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Bucket list trip:

Tuscany 10-day Itinerary

  • Italy

Last updated: 06 June, 2024

Where to go and what to see in Tuscany to get the most from your trip – a 10-day itinerary from destination expert and travel writer Nicky Swallow.

Editor note – Nicky has not included specific recommendations of where to stay each day unless it’s necessary. Instead, see the ‘Where to stay’ section in our Tuscany destination guide.

Day 1 Florence

4

Start your day in Florence with one of the city’s big hitters. Grab a coffee at Café Rivoire before picking up your pre-booked tickets for the Uffizi gallery; allow at least two hours.

Pop into nearby Vini e Vecchi Sapori for a restorative plate of pasta with zucchini flowers before tackling the mighty Duomo. Climb the 400-odd steps of Giotto’s bell tower for a bird’s eye view of the terracotta rooftops.

Sip a sunset aperitivo at panoramic La Terrazza (Hotel Continentale) before a vast T-bone at Regina Bistecca.

  • Florence, Tuscany, Italy

Uffizi Gallery

Bucket List Experience

Uffizi Gallery

Containing some 5,400 works, the Uffizi’s collection spans art history from ancient Greece through to 18th-century Venetian painting. But most of all, it is known as the world’s largest and most important collection of Renaissance and Mannerist art.

You could spend all day wandering the galleries, but the best bet is to pick out the works you want to see beforehand and head straight for those. The website has helpfully selected its must-see masterpieces and provided some useful background information on each – worth reading before you go.

Adult price: £10

Good for age: 18+

  • Florence, Tuscany, Italy

Completed in 1436, this multi-colored marble megalith is crowned with one of the marvels of the Renaissance world; Brunelleschi’s vast double-shelled dome – built without scaffolding – was a breathtaking feat of engineering.

If time is short, skip the cathedral’s barn-like interior and visit the dome (463 steps) and Giotto’s magnificent bell tower (414 steps).

Adult price: £16

Good for age: 18+

Giotto’s Bell Tower

  • Florence, Tuscany, Italy

Giotto’s Bell Tower

Experience

Giotto’s slender pink, green and white Gothic-style campanile soars 280 feet above the surrounding streets, its great bell regularly booming over the city. The original sculptural reliefs that decorated the building are now mostly in the Cathedral Museum.

Good for age: 18+

  • Florence, Tuscany, Italy

  • Official star rating:

The Continentale is the most contemporary and playful of the Ferragamo family’s four Florentine hotels, dressed up in stylish, retro decor by interiors-whizz Michele Bonan.

Inside, the interior has an edgy vibe – tent-like curtains surround the beds; the clocks run in reverse; pops of bubbly gum colours break the white mood.

At sunset, grab a table on the hotel’s smart rooftop terrace bar, order a Campari Spritz and soak up the panoramic city views alongside a hip Florentine crowd.

It boasts a prime spot in the heart of the city, almost on top of the Ponte Vecchio. It’s the perfect choice for well-heeled weekenders looking to stay in the thick of the Florence action.

Average £420

Extra beds

Pool

2+ bedrooms

Beach

Kids menu

Fitness center

Kids club

Day 2 Florence

4

Start the day at the Accademia Gallery (pre-book) to admire Michelangelo’s David.

Then drop by Benozzo Gozzoli’s tiny Chapel of the Magi en route to the foodie heaven of the Mercato Centrale. Spend the rest of the morning browsing the gourmet offerings and stay for lunch, or sign up for a tour/cooking lesson.

Book a guided walking tour of the centro storico, and wind up with a prosecco at old-fashioned Procacci in Via Tornabuoni.

After a rest, head to hip La Menagere for cocktails and dinner.

  • Florence, Tuscany, Italy

Exterior of the entrance to the museum

Bucket List Experience

Accademia Gallery, Florence

Florence’s other big-name art museum (with the Uffizi) has a world-class collection of 14th- and 15th-century art, but those endless queues of people are really here to see one thing: Michelangelo’s 1504 4m-high statue of David.

Moved here in 1873 from Piazza della Signoria, the iconic sculpture appears quite different in the flesh: the head and hands are larger than expected (a trick of perspective; originally the statue was placed higher up).

