10 days in Tuscany - the ultimate Tuscany itinerary

The dusky set of an Italic melodrama, Tuscany wows even the most stoic of travellers with its artistic legacy and historic charms on a dramatic landscape of Chianti vineyards and indigo seas. Named after the ancient Etruscans who rivalled the Greeks from 5BC onwards, Tuscany comes with much cultural clout in the boot of the nation. Forego pre-packaged Tuscany tours and go your own way with a helping hand from our guide to the 7 best places to experience gay Italy and our 10 day Tuscany itinerary below.

Tailor Made Journey

Tailor-Made Italy: The Vatican to Venice

On a privately guided journey that reveals Italy's splendours at their most compelling, enjoy a special early entrance to the Vatican, view the artistic treasures of Florence, learn about an art restoration project and sample Italian cuisine with tastings in Tuscany and a food tour in Venice.

Photo: Siegfried Poepperl

Why visit Tuscany?

First came the Etruscans with their enduring art and cultural institutions, followed by the House of Medici which further influenced politics, religion and architecture across Italy. Tuscan’s central city of Florence lays claim to the poet who set the foundations for the modern Italian language, while later in the 15th century, the city became a hotbed for Renaissance ideals, bringing with it an era of artistic and intellectual progress for Italy. As a result, you’ll find the whole of the region comes littered with art across its museums, churches and galleries, as well as plenty of cultural attractions and historic sites, kept alive with an array of traditional festivals.

Peep centuries-old palazzo floor frescos, world-famous artworks by Da Vinci and even climb the stairs of the most famous leaning tower, stopping by a cucina contadina for a homecooked meal like no other. From Florence and Siena to Pisa and Lucca, there’s something in Tuscany’s biggest cities for everyone, with evermore to be discovered across the rolling Tuscan countryside where small towns and infamous wineries come close to 400 kilometres of Tyrrhenian Sea coastline.

Photo: Patrick Schneider

Florence | Photo: Martin Dubreuil

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From Florence and Siena to Pisa and Lucca, there’s something in Tuscany’s biggest cities for everyone, with evermore to be discovered across the rolling Tuscan countryside

Best time to visit Tuscany

Though there is no wrong time to visit Tuscany, travellers should note that July and August mark the height of summer and can be both humid and busy in central areas, such as in Florence and along the coast. For a slightly quieter trip, try the shoulder seasons from April to early June and September to October for optimum temperatures and clear days with fewer crowds. February is also a consideration for its cooler weather and post-New Year’s Day quietude. All foodies considered, however, later in the year between October and November could be time to visit, as the region celebrates its annual harvest by way of wine, truffle and chestnut festivals.

Florence | Photo: Raghu Nayyar

Getting Around Tuscany

The beating heart of the region lies in Florence, a city easily reached via Aeroporto di Firenze (FLR) which is just 4 kilometres west of the city centre. Other international airports such as Pisa International Airport and Galileo Galilei Airport are also good options, based even closer to their respective centres. While there are no direct flights from the United States, US travellers can transfer through a wide number of European city hubs, including London, Paris and Amsterdam.

From the airport, get a taxi or try the bus service into town, moving onto foot within the historic pedestrian-only centres. For transport between cities, trains are dependable and offer connections from Florence on to major spots such as Lucca and Arezzo. If heading from Florence to Siena, or onwards to the hilltop towns of San Gimignano and Volterra, the bus is the next best thing to a car. Exploring Tuscany with your own vehicle is the hands-down winner, however, allowing you the freedom to ride across the entire region at any pace you choose. Pick up a rental at one of the bigger towns and cities, requesting an automatic in advance if shifting gears manually seems a hassle.

Crete Senesi | Photo: Jarno Cobbaert

Photo: Karl Muscat

The ultimate Tuscany itinerary

10 days in Tuscany will go flying by as you tick off the hottest destinations in capital ‘Firenze’ before working your way out to medieval hubs like Siena and Lucca, which offer neat jumping-off points to the coast, world-class wineries and more rural parts.

1. Florence

A likely first stop on your trip through Tuscany is the UNESCO World Heritage city of Florence which deserves at least a day of love from all its visitors. Become entranced by morning on the banks of the Arno river, getting lost among the goldsmiths of cobbled backstreets before going gourmet in a market trattoria come lunchtime. For the afternoon, the Uffizi Gallery provides easy insight into the city’s artistic past, with Botticelli and Michelangelo showstoppers, while out of doors, marble basilicas, 16th-century palaces and Italy’s greatest fashion houses (Hello, Guccio Gucci) vie for space among artisan boutiques and blossom-laden palazzos.

Besides getting hooked on haute couture, visitors to Florence can get into nature with a sunset hike to Piazzale Michelangelo, venturing out on optional day trips to both Arezzo (1-hour drive) and Lucca (1 hour 30 minutes). Get the whole rundown on where to stay and what to do with our dedicated Florence travel guide.

