Day Trips from Tuscany to Chianti

Semi-private tour to Discover the enchanting Chianti Classico region on a meticulously crafted wine tour that immerses you in Tuscany's lush vineyards and celebrated wineries. Enjoy scenic drives in a luxury minivan, visit two organic wineries, and indulge in a delightful lunch paired with exquisite local wines. Led by expert guides with deep local knowledge, this tour offers insights into the winemaking process from passionate artisans. Perfect for wine lovers and food lovers, this experience caters to small groups and ensures a personalized itinerary for a memorable day in Tuscany. - Enjoy a full 5-hour tour of the Chianti Classico region - Semi-private for a maximum of 7 guests. - Visit 2 organic wineries with exclusive tastings of Chianti Classico and supertuscans wines - Savor a delicious locally-sourced lunch at a winery - Travel in luxury transportation from Florence with an expert guide -Scenic roads for a great experience - No pressure on buy wines

Enjoy our private tour through the rolling hills of the Chianti Classico area, the land of the famous Black Rooster. Sit back and relax as we drive along scenic countryside roads surrounded by vineyards, olive groves, and cypress trees, stopping at panoramic points to take photos of the breathtaking Tuscan landscapes. During the journey, you will pass through and visit charming medieval villages such as Panzano, Greve in Chianti, and Montefioralle, the birthplace of the historic Vespucci family. You will have time for short walks through their historic centers, soaking in the authentic atmosphere of rural Tuscany. The experience concludes at a local winery, where you will enjoy a guided tasting of authentic Chianti Classico wines, paired with traditional Tuscan antipasti made with local products.

Enjoy a day trip to three of Tuscany’s most iconic destinations: Montalcino, home of the famous Brunello wine; Pienza, renowned for its Pecorino cheese; and Montepulciano, known for its prestigious Nobile wine. Travel through the UNESCO-listed Val d’Orcia aboard a premium air-conditioned minivan with an English-speaking driver and complimentary water. Small group experience, maximum 8 participants. Why choose us? • Guaranteed departures • Secure booking • 24-hour cancellation policy • Best rates guaranteed For operational reasons, the itinerary order may vary between Montepulciano and Montalcino.

Take an early high-speed train from Rome to Florence, where your driver will meet you outside the station. Enjoy a full-day journey through the stunning Val d’Orcia, a UNESCO World Heritage Site. Visit Montepulciano and explore its fascinating underground cellars while tasting local wines and specialties. Continue to Pienza, the charming Renaissance village famous for Pecorino cheese, where you'll enjoy a seasonal lunch. In the afternoon, discover a prestigious Brunello di Montalcino winery with a guided visit of the vineyards and cellars, followed by a premium wine tasting. Travel comfortably throughout the day in a premium minivan with an English-speaking driver before returning to Florence station for your train back to Rome. For operational reasons, the order of visits between Montepulciano and Montalcino may vary.

Experience the essence of Tuscany on this immersive Brunello tour through Val d’Orcia. This tour is specially crafted for Brunello enthusiasts and curious wine lovers eager to experience the elegance and rich story behind Tuscany’s most iconic red. This tour offers much more than wine tasting — it is a celebration of Tuscany’s landscape, heritage, and the passionate people who bring Brunello di Montalcino to life.

Enjoy a day trip through Tuscany's iconic Val d'Orcia, a UNESCO World Heritage Site. Visit Montalcino, home of Brunello wine, Pienza, famed for Pecorino cheese, and Montepulciano, celebrated for Nobile wine. Travel comfortably in a premium minivan with an English-speaking driver. Indulge in wine tastings, a superior lunch, and guided vineyard and cellar tours.

One full day of a beautiful guided sightseeing tour driving through symmetrical vineyards, olive trees, wooded groves, stone farm houses, late Renaissance villas and old villages, castles and medieval hamlets.

Visit one of Tuscany’s most respected wine regions on this tour from Florence to Brunello di Montalcino. In a private, air-conditioned car with a guide, drive first to Montalcino, a hilltop medieval walled city to explore the ancient town. Next, visit family-owned wineries in the Brunello countryside like Poggio Rubino and Capanna. Your guide will also take you to see the beautiful Abbey of Sant’Antimo, which is thought to date back to the sixth century.

Fiat 500 represents the emblem of Italian Style. Shape, size and its unique charm make of this car a special and authentic symbol beyond it’s simple use as a vehicle. Ideal both on city’s tiny alleys and on the famous country-side windy roads. We will be visiting typical medieval villages, get in touch with local wine and food producers as well as artisans, and stop along the way to take some picturesque photos that will become indelible memories. An experienced tour guide will lead you around and show you the way as only a local can. The tour ends in a local farm where we will be hosted by a family that has been living there since centuries, producing their own wine, Chianti Classico. We will have the chance to visit the property including the cellar and then relax where a traditional Tuscan lunch will be served, all accompanied by their wines. Pick up and drop off from your accomodation in Siena included.

Cruise through Tuscan wine county in true Italian style — behind the wheel of a vintage Fiat 500. Learn how to drive the classic Italian car with a brief lesson, then hit the road with a private guide for a joy ride along scenic country roads. Stop at a typical Chianti village, a medieval hamlet, and an antique farmhouse, where you'll be treated to a homemade lunch and tasting of wine, grappa, and olive oil.

Surround yourself with the unrivaled scenery of Valle de Orcia while trying some of its epicurean delights on a private tour from Siena. Begin in the hill town of Montalcino, where you'll sip on locally produced wine at a popular winery. Later, head to the historic center of UNESCO-listed Pienza, where you'll enjoy free time to explore independently. A typical Tuscan lunch, cheese tasting, and hotel pickup are included.