Walk around the back to see David’s sling, a tree stump – and those famous buttocks.

Adult price: £10

Good for age: 18+

Magi Chapel

  • Florence, Tuscany, Italy

Magi Chapel

Experience

Benozzo Gozzoli’s glorious fresco depicting the Procession of the Magi dates from 1459 and covers the tiny ‘Cappella dei Magi’ in Palazzo Medici-Riccardi. Painted in brilliant jewel colours, it shows a procession of richly-attired kings, knights and servants travelling through a fairytale rural landscape.

Adult price: £6

Good for age: 18+

Florence’s Central Market

  • Florence, Tuscany, Italy

Florence’s Central Market

Experience

The first floor of Florence’s traditional produce market, Centrale Mercato, was transformed in 2014 into a dazzling food hall where producers offer everything from freshly-made mozzarella, truffle pasta, barbequed ribs, artisan bread and cheeses to hand-made chocolates. Pair a guided tour (to find ingredients) with a Tuscan cooking class after.

Good for age: 18+

MaMa Florence Cooking School

  • Florence, Tuscany, Italy

MaMa Florence Cooking School

Experience

For visitors who want to learn to make as well as eat the local specialities, this cooking school is a good place to start. Hands-on classes taught by pro chefs include making pasta, pizza, gelato, Tuscan meat and vegetarian. You can opt to tour the Central Market first too.

Adult price: £100

Good for age: 13+

Duration: 3-4 hours

When: Daily

Freq: daily

Day 3 Florence

4

A day in the Oltrarno…

After a cappuccino in Piazza Santo Sprito, discover the vast, ornate Pitti Palace and wander the shady Boboli Gardens before stopping at nearby Le Volpi e L’Uva wine bar for a lunchtime snack.

Explore the artisan workshops that line the surrounding narrow lanes, and don’t miss a gelato at award-winning Gelateria della Passera.

Squeeze into the tiny Santino wine bar for a glass of fizz before a Tuscan-with-a-twist dinner at Il Santo Bevitore (booking essential).

  • Florence, Tuscany, Italy

Pitti Palace

Bucket List Experience

Pitti Palace

Florence’s most imposing building was once home to the Medici court and later to the Savoy kings. Now this vast former palace houses multiple museums, the largest – and most important – of which is the Palatina Gallery.

The Palatina is laid out in a series of grand rooms on the first floor with fabulous frescoed ceilings under which hang masterworks by the likes of Raphael, Rubens, Botticelli and Van Dyck in elaborate gilded frames.

The other museums include the Treasury of the Grand Dukes, the Gallery of Modern Art and the Museum of Costume and Fashion. A new ground-floor gallery opened in late 2021 housing the oldest collection of Russian icons in Western Europe.

Adult price: £9

Good for age: 18+

  • Florence, Tuscany, Italy

Boboli Gardens

Experience

Boboli Gardens

Laid out on the hill that stretches up behind the Pitti Palace, this 16th-century former playground for the Medici family is one of the most beautiful gardens in Italy.

This shady green oasis makes a wonderful escape on a hot, summer’s day and is criss-crossed by pathways, dotted with fountains and scattered with lichen-covered statues.

At the top is the walled Giardino del Cavaliere with wonderful views over the rural outskirts of Florence. Walk down via the Neptune fountain and the amphitheatre which was built to hold Medici court spectacles.

Adult price: £5

Good for age: 13+

Le Volpi e l’Uva

  • Florence, Tuscany, Italy

Le Volpi e l’Uva

Experience

This small wine bar specialises in wines from small, independent producers and always has something interesting on offer. Order one of the bubbling, melted cheese-topped crostini to soak it up; the one with truffle-infused sausage is particularly good.

Good for age: 18+

Gelateria della Passera

  • Florence, Tuscany, Italy

Gelateria della Passera

Experience

This hole-in-the-wall ice cream shop (on pretty Piazza della Passera in the Oltrarno) dishes up some of the best gelato in the city centre, all made in small batches from fresh ingredients and without any kind of artificial flavourings. Think pistachio, pink grapefruit, zabaglione and coffee; flavours move with the seasons.

