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Bucket list trip:

Last updated: 21 June, 2023
Expert travel writer: Nicky Swallow

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.

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.

Uffizi Gallery

Florence, Tuscany, Italy

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Bucket List Experience
Uffizi Gallery

The world’s largest and most important collection of Renaissance and Mannerist art, home to 5,400 works spans art history from ancient Greece through to 18th-century Venetian painting.

Adult price: £10

Best for ages 18+

Giotto’s Bell Tower

Florence, Tuscany, Italy

Giotto’s Bell Tower

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.

Best for ages 18+

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Hotel Continentale Florence

Florence, Tuscany, Italy

|Official star rating:

Hotel Continentale Florence

Cool, edgy Ferragamo-owned design hotel by the Ponte Vecchio in the heart of the city – the perfect base for sightseeing.

Average £420

Extra beds

Pool

2+ bedrooms

Beach

Kids menu

Fitness center

Kids club

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.

Accademia Gallery, Florence

Florence, Tuscany, Italy

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Bucket List Experience
Exterior of the entrance to the museum

One of Florence’s two big-name art museums, home to a world-class collection of 14th- and 15th-century art, and Michelangelo’s iconic masterpiece David.

Adult price: £10

Best for ages 18+

Magi Chapel

Florence, Tuscany, Italy

Magi Chapel

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

Best for ages 18+

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Florence’s Central Market

Florence, Tuscany, Italy

Florence’s Central Market

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.

Best for ages 13+

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MaMa Florence Cooking School

Florence, Tuscany, Italy

MaMa Florence Cooking School

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

Best for ages 13+

Duration: 3-4 hours

When: Daily

Frequency: daily

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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).

Pitti Palace

Florence, Tuscany, Italy

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Bucket List Experience
Pitti Palace

Housed in the city’s most imposing palazzo, Florence’s second-largest art gallery is home to masterpieces by Raphael, Rubens, Botticelli and Van Dyck.

Adult price: £9

Best for ages 18+

Boboli Gardens

Florence, Tuscany, Italy

Boboli Gardens

This shady green oasis in the centre of Florence is one of the most beautiful gardens in Italy and makes a wonderful escape on a hot, summer’s day.

Adult price: £5

Best for ages 13+

Le Volpi e l’Uva

Florence, Tuscany, Italy

Le Volpi e l’Uva

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.

Best for ages 18+

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Gelateria della Passera

Florence, Tuscany, Italy

Gelateria della Passera

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.

Best for ages 4+

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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.

Leaning Tower of Pisa

Pisa, Tuscany, Italy

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Bucket List Experience
Leaning Tower of Pisa

One of Italy’s most popular sights, an astonishingly beautiful but leaning belltower dating back to 1173, doomed from the outset having been built on unstable sand and clay.

Adult price: £15

Best for ages 10+

Field of Miracles

Pisa, Tuscany, Italy

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

Pisa’s Field of Miracles is an extraordinary complex of historic buildings set on a wide green lawn, encompassing the iconic Leaning Tower, the Cathedral, the Baptistery and the Campo Santo.

Best for ages 18+

Museum of Ancient Ships

Pisa, Tuscany, Italy

Museum of Ancient Ships

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

Best for ages 4+

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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.

Truffles in Tuscany

Tuscany, Italy

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Bucket List Experience
Truffles in Tuscany

Learn about these extraordinary tubers – the most highly prized of Tuscany’s rich food harvest – on an expert-led truffle hunt in traditional Tuscan countryside. Hunts are often combined with truffle-based lunches or cooking lessons with truffles.

Best for ages 13+

Duration: -

Cucina Giuseppina Cooking School

Certaldo, Tuscany, Italy

Cucina Giuseppina Cooking School

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.

Adult price: £120

Best for ages 13+

Duration: 3-4 hours

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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.

A day in Lucca

Lucca, Tuscany, Italy

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Bucket List Experience
A day in Lucca

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.

Best for ages 18+

Walk or cycle Lucca’s city walls

Lucca, Tuscany, Italy

Walk or cycle Lucca’s city walls

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.

Best for ages 4+

Duration: 1 hour

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St Martin’s Cathedral

Lucca, Tuscany, Italy

St Martin’s Cathedral

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.

Best for ages 18+

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Giacomo Puccini Museum

Lucca, Tuscany, Italy

Giacomo Puccini Museum

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

Best for ages 18+

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Gelateria De’ Coltelli

Lucca, Tuscany, Italy

Gelateria De’ Coltelli

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.

