Day Trips from Florence to Arezzo

Brunello di Montalcino is one of Tuscany’s signature wines, available only at premium price points outside Italy. Indulge without worrying about choosing a designated driver on this private day trip, direct from your Florence accommodation. As well as a wine tasting, enjoy the chance to sample Pienza’s famous pecorino sheep cheese: Upgrade to enhance your visit with a licensed guide to show you the towns and answer your food questions.

Make the most of your time and avoid the delays of public transportation on this private Montepulciano and Pienza day trip from Florence. Set off directly from your hotel and enjoy free time to sightsee and shop in both Tuscan towns, plus exclusive wine and cheese tastings with local producers. Upgrade to include guided walking tours or explore at your own pace with the recommendations of your English-speaking driver.

Discover the beauty of Tuscany on a private DA Florence to Cortona and Montepulciano tour. Start your adventure in Cortona, where you will explore the historic center, listening to fascinating stories told by your Guide. Next, head to Montepulciano for a guided tour of a historic winery, where you will have the opportunity to taste fine wines and enjoy a light lunch. This tour is perfect for wine and history lovers, offering an authentic experience of Tuscany. - Private DA Florence to Cortona and Montepulciano tour with driver - Guided tour in the center of Cortona with local stories - Wine tasting in a historic winery in Montepulciano - Light lunch included during the tour

Sample the top Tuscan specialties in the hills where they’re produced with this unique wine, cheese, and olive oil tour from Florence. Save time with pickup directly from your hotel and head south into the heart of Tuscany. Visit an olive oil mill in Chianciano for a tour and tasting, followed by a stop at a Montepulciano winery to sample the local Nobile and other wines. End with a stroll through Pienza’s old town and a pecorino cheese tasting.

Journey to the origins some of Italy’s most celebrated ‘vino’ on a private, full-day tour designed for wine lovers and connoisseurs. Visit the medieval town of Montalcino at the famed of Brunello di Montalcino wine. Taste this prized elixir at a winery. Learn about the area’s history and winemaking heritage from a private guide and meet local producers. Price is per group, with a maximum of either 3 or 8 passengers, depending on season and vehicle type.

Leave Florence behind and cross the rolling hills of southern Tuscany on a wine tour in the heart of the Val d’Orcia, a UNESCO World Heritage Site. The first stop is Montepulciano, a historic hill town where food and wine come together in an authentic Tuscan experience. Enjoy a traditional lunch based on local products, with typical cold cuts and cheeses, followed by homemade Pici with slow-cooked meat sauce or tomato sauce for vegetarian option. During lunch, take part in a guided tasting of Rosso di Montepulciano and Nobile di Montepulciano. In the afternoon you reach Pienza, a Renaissance jewel overlooking the Val d’Orcia. You will have free time to stroll through its streets, visit craft shops and admire beautiful views. The last stop is Montalcino, home of the famous Brunello. Here you will visit a local winery and participate in a guided tasting, discovering the traditions and secrets of one of the most prestigious wines in Italy.

Dive into the enchanting UNESCO wonderland of Val D'Orcia! Start your day soaking up Tuscany’s breathtaking views and exploring the hidden gems of Montalcino, home to the legendary Brunello wine. Savor a delicious Tuscan lunch with pasta, local cheese, and olive oil in Pienza, famous for its "pecorino" cheese and timeless charm. Wrap up with a wine tasting in Montepulciano. With comfy transport and culinary delights, this tour is the ultimate Tuscan escapade for foodies and wine lovers.

Optimize your logistics and make the most of your time with this private transfer from Florence to Assisi that includes stops to visit the Tuscan hill towns of Montepulciano and Cortona. Enjoy the ease of pickup at your Florence hotel and explore towns worry-free while your driver stays with the vehicle and your luggage. Sightsee, shop, and dine at your own pace, then end your day with seamless drop-off directly at your Assisi hotel.

Visit three of the most captivating towns in Tuscany in a single day with this tour that includes time-saving transportation directly from Florence. Enjoy a guided tour of Siena to take in the Piazza del Campo and Duomo, then relax over a traditional Tuscan lunch with wine at a local cellar. Spend your afternoon exploring first San Gimignano and then Pisa—including the iconic Leaning Tower—at your own pace. Hassle-free transport from Florence to see Siena, San Gimignano, and Pisa Delve into the history and architecture of Siena with a guided walking tour Sample tagliatelle pasta, salami, cheeses, and local wines at lunch Free time to explore San Gimignano and Pisa’s Piazza dei Miracoli

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.

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 from the crowds of Florence and discover Arezzo and Cortona on a private 9-hour. All-inclusive private transportation from your hotel allows you to comfortably see a long list of attractions in a short amount of time. Visit historical sites, including the 9th-century Etruscan Atrium, as well as filming locations for “Life is Beautiful” and “Under the Tuscan Sun”. Enjoy ample free time to explore both Tuscan towns.

The city is rich in artistic and architectural heritage of two of the greatest Italian Renaissance masters, who were born, lived and worked here: the architect and historiographer Giorgio Vasari and the painter Piero della Francesca. You will visit Piazza Grande, particularly famous for its peculiar trapezoidal shape, where you will see churches, historical buildings such as the Palazzo delle Logge (designed by Vasari), artisans and workshops

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.

Indulge in a day of designer shopping on a private outlet tour from Florence. Travel in a luxury minivan with space for up to seven and enjoy a day of designer deals. Start at the Prada outlet in Levanelle before heading to The Mall, Tuscany’s top designer outlet, featuring brands such as Valentino, Burberry, Gucci, and Armani.

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.

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.

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 Tuscany’s wine and cheese traditions on this full-day private tour from Florence. Visit Montepulciano to taste Vino Nobile at a local winery with insight into how it is produced. Continue on to Pienza to sample pecorino cheese and discover the town’s Renaissance architecture. Travel in comfort with round-trip transportation, and explore solo or upgrade to be joined by a guide.

Discover the essence of Tuscany on the Brunello di Montalcino Wine Tour, a full-day adventure through Val d’Orcia. Marvel at rolling hills and cypress trees as you visit a boutique winery for an organic Brunello tasting, learning about the winemaking process directly from passionate artisans. Enjoy a farm-to-table lunch featuring local ingredients, and explore charming hilltop villages like Pienza or Monticchiello. This tour is designed for wine enthusiasts seeking authentic experiences, all within a picturesque setting. - Full-day tour lasting 10 hours through the stunning Val d'Orcia region - Taste organic Brunello wines at a family-owned boutique winery - Enjoy a delicious farm-to-table lunch with sweeping valley views - Explore quaint hilltop towns for an intimate glimpse of local life

Embark on an unforgettable journey through the enchanting landscapes of Tuscany and Umbria, departing from the art-filled city of Florence. This exclusive tour offers the perfect blend of stunning views, rich heritage, and world-class wines, providing an immersive experience that will stay with you long after the trip ends. Your adventure begins in Tuscany, in one of the region's most prestigious estates. Here, you’ll be treated to a curated wine tasting amidst the beauty of rolling hills and lush vineyards. Then, indulge in a delightful lunch in Cortona, one of Tuscany’s most picturesque hill towns. Enjoy a traditional, farm-to-table meal in a charming trattoria, where every dish highlights fresh, regional ingredients. Next, you'll continue your journey to Castiglione del Lago, a hidden gem on the shores of Lake Trasimeno in Umbria.

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 with beautiful Tuscan views (indoors during winter months, bad weather, and always on Mondays). 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.