Day Trips from Tuscany to Chianti

Wine tasting is no fun when one of you has to be the designated driver. Leave Tuscany’s winding roads to your chauffeur when you book this fully customizable wine tour, with private transfers direct from your Florence address. The standard stops are Montalcino, Pienza, and Montepulciano, historic towns with rich wine and food traditions. Book your preferred wineries directly or ask for recommendations then pay as you go.

This customized day trip pairs the otherworldly landscapes of southern Tuscany with the region’s frozen-in-time villages and prized flavors. Relax and take in the views from a luxury vehicle while a private guide and driver handles the country roads. Taste famed Brunello wine in Montalcino and Pecorino cheese in lovely Pienza, visit a medieval monastery, and get hand-picked recommendations for an authentic Tuscan lunch.

Explore southern Tuscany with your own private guide on a full-day wine and food tour from Siena. Visit Pienza, Val d'Orcia, Montalcino, and more as you take in small towns, a 14th-century monastery, and sample Brunello di Montalcino, the famous wine of the region. Ride in comfort in a luxury vehicle with a private guide who shares the best of the region.

With ancient vineyards, Renaissance architecture, and colorful local culture, the UNESCO–listed Val d'Orcia is one of Tuscany’s must-see attractions, but exploring the area independently can be difficult. With this convenient day tour, start at your Florence hotel and travel into the Tuscan countryside by comfortable minivan, visiting the hillside towns of Montepulciano, Pienza, and Montalcino.

Take a break in the countryside with a private tour that includes visits to boutique wineries and a sustainable, family run cheese farm. Enjoy a full day dedicated to wine and cheese, exploring the heart of Tuscany. Drive through the Val d'Orcia, a UNESCO World Heritage Site, and savor some of the region’s finest red wines, including Vino Nobile di Montepulciano and Brunello di Montalcino. Stroll through the medieval squares of Pienza and sample authentic Tuscan cheeses at a historic estate, featuring one of the most breathtaking terraces overlooking the Orcia Valley.

Savor the sights and tastes of Tuscany on this private wine-tasting tour of the famed Chianti region. From Florence, journey across the Chianti hills, covered with vineyards and olive groves, toward Greve where you will make a first stop before heading for a respected Chianti winery to visit the cellars and learn about the production methods of the Chianti Classico. After a Tuscan-style lunch paired with wine, you'll head towards a second Chianti winery for another wine tasting.

Feast your senses on the palatal pleasures and verdant beauty of the Tuscan Brunello vineyards on private full-day trip from Florence. Travel deep into the Italian countryside to discover the renowned wine-producing areas of Montalcino and Montepulciano — famed for their refined wine varietals. In Montalcino, explore the village’s historical town center and taste fine wines before you absorb stunning views from Montepulciano village’s hilltop perch. On this private tour, you’ll receive undivided attention from your guide and relish the opportunity to customize your itinerary according to your interests.

Discover the wonders of Chianti and San Gimignano on a private day tour from Lucca. This customized excursion is perfect for travelers seeking an authentic Tuscan experience. With a private chauffeur at your disposal, you’ll immerse yourself in the charming Chianti countryside, enjoy tastings at renowned wineries, and witness skilled artisans at a terracotta workshop. Later, explore the UNESCO World Heritage site of San Gimignano, with its iconic medieval towers.

Tuscany’s Chianti region is a hassle to explore with public transport, and the country roads are confusing to navigate on your own. With this private day tour, cover more ground and focus on the views rather than the map with a private driver. Set off directly from your accommodation in Montecatini for a scenic drive through Chianti, including stops at two picture-perfect villages. Cap off your day with time to explore San Gimignano.

Livorno is the gateway to northern Italy and this private full-day shore excursion ensures you maximize your time and enjoy an itinerary tailor-made for you. Spend a day exploring the Tuscan Hills, enjoy wine tasting in the Chianti wine region, and admire the medieval monuments of UNESCO-listed San Gimignano.

Treat your senses to a memorable day in the world-famous Chianti wine region on this private tour from Florence. Travel in a luxury minivan through a landscape of historic vineyards, rolling hills and medieval villages, with a private driver at your disposal throughout the day. Taste renowned Chianti wines and authentic Tuscan cuisine at estates of your choosing, or let your local driver make suggestions for the best places to wine, dine and explore.

Trade the busy streets of Florence for the ancient vineyards, medieval villages, and scenic landscapes of the Chianti wine region on this half-day tour. Let a knowledgeable local driver take you to some of the area’s best family-run wineries, where you can learn about traditional production methods and taste the local bounty like extra-virgin olive oil and renowned wine varietals like Chianti Classico. The private tour can be customized to suit your interests, such as a stop for an authentic Tuscan lunch at a local farm.

