Day Trips from Tuscany to Chianti

Experience the highlights of southern Tuscany on a full-day small group tour from Florence through the rolling landscapes of the Val d’Orcia. Travel in comfort and enjoy a perfect blend of food, wine, history, and scenery. Your first stop is Montepulciano, where you’ll enjoy an authentic Tuscan lunch featuring local cured meats and cheeses, followed by handmade Pici pasta with ragù, or tomato sauce for vegetarian guests. During lunch, take part in a guided tasting of Rosso di Montepulciano and the renowned Nobile di Montepulciano, perfectly paired with the regional cuisine. Continue to Pienza, the “ideal Renaissance city,” and enjoy free time to stroll its picturesque streets, admire panoramic countryside views, and browse artisan food shops. In the afternoon, reach Montalcino, home of the prestigious Brunello di Montalcino. Visit a local winery for a guided tasting and learn about the traditions and aging process behind one of Italy’s most celebrated wines.

Benefit from a private full-day tour of Tuscany with round-trip transportation from your accommodation. Have free time during your visits to Montalcino, Pienza, and Montepulciano, and have the option to stop for lunch, and wine or cheese tastings in the countryside. Travel in comfort in an air-conditioned private vehicle with hotel pickup and drop-off included.

Pedal through the Tuscan countryside during this half-day e-bike tour through Brunello. Bike along unpaved roads with ease on your electric bike towards local Tuscan vineyards. Enjoy a wine tasting at the Abbey of Sant’Antimo and learn about the ancient winemaking process. Sample three glasses of wines, including the Brunello di Montalcino, before heading to the medieval town of Montalcino to explore.

Tuscans were making wine long before Roman times. Discover the region’s rich wine traditions, the fine art of winemaking, and a wealth of local delicacies on this private tour. Taste wines including Chianti Classico, Chianti Reserva, and super Tuscans; visit two separate wineries; sample olive oil, balsamic vinegar, cold cuts, and pecorino cheese; and enjoy a light lunch with wine.

Visit the historic town of San Gimignano and discover hidden gems—local wineries with views almost as good as the wine. Wander through two wineries, take in views of the vineyards and surrounding rolling countryside, and learn how wine is made. Then taste local wine with your hosts and visit the cellars where wine ages in wooden barrels.

Tuscany produces one of Italy’s flagship wines: Brunello di Montalcino. Exploring the countryside where these wines are produced, however, means navigating confusing rural roads and searching for remote wineries. With this wine tour, leave the hassle of driving to the experts and instead enjoy a stress-free day of wine tasting and sightseeing. Visit two winereis and a cellar.

Immerse yourself in Italian wine culture on this half-day tour around the revered Chianti Classico wine region. There’s no crowding into cellar doors on this small-group tour of the region. Instead, spend your afternoon exploring the cellars and sampling the products of some of the region’s vineyards. All transport is provided, so you can fully enjoy your tastings.

Discover the essence of Tuscany on this immersive wine tour through the beautiful Chianti region. Visit three distinct wineries, where you'll explore traditional vineyards and enjoy multiple tastings of exquisite Chianti wines. With a knowledgeable guide leading the way, you’ll learn about the art of winemaking while soaking in the stunning countryside views. Perfect for adults seeking a delightful day of wine and camaraderie.

Experience medieval Tuscany on a group day trip. Visit the fortified town of Monteriggioni with tickets to its Templar Museum and access to its medieval walls. Continue on to the UNESCO heritage area of Val d'Orcia and stop at the medieval village of Montalcino for an optional taste of local wine and nibbles. Finish your tour with a wander through Pienza before the scenic drive back to Florence.

