Introduction
Tuscany is a place to savour the finer pleasures in life: from long al fresco lunches in a picturesque vineyard to cruising through the rolling hills in a convertible, there are few places that capture the essence of “la dolce vita” more than this. Exploring Tuscany is akin to unearthing a masterpiece, each stroke of its landscape contributing to an unrivaled canvas of beauty. The winding roads lead not only to iconic destinations but also to hidden gems waiting to be discovered. There's an innate charm in losing oneself amidst the undulating hills, vineyards, and olive groves that adorn this region. Beyond the enchanting landscapes, Tuscany is a tapestry woven with threads of history, culture, and artistry. From the ancient allure of its medieval towns to the vibrant spirit of its locals, every moment here is an immersion into a timeless legacy. In this place of serenity and wonder, one can't help but find a piece of their heart left behind, yearning for the day they return to indulge once more in its magic.
If you’re planning a trip to Tuscany, I’m sure you want to make the most of it, so I have written a detailed roadtrip itinerary below, complete with suggestions for hotels and restaurants.
Where to stay?
Below is a list of some of the finest luxury hotels in Tuscany, in no particular order.
Castello Banfi Al Borgo – an exclusive medieval castle-turned wine resort with just 14 rooms, spread over 7,100 acres of grounds and nestled in the famous Brunello di Montalcino wine region.
Badia di Pomaio – an ethereal 17th century monastery-turned-boutique hotel, which opened in 2019 after a two-year restoration process and is located in the deep in the peace and quiet of the forest surrounding the town of Arezzo.
Hotel Le Fontanelle – a 13th century estate located in the Chianti Classico (the historical heart of Chianti winemaking), this hotel is designed in traditional style and boasts stunning gardens with panoramic views over the rolling hills.
Castello di Casole, a Belmond hotel – approached along a winding road lined with Cypress trees, the Belmond occupies a restored medieval castle set in an authentic farm estate amidst the undulating landscape of vineyards and olive groves.
Villa di Piazzano – a historic estate that was originally the hunting lodge of Cardinal Silvio Passerini, a favourite of Florence’s Medici family, the Villa di Piazzano occupies a historical manor house and offers down-to-earth luxury.
Villa Le Calvane - occupying a building dating from the 15th century, Villa Le Calvane is perched on a hill top overlooking olive groves and vineyards between Florence and Siena and offers tranquil views from its infinity pool.
Rosewood Castiglion del Bosco - situated within the UNESCO-listed Val d'Orcia Natural Park and in the heart of the Brunello di Montalcino wine-making region, the Rosewood is a 5000-acre country estate with 53 rooms and villas.
Monastero di Cortona - as the name suggests, this property is a fifteenth century monastery in the historic hilltop town of Cortona. It was renovated in 2019 to faithfully preserve the architectural details of the original monastery.
Where to eat?
I have listed below some of the best restaurants in Tuscany, where you will find authentic and delicious Italian cuisine.
Fonte alla Vena – this informal and simply furnished establishment in the Val d’Orcia region serves traditional Tuscan staples which are full of robust and delicious flavours.
La Bucaccia – a top choice for Tuscan cuisine in Cortona. You can take your pick between a table on the main street of the historic centre or a spot in one of the rustic interior dining rooms.
Osteria Le Panzanelle – this rural trattoria in the Chianti Classico region has a simple and casual vibe and serves generous portions of regional Tuscan cuisine, including homemade pastas.
Da Pode – located on the outskirts of the medieval town of San Gimignano, this restaurant overlooks a sweeping valley of cypresses, vineyards and olive groves and is the perfect spot for a long lunch over homemade Tuscan food.
Futura Osteria – occupying the cellars of a former monastery in a small medieval village, this place focuses on simple and seasonal Tuscan cuisine and offers a secluded terrace.
La Solita Zuppa – in the historic centre of Chiusi, this place is a classic Tuscan trattoria which adheres faithfully to traditional recipes. The traditional vaulted ceiling, which is typical of Tuscan trattorias, completes the picture.
Silene – located in a sleepy little mountain village, the dishes at this owner/chef-operated restaurant are prepared largely from ingredients grown in the kitchen garden and are full of classic and intense Tuscan flavours.
Il Falconiere – as a part of the beautiful Baracchi farm estate, this exclusive restaurant makes use of many ingredients produced in-house to create dishes that are evocative of the robust flavours of Tuscan cuisine.
