Tuscany private guided tours & experiences
Published 08 June 2025
Tuscany private guided tours & experiences including wine-tasting, cookery, hiking, olive-oil tasting, history and architectural guided visits
Tuscany is home to some of the most intrinsically Italian authentic experiences and with an Expressions luxury holiday to Tuscany you can appreciate the best this region has to offer. We can offer you private guided tours, experiences and excursions with a driver and guide as appropriate. You are collected from your hotel in Tuscany and returned at the end.
The private guided tours and excursions range from half-day experiences such as a private walking tour with guide in Siena to a six-hour experience that incorporates a winery visit with wine-tasting, virgin olive oil tasting, a visit to a cheese producer with tasting and a typical Tuscan lunch.
As well as wine, cheese and olive oil tasting experiences, Expressions offers you hiking in the Tuscan countryside accompanied by a local guide, cookery lessons, visits to a saffron farm, and truffle hunting. The areas we tend to cover are the Chianti region and the Val d'Orcia-Montalcino region, but Siena and other cities can be visited too. These private tours, excursions and experiences can be added to most of our hotel holidays in Tuscany, depending on the location of the hotel.
Below is just a selection of all the Tuscany private guided visits, excursions and experiences Expressions can offer you.
Tuscan Taste Track in Chianti
Flavours and smells are memories that we will always bring with us. That’s what we offer, an unforgettable experience around the Tastes of Tuscany. Following our expert local guide off the beaten path of Chianti, you will discover our local products and people behind those.
We start the tour visiting a cheese farm, from the barn through all the steps of the production that will end up in our plates. The authentic passion of a Shepherd that translates his hard work in pecorinos, ricottas and so much more, a jubilation for the palate! Something special will then follow, as we will be attending to a proper tasting of Extra Virgin Olive Oil. You will be introduced by a local producer to all the characteristics, uses, properties and benefits that this product, so valuable, has to offer.
Our journey will continue in the world of wine. We know that there is no better way of enjoying the area if not going to visit an organic Winery... will be kindly hosted by a family that has been making wine for centuries in the Chianti Classico. We will walk around the property and the cellar to find out some of their secrets. The stunning view of cypresses, vines and olive groves will be then a perfect frame to our lunch based on typical Tuscan products paired with their different wines.
Tour includes:
• Private Tour with a Driver Guide
• Pick-up and drop-off at your accommodation on request
• Cheese farm visit with cheese tasting
• Extra Virgin Olive Oil Tasting
• Winery visit with Wine Tasting
• Typical Tuscan Lunch
Classic Wine Tour in Chianti
Chianti Classico, the land of wine. More than just a business it’s our lifestyle. With this tour we mean to share with you all what lays behind it.
A tradition that in the area was first implemented by the Etruscan way before the roman empire, that nowadays we have refined and made our mark. Specifically, thanks to our territory, that is not just a series of stunning views, rolling hills blending with tall woods, but also has characteristics in the soil that makes it so rich in minerals and nutrients, and allows us to live in a perfect ecosystem for the vines to grow. Wine, we know, is a mixture of art, science, passion, hard work, tradition and instinct... we will lead you through all the steps of the production, harvest, fermentation and aging. We will talk about the characteristics and the rules that make Chianti Classico and all its appellations so special. During the experience we will be able to visit two different wineries and taste their wines.
They differ in style and techniques. We will go to one of the most important producers in the area, a renowned reality, that focuses on the production of exceptionally fine and elegant wines following the dream of his first owner to become the greatest. We will then go to a small family run business, where new technologies are still far away, but where the love that ‘Grandpa’ has always shown for his fruits it’s evident in the final product. We will be hosted for lunch in the perfect set up of this organic farm with terraces overlooking the hills and the vines.
Tour includes:
• Private Tour with a Driver Guide
• Pick-up and drop-off at your accommodation on request
• 2 Winery visits including Wine
• Typical Tuscan Lunch
Extra Virgin Olive Oil Tour in Chianti
Together with the vines, olive trees were plants introduced in Tuscany by the Etruscan many centuries ago. Now they both characterize this land of such rare beauty and abundance.
In Tuscany extra virgin olive oil it’s an essential ingredient of our dishes and the perfect topping for salads. The oil mill is the special place for the production of EVO, determining in a very short time the organoleptic properties of this fresh and wonderful olive juice. With the help of the local guides you will discover all the secrets of the production. The extraction takes place through mechanical procedures and is carried out strictly cold. The pressing method is constantly differentiated to get the best out of every variety with the use of hammer, disc and dripper crushers. We will visit two oil mills very different from one another in style and techniques, producing high quality varieties of Tuscan EVO that differ in their aromas and flavours. Lunch will be served in the farm where you will enjoy all the best of the extra virgin olive oil and its pairing with food. Learn all about the different characteristics, culinary uses and all the many health benefits of this incredible product, always surrounded by charming views.
Tour includes:
• Private Tour with a Driver Guide
• Pick-up and drop-off at your accommodation on request
• 2 Oil Mills visits including Extra Virgin Olive Oil Tastings
• Typical Tuscan Lunch including beverage
Truffle Hunting with Wine Tasting in Chianti
Tuscan hills hide treasures and we will accompany you on a guided tour in the middle of the Chianti woods. We will reveal some of the most intricate secrets about truffles, including insights on the environment, their biological cycle and how truffle dogs are trained.
Our hunter and his dog will introduce you to the exclusive world of truffles, from hunt to table. We will lead you along this experience that will become an indelible memory. You will spend an entertaining and enriching morning hunting for ‘edible gold’ in the scenic woods of Tuscany. With truffle in our hands our experience will continue in a local organic farm having lunch based on Tuscan specialties combined with the truffle you just found. You will relax and enjoy a tasting of their wines and other typical products.
Tour includes:
• Private Tour with a Driver Guide
• Pick-up and drop-off at your accommodation on request
• Approx. 1-hour Truffle Hunt with professional hunter and trained dog
• Truffle based Tuscan Lunch
• Wine Tasting
Cooking Class with Wine Tasting in Chianti
Culinary tradition is a protagonist of Tuscan culture, and a major part of the experience visiting the region.
We will be hosted in an organic farm, in the heart of Chianti Classico area. A typical farmhouse where a Tuscan family lives since many generations. It’s a charming set up, surrounded by rows of vines, olive groves, flowers and vegetable gardens. Here we will have to roll our sleeves up and start cooking our meal. With the help of a local Tuscan Lady you will learn traditional secrets of our cuisine as well as cooking techniques. Success is guaranteed. Starters like bruschettas and crostini, cold cuts, cheeses and their pairing with honeys and jams. Pasta, and its fascinating world. We will make our own fresh home-made pasta from scratches, the old-fashioned way with a wooden rolling pin! Since any great meal ends with a dessert, we will be making something traditional to be enjoyed at the end of our lunch too. A tasting of various wines and spirits produced in the farm is included in the experience, as well as the visit of the property and cellar.
Tour includes:
• Private Tour with a Driver Guide
• Pick-up and drop-off at your accommodation on request
• Cooking Class with preparation of a 3-course meal
• Typical Tuscan Lunch with dishes you prepared
• Wine Tasting