Good for age: 4+

Day 4 Pisa

3

Catch an early train from Florence and book an early slot to climb the Leaning Tower, then visit the Duomo, the Baptistery and the Camposanto (Field of Miracles). Head south through Piazza dei Cavallieri and down porticoed Borgo Stretto; stop for coffee at Pasticceria Salza.

Explore the old Mercato delle Vettovaglie with lunch at Osteria La Mescita. After, check out the current exhibition at Palazzo Blu and wander west along the river to the tiny Gothic church Santa Maria della Spina. Cross the Arno and finish the day at the fascinating Museum of Ancient Ships.

On return to Florence, order a Neapolitan pizza at Giotto.

  • Pisa, Tuscany, Italy

Leaning Tower of Pisa

Bucket List Experience

Leaning Tower of Pisa

One of Italy’s most popular sights, this astonishingly beautiful belltower dates back to 1173. An architectural marvel at the time, the tower was doomed from the outset, having been built on unstable sand and clay.

It began to lean once the third storey was completed; work was suspended for a hundred years, with the tower only being completed in the late 14th century. It housed seven bells, one for each musical note, and eventually reached a height of just over 58m.

In 1993, at 15 feet off the vertical, the tower seemed so close to collapse that an expensive rescue bid was made involving vast counterweights, steel cables and lots of digging. It worked to a degree; the building is once again safe and open to the public (but with enough lean to keep the hordes coming).

The still-famously titling tower still attracts millions of visitors a year, for the unnerving climb up its 293 steps.

Adult price: £15

Good for age: 13+

  • Pisa, Tuscany, Italy

Cathedral and leaning tower at Piazza dei Miracoli in Pisa, Italy.

Bucket List Experience

Field of Miracles

Pisa’s so-called ‘Field of Miracles’ (Campo dei Miracoli) is an elegant complex of monumental, unique buildings set on a wide green lawn just inside the northern city walls. It encompasses the iconic Leaning Tower, the Cathedral, the Baptistery and the Campo Santo.

First constructed was the huge Romanesque Cathedral, begun in 1063, with an intricately-tiered marble façade. Then came the Baptistery (1152), the biggest of its kind in Italy; it has a magnificent pulpit by Nicola Pisano. Building started on the emblematic Leaning Tower (a bell tower) in 1173, and it almost immediately began to lean.

Finally came the Camposanto (‘Holy Field’) cemetery, a roofless rectangle of gleaming white marble begun in 1277. It was once adorned with fabulous frescoes by Benozzo Gozzoli, but Allied bombing in 1944 caused the roof to collapse all but destroying them; today just fragments remain.

This is one of the most visited sites in Tuscany, although most people have their sights set on the Leaning Tower.

Good for age: 18+

Museum of Ancient Ships

  • Pisa, Tuscany, Italy

Museum of Ancient Ships

Experience

Housed in the atmospheric, 17th-century ex-Arsenal, this archaeological museum traces the fascinating 1,000-year history of seafaring and ships in Pisa, once a great Maritime Republic. Star exhibits include the collection of restored Roman vessels, unearthed in the San Rossore area.

Adult price: £6

Good for age: 4+

Day 5 Truffles

2

Sign up for a truffle hunting and cooking experience at Cucina Giuseppina which is based in the old town of Certaldo; catch a train or bus (40-minutes) from Florence.

An experienced truffler and his dog will lead the hunt through the woods followed by a truffle-based lunch or a cooking lesson.

In the late afternoon, explore Medieval Certaldo Alto (the old town): visit the 14th-century Palazzo Pretorio, the Casa di Boccaccio and wander the pretty cobbled streets.

Head back to Florence for dinner and the night.

  • Tuscany, Italy

Truffles in Tuscany

Bucket List Experience

Truffles in Tuscany

Of all the food and wine ingredients indigenous to Tuscany, the white truffle is probably the most highly-prized – yet it’s one of those things that you will either love or hate; it has a heady yet strange, earthy, musky aroma and a delicate flavour that lends itself particularly well to eggs and buttery tagliolini pasta

Different types of truffles grow year-round in Tuscany and in various areas, the most prolific of which are San Miniato, the Mugello and the Crete Senese. They are, however, elusive. White truffles will only thrive in just the right conditions, growing on the roots of trees and normally hidden by layers of damp leaves and earth.