The Ultimate Roadtrip Itinerary
I would recommend allowing at least 7 days to comprehensively explore southern Tuscany. If you are less pressed for time, you can add a day here or there (or even longer!) to make the trip more leisurely. I have crafted for you below a comprehensive roadtrip itinerary through the timeless region of southern Tuscany, from the charming medieval towns to the breathtaking countryside, this itinerary promises an immersive experience filled with history, culture, and natural beauty.
San Gimignano (1-2 days)
San Gimignano is a medieval time capsule built on the ancient Via Francigena. To visit this city is to retrace the footsteps of the pilgrims who walked through the city on the way to Rome many moons ago. Today, it is one of Italy’s most well-preserved old towns. A UNESCO World Heritage, its layout is essentially unchanged since the 14th century. San Gimignano is primarily known for its stunning skyline dominated by a collection of well-preserved medieval towers, which earns it the moniker of the "Medieval Manhattan." This “City of Towers” was once home to around 72 towers, built by wealthy families in the Middle Ages as symbols of power and prestige. Today, 14 of these towers still stand and the town’s narrow, winding streets are lined with artisan shops and quaint cafes.
Be transported to 11th-century Italy at Piazza del Duomo (Cathedral Square), pictured below. The Palazzo Communal (town hall), Palazzo Vecchio del Podesta (Old Mayor’s Palace) and Duomo cathedral look the same as they did in the medieval period. Admire the simple yet exquisite beauty of their mullioned windows, detailed stonework and frescoes. Another icon is the 14th century Torre Grossa (“Big Tower”) - climb its belfry walkway to the top with the best views of the town. Consecrated in 1148, the interior of the Collegiate Church of Santa Maria Assunta features stunning frescoes (mural paintings) by Renaissance artists.
Pictured below is the Piazza della Cisterna, a town square surrounded by medieval towers. At the center is a 13th-century well that epitomises the romantic atmosphere of the square. During the medieval period, the square was a marketplace devoted to local culture. Today, it is lively with cafes and shops. Grab a gelato at the world champion Gelateria Dondoli.
During the medieval period, the Romanesque architectural style was prevalent in Italy. This style favoured semi-circular arches for windows and doorways. San Gimignano's historic centre is characterised by narrow winding streets and stone buildings, which offer a glimpse into the town’s medieval past. Take a stroll down one of the lesser-known streets, like Via del Castello (pictured below), to discover peace away from the crowds.
Pictured below are the backstreets of Val del Corbizzo and Via di Berignano, the latter’s whose steep descent is perfect for photography. These little streets are some of the best ones to stroll down, as they are quiet, local streets flanked by old stone houses with laundry drying on the wrought iron balconies and the smell of nonna’s cooking.
Via Palestro (pictured below) is another picturesque street full of weathered stone buildings decorated with colourful pots of pansies. Wander past artisans’ workshops and hidden courtyards for a window into daily life in a medieval Tuscan town.
Walking the town walls or climbing one of the remaining medieval towers affords breathtaking panoramic views of the surrounding Tuscan countryside, with its rolling hills, vineyards, and olive groves.
Siena (1-2 days)
In today’s fast-paced, hyperactive society, I always look for opportunities to be inspired and humbled by old-world places such as Siena. Here, stunning edifices such as the Siena Duomo were built in a bygone era when things were made slowly, thoughtfully and exquisitely. Siena's magic lies in its rich history, which is impeccably preserved in its art and architecture. These showcase a rich blend of Gothic and Renaissance styles - from ornate frescoes to intricate sculptures and from flying buttresses to marble mosaics.
The Duomo di Siena (Siena Cathedral), pictured below, stands majestically as the crown jewel of the city - a masterpiece of Italian Romanesque-Gothic architecture known for its stunning facade, intricate marble work, magnificent interior, and breathtaking frescoes.
Pointed or lancet arches are the predominant and defining architectural feature of the Gothic style. They create an upward, vertical emphasis and allow for taller and more spacious buildings compared to previous structures.
Siena thrives on a vibrant cultural tapestry, where local traditions and community pride run deep. The city has 17 neighbourhoods (contrade) and each contrada has its distinct flag, emblem and competes with rival contrade in the spirited centuries-old event that is the Palio horse race. As you get lost in Siena’s labyrinthine streets, you can’t help but wonder - if these weathered cobblestones and walls could talk, what tales would they tell?
