Siena:
 A Le Collectionist Guide

Allow Siena to put its spell on you with its impressive architecture, labyrinth-like streets and traditional Italian gastronomy.

Experience the essence of Tuscany by indulging in a wine-tasting adventure in the Chianti region. This picturesque area is renowned for its rolling vineyards, charming wineries, and world-class wines, primarily the Chianti Classico. Visitors can savour a variety of exquisite red wines while enjoying breathtaking countryside views and learning about the winemaking traditions that have thrived here for centuries.

Led by expert Tuscan chefs, participants engage in hands-on cooking, learning to create traditional Tuscan dishes from scratch. Tuscan topography produces some of the most spectacular produce so why not learn the secrets behind the wild boar ragu pappardelle and black truffle tagliatelle that have already put a spell on you in Siena’s quaint trattorias.

Nestled in the heart of Tuscany, this UNESCO World Heritage site is home to narrow cobblestone streets and a stunning cathedral. It's a place where history comes alive, offering visitors a chance to explore magnificent Gothic and Renaissance landmarks.

Every July and August, the ancient square of Siena, Piazza del Campo, transforms into a track for the infamous bareback horse race that dates back to the 17th century. The Palio is much more than a race; it's a deeply ingrained tradition, a source of civic pride, and a vibrant display of pageantry, with parades, colourful flags and elaborate ceremonies.

Though it’s a bit far away, it’s well worth taking the time to head to Santo Spirito, the historic heartland of the most famous Florentine crafts. Rummage through this treasure trove of artisanal creations, and discover the city’s finest leather creations, intricately handcrafted mosaics and mesmerising jewellers. With the assistance of a local guide, explore the winding, charming streets and unveil the area’s monuments and heritage of fine craftsmanship.

Situated in the province of Siena and just 56 km south of Florence, the magnificent skyline of this small mediaeval town earns it the name of ‘town of fine towers’. Once a stopping point for pilgrims journeying to Rome, San Gimignano invites you to follow in their footsteps and explore. With its tower houses, encircling town walls and Gothic and Romanesque architecture, it appears frozen in time.

Castellina in Chianti is a treasure trove of vineyards and wineries where classics such as Chianti Classico reign. Nestled among the undulating hills and lush fertile fields, you will discover beautifully restored farmhouses and exquisite villas. In this region nature is always the guest of honour.

The gently sloping hills of the Orcia Valley are dotted with constellations of picturesque towns and villages while the river meanders through the verdant valley. Whether you’re marvelling at the first examples of Renaissance architecture in Pienza, the mediaeval walls of Montalcino, the small commune of Radicofani or sampling the delightful red wines of Montepulciano, the Orcia Valley is guaranteed to delight.

Duomo di Siena is a testament to Italian artistry with its striped marble façade and statues sculpted by the finest Italian artists of the era such as Nicola and Giovanni Pisano, Donatello and Bernini. Completed in the 13th century, its Romanesque-Gothic architecture is elaborate and ornate. No corner is left unadorned and as you wander through the cathedral, make sure to cast your gaze down to the marble intarsia images that adorn the floor. 

Wander around this historic fortress built in the 16th century on the orders of Duke Cosimo I de’ Medici. Once a vital site for military strategy, it has now been transformed into a public park which frequently hosts art exhibitions, concerts and is home to the Siena Jazz Festival. Bask in the golden glow of the afternoon sun and enjoy the panoramic views of Siena.

Venture off the beaten path and evade tourists in this charming village just 20 minutes from Siena.  Fiercely protected by its extensive fortifications, it has remarkably managed to preserve its mediaeval charm. Wander through the cobbled streets and find yourself transported back through time. 

At La Taverna di San Giuseppe the cuisine is firmly rooted in Tuscan tradition. There is no better way to get to know Siena than through tasting the local Tuscan delicacies in dishes which put regional produce at the forefront. In this Michelin-star restaurant, enjoy perfectly executed, stripped-back dishes which are expertly paired with one of their 600 labels of wines.

