Top Chianti Holidays

Enjoy Tuscany to the fullest on a private vineyard picnic. Discover our winery on a guided tour (optional), taste wine in a cozy atmosphere overlooking Montalcino, and enjoy your picnic basket filled with delicious homemade Tuscan specialties.

For true wine-lovers, there’s no greater thrill than seeing where Tuscany’s specialty red is made. During this in-depth tour of an organic, family-run winery, you’ll learn the ins and outs of Chianti Classico. Tour the scenic vineyard and sample four different red wine varieties inside the atmospheric on-site cellar. Pair your tasting with fresh cheeses and salami, all made from fresh regional products.

Learn how to create up to three classic Italian dishes—including homemade pasta—during this private cooking workshop in Chianti. Head to a scenic countryside home for an intimate lesson led by a pair of local cooks. Workshops include a wine and olive oil tasting and home-cooked meal with vegetarian and vegan options available.

Discover Tuscany and biodynamic viticulture on a winery tour with a breathtaking view of Montalcino while you learn about our philosophy. During a seated wine tasting, we will serve you 6 different wines and give you a short introduction to each of them. Then you will have the possibility to taste them independently.

Join us for a delightful wine tasting experience, complemented by a traditional Tuscan lunch. Stroll through our organic vineyard and take in the stunning views while savoring two distinct wines alongside a delicious three-course meal. Admire the picturesque Tuscan landscape as you learn about the traditional methods and techniques used to produce our high-quality wines. The lunch menu features a selection of cured meats and cheeses, handmade pasta with flavorful sauces, and delightful desserts. A vegetarian option is available; please let us know at the time of booking if you would like this alternative.

Our experienced sommelier will guide you through a tasting of four fine wines, including a white wine and three different red wines, each with its own unique characteristics and nuances. The red wines will surprise you with their colours from ruby red to deep dark red; you will learn to recognise the flavours, from the softest to the most tannic; you will discover the many aromas hidden in a wine, belonging to the families of spices, fruits, woods and many others such as leather and tobacco. White wine will refresh you and offer delicate and complex notes, also all to be discovered and analysed. The expert sommelier who will guide you through the tasting will not only introduce you to the wines, but also talk to you about the best pairings to make with food, local and otherwise. Once the tasting is over, it will be time for dinner, based on fresh, local and typical products, to be enjoyed in the beautiful SiChef Villa, framed by the Tuscan hills.

Imagine stepping into a secluded haven, nestled among the rolling hills of Montalcino's northwestern slopes. Paradiso di Cacuci welcomes you, by appointment, to an intimate and personalized wine and culinary experience. Our guided tastings, reserved for individual visitors and small groups, take you on a sensory journey through the Brunello di Montalcino production process. Our tastings, exclusively private and by appointment, are designed to offer personalized attention and an unforgettable experience. Be captivated by the landscape's beauty, our region's history, and the quality of our wines. Reserve your private tasting today and uncover the true meaning of Paradiso di Cacuci.

Visit a family-run winery in Chianti to experience the traditional side of local winemaking. With an included tasting of several house wines, this tour of Montefioralle Winery goes from Chianti classic to sweet vin santo. In warm weather, you can sample the wine in a scenic outdoor spot with views of the vines and the surrounding historic village.

Walking, discovering, and tasting: In the heart of Tuscany, through the lands of the Chianti region, we accompany you on daily excursions combined with original experiences to search for artistic, wine, gastronomic, and artisanal treasures. We walk to come into contact with this region’s nature: the hills, the streams, the woods, the trails through vineyards, and the wildest corners. We discover hidden gems: old farmhouses, parish churches, castles, and workshops where craftsmen create as they did once upon a time. We taste the fruits of this land: Chianti wines together with traditional dishes, but we also take in the scents of the flowers, the colors of the fields, and the sounds of every setting that we pass through. Each hike reveals an aspect of this land and combines outdoor activities with unique experiences to be enjoyed together, sharing every step, every taste, and every emotion.

Make the most of your time while in port in Livorno and avoid wasting hours trying to explore Tuscany by public transportation or rental car on this full-day private wine tour in the Chianti hills. Led by a wine-focused guide, take a scenic drive into the heart of the Chianti wine region and visit a local winery to learn about the winemaking process and sample local blends. Taste top-quality wine and Tuscan olive oil while admiring the rolling landscape before heading back to your cruise ship.

Tour the cellars of Monterinaldi Castle with a sommelier as your guide. This historic castle in the heart of Chianti is the perfect setting to learn all about the winemaking process. After your private tour of the cellars, enjoy a 3-course Tuscan lunch with wine pairings in an 18th century villa.

Guests will be immersed in the countryside of the southern area of Montalcino and will enter the atmosphere of Molino di Sant'Antimo and the tradition of the Vittori family. This experience, which includes a visit to the cellar and a 4-course lunch, will lead our guests to discover the typical dishes of Tuscan cuisine proposed by the Vittori family in the Montalcino company. During the experience the wines of our production will be tasted such as: Gina Rosato or Il Bianco Chardonnay Igt Red of Montalcino Doc Brunello di Montalcino DOCG This selection is designed as an introduction to our winemaking history. Rosso and Brunello are central wines in Molino. Gina is the idea outside the box, an Italian Rosé with a French soul.

Immerse yourself in the authentic culture of Chianti with a wine tasting in Radda, a medieval village nestled in the Tuscan hills. Surrounded by Sangiovese vineyards, this experience offers more than just a tasting—it’s a journey into local tradition. Guided by an expert, you’ll explore the full winemaking process, from fermentation to barrel aging, before sampling three typical Tuscan wines and a Vermouth. A perfect way to connect with the land, its history, and its flavors.