A truffle hunt with an expert trifulau (truffle hunter) and his dog is a compelling way to discover how the truffle-hunting world works. The stakes are high – white truffles sell for huge amounts of money. In 2007, a 1.28kg tuber sold at auction in the US for an astonishing $330,000.

The most highly prized of Tuscany’s rich food harvest, the white truffle is also the most elusive. An expert-led truffle hunt is an ideal way to discover and taste these extraordinary tubers.

Good for age: 13+

Duration: -

Cucina Giuseppina Cooking School

  • Certaldo, Tuscany, Italy

Cucina Giuseppina Cooking School

Experience

A 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.

Adult price: £120

Good for age: 13+

Duration: 3-4 hours

Day 6 Lucca

5

From Florence, travel to Lucca by train or bus. Start with a cappuccino in oval Piazza del Anfiteatro. Explore the wonderful old shops on Via Fillungo and pop into the Puccini museum. Visit the Cathedral of San Martino; don’t miss the beautiful tomb of Ilaria del Carretto.

Hire a bike in Piazza Santa Maria to explore the 16th-century ramparts for an hour before a slap-up lunch at the famous Buca di Sant’Antonio (book ahead).

Climb the Torre Guinigi for spectacular views and take a stroll around the gardens of Palazzo Pfanner; finish the day in the church of San Michele in Foro.

Order a Campari spritz in Piazza del Anfiteatro before heading back to Florence and dinner at Trattoria del Carmine.

  • Lucca, Tuscany, Italy

A day in Lucca

Bucket List Experience

A day in Lucca

Lucca is a compact gem of a town, a perfect ensemble of Medieval and Renaissance buildings enclosed by a well-preserved set of 16th-century walls. Aside from its handsome piazzas and palazzi and exquisite churches, it boasts some lovely old shops, excellent restaurants and atmospheric cafés, all lining a network of pretty cobbled streets. Its overall attraction lies in the fact that it never feels overwhelmed by tourists, thus offering an authentic sense of local life.

A coffee in oval Piazza del Anfiteatro (built on the site of the Roman amphitheatre) is a good place to start a tour of the town. There are some wonderful old shops with their original storefronts in and around nearby Via Fillungo.

Historic, atmospheric Caffè di Simo (Via Fillungo 58) is another good place for a cappuccino and a pastry while the Buca di Sant’Antonio restaurant (open since 1782, Via della Cervia 3) serves up Lucchese specialities with a modern twist.

Good for age: 18+

Walk or cycle Lucca’s city walls

  • Lucca, Tuscany, Italy

Walk or cycle Lucca’s city walls

Experience

Don’t miss a stroll or bike ride around the 2.5 miles of walls; the locals love their ramparts and cycle, walk, jog and picnic here regularly (in summer, go early or late in the day to avoid the heat). You can hire bikes from Cicli Bizzari in Piazza Santa Maria, from where there is access to the ramparts.

Good for age: 4+

Duration: 1 hour

St Martin’s Cathedral

  • Lucca, Tuscany, Italy

St Martin’s Cathedral

Experience

The most important church in Lucca. Begun in the 11th-century, it has a magnificently carved marble façade and houses the tomb of Ilaria Carretto, a beautiful work in marble by Jacopo della Quercia.

Good for age: 18+

Giacomo Puccini Museum

  • Lucca, Tuscany, Italy

Giacomo Puccini Museum

Experience

Opera buffs shouldn’t miss the small museum dedicated to Giacomo Puccini, Lucca’s most famous son. He’s regarded as the greatest and most successful proponent of Italian opera after Verdi.

Adult price: £2

Good for age: 18+

Gelateria De’ Coltelli

  • Lucca, Tuscany, Italy

Gelateria De’ Coltelli

Experience

Seasonal fruit, local ingredients and organic milk, cream and eggs are the mainstays of this artisanal ice cream. Flavours vary with the seasons, but look out for the sinful De Bondt chocolate and candied orange peel and the pistachio ice creams, and the refreshing Sicilian-style granitas (almond, maybe) in summer.