Siena’s cobblestone streets, secret courtyards and sweeping viewpoints create a sense of romanticism and mystery that the city is known for. As a visitor, you can really get immersed in the Sienese life by getting lost in the labyrinthine streets, stopping to daydream in quaint cafes and devouring some hearty pici pasta and ribollita soup that simply hit the spot.
Chianti (1 day)
The Chianti region boasts rolling hills, olive groves, cypress trees, and medieval villages. It’s biggest claim to fame, however, is as a renowned wine region, famous for the cultivation of the Sangiovese grape varietal, which thrives in the hilly terrain. Chianti Classico wines, the most famous of Chianti wines, typically showcase a balance of fruitiness, acidity, and earthy characteristics. Pairing Chianti wines with local dishes like wild boar stew, ribollita (a hearty soup), Pappa al Pomodoro (tomato bread soup), and Tuscan pecorino cheese is an unmissable part of any Tuscany trip.
Indulge in a gourmet lunch savouring the bucolic landscape of the Chianti wine region. Pictured above is the romantic restaurant, La Colonna restaurant, with breathtaking views of the Chianti countryside.
There is nothing more classically Tuscan than exquisitely manicured gardens, lines of ancient olive groves (that have been nurtured for centuries to produce the liquid gold that is Italian olive oil) and avenues of cypress trees, against the background of the rolling hills of Chianti and its vineyard-covered landscape.
Crete Senesi and Asciano (1 day)
Crete Senesi
Crete Senesi, also known as the Senese Clays, is defined by its undulating hills covered with clay-rich soil that takes on various hues throughout the year, from shades of grey to earthy browns and from silvery tones to deep ochres. It is a barren yet beautiful, otherworldly and almost lunar-like landscape. Scattered among these hills are small, charming villages and hamlets. The interplay of light and shadow over the rolling hills, especially during sunrise or sunset, creates an ethereal atmosphere.
A must do-in Tuscany is to drive or bike along the Strada Provinciale 438, an immersive scenic route that will take you deep into the gentle soul of Tuscany, floating through the undulating landscape of rolling hills with those iconic cypress trees marking the way in all directions. Endless panoramic photo opportunities await. Amidst the clay hills, solitary cypress trees dot the landscape, adding to its picturesque beauty.
Asciano
Asciano is a charming town located in the heart of the Crete Senesi region. It boasts rows of pastel buildings, ancient churches, charming laneways and atmospheric restaurants. However, what makes Asciano special is that it offers a serene and authentic experience away from the bustling tourist centers, perfect for travellers seeking a taste of real Tuscan life, including the rustic local cuisine.
Wooden doors in Tuscany are often crafted by skilled artisans and exemplify their expertise in woodworking techniques.
Take a seat in the piazza, the vibrant heart of Italian communal life.
Val d’Orcia (2 days)
The Val d'Orcia is a UNESCO World Heritage-listed region celebrated for its iconic and idyllic landscapes of gentle, rolling hills. This magical valley captivates the soul with its undulating hills blanketed in vibrant shades of green, golden wheat fields swaying in the gentle breeze and rows of cypress trees lining the horizon like elegant guardians. Amidst this picturesque landscape lie medieval villages perched atop hills, each cobblestone street whispering tales of ancient history and artistic heritage. The ethereal beauty of Val d'Orcia emanates tranquility, inviting wanderers to lose themselves in its timeless charm.
Pictured below is the Agriturismo Baccoleno, an iconic postcard post that is a 250-hectare farm that has been owned by a local family for 60 years. The farmhouse is an agriturismo-style hotel that visitors can stay at.
The Val d'Orcia is known for its vast expanses of wheat fields. The appearance of the fields changes with the seasons, from lush green sprouts in the spring to golden waves of wheat ready for harvest in the summer. The cultivation of wheat has been practiced in Val d’Orcia for centuries, influencing the local economy and culture. Farmers in the area continue to cultivate wheat using techniques that have been passed down through generations, which has earned the region its UNESCO World Heritage status.
Strada di Terrapille (pictured below) is the shooting location for the iconic ending scene of the film “Gladiator”. Photos simply don’t do this place justice. Walking through these gentle hills at sunset is an incredible experience.