La Compagnia dei Vinattieri promises an unpretentious atmosphere that encourages you to take pleasure in the art of eating well. Local Tuscan produce is beautifully plated, resulting in not just a meal but an experience. In true Italian fashion, it executes flawlessly the paradox of being both rustic and elegant simultaneously. 

Head through the arch of floral ivy and find the perfect destination to grab a lunchtime sandwich during a busy day of sightseeing at Gino Cacino di Angelo La Pagina. With a plethora of filling options, choose from prosciutto, cheese and vegetables as the owners assemble an unexpected feast before your eyes.

Il Convito di Curina* is emblematic of traditional Tuscan elegance, with dishes centering seasonal vegetables and herbs grown from the garden. Boasting a Michelin-star, when it comes to flavour nothing is left to chance. Enjoy their refined and elegant dishes overlooking the rolling Tuscan hills for an unforgettable experience.

Allow your little ones to become explorers for the day as you cycle through the breathtaking surrounding landscape. Passing by verdant natural beauty, terra-cotta houses and picturesque villages, take a moment to slow down your pace to absorb the sights around you. After working up an appetite, stop off at one of the many charming villages that line your route, welcoming you in with their warm hospitality and traditional produce. 

In a nutshell
Bike ride/ Spectacular landscape

Young and old alike will delight in tasting some of Italy’s finest gelatos. Why not visit San Gimignano, where you can sample the world’s best gelato at Gelateria Dondoli? Opt for tried and trusted flavour combinations or embark on a taste adventure with options such as saffron and pine nut cream or pink grapefruit and local sparkling wine. With such moreish offerings, even in the midday Tuscan sun, finishing the ice cream before it melts won’t be a problem! 

In a nutshell
Gelato/ Unusual flavours

Siena and San Gimignano’s mediaeval towers dominate their skyline and visitors crane their necks admiring such spectacular edifices. Why not let the whole family enjoy the view from above, climbing the towers for stunning panoramas of the city and verdant countryside?

In a nutshell
Historic towers/ Breathtaking views

Siena’s fertile countryside is renowned for producing some of the most exquisite wines, each a testament to generations of winemaking expertise. Immerse yourself in these enchanting vineyards, as they unveil the secrets of their centuries-old craft. Allow us to organise a tailor-made private wine tasting at these picturesque vineyards, savouring their vintages.

In Siena, recipes for local dishes are like palimpsests that have been perfected and reworked over centuries. Learn these generational secrets such as how to perfect the iconic pasta shape pici by hand for the best souvenir that doesn’t have to fit in your suitcase.

Defy gravity and see the rolling Tuscan hills from a unique vantage point. Allow us to arrange the most spectacular journey, as a hot air balloon carries you into the skies. Glide over the remarkable landscape, dotted with quaint mediaeval villages, vineyards and olive groves, savouring the unforgettable panoramic views. 

Blessed by the Mediterranean sun, Siena is typical of so many Italian regions that retain the elusive charm all year round. Whether you want to evade the museum crowds in winter or lounge in the shade of the trees in summer, Siena is the dream destination for your cultural getaway.

In this season of rebirth, emerge from your winter hibernation and embrace the timeless charm of Siena. Make the most of the temperate Mediterranean climate in Italy, as average maximum temperatures reach 24°C, and admire the fruitfulness of the lush landscapes surrounding you. Evade the summer hoards this spring in Italy for an escape filled with natural beauty and culture in equal measure.

Although Siena retains its charm all year round, during the vibrant summer months it truly flourishes. Don't miss out on unforgettable events like the Palio di Siena, held in July and August, where this historic town comes alive in all its glory.

For connoisseurs and wine lovers, autumn is the perfect time to visit Siena for it marks the grape harvest season. Explore the nearby vineyards, sampling their creations. Additionally, with fewer tourists and pleasant weather, it's an ideal time to visit and immerse yourself in the magic of Siena.

Explore Siena’s cultural riches away from the crowds during the winter months. With the weather in December still hovering around 11°C during the day, wrap up warm and wander through the ancient winding streets of this historic city. Embrace the dolce vita lifestyle all year around this winter in Italy.

Things to do in Italy in December
Things to do in Italy in January
Things to do in Italy in February