Good for age: 4+

Day 7 San Gimigano

6

Editor: for the next few days of this itinerary exploring the regions south of Florence, including this one, it’s much easier if you hired a car…

From Florence, catch a bus or drive to San Gimignano. Begin the day by climbing the Torre Grossa (218 steps) for views of the town’s Medieval towers and red rooftops.

Then discover the treasures in the Museo Civico and climb the ruined Rocca. Pop into the Galleria Gagliardi to see its contemporary sculpture collection.

Stop for lunch at Gustavo Mescita Vini, a wine bar with food on the main drag. Then sample the fantastic gelato at world-famous Dondoli in Piazza della Cisterna. Visit the astonishing frescoes in the Collegiata church and sign up for a tasting of the local Vernaccia wine. Finish with a prosecco in Piazza Cisterna.

Either return to Florence, or head to Borgo San Felice (1 hour’s drive) or Hotel Palazzo Ravizza in Siena (30 mins drive) as your next base for exploring Tuscany’s southern region.

  • San Gimignano, Tuscany, Italy

A day in San Gimignano

Bucket List Experience

A day in San Gimignano

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.

Good for age: 18+

Civic Museum of San Gimignano

  • San Gimignano, Tuscany, Italy

Civic Museum of San Gimignano

Experience

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.

Good for age: 18+

Gelateria Dondoli

  • San Gimignano, Tuscany, Italy

Gelateria Dondoli

Experience

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).

Good for age: 4+

Collegiata di Santa Maria Assunta

  • San Gimignano, Tuscany, Italy

View of the Collegiate Church of Santa Maria Assunta, iconic basilica and major landmark in the historic centre of San Gimignano

Experience

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.

Good for age: 18+

  • Tuscany, Italy

  • Official star rating:

Borgo San Felice

Place to Stay

Borgo San Felice

A medieval stone village converted into a luxurious resort in the heart of south-eastern Chianti, Borgo San Felice is also a working wine estate, producing award-winning wines and olive oil. Immersed in vineyards and olive groves, it is a sophisticated country retreat with particular appeal for oenophiles.

The restoration has left typical Tuscan features, such as beamed ceilings and brick arches intact, but updated the look for the 21st century.

Rooms are spread through the main palazzo and village buildings; the old schoolhouse, the olive press, the cellars and the bakery.

There’s an excellent spa and two restaurants, one with a Michelin star.

Although this is the sort of place where you could throw your car keys away on arrival, there is lots to do close by. Siena is a twenty-minute drive away and Florence is an hour. This part of Chianti is stuffed with wine estates, so it’s a brilliant launch pad for wine tastings and vineyard tours.

Average £600

Extra beds

Pool

2+ bedrooms

Beach

Kids menu

Fitness center

Kids club

  • Siena, Tuscany, Italy

  • Official star rating:

With its quiet yet central location, reassuringly old-fashioned atmosphere and delightful Italianate garden, aristocratic Palazzo Ravizza is a great base from which to explore Siena.

Dating from the 18th century and still owned by the noble Ravizza family, it has been welcoming guests since 1922, and retains a nostalgic air, while providing 21st-century comforts.

Public spaces and bedrooms are furnished with antiques and artworks, and guests are welcome to play the Steinway in the elegant grand salon.

But the real USP is the marvellous formal garden that looks over the open Sienese countryside; a stunning spot for breakfast or a post-sightseeing aperitivo.

Anyone looking to extend a visit to Siena beyond a day will struggle to find a more authentic place to stay.

Average £150

Extra beds

Pool

2+ bedrooms

Beach

Kids menu

Fitness center

Kids club

Day 8 Chianti

4

Rise early and start with a visit to in Greve-in-Chianti before heading south along the vineyards along the SS222 stopping off at pretty Panzano; visit Dario Cecchini’s famous butcher’s shop.