Another iconic Tuscany postcard location - this S-shaped road that leads to the town of Monticchiello is lined with cypress trees, making it a beloved photography location that is quintessentially Tuscan.
The Cipressi di San Quirico d'Orcia (pictured below) is a hilltop vantage point with cypress trees arranged in a circular formation, with their slender silhouettes reaching towards the sky. Their presence is emblematic of the region's beauty, adding a touch of elegance and harmony to the breathtaking Tuscan countryside.
Cappella della Madonna di Vitaleta - a 17th-century chapel built on the spot where legend says the Virgin Mary appeared to a shepherdess.
Genna Borborini Maria Eva, another shooting location for the film “Gladiator”
Photos below were taken from the Strada Provinciale 146, an iconic road that stretches across the agricultural countryside of Val 'd’Orcia. As you drive or bike along this road, you are greeted with a visual symphony of vineyards, cypress trees and wheat fields that stretch to the horizon. The picturesque Tuscan farmhouses create captivating focal points for composition, while the verdant olive groves offer intricate textures and patterns for photography. The iconic cypress trees, with their slender silhouettes, provide dynamic leading lines that draw the viewer's eye into the frame and their uniformity is ideal for creating strikingly compressed shots using a zoom lens.
Pienza (1 day)
Pienza is my favourite town in Tuscany - I fell in love with it instantly. A peaceful hilltop town with well-preserved Renaissance roots, it has a distinctively sophisticated spirit. After reading more about its history at the Diocesan Museum, I realised why. Pope Pius II (a leading humanist with Sienese roots) designed Pienza as the ‘ideal city’ during the Renaissance, transforming it into an elegant city inspired by the architectural and urban planning principles of the Renaissance. Giovanni Pascoli described Pienza as "born from a thought of love and a dream of beauty". And it still is today.
The town’s main square, Piazza Pio II, boasts an elegant layout, harmonious proportions, and panoramic views from its strategic hilltop position of the surrounding Val d'Orcia countryside. The Cathedral of Santa Maria Assunta, located in Piazza Pio II, is a beautiful example of Renaissance architecture. The historic centre of Pienza has itself been recognised as a UNESCO World Heritage Site since 1996.
A stroll along the town wall of Pienza delivers uplifting vistas of the Val d’Orcia countryside.
During the hot Tuscan summers, shutters provide shade while allowing for airflow when windows are open.
Montepulciano and Montalcino (1 day)
Montepulciano
Montepulciano is a hilltop town boasting panoramic views and full of ancient churches and fortresses, elegant Renaissance palaces, charming gardens and town squares. Volturi scenes from the “Twilight” movies were shot here, reflecting how well-preserved its ancient architecture is. Time stands still in this old-world town.
The contrast between narrow streets hemmed in by medieval stone walls and open vistas of the surrounding countryside is a hallmark of Tuscany’s hilltop towns.
The epitome of idyllic Tuscan country living - here, you will find quaint little corners and a world where we still paint by hand rather than using AI.
Tuscany’s rich spiritual heritage is interwoven into the landscape at every corner.
Montepulciano offers panoramic views of the surrounding valley of Val d’Orcia, as it is a hilltop town perched high on a 600-meter limestone ridge.
Montalcino
Montalcino is a hilltop town set within fortified walls, renowned for its history and viticulture (as it produces the prestigious Brunello di Montalcino made from the Sangiovese grape). Climb the fortress walls of its ancient castle to enjoy panoramic views, stroll through Piazza del Popolo and the labyrinth of cafes and restaurants, step back in time at the 14th century palace Palazzo dei Priori and the Romanesque Abbey of Sant’Antimo and learn about the town’s Etruscan heritage at the Civic and Diocesan Museum. The imposing fortress, the Fortezza di Montalcino, is the icon of Montalcino - offering panoramic views of the surrounding countryside.
Ultimately, a road trip through Tuscany isn't just a journey - it's an immersion into a captivating world of art, history, and natural splendour. Every turn reveals a new facet of this enchanting region, where getting lost only leads to discovering its hidden treasures. From the rolling hills to the ancient towns, the heartwarming locals and the exquisite cuisine, Tuscany is a testament to the beauty of simply embracing the moment. So, let yourself wander, soak in the charm, and relish every moment spent in this timeless Italian gem.