visits to the Cappelle Medicee, home to several of the master’s sculptures. Pop into San Lorenzo, the Medici’s parish church, then see the David in the Accademia (see “Insider Tips” below).

Alternatively, skip the Cappelle Medicee for the food stalls of the Mercato Centrale and the art-filled interior of Santa Maria Novella, the most important of Florence’s churches after Santa Croce.

North of the Accademia is the Museo di San Marco, devoted to the sublime art of Fra Angelico. Make a call on this, depending on time and inclination, ditto the lovely frescoed chapel by Benozzo Gozzoli in the Palazzo Medici-Riccardi. Tickets for both can be booked online.

Next, head to the Oltrarno, the traditional artisans’ quarter across the Arno, full of galleries, small workshops and restaurants, with Trattoria 4 Leoni a good spot for lunch.

For more art, the Palazzo Pitti-Galleria Palatina contains the city’s finest collection after the Uffizi. Or pre-book a slot to see Masaccio’s ground-breaking frescoes in the Cappella Brancacci. 

Your final afternoon in Florence could be spent relaxing in the Boboli Gardens, behind the Palazzo Pitti, or else commit to an uphill walk to San Miniato al Monte, arguably Italy’s loveliest Romanesque church. Return via Piazzale Michelangelo, the city’s most famous viewpoint, and walk through the gardens below to the emerging little San Niccolò neighbourhood.

Raise a glass

Pick up your car and head south into Chianti, an enclave of pastoral hills covered in olives, oak woods and vineyards. Perhaps start with a visit to the moving Second World War American Cemetery just south of the city: otherwise take the SS222, with stops in Greve in Chianti and a coffee break at La Bottega in charming little Radda in Chianti.

Drive four miles farther for a pre-booked tour and relaxed wine tasting at the Badia a Coltibuono, a tranquil 11th-century abbey (with rooms) high in the hills, followed by lunch in the winery’s excellent restaurant (nominate a driver). 

Chianti offers countless other wineries: the most famous is Antinori, known for its striking contemporary architecture. You could visit after the Cemetery (15 minutes’ drive to the north) and winery before wending back into the hills towards Greve.

Devote the afternoon to a meandering drive via Gaiole and Castelnuovo Berardenga through some of Chianti’s prettiest countryside. Your target is Gargonza (doubles from £160), a converted fortified medieval hamlet, and a peaceful and fascinating place to dine and spend the night. 

Arezzo and Cortona Day 5

Head for the hills

A short drive down from the hills brings you to Arezzo, blessed with a lovely historic core that centres on a fine cathedral and Piazza Grande. Explore, ensuring you see the sublime frescoes of Piero della Francesca in the church of San Francesco (booking is obligatory at discoverarezzo.ticka.it).

It’s a 50-minute drive south from Arezzo to Cortona, your target for the night, but consider taking a detour through the mountains to Monterchi and then Sansepolcro – a first-rate Tuscan town in its own right.

Cortona is a striking, many-levelled and ancient hill-town made (more) famous by Frances Mayes’ book (and subsequent film), Under the Tuscan Sun. Stay centrally at the simple but first-rate Dolce Maria (B&B doubles from £75) or fancier San Michele (from £95) and eat a lunch of traditional Tuscan dishes (leave room for some fabulous cheeses) at La Buccacia.

The afternoon see the Etruscan collections in the excellent MAEC museum and two glorious paintings by Luca Signorelli and Fra Angelico in the Museo Diocesano. Cortona’s main rewards, though, are exploring its many medieval nooks and crannies and admiring the shimmering hills and plains of the Val di Chiana below from a variety of viewpoints. 

Val d’Orcia Day 6

The perfect view

Today is devoted to the Val d’Orcia, whose villages and landscapes are so lovely they have been designated a World Heritage Site.

Make the short drive – perhaps via nearby Lake Trasimeno – from Cortona to Montepulciano, the highest of the Tuscan hill-towns, where you should allow an hour to wend upwards towards Piazza Grande to explore the cathedral and its medieval surroundings.

From Montepulciano drive the backroads for a quick look at tiny Montichiello and then on to Pienza, which is a gem, its heart part of an unfinished 15th-century papal project to create an ideal Renaissance city. Visit the Diocesan Museum, Palazzo Piccolomini and cathedral, the last filled with glorious medieval altarpieces. Above all, though, walk the old walls behind the cathedral for some of Tuscany’s finest views.

Book outside tables for lunch with these views at La Terrazza del Chiostro or the more down-to-earth Terrazza della Val d’Orcia.

Options after lunch: a looping scenic drive for more classic countryside and the villages of Petroio, Montisi and Castelmuzio; and – or – a more direct route via San Quirico and Bagno Vignoni to your destination for the night, Montalcino. In either event, be certain to visit one of Italy’s most beautiful abbeys, the ninth-century Sant’Antimo, before it closes. 

Stay at the three-star Dei Capitano (doubles from £80) within Montalcino’s walls and try the long-established Grappola Blu for dinner. 

Tuscany’s second city

Devote around two hours to Montalcino this morning, longer if you want to drive – perhaps en route for Siena (see below) – to one of the area’s celebrated Brunello vineyards (winery details at consorziobrunellodimontalcino.it). Note, though, that the town itself has places to taste and buy wine, not least the enoteca in the old fortress. Don’t miss the art-filled Museo Civico and Sant’Agostino church.

If you have only one night in Siena, Tuscany’s second city, push on to arrive in time for lunch or earlier. If not, and you relish Renaissance art, the Abbazia di Monte Oliveto Maggiore, five miles (8km) northeast of Buonconvento, has one of Tuscany’s foremost fresco cycles, The Life of St Benedict, by Sodoma and Luca Signorelli.