Break for wine tasting at Fontodi before continuing down the SS222 to Castellina in Chianti, another wine centre; sample some more wines at Enoteca Squarcialupi. Then drive on to Fonterutoli, one of Chianti’s foremost producers, for a cellar tour and lunch. Leave the SS222 and drive east to the Castello di Brolio which is where the history of Chianti wines began.

Finally, head (back) to Borgo San Felice leaving time for a tasting of their excellent wines and dinner at their gourmet restaurant Poggio Rosso.

  • Chianti, Tuscany, Italy

Chianti Wine Region

Bucket List Experience

Chianti Wine Region

Some of Italy’s best wines are produced in the DOCG Chianti Classico, 177,500 acres of undulating, vine-striped land stretching between Florence and Siena. Dozens of wine estates share this fertile terroir, many of which offer tastings and vineyard tours and an opportunity to buy wines from source. Some also have very good restaurants and accommodation.

The history of wine-making in the region dates back hundreds of years. Early Chiantis were a blend of Sangiovese, Canaiolo and Malvasia Bianca grapes; today, a DOC Chianti must be made with at least 80% Sangiovese.

The main Chianti growing area is divided into eight sub-zones. The most famous is Chianti Classico, located between Florence and Siena, which produces some 25 million bottles a year, including some of the region’s greatest wines. Most bottles sport the image of a black rooster on a gold background, a guarantee of quality.

Good for age: 18+

Castellina in Chianti

  • Castellina in Chianti, Tuscany, Italy

Castellina in Chianti

Experience

Lying directly on the SS222, hill-top Castellina was once a bastion of Florentine dominance as seen in the imposing fortifications and tower. It’s a very pleasant town to wander around and there are lots of places to buy and taste wine.

Good for age: 18+

  • Tuscany, Italy

  • Official star rating:

Borgo San Felice

Place to Stay

Borgo San Felice

A medieval stone village converted into a luxurious resort in the heart of south-eastern Chianti, Borgo San Felice is also a working wine estate, producing award-winning wines and olive oil. Immersed in vineyards and olive groves, it is a sophisticated country retreat with particular appeal for oenophiles.

The restoration has left typical Tuscan features, such as beamed ceilings and brick arches intact, but updated the look for the 21st century.

Rooms are spread through the main palazzo and village buildings; the old schoolhouse, the olive press, the cellars and the bakery.

There’s an excellent spa and two restaurants, one with a Michelin star.

Although this is the sort of place where you could throw your car keys away on arrival, there is lots to do close by. Siena is a twenty-minute drive away and Florence is an hour. This part of Chianti is stuffed with wine estates, so it’s a brilliant launch pad for wine tastings and vineyard tours.

Average £600

Extra beds

Pool

2+ bedrooms

Beach

Kids menu

Fitness center

Kids club

  • Siena, Tuscany, Italy

  • Official star rating:

With its quiet yet central location, reassuringly old-fashioned atmosphere and delightful Italianate garden, aristocratic Palazzo Ravizza is a great base from which to explore Siena.

Dating from the 18th century and still owned by the noble Ravizza family, it has been welcoming guests since 1922, and retains a nostalgic air, while providing 21st-century comforts.

Public spaces and bedrooms are furnished with antiques and artworks, and guests are welcome to play the Steinway in the elegant grand salon.

But the real USP is the marvellous formal garden that looks over the open Sienese countryside; a stunning spot for breakfast or a post-sightseeing aperitivo.

Anyone looking to extend a visit to Siena beyond a day will struggle to find a more authentic place to stay.

Average £150

Extra beds

Pool

2+ bedrooms

Beach

Kids menu

Fitness center

Kids club

Day 9 Siena

7

Begin the day with a coffee in historic Piazza del Campo, then climb the Torre di Mangia for wraparound views. Visit the dazzling collections of paintings in the Civic Museum and the Pinacoteca. Grab a quick lunch at Enoteca I Terzi.

Visit the zebra-striped Duomo and explore the ancient streets and alleyways of the old town, keeping an eye open for Palio symbols on the old street signs. Stop at Caffé Nannini for a slice of panforte. Visit the ex-hospital of Santa Maria della Scala for its brilliant archaeological museum and frescoed Pilgrim’s Hall.

