Tuscany is an ideal destination for a short getaway thanks to its timeless beauty and its natural, cultural, and of course culinary richness! More and more people are choosing to spend a spring weekend at a farmhouse, a perfect way to immerse yourself in the peaceful countryside, enjoy traditional dishes made with local ingredients, and rediscover the slow rhythm of nature.
Farmhouses also serve as a strategic starting point to explore the region's main attractions — such as art cities, charming villages, and thermal baths — away from the hustle and bustle of the city. They often offer guests the chance to enjoy authentic experiences, from wine tastings and picnics in the vineyards to cooking classes.
Where to go in Tuscany in May and enjoy the spring?
For lovers of the countryside and quiet, ancient villages, the Val d'Orcia is without a doubt one of the most charming destinations. Over the course of a three-day itinerary, you can truly unplug and be enchanted by the peaceful landscapes surrounding medieval towns like Montepulciano, Montalcino, and Pienza — not to mention the iconic views of Siena. Our spring itinerary begins right here, in the city known worldwide for its historic Palio.
Art, hiking, and hot springs between Siena and Montepulciano
An ideal starting point for a short itinerary through the Val d'Orcia is Siena, with its intimate city atmosphere and historic center revolving around the world-famous Piazza del Campo. Every year, in July and August, thousands of visitors from around the globe gather here to witness the Palio horse race. Within the stunning perimeter of the square, you can admire the Fonte Gaia, the Palazzo comunale, and the magnificent Torre del Mangia.
A stroll to Piazza del Duomo offers a view of the beautiful Cathedral of Santa Maria Assunta and the chance to visit the Santa Maria della Scala museum complex. Spread over seven levels, it's now a major cultural hub hosting exhibitions and permanent collections. For lovers of aristocratic residences, there's also the opportunity to take a guided tour of Palazzo Chigi Saracini, home to masterpieces by Botticelli, Sodoma, Sassetta, Beccafumi, and Cassioli.
Among the must-see stops for lovers of the Tuscan countryside and the captivating blend of landscape, small towns, and fine wine, there is Montepulciano. Here, in the land of Vino Nobile, you can visit the beautiful medieval village, with its vibrant heart in Piazza Grande, featuring the 14th-century Palazzo comunale, the Cathedral, and the Torre di Pulcinella. Montepulciano is also the ideal spot for fans of walking or hiking, where you can plan an excursion to the lake and visit the surrounding natural park.
For those looking to relax and unwind, the town also offers a thermal spa, where you can experience the healing benefits of baths in the sulfurous salsobromoiodic waters.
The gastronomic experience at Fattoria del Cerro, where taste, elegance, and tradition come together
When traveling along an itinerary in the Val d'Orcia, it's worth planning a stop at Fattoria del Cerro, the historic producer of Vino Nobile located in Acquaviva.
The estate offers the perfect solution for a three-day stay at an farmhouse: the elegant rooms with views at Relais Villa Grazianella — 11 in total — welcome guests in an intimate and refined atmosphere. During a stay at Fattoria del Cerro, you can also enjoy various experiences, such as exploring the vineyards on an e-bike or off-road vehicle, or even having a picnic in the vineyards to connect with the intimate and rural nature of the Tuscan territory.
The estate's formula will also win over food lovers, thanks to the chef of the L'Antica Chiusina restaurant at Villa Grazianella and his traditional Tuscan dishes, which can be savored at dinner or, why not, tried directly in the kitchen during a cooking class.
Tuscan villages to visit in spring
Another perfect stop on a spring tour is Pienza. This small village, recognized as a UNESCO World Heritage Site, is famously known as the “ideal city" of the Renaissance. To experience its charm and treasures, all it takes is a leisurely stroll through Piazza Pio II and the Palazzo Ducale, followed by a visit to the stunning hanging garden of Palazzo Piccolomini, which offers an unforgettable view over the Val d'Orcia.
Those who love the peace and quiet of small historic towns will fall in love with the village of San Quirico d'Orcia. This beautiful medieval town along the Via Francigena is a true gem, filled with charming sights such as the Collegiate Church of San Quirico and Giuditta and the Horti Leonini—gardens designed by Diomede Leoni in 1540.
Before setting off toward the next destination, whether by car or perhaps by motorcycle, it's well worth stopping to admire the iconic cypress trees of San Quirico, perched on a hill and now a symbol of the Tuscan landscape.
A short itinerary through Tuscan villages wouldn't be complete without a stop in Montalcino, the homeland of the renowned Brunello wine. This charming town is nestled within the Val d'Orcia Natural Park, a UNESCO World Heritage Site. Here, you can immerse yourself in an atmosphere that has preserved its medieval character through the centuries.
To truly experience it, head to the Abbey of Sant'Antimo, where you can attend mass and listen to the evocative Gregorian chants still performed today by French monks.
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In spring, Tuscany transforms into a true open-air botanical spectacle. The landscapes burst into vibrant colors, the scents grow more intense, and the travel experience becomes even more thrilling for those who love nature and its seasonal rhythms.
In the Val d'Orcia, sweeping fields of red poppies and golden broom sway between rows of vines and centuries-old olive trees, creating a stunning contrast with the stone villages and rolling hills.
In San Quirico d'Orcia, the elegant Horti Leonini offer one of the season's most enchanting blooms. Designed in the 16th century, these formal gardens are a triumph of symmetry, perfectly trimmed hedges, and unforgettable photo-worthy views—especially between April and May.
Pienza also reveals itself in all its splendor: here, balconies and loggias are decorated with fragrant plants, while the hanging gardens of Palazzo Piccolomini offer a flower-filled view over the valley that alone is worth the trip, an ideal spot for lovers of nature photography and slow tourism.
Anyone wishing to immerse themselves in the green heart of Tuscany can easily reach Chianti, where spring paints landscapes like a watercolor: wild irises, ancient roses, fragrant brooms and budding vineyards color the scenic roads between Greve, Radda, Castellina, and Gaiole.
Discovering wine along the roads of tradition
Whether you opt for the Val d'Orcia or a mixed itinerary, the most authentic soul of Tuscany can be discovered in the winery, savoring the aromas and flavors of the land in a good glass of wine.
Those who choose to stop at Fattoria del Cerro will have the opportunity to appreciate the fine Vino Nobile di Montepulciano. The estate's new winery, nestled among the Prugnolo Gentile vineyards, will open its production site to guests starting from Easter 2025. The fully renovated spaces, such as the wine cellar and the Acquario Room, will offer new tasting experiences to discover. Guided tours, with dedicated times and information, will lead guests through a unique sensory and cultural journey.
This is yet another opportunity to choose this estate and enjoy the Vino Nobile di Montepulciano DOCG, produced here in the "Riserva DOCG", and "Antica Chiusina" varieties.
Those who include a stop at Poderina along their itinerary will have the opportunity to discover how Brunello di Montalcino is made. Here, in the estate's winery, guests can observe all stages of production and taste the wine paired with local cheeses and cured meats. Four wines are offered for tasting: Brunello di Montalcino DOCG, "Poggio Abate Brunello di Montalcino Riserva DOCG", "Rosso di Montalcino DOC", and "Moscadello di Montalcino DOC". A Sangiovese tasting can also be booked at the winery.
For those who decide to stop at Tenuta di Monterufoli, a wine-tasting experience in the cellar awaits, offering the chance to discover and appreciate Vermentino di Toscana IGT and Poggio Miniera Val di Cornia Rosso DOCG.
Tuscany is perfect for those who love immersive experiences in history, blooming landscapes, and authentic flavors. Are you ready to book your stay in this beautiful region?