This private tour is designed to offer an authentic experience with maximum comfort and local insight. It starts directly from your hotel in a fully licensed Mercedes van with air conditioning for a smooth and relaxing ride. Accompanied by a professional driver-guide-certified sommelier, fluent in English and Italian born and raised in the Montalcino area. Travel through the stunning Val d’Orcia admired worldwide for its rolling hills and iconic landscapes. The highlight of the tour is an exclusive visit to a family-owned, organic Brunello winery, where you will walk through the vineyards, tour the cellars, and enjoy a guided tasting of selected red wines, including the celebrated Brunello di Montalcino, accompanied by a tasting extra virgin olive oil. The experience concludes with free time in the medieval town of Montalcino, the heart of the Brunello wine region, where you can explore historic streets, admire monuments, and browse charming local shops at your own pace.

One of the best wine region of the world with a local driving-guide and wine connoisseur, born and raise in the area.Private tour in two boutique wineries , driving through the most scenic road of Val d'Orcia with chance to stop for the best Tuscan countryside pictures.

With spotty public transportation and winding rural roads, the Brunello di Montalcino wine country can be tricky to explore on your own. Discover the history and flavor of one of Italy’s premier wines with ease on this full-day tour from Florence. Travel through the Tuscan countryside to the Brunello hills and the village of Montalcino. Visit a small, family-run winery to learn about traditional production methods and taste renowned varietals like Brunello DOCG and Rosso di Montalcino DOC. Savor a farm-fresh lunch of Tuscan specialties at the estate, and finish the day with more tastings at another local winery.

Discover the enchanting Chianti region with visits to two picturesque wineries. Enjoy tastings of world-renowned Chianti wines paired with local delicacies, olive oil, and balsamic vinegar. Relax on a scenic drive through rolling Tuscan hills, guided by an expert escort. This unforgettable journey offers a perfect blend of wine, culture, and breathtaking landscapes, making it an essential Tuscan experience.

Escape to Tuscany's Chianti Hills from Florence for a wine lover's paradise. Roam vineyard-covered landscapes, taste Chianti's renowned wines, and uncover the artistry behind each bottle. A toast to unforgettable memories! Be prepared to be mesmerized by a tapestry of natural beauty. Endless vineyards dressed in vibrant greens stretch towards the horizon, while the ancient olive groves and charming medieval towns provide a sense of timelessness. The countryside whispers stories of generations who have toiled to create this captivating vista. Chianti is more than just a wine; it's a testament to the harmony between the land and the hands that nurture it. Traverse the vineyards, touch the soil, and grasp the meticulous care that goes into every grape. Expert vintners will guide you through tastings that allow the flavors to unfold on your palate, showcasing the nuances that make Chianti wines revered worldwide.

Experience the ultimate Tuscan day out, combining the open-air thrill of a panoramic ride with the luxury of a private wine tour. Start your morning zipping through the Florentine hills in a private, eco-friendly Golf Cart, taking in breathtaking views away from the crowds. Then, transition into a luxurious, climate-controlled Private Van for a scenic drive along the famous Via Chiantigiana. Arrive at a historic winery near Greve in Chianti for a guided tasting and an authentic Tuscan lunch.

Brunello di Montalcino is one of Italy's most prestigious wines, but navigating to the rural wineries outside of Montalcino on your own can be stressful. On this private wine tour, let your driver take the wheel and focus on vineyard views as you make your way to the top wine estates and cellars for exclusive tasting experiences. Explore stunning vineyards, learn about traditional winemaking techniques, and savor the rich flavors of Tuscany with guided tastings and a traditional lunch.

Get a taster of Tuscany on this private tour that features a selection of the region's highlights. Visit Siena, the Chianti countryside, and San Gimignano all in the same day, without having to hire your own car. Enjoy an itinerary that includes historic sightseeing and regional wineries, with the option to try local varietals (extra cost). Ideal for travellers who are only in the area for a short time.

Spend a day in the Tuscan countryside without having to puzzle through tricky transportation on this Chianti and San Gimignano day trip that includes a driver from Florence. Stop in Montefioralle for photos, then visit a Tuscan winery in Greve in Chianti, where you’ll tour the vineyards, learn about the wine-making process, and enjoy tastings of Chianti Classico and other regional specialties. Next, explore the medieval town of San Gimignano before heading to a nearby farm for a light lunch with Tuscan appetizers, wines, and oils.