Book dinner at elegant Osteria Le Logge, or head direct to your next base at Hotel Lupaia (45 min – 1 hour drive).

  • 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

Bucket List Experience

A day in Siena

According to many of its citizens, Siena is the most perfect medieval city in the world. A glorious ensemble of red brick buildings and exquisite monuments, it’s famous for its fan-shaped Campo and the twice-yearly Il Palio horse race.

Any visit to the city should begin in the sloping Piazza del Campo, the city’s main square, fringed with cafes that are perfect for a doppio espresso and a spot of people-watching. The square is dominated by the Mangia Tower and the Palazzo Pubblico – and climbing the tower is a great way to start your visit, giving wraparound views of the city and surrounding countryside.

The old town is relatively compact and the best way to explore is simply by strolling through the ancient streets and alleyways.

Good for age: 18+

Civic Museum of Siena

  • Siena, Tuscany, Italy

exterior of the The Pubblico Palace in Siena

Experience

A must-see for its collection of paintings by Lorenzetti, Simone Martini and other Sienese masters. One of the highlights is Simone Martini’s Maesta fresco (1315); another is Lorenzetti’s fresco cycle The Allegory of Good and The Effects of Bad Government (1338-40).

Adult price: £8

Good for age: 18+

National Pinacoteca Siena

  • Siena, Tuscany, Italy

Pinacoteca Nazionale exterior entrance door

Experience

A 15th-century palazzo housing more than 1,500 artworks, one of Italy’s foremost collections includes an array of dazzling Sienese fondi d’oro paintings (with gilded backgrounds). Expect works by Guido da Siena, Lorenzetti, Sodoma and Beccafumi.

Adult price: £7

Good for age: 18+

Siena Cathedral

  • Siena, Tuscany, Italy

The facade of the Siena Cathedral in the sunlight and the circular window

Experience

The magnificent Gothic, zebra-striped Duomo houses a celebrated polychrome floor, often covered for protection but normally visible in August and September. Look out for Nicola Pisano’s superb marble pulpit and the young Michelangelo’s Piccolomini altar.

Good for age: 18+

Santa Maria della Scala

  • Siena, Tuscany, Italy

Santa Maria della Scala

Experience

This ex-hospital building was founded in the 9th century (making it one of Europe’s oldest), and only closed relatively recently; the author Italo Calvino died here in 1985. It houses an excellent archaeological museum and the wonderful ‘Pilgrim’s Hall’ decorated with 15th-century frescoes depicting the history of the hospital.

Adult price: £8

Good for age: 18+

  • Siena, Tuscany, Italy

  • Official star rating:

With its quiet yet central location, reassuringly old-fashioned atmosphere and delightful Italianate garden, aristocratic Palazzo Ravizza is a great base from which to explore Siena.

Dating from the 18th century and still owned by the noble Ravizza family, it has been welcoming guests since 1922, and retains a nostalgic air, while providing 21st-century comforts.

Public spaces and bedrooms are furnished with antiques and artworks, and guests are welcome to play the Steinway in the elegant grand salon.

But the real USP is the marvellous formal garden that looks over the open Sienese countryside; a stunning spot for breakfast or a post-sightseeing aperitivo.

Anyone looking to extend a visit to Siena beyond a day will struggle to find a more authentic place to stay.

Average £150

Extra beds

Pool

2+ bedrooms

Beach

Kids menu

Fitness center

Kids club

Lupaia

  • Montepulciano, Tuscany, Italy

  • Official star rating:

Lupaia

Place to Stay

Lupaia

This beautiful, stylishly-restored 17th century farmhouse complex has been turned into a luxury country retreat, hidden away down a long winding lane in the UNESCO-designated Val d’Orcia.

The 12 bedrooms – which size-wise are more like suites – inhabit the old stone farm buildings, and are done out in luxe-rustic style with massive beds, splendid bathrooms and private garden areas.

The heart of the hotel is the restaurant, with its open kitchen and vast fireplace; meals are served here in cooler weather, or on the romantic terrace decorated with fairy lights in summer.