Photo: Josh Hild

2. Lucca

Oft overlooked in favour of nearby Pisa, Lucca has a lot to offer those looking for authentic Tuscany at a slower pace. Centrally located on the Serchio River, Lucca is a vibrant town laden with important architecture such as its Roman amphitheatre, the 11th century Diavolo Bridge and the medieval towers of Torre Guinigi and Torre dell Ore. Alongside all of that, Lucca hosts several famous churches spanning human history, the oldest being the Church of San Michel which was written about as early as 795AD.

One of the top things to do in Lucca is to cycle or walk along the perimeter walls, learning of the town’s Etruscan and ancient Roman foundations, all the while soaking up the view over Villa Reale di Marlia and its gardens. Downtown, Via Fillungo, can keep you busy with its maze of interconnected streets both old and new, while the Piazza dell’Anfiteatro is worthy of congregating on for Lucchesi wine and rustic fare. Those willing to rent a car can go the way of homegrown composer Giacomo Puccini, taking to the surrounding hills for villa lifestyles and thermal baths at Montecatini Terme. In easy reach along the river, Garfagnana is also one for adventurers, allowing for stand-up paddleboarding, horse riding and more.

Lucca | Photo: Miti

Lucca | Photo: Djedj

3. Volterra and San Gimignano

A small Etruscan hill town around 90 minutes from Lucca is Volterra, a site boasting three thousand years of history and one of the country’s prettiest piazzas. Known as Piazza dei Priori, this medieval square will link you to all that’s good in the town, branching out along narrow alleys and old shopping streets of alabaster façades. Find Via Porta all’Arco (or Artisan Lane) to glimpse the town’s handicraft and art industry at work, looking up to the skyline to set eyes on the 14 towers of San Gimignano, an eastern outpost about 45 minutes’ out of town. Take a morning trip here to see the towers of ‘medieval Manhattan’ up close, seeing the Sienese frescoes at the Basilica of Santa Maria Assunta and climbing up Torre Grossa to reach the highest point in town. While here you’ll also learn about how the towers came to symbolise status and wealth in Etruscan times, before a plague in the 14th century wiped our much of the population and forced submission to Florence in 1354.

San Gimignano | Photo: Ztx

4. Monteriggioni, Chianti

A pair of sleepy drunks, Monteriggioni and Chianti are in fact Italy wine region’s most valued players. Monteriggioni comes first after Volterra, just 45 minutes drive east and uphill towards the ‘Gateway of the Middle Ages’. Here you’ll discover a lofty village packed with craft stores and cafés as well as 13th-century fortifications and the Church of Santa Maria Assunta, best seen in the morning or later in the evening when the tour groups disperse and a cosy assortment of bars open.

From there, it’s just 20 minutes to Castellina, the so-called gateway to Chianti wine region. Castellina gives more medieval vibes and rolling views with an intriguing vaulted passageway that leads through its town walls. Take a day to drive aimlessly in all directions from Castellina, up and down through the hills and vineyards to wind up at the quiet hamlet of Montefioralle, the main town of Greve, photogenic Radda or the market town of Gaiole, all of them worthy of an afternoon and a bottle of red.

A little more about the Chianti region:  this is the picture-perfect part of Tuscany responsible for producing both Chianti and Chianti Classico, two reds sold under Gallo Nero. As well as wines, Chianti is also known for its olive production, with groves, vineyards and forests overlooked by stone farmhouses, remote Romanesque churches, Middle Age castles and Renaissance villas.

Castellina In Chianti | Photo: Rowan Heuvel

Photo: Roman Odintsov

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This is the picture-perfect part of Tuscany responsible for producing both Chianti and Chianti Classico, two reds sold under Gallo Nero

5. Siena

A big one on the traveller’s trail is the Province of Siena, our next stop. More medieval beauty is a given while in Siena, most concentrated on the capital city of the same name which comes split into 17 distinct neighbourhoods, each with their own constitution, traditions and history. In amongst this melting pot, Siena’s UNESCO World Heritage centre stands out for its architecture, museums and bustling piazzas, such as the Piazza del Campo on which the biannual Palio horse racing festival takes place. Downtown is where to go for lunch, followed by a guided tour of the town’s best bits, encompassing the 13th-century Palazzo Pubblico (home of the Civic Museum) and the 500-step Torre del Mangia with its worthwhile panoramas over the region and the fanciest hillside villas. An alternative view of the city and surrounding wine region can also be had via hot-air balloon, taking off from the outskirts of Siena City.

The green and white duomo of the Piccolomini Library is hard to miss while you’re up in the air, but the interiors are equally as arresting, thanks to huge Pinturicchio frescoes that cover the library walls. Also on your radar should be the Museo dell’Opera Metropolitana art museum, and churches such as the Basilica dell’Osservanza, Santo Spirito and the Sanctuary of Santa Caterina. Otherwise, big spenders can take the afternoon for designer shopping at Valdichiana Outlet Village, while those wishing to learn of the province’s craftmanship and get a few ceramic souvenirs can head to Ceramiche Bianco e Nero di Staccioli.