Embark on a private journey through the heart of Chianti along the iconic Chiantigiana Road, with scenic views of rolling hills, vineyards, and olive groves. Before leaving Florence, we will stop at Piazzale Michelangelo to admire the stunning view of the city. Our first stop is Greve in Chianti, where we will visit the main square and a famous grocery store to sample typical Tuscan products like salami and cheese. We will then continue through picturesque villages like Montefioralle and Badia di Passignano. Next, we’ll visit the medieval town of San Gimignano, a UNESCO World Heritage Site, known for its 13 towers. After free time to explore, we’ll head to a local farmhouse for a 2-hour group cooking class, followed by a delicious lunch and generous wine tasting. At the end of this unforgettable experience, we will return to Florence.

Departing from Florence, enjoy a scenic drive through the Tuscan hills before reaching Trequanda, a charming medieval village in the Val di Chiana. Here, you can explore the Rocca di Trequanda, a well-preserved fortress with Ghibelline battlements, and the nearby Church of Saints Peter and Andrew, known for its stone&brick façade. The highlight of the stop is a visit to a local farm, where you’ll learn the techniques behind creating a Supertuscan wine. You’ll even blend and label your own bottle, becoming a winemaker for a day and taking home a unique souvenir. The journey continues to Montalcino, famous for its prestigious Brunello wine. Enjoy views over the Val d’Orcia, visit the impressive Montalcino Fortress, and stroll through Piazza del Popolo. A short distance away stands the beautiful Abbey of Sant’Antimo, an excellent example of Romanesque architecture. Your day concludes at a local winery with a guided tour and a Brunello tasting, celebrating an authentic flavor of Tuscany.

The day starts with departure from Florence in a private car or minivan. You’ll leave the city and head into the Tuscan countryside, with its rolling hills, vineyards, and medieval villages. The first stop is Montalcino, famous for its Brunello wine. After a visit to the historic center, you’ll tour a renowned winery, walking through vineyards and cellars, and participate in a guided tasting, including local extra virgin olive oil. A farm lunch with traditional Tuscan dishes and estate wines follows. In the afternoon, you’ll travel to Siena. Discover Piazza del Campo, the Cathedral, and other historic sites. You’ll also have free time to explore at your own pace, perhaps enjoying a sweet treat from a local pastry shop. The day ends in Monteriggioni, one of Tuscany’s best-preserved fortified villages. Walk along its intact city walls, then enjoy a wine and local product tasting at an authentic winery inside the village. A perfect blend of history, flavors, and breathtaking views.

The Val d’Orcia is one of Tuscany's most picturesque areas, but scarce public transportation and confusing rural roads make exploring on your own tricky. Leave the driving to a professional and focus on views of the UNESCO-listed landscape on this tour of Pienza and Montepulciano from Florence. Marvel at historic architecture and rolling hills, plus enjoy a light lunch and tasting of local Vino Nobile di Montepulciano wines.

What better way to end your day in Florence than with a drive through Tuscany's wine country. Sample wines like a pro during this private half-day tour in Chianti. Set off in the afternoon and enjoy a scenic drive through the rolling vineyards and olive groves. Stop at a family-run winery to sample four Chianti Classico and Super Tuscan wines, as well as olive oil, local cheeses, and artisan chocolate.

Explore Tuscany's countryside without hiring a car with this private driving tour of the region. Perfect for travelers staying in Florence, enjoy hotel pickup and relax as you are taken to a range of destinations based on your interests. Visit the Florence American Cemetery, the medieval hamlet of Castello di Montefioralle, and take in the view at Piazzale Michelangelo. For wine lovers, opt to visit a Chianti winery (at an additional cost) and enjoy tastings of local varities.