Experience the treasures of Tuscany on a private day trip from Florence. Travel by luxury minivan through countryside full of historic vineyards, medieval villages, and olive groves. Visit the charming medieval city of Siena and the town of Montalcino. Your professional, English-speaking driver shares local history and can recommend the best places to visit, shop, and dine for a customized experience.

Get a personal introduction to Siena and Chianti with a full-day, private tour from Florence in a luxurious van. Stroll Siena’s gothic streets with a local guide, and discover the art and black-and-white architecture of its UNESCO-listed historic center. Explore rolling vineyards and olive groves then taste your way through famous wineries, family cellars, local olive oils and aged balsamic vinegar.

Explore the Heart of Tuscany with an Authentic Culinary and Wine Experience! Calling all food lovers and wine enthusiasts! Embark on a truly unforgettable journey where the timeless traditions of Italian cuisine meet the captivating heritage of Chianti wine country. Highlights of this Experience: Chef with a Michelin-star background Hands-on and Interactive pasta-making class Curated wine tasting at local wineries Unforgettable Chianti wine tour Visit 2 family owner wineries Unforgettable Tuscan memories What’s included in this Experience? - All cooking tools and fresh ingredients provided - Drinks And Wine offered - Downloadable e-recipe book to take home - Private transfers with a knowledgeable sommelier Start your day mastering fresh pasta with a Michelin-star chef, then head to Chianti for a scenic wine tour with our sommelier. Visit local wineries, taste exquisite wines, and immerse yourself in Tuscan culture. A perfect mix of cooking, sipping, and discovery!

Experience the true flavor of the Tuscan countryside—and enjoy wine tasting without designating a driver—on this Chianti wine tour from Florence. Visit local wineries in scenic villages to sample revered Tuscan wines and learn winemaking secrets. Alternatively, enhance your day with a morning cooking class preparing traditional Tuscan recipes paired with premium wines.

Get a taste of Tuscan landscape, wine, and food on this full-day private tour from Florence. Led by an English-speaking driver, discover the regions of Chianti and Val d’Orcia, soaking up the local flavor with several wine tastings. Explore the charming towns of Castellina and Montepulciano, and savor a traditional Tuscan lunch at a farmhouse in Montalcino.

Explore the enchanting Tuscan countryside on this self-drive adventure with an electric Vespa. With a dedicated guided app, drive through Chianti’s winding roads, surrounded by vineyards, olive groves, and cypress trees. Discover charming medieval towns like Montefioralle and Greve in Chianti, and stop to feast on a delicious Tuscan lunch in a typical trattoria.

Discover Tuscany's most iconic hilltop gems on this full-day excursion from Florence. Organizing a trip to the region’s scattered medieval villages can be challenging without local insight or a grasp of the Italian language. This group experience covers the logistics, so you can spend your time basking in the beauty of Val d'Orcia, sipping wine at a rural vineyard, and exploring medieval fortresses along the way.

Visit two of Tuscany's beautiful hilltop towns, plus enjoy tours and tastings at boutique wineries in Chianti and Montalcino on this small-group tour from Siena. All transport is included for a hassle-free experience, with free time to explore Pienza. Sample top Chianti, Brunello, and Super Tuscan wines, and relax over a Tuscan lunch featuring local specialties.

Discover the history of the Chianti region, visit Montalcino's medieval fortress, and enjoy a scenic drive through Val d'Orcia on this small-group tour from Siena. Taste Chianti Classico and Brunello wines paired with Pecorino cheese, bruschetta, salame, and extra virgin olive oil. Explore the historic cellar and learn about the wine production process in a boutique family-owned winery.

Cross the Tuscan hills in search of fine wine, local food, and unforgettable views. This small group tour from Florence takes in UNESCO heritage sites, charming medieval towns, and a landscape that captivated Renaissance painters. Stop in Montalcino for a lunch of local fare and a tasting of some of the best wines in the world. And head to Montepulciano to wander its picturesque palazzos and visit the historical wine cellars.

Explore the rolling green hills and medieval villages of Chianti with a private 5-hour tour. Enjoy riding in a luxurious minivan and being chauffeured to some of the finest small organic wineries in the region. Learn about traditional production methods as you sample artisanal extra virgin olive oil and beloved Chianti Classico while soaking up the views at every turn. Your unique experience is fully customizable for an unforgettable journey through Italy's most famous vineyards.

Escape far from the crowds and traffic—and enjoy an immersive way to explore the iconic Chianti countryside that few other visitors get to experience—on this small-group, full-day hiking tour from Florence. Ramble for 4 miles (7 kilometers) on trails through vineyards and olive groves to really soak up the scenery. Along the way, visit three wineries to sample up to 10 wines, and enjoy Tuscan specialties for lunch.