Allow time to park and transfer to your Sienese hotel, with the five-star Grand Hotel Continental (doubles from £255) the upmarket choice or the Duomo (from £78) the best-located three-star option. 

Take a brisk lunch at Il Carroccio (Casato di Sotto 32; 0577 41165; no website), then start exploring the city in the nearby Campo, Europe’s finest medieval square and the setting for Siena’s famous Palio horse race. See the sublime frescoes and other artworks inside the Museo Civico and consider climbing the adjacent Torre del Mangia (no lift) for sweeping views.

San Gimignano Day 8

A medieval Manhattan

You need another morning in Siena to do justice to the Duomo, spectacular inside and out, and to the Museo dell’Opera, filled with art that includes Duccio’s Maestà, one of Italy’s seminal medieval paintings. Less visited, but worthwhile, is Santa Maria della Scala opposite the Duomo, celebrated for its extraordinary 15th-century fresco cycles.

The Pinacoteca Nazionale offers an exhaustive summary of Sienese art, but you probably want to leave time simply to explore the city’s many lovely streets, especially those south of the Campo and southwest of the Pinacoteca.

With a full day in Lucca tomorrow, you have options this afternoon. More time in Siena and/or a 40-minute drive to San Gimignano (admire fortified Monteriggioni en route), Tuscany’s most-visited village, known for its many medieval towers. Be certain to see the Musei Civici and the frescoed Collegiata and Sant’Agostino church.

At a push, you could visit another fine hill-town, Volterra, but it’s 40 minutes from San Gimignano (a scenic drive) and another 90 minutes from Volterra to Lucca.

Stay within Lucca’s walls at the Ilaria (from £97), a long-established mid-range choice, or the revamped Grande Universe Lucca (from £190), the best smarter option. 

Days 9 & 10

A laid-back beauty

Lucca is many people’s favourite Tuscan town, a tranquil place of immediate charm, still entirely medieval in aspect within its extraordinary walls. At some point today walk, or rent a bike (biciclettepoli.com) in Piazza Maria, to explore these tree-lined, car-free ramparts.

Start, though, in Piazza San Michele, graced with one of Tuscany’s loveliest churches, San Michele, then visit the Duomo, its adjacent museum and the Roman remains below nearby Santi Giovanni e Reparata.

Now walk north past the Torre Guinigi, a tree-topped medieval tower, and on to Piazza dell’Anfiteatro, a picturesque piazza built over the city’s Roman amphitheatre. Visit San Frediano for its mosaic façade and interior art then wend westward to see Casa Puccini, former home of Lucca’s most famous son. 

At lunch, try the traditional Da Giulio or more upmarket Buca di Sant’ Antonio, in business since 1782.

Lucca could keep you occupied all day, but garden-lovers might want to drive to one or more of the villas in the city’s hinterland, notably the Villa Reale, Villa Torrigiani and Villa Garzoni. 

Homeward bound

Booking a late flight home leaves extra sightseeing time whether you are departing Florence or Pisa. A morning is plenty to see Pisa’s Leaning Tower and the adjacent cathedral, baptistery and Museo dell’ Opera. Book tickets to climb the tower. You should also have time to explore nearby Piazza dei Cavalieri, Pisa’s medieval heart.

Returning to Florence, choose between Pistoia and Prato. Both have attractive historic centres, with Pistoia smaller and easier to negotiate, but Prato home to the more significant monuments.

How to do it

When to go

Tuscany’s landscapes are at their best in April and May, when the weather should also be ideal for city sightseeing. September and October offer the grape harvest and autumnal colours but avoid July and August – too hot and crowded – and time your days in Florence to miss weekends, which are busy year-round. 

What to book

Italian specialist Citalia (01293 324514; citalia.com) can tailor-make itineraries to Florence and Tuscany. If you prefer a small-group escorted tour, Jules Verne (020 3553 6528; vjv.com) offers a seven-night, single-base “Tales of Tuscany trip”, with a visits to Florence, Lucca and Pisa, and a free day you could use to see Siena. From £1,045 per person, including B&B and flights.

What to pack

If you come off-season to avoid the heat and the crowds note that Florence and the countryside can be surprisingly cold from November to March. Pack warm. October and November are the wettest months, so be prepared. Many museums have airport-like security screening, so travel light for sightseeing, preferably without a backpack. 

Holiday reading

If Dante, Machiavelli and Petrarch are too weighty for holiday reading, opt for Still Life by Sarah Winman (Fourth Estate), which fuels the fantasy of an escape to Florence, while Iris Origo’s classic War in Val d’Orcia (Allison & Busby) is an evocative portrait of life in Tuscany’s rural heartland during the Second World War. 

Expert tips

Fly to Pisa (more flights) or Florence (more convenient) but spare a thought for your departure (see Day 10) and – especially – your hire car. Parking in Florence is all but impossible (Siena too), so pick up your car, if possible, on the morning of Day 4. Note, too, that with the odd taxi and tweak, much of this itinerary can be done by train (trenitalia.com).

Be sure to book timed tickets online for Michelangelo’s David at the Accademia; the Cappelle Medicee; and the Uffizi, noting that all three are often quieter in late afternoon. Slots can be fully booked months in advance and while third-party agencies often have tickets, beware service and booking fees.

Florence’s Duomo (cathedral) often involves long queues for entry, especially if you wish to climb the dome (€30/£26.40). Of the three advance passes available online, consider the “Giotto” (€25/£22), which excludes the dome but includes the adjacent Campanile plus the Baptistery and Museo dell’ Opera.

Queues are not usually as bad in Siena, but you can still save money and time –especially for entry to the Duomo – by buying an Opa Sì Pass, which offers entry to the Duomo and other key sights nearby. It is valid for three days. 

Have you been to Tuscany? Which places would be on your perfect itinerary? Please leave your comments below.