Best for ages 4+

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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.

A day in San Gimignano

San Gimignano, Tuscany, Italy

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Bucket List Experience
A day in San Gimignano

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.

Best for ages 18+

Civic Museum of San Gimignano

San Gimignano, Tuscany, Italy

Civic Museum of San Gimignano

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+

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Gelateria Dondoli

San Gimignano, Tuscany, Italy

Gelateria Dondoli

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+

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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

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+

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Borgo San Felice

Tuscany, Italy

|Official star rating:

Borgo San Felice

A rambling luxe retreat set in a timeless Tuscan landscape of vineyards and olive groves; it’s also a working wine estate producing award-winning vintages.

Average £600

Extra beds

Pool

2+ bedrooms

Beach

Kids menu

Fitness center

Kids club

Hotel Palazzo Ravizza

Siena, Tuscany, Italy

|Official star rating:

Hotel Palazzo Ravizza

With its old-fashioned atmosphere, central location and wonderful Italianate garden, three-star, aristocratic Palazzo Ravizza is a great base for exploring Siena.

Average £150

Extra beds

Pool

2+ bedrooms

Beach

Kids menu

Fitness center

Kids club

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 Wine Region

Chianti, Tuscany, Italy

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Bucket List Experience
Chianti Wine Region

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+

Castellina in Chianti

Castellina in Chianti, Tuscany, Italy

Castellina in Chianti

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.

Best for ages 18+

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Borgo San Felice

Tuscany, Italy

|Official star rating:

Borgo San Felice

A rambling luxe retreat set in a timeless Tuscan landscape of vineyards and olive groves; it’s also a working wine estate producing award-winning vintages.

Average £600

Extra beds

Pool

2+ bedrooms

Beach

Kids menu

Fitness center

Kids club

Hotel Palazzo Ravizza

Siena, Tuscany, Italy

|Official star rating:

Hotel Palazzo Ravizza

With its old-fashioned atmosphere, central location and wonderful Italianate garden, three-star, aristocratic Palazzo Ravizza is a great base for exploring Siena.

Average £150

Extra beds

Pool

2+ bedrooms

Beach

Kids menu

Fitness center

Kids club

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).

A day in Siena

Siena, Tuscany, Italy

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Bucket List Experience
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.

Best for ages 18+

Civic Museum of Siena

Siena, Tuscany, Italy

exterior of the The Pubblico Palace in Siena

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

Best for ages 18+

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National Pinacoteca Siena

Siena, Tuscany, Italy

Pinacoteca Nazionale exterior entrance door

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

Best for ages 18+

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Siena Cathedral

Siena, Tuscany, Italy

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

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.

Best for ages 18+

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Santa Maria della Scala

Siena, Tuscany, Italy

Santa Maria della Scala

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

Best for ages 18+

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Hotel Palazzo Ravizza

Siena, Tuscany, Italy

|Official star rating:

Hotel Palazzo Ravizza

With its old-fashioned atmosphere, central location and wonderful Italianate garden, three-star, aristocratic Palazzo Ravizza is a great base for exploring Siena.

Average £150

Extra beds

Pool

2+ bedrooms

Beach

Kids menu

Fitness center

Kids club

Lupaia

Montepulciano, Tuscany, Italy

|Official star rating:

Lupaia

A beautiful, stylishly-restored 17th-century farmhouse complex is a romantic retreat for couples or those looking for an intimate, authentic place to stay.

Average £600

Extra beds

Pool

2+ bedrooms

Beach

Kids menu

Fitness center

Kids club

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.

A day in the Val d’Orcia

Val d'Orcia, Tuscany, Italy

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

One of the most beautiful areas of Tuscany, the Val d’Orcia is a ravishing expanse of open, undulating farmland, dotted by atmospheric hill towns and dominated by Monte Amiata, an extinct volcano.

Best for ages 18+

Bagno Vignoni

Bagno Vignoni, Tuscany, Italy

Bagno Vignoni

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.

Best for ages 13+

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Montepulciano

Montepulciano, Tuscany, Italy

Montepulciano

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.

Best for ages 18+

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Lupaia

Montepulciano, Tuscany, Italy

|Official star rating:

Lupaia

A beautiful, stylishly-restored 17th-century farmhouse complex is a romantic retreat for couples or those looking for an intimate, authentic place to stay.

Average £600

Extra beds

Pool

2+ bedrooms

Beach

Kids menu

Fitness center

Kids club