Explore Val d’Orcia, a UNESCO World Heritage site known for its stunning landscapes, art, and rich food traditions on this private tour. Visit Montalcino, home of the renowned Brunello wine, where you'll enjoy a guided winery tour and lunch. Then, head to Montepulciano, a medieval city with Renaissance palaces and sweeping valley views, famous for its Vino Nobile wine. Enjoy wine tastings in both towns while taking in their historical and scenic beauty.

Explore rolling hills, sunflower fields, and cypress-lined roads in Tuscany, savoring two local treasures: red wine and Pecorino cheese. Begin in Pienza, a Renaissance gem in Val D’Orcia, with a tasting of its famed Pecorino cheese at a traditional “bottega.” Next, visit Montalcino, home of world-renowned Brunello wine. Enjoy a private winery tour, a cellar visit, and a Tuscan lunch perfectly paired with Brunello wines to cap off your culinary journey.

Escape the bustle of Florence with this private Vespa tour through the rolling hills of Tuscany. Hop on your scooter and follow your guide through the Chianti countryside, stopping to visit medieval hill towns and taking a break at a Tuscan vineyard for a wine tasting and freshly–prepared lunch. Take in sweeping views as you zip through Tuscany on your Vespa far from the crowds and discover corners of the region that most tourists miss.

We will spend an entire day crossing the most characteristic and beautiful part of the Tuscan countryside: the Chianti. Here we will visit small villages and admire unique landscapes ... without forgetting to taste some good wine!

Skip the rush of big group tours and enjoy a personalized private tour of the Chianti region with this half-day excursion from Florence. With just your group and dedicated driver-guide, explore Greve in Chianti and Montefioralle, then visit a local winery to learn about Sangiovese grapes and taste Chianti.

Explore the Tuscan countryside on this full-day outing to the Italian countryside from Florence to discover the region's wine-making culture. Visit the medieval hill town of Montalcino for a stroll through its streets. Then, continue to Montepulciano—which is famous for the variety of grapes that bear its name—for a wine tasting and a visit to the underground city. On the return journey, drive through the UNESCO-listed Val d’Orcia and make a couple of panoramic stops.

You will have an unique experience with speaking English driver, you will feel the real atmosphere of Tuscany in the beauty of the Nature and good food. Enjoy and book this incredible experience through the beauties of Tuscany. Join our guide and enjoy this incredible experience.

Live an authentic experience in the heart of Chianti Classico with a visit to two family-run wineries, where you will be welcomed directly by the producers. In an intimate and relaxed atmosphere you can taste excellent wines, extra virgin olive oil, cheeses and typical cold cuts, discovering the most genuine flavors of Tuscany. The Guide, born and raised in the region, will accompany you by private car, telling the history, traditions and curiosities of the territory. Along the way there is also a stop in a small village in Chianti, to immerse yourself even more in local life. The tour is designed for those looking for a personal and non-tourist experience: familiar and welcoming wineries, direct dialogue with the owners, quiet rhythms and an authentic contact with Tuscan wine culture.

Wine lovers, this trip into Tuscany from Florence is designed just for you. You’ll leave the city behind and head to the Chianti region, known around the world for its red wines. You’ll be picked up from the meeting point in Florence and driven to Tuscany and the Chianti region. Your first stop is the Medieval village of Greve. Then, you’ll head to Montefioralle, which has been perfectly preserved since the 12th century. Chianti Classico, one of the most iconic Italian red wines, has a black rooster on its label – you’ll hear the backstory for this during your time in Montefioralle. From here, you’ll head to a family-run wine estate for lunch and a wine-tasting session. The cellars have been around since Medieval times, and they use oak barrels to do a lot of their aging. You can expect Italian classics prepped with ingredients grown on the property. You’ll have three different Chiantis to sample. This region is also known for its olive oil, so you can try some of that, too.

Ciao, solo travelers, and welcome to Tuscany! Here's your chance to explore the charming Tuscan countryside on a scooter — feel the fresh air, feel the freedom, and let me take you to the movie-worthy, magical places and villages you never knew existed. Come for a ride with me, your private guide, who knows how to enjoy life "like an Italian" and is passionate about riding a scooter through the Chianti hills, exploring the crème de la crème of Tuscany, and sharing all this beauty, flavor, and these hidden gems with you. Along the way, you'll have the chance to stop anywhere it's safe to take photos, soak in the view, and immerse yourself in the ever-changing yet timeless beauty of the Tuscan valleys.

Unlike standard Chianti tours, this experience blends wine tasting with a behind-the-scenes look at Impruneta’s centuries-old terracotta tradition, followed by authentic village stops, boutique winery experience and a relaxed gelato break—creating a well-rounded journey into Tuscany’s art, craft, and flavors.

Welcome to a unique experience in the heart of beautiful Tuscany! Our Chianti tour invites you to discover the essence of this legendary wine region, all with the luxury and comfort of our exclusive chauffeur service included. From the moment we pick you up at your accommodation, you will immerse yourself in a dream journey through the most impressive landscapes in Italy. Our expert drivers, knowledgeable about the area, will guide you through the winding roads between hills, dotted with vineyards, olive groves and cypress trees, giving you panoramic views that will leave you breathless. During the tour, you will have the opportunity to see family-owned vineyards, where you will be greeted with warm Tuscan hospitality and have the opportunity to taste some of the most exquisite wines in the region. From the iconic Chianti Classico to other local varietals, each sip will transport you to centuries of wine tradition.

we will make you experience Chianti as we do, in its beauty, goodness and simplicity, with fun and light-heartedness