Day Trips from Florence to Montepulciano

Navigating Tuscany’s rolling vineyards and medieval towns by public transportation or rental car can be stressful and time-consuming. With this private day trip, leave the driving to a professional and relax as you take in views of the Crete Senesi, Montepulciano, and Siena. Stop at a winery to taste Tuscan reds and whites and enjoy free time to explore the old towns of these two iconic destinations with included hotel pickup.

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

Discover two of Tuscany's most beautiful cities, Montepulciano and Siena, in just one day on this private trip. From Florence, journey in an air-conditioned vehicle to Montepulciano, with time to take in hilltop views from the Torre di Pulcinella. Next, visit Siena, where you can explore a medieval square and the local Gothic cathedral—climb to the top for views over the city.

Enjoy a stress-free private transfer from Florence to Rome with a sightseeing stop, driven by a friendly, English-speaking driver and a comfortable, air-conditioned vehicle. Customize your journey with an optional stop at a scenic destination like San Gimignano, Siena, or Orvieto, adding a touch of exploration to your trip. With door-to-door service, luggage assistance, and bottled water included, this transfer ensures a smooth and enjoyable travel experience.

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.

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.

Escape Florence for a full-day journey through the heart of Tuscany’s Val d’Orcia, a UNESCO World Heritage landscape of rolling hills, vineyards, olive groves, and cypress-lined country roads. Visit three of the region’s most beautiful towns, Montalcino, Pienza, and Montepulciano, each known for its history, views, and authentic Tuscan character. Begin in Montalcino, home of the world-famous Brunello wine, where you’ll visit a wine cellar and enjoy a tasting. Continue to Pienza, the Renaissance “ideal city,” famous for its architecture, panoramic views, and Pecorino cheese. Finally, explore Montepulciano, renowned for Vino Nobile, and enjoy another wine and Pecorino tasting inside a historic underground cellar before returning to Florence.

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.

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.

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.

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. 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.

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.

Taste some of Tuscany's most renowned varietals on a full-day private Chianti wine tour from Florence. Visit the charming medieval towns of Montalcino, Montepulciano, and Greve, where historic castles and towers appear untouched by time. In each village, stop at wineries and wine bars to sample pours of Nobile, Brunello, and Chianti Classico wines and learn about the cultivation of these prized grapes.

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.

Join this full-day sensory-filled journey through Val d'Orcia with exquisite wine and cheese tastings. Spend your day immersed in Tuscany's charming medieval towns while enjoying the world-renowned Nobile di Montepulciano and award-winning Pecorino di Pienza. And don't forget about the lunch and refreshing alcoholic beverages included. All these wonderful experiences will take place in a comfortable air-conditioned vehicle. It's a full-day adventure you won't want to miss.

Embark on an unforgettable journey through Tuscany and discover historic cities, cinematic landscapes, and world-famous wines. Departing from Florence, explore enchanting destinations such as Cortona, Montepulciano, and Montalcino, immersing yourself in the region's unique culture, architecture, and flavors. In addition to the experience during the trip, you will also receive an exclusive ebook to complement your journey and make your discoveries even more special. The material includes historical curiosities, references to films shot in Tuscany, information about the famous local wines, cultural tips, and details about each destination visited. A perfect guide to deepen your connection with the Italian essence before, during, and after the experience.

Escape Florence and journey into the heart of Tuscany on this exclusive full-day private van tour, meticulously crafted for fans of "Under the Tuscan Sun". Travel in ultimate comfort with a professional English-speaking driver to explore the charming medieval streets of Cortona, discover the real Villa Bramasole, and marvel at the Renaissance beauty of Montepulciano. What makes this tour truly unique is the interactive "movie-star" experience! Throughout the day, you will step straight into the film by recreating its most iconic scenes for unforgettable photos. Write a postcard on the stone steps of Cortona, capture the magic of seeing Villa Bramasole, channel your inner Katherine in Montepulciano's Piazza Grande, and celebrate at the romantic San Biagio wedding location. Become the protagonist of your very own Tuscan dream!