Located in the heart of the Val d’Orcia, just outside Montepulciano, Lupaia makes a perfect base for exploring the area; Pienza, Bagno Vignoni and San Quirico d’Orcia are all within a 30-minute drive.

The owner-managers are always on hand and full of helpful advice about how to get the best from the area, giving the place a really personal, intimate feel.

It’s a great choice for couples and those who want to really immerse themselves in Tuscan life.

Average £600

Extra beds

Pool

2+ bedrooms

Beach

Kids menu

Fitness center

Kids club

Day 10 Val d'Orcia

4

Start your exploration of the stunning Val d’Orcia with a wander round lovely, Renaissance Pienza. Then take the SP71 to San Quirico d’Orcia, and visit the Collegiata church.

Drive south along the SR2 to the spa town of Bagno Vignoni, and take a salutary soak in the pool at the hotel Posta Marcucci where you can also have a bite of lunch.

Head east across the valley towards Montepulciano, stopping off at tiny Montichiello. Finish up in hilltop Montepulciano; visit the church of San Biagio, the Duomo and taste some Vino Nobile wine.

Order a prosecco at Caffé Poliziano before returning to Hotel Lupaia for dinner.

  • Val d'Orcia, Tuscany, Italy

Beautiful view of the green hills and villa in the valley of Val d'Orcia.

Bucket List Experience

A day in the Val d’Orcia

The UNESCO-protected Val d’Orcia is one of the most beautiful areas of Tuscany, a ravishing expanse of open, undulating farmland broken by cypresses in soldier-straight lines and dominated by Monte Amiata, an extinct volcano.

Atmospheric hill-top towns dot the countryside, many dating back to medieval times, when settlements were built on outcrops of rock or hill summits; both easier to protect and harder to invade.

Pottering between two of three of the towns is a glorious way to spend a day; Pienza and Montepulciano are the biggest draws, but other highlights include the spa village of Bagno Vignoni – where a thermal pool takes the place of the central piazza – and San Quirico d’Orcia, with its magnificent Collegiata church. Close to Montepulciano is Villa La Foce, with a beautiful garden open to visitors.

Unpaved white roads link many of the smaller villages in the area, making this ideal walking and cycling country. Weaving through these unspoilt landscapes on either foot or two wheels is a fabulous way to appreciate some of the most beautiful rural landscapes in Italy.

Good for age: 18+

Bagno Vignoni

  • Bagno Vignoni, Tuscany, Italy

Bagno Vignoni

Experience

This small, enchanting village, situated on a hill above the Val d’Orcia, is famous for its central square, which is a large pool filled with hot springs water. You can’t bathe in it these days, so head for Hotel Posta Marcucci instead.

Good for age: 18+

Montepulciano

  • Montepulciano, Tuscany, Italy

Montepulciano

Experience

Famous for its production of robust red wines (which can be sampled at the town’s many enotecas), hilltop Montepulciano is also worth visiting for its grand palazzi, the Duomo, and, just outside the walls, Sangallo’s church of San Biagio.

Good for age: 18+

Lupaia

  • Montepulciano, Tuscany, Italy

  • Official star rating:

Lupaia

Place to Stay

Lupaia

This beautiful, stylishly-restored 17th century farmhouse complex has been turned into a luxury country retreat, hidden away down a long winding lane in the UNESCO-designated Val d’Orcia.

The 12 bedrooms – which size-wise are more like suites – inhabit the old stone farm buildings, and are done out in luxe-rustic style with massive beds, splendid bathrooms and private garden areas.

The heart of the hotel is the restaurant, with its open kitchen and vast fireplace; meals are served here in cooler weather, or on the romantic terrace decorated with fairy lights in summer.

Located in the heart of the Val d’Orcia, just outside Montepulciano, Lupaia makes a perfect base for exploring the area; Pienza, Bagno Vignoni and San Quirico d’Orcia are all within a 30-minute drive.

The owner-managers are always on hand and full of helpful advice about how to get the best from the area, giving the place a really personal, intimate feel.

It’s a great choice for couples and those who want to really immerse themselves in Tuscan life.

Average £600

Extra beds

Pool

2+ bedrooms

Beach

Kids menu

Fitness center

Kids club