Take a look behind the wine cellar scenes during an exclusive Brunello barrel tasting. Hand in hand with us, you can taste and discuss the wines in a personal atmosphere in our vaulted cellar. Afterward, a set table awaits you, where you will get served 6 Brunelli with matching, individually developed Gourmet Bites.

If you do not have much time but still want to visit the beauties of Chianti and have the opportunity to taste the famous wine of the Chianti lands, immersed in the green countryside, this is the tour for you. The small group size of no more than 6 pax will make you appreciate the tranquility and peace of Chianti

Embark upon a journey into the heart of Tuscany, nestled amidst the rolling hills of the Chianti region, renowned for its storied vineyards and centuries-old wineries. Begin your day with a visit to an ancient Etruscan cellar. Here you'll discover the secrets of Italian vinification, from grape selection to maturation, that contribute to the distinctive character of each vintage. After exploring the historic cellar, indulge in a sumptuous four-course lunch, meticulously prepared to reflect the rich culinary heritage of this enchanting region. Each course is thoughtfully paired with one of six prestigious wines produced on-site. The wines, ranging from robust reds to vibrant whites, allow you to explore the breadth and depth of the winery's craftsmanship. With every sip, uncover the nuanced taste profiles influenced by the fertile soils, unique microclimate, and expert cultivation of the vineyard's Terroir.

Join us for a delightful wine tasting experience, complemented by a traditional Tuscan lunch. Stroll through organic vineyard and take in the stunning views while savoring two distinct wines alongside a delicious three-course meal. Admire the picturesque Tuscan landscape as you learn about the traditional methods and techniques used to produce high-quality wines. The lunch menu features a selection of cured meats and cheeses, handmade pasta with flavorful sauces, and delightful desserts. A vegetarian option is available; please let us know at the time of booking if you would like this alternative. Tasport From Montalcino

Your experience will start directly at your hotel, where you will climb aboard an air-conditioned vehicle with a professional driver. You will visit a historic wine cellar to discover the aromas of the barrel room and the quiet of the cellars. Enjoy different vintages of local Chianti Classico wines. After, you will be welcomed to a family-run winery to visit the cellar, have a wine tasting, and enjoy a full lunch accompanied by locally produced wines for those who wish to discover the pleasure of local cuisine. In the end of the tour, you will visit a third winery, a biological one. You will visit the cellars and enjoy a guided tasting of three local wines with tastings of olive oil with bread and Cinta Senese Dop cured meats. Please note that the order of visits and the wineries could change due to availability. When select SELF DRIVE OPTION, you have to travel with your OWN car. NO TRANSFER is included. It is NOT possible to take the tour using public transportation.

Enjoy an unforgettable day: let yourself be guided through the rolling hills and vineyards while admiring the beautiful Tuscan landscapes! Our tour will combine the perfect Brunello di Montalcino wine with our typical Tuscan cooking.  Thanks to this tour you will be able to appreciate wines and food and to learn more about our history and traditions: in two words, our Tuscan life style!

Enjoy an exclusive one-hour wine tasting experience, complemented by warm homemade bread and exquisite Tuscan olive oil. Stroll through the vineyard before indulging in a guided tasting of three exceptional local wines. Discover the traditional methods and techniques used in producing high-quality wines. During the tasting, you’ll savor three outstanding selections, including the world-renowned Brunello and Rosso di Montalcino. Plus, you’ll have the unique opportunity to taste wine straight from the wooden barrel! Capture your unforgettable moments and feel free to share your experience on social media!

Paradiso di Cacuci is a winery located in a small “corner of Paradise“ in the northwestern area of ​​Montalcino. Our wine production is centered on the perpetuation of the tradition which, together with a more modern model and in compliance with the values ​​of the Brunello Consortium, uses only from our vineyards which are respectively divided into; 5 ha Brunello di Montalcino, 1 ha. Rosso di Montalcino and 5 ha. di I.g.t. Sangiovese. Welcomes, by reservation, individual visitors and small groups offering guided tastings that give the opportunity to get to know the production directly, starting from the wine making process to the discovery of the final result, giving a unique and unforgettable experience. Our tastings are only private and by appointment only to guarantee you our best services.

Discover Tuscany’s culinary heritage at a historic 17th-century villa in the heart of Chianti Classico. Start your day with an Italian moka coffee while learning about the villa’s winemaking history. Enjoy a guided walk through the vineyards, olive groves, and gardens, and uncover the art of wine production and organic farming. Delve into the family’s 3-generation tradition of Extra Virgin Olive Oil (EVOO) production, followed by a professional EVOO tasting to distinguish the finest varieties. The experience continues with a delicious Tuscan light lunch, featuring local cheeses, cured meats, homemade pasta, and villa-crafted wine, all set against the breathtaking Tuscan hills. Perfect for food and wine enthusiasts, this farm-to-table experience offers an authentic taste of one of Italy’s most celebrated wine regions.

Imagine stepping into a secluded haven, nestled among the rolling hills of Montalcino's northwestern slopes. Paradiso di Cacuci welcomes you, by appointment, to an intimate and personalized wine and culinary experience. Our guided tastings, reserved for individual visitors and small groups, take you on a sensory journey through the Brunello di Montalcino production process. Our tastings, exclusively private and by appointment, are designed to offer personalized attention and an unforgettable experience. Be captivated by the landscape's beauty, our region's history, and the quality of our wines. Reserve your private tasting today and uncover the true meaning of Paradiso di Cacuci.