Siena | Photo: Alessandro Rossi

6. Crete Senesi

Venture deeper into the Tuscany landscape by heading southeast of Siena to Crete Senesi. The area is said to hold some of Tuscany’s best drives, made all the more interesting by undulating lunar hills and pretty villages. The clay hills, today brightened up by olive groves, wheat fields and cypress avenues, once led under the Pliocene Sea some 3 million years ago. Now referred to as the Desert of Accona,  Crete Senesi still offers traces of its more recent history, by way of small medieval settlements, traditional festivals and ancient cultural customs. Visit the towns of Asciano, Buonconvento and Serre di Rapolano to sample local culture and cuisine, making sure to stop at the Abbey of Monte Oliveto Maggiore, the thermal springs of Rapolano Terme and San Giovanni d’Asso to stock up on white truffles on the way.

7. Val d’Orcia

An hour south and into the valleys brings us to Val d’Orcia, a UNESCO World Heritage site and key player for ‘Agriturismo Tuscany’. With such fertile soil protected by imposing hilltop fortifications, Val d’Orcia has both gastronomic and historic appeal, perfect for an overnight stay in any of the towns and villages within. Pienza in the northeast is good for overnight stays within its historic centre, visiting the many abbeys and medieval hamlets in neighbouring settlements by day. San Quirico d’Orcia in particular is known for its Collegiate Church, Palazzo Chigi Zondadari and its Horti Leonini Gardens, while Monticchiello is a fortified joy to explore. Those wanting to play damsel for the day can also try the region’s best castles, such as Fortezza di Montalcino or Fortezza di Radicofani.

San Quirico d'Orcia, Italy | Photo: Luca Micheli

8. Montepulciano, Cortona

More time-old churches, palaces and wines await ahead, first in the medieval hill town of Montepulciano, just 30 minutes drive east of San Quirico, and then onto Cortona Italy, fondly known as Tuscany’s breadbasket. Once in Montepulciano, you’ll need just a few hours to see the best sights, starting at Piazza Grande with good shoes to go up and down the steep main ‘corso’ to find forts, the Church of Saint Agostino and Sangiovese vineyard views. Though Montepulciano’s heyday is well behind it – its many palaces designed in the 1400 and 1500s by Renaissance architects such as Michelozzo, Sangallo, Vignola et al – today the excellent food and wine is the main lure, best enjoyed at loftier points in town overlooking Valdichiana below.

Then to Cortona, another high-up spot with vistas over the plains, as well as added intrigue by way of local art, crafts and market hubbub. Cortona is also where you can get your paws on the famous bistecca alla Fiorentina, a Porterhouse steak dish made from native white Chianina beef. Once filled with protein, we can better make our way around town, starting in the central street of Via Nazionale and branching out to the magnificent Palazzo Comunale that edges the Piazza Della Repubblica. Come on a Saturday for extra market action, revelling in the diverse produce on offer and sourcing hand-painted ceramics locally manufactured using traditional methods.

Montepulciano | Photo: Rowan Heuvel

9. Valtiberina

Following a winding journey from Cortona, we come to Valtiberina on the eastern border to Umbria. Relatively little known among tourists, this corner of the region is a great extension for gay Tuscan vacations, as the birthplace to artists Michelangelo and Piero Della Francesca both. The Scale Museum in Monterchi or the Civic Museum in Sansepolcro are the places to go for artwork, while the old town of Anghiari focuses more on artisanship and stone carving. Taking its name from the Tiber River that runs through it, Valtiberina is also a meeting point of culture and civilisations of old, including the Byzantines, Etruscans, Lombards and Umbrians. In its strategic position, the valley was also fought over for centuries by Arezzo bishops, Rimini lords, Roman popes and the Florentines. Mementos of this history are scattered throughout the area, inclusive of Roman ruins, medieval churches and various fortified castles. To indulge in parish history and chill along the river, try Pieve Santo Stefano also home to the National Dairy Archive.

10. Arezzo

Arezzo Italy is our final destination to wrap up 10 days in Tuscany, lying just 40 minutes outside of Sansepolcro. Arezzo, despite being the capital of eastern Tuscany at the crossroad of four valleys, is far less visited than the likes of Florence or Siena, meaning that the beauty of the town, as well as its fantastic art and architecture, remains as authentic as it always has been. Centre yourself on historic Piazza Grande (the main square that holds bi-annual jousting competitions and features in the Benigni movie “La Vita è Bella”), before walking around to learn of WWII bombings and Roman Empire takeovers from the monuments and artifacts dotted around.

While the city itself was founded in 9BC to become a key player in the region, human history dates back much further, evidenced by the locally unearthed Man of the Elm whose bones date back to the Palaeolithic era. To cover more recent happenings, Arezzo still has much to explore, including the Roman amphitheatre and newly restored Medicean Fortress. As for churches, Arezzo is not lacking, its best being the Church of San Francesco, the Church of San Domenico and a bonus cathedral dedicated to San Donato.

Arezzo | Photo: Jur Wiersema

Photo: Stefan Stefancik

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Florence | Photo: JLB1988

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