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Romantic weekend in Tuscany: 10 unforgettable experiences

  • 04/02/2025

​​There must be a reason, or perhaps more than one, why Tuscany is always the perfect destination for those looking to spend a romantic weekend. Maybe it’s the gentle curves of its rolling hills, the exquisite food and world-class wine, the timeless villages, or the relaxed atmosphere that makes it the ideal backdrop for a getaway for two.

If you're looking for inspiration for a romantic weekend in Tuscany, you're in the right place! Here are 10 ideas, including must-visit places, unique experiences, and charming farm stays, to create an unforgettable escape with your special someone.


10 ideas for a romantic weekend in Tuscany 

A romantic weekend in Tuscany is the perfect opportunity to spend unforgettable moments with your partner, away from the hustle and bustle of everyday life. Explore picturesque villages, breathtaking landscapes, and experiences that celebrate beauty and... complicity.

Let’s discover some ideas and inspiration to make your getaway truly special!


1. Explore the alleys of Montepulciano

If you're a couple who loves charming villages, then you can't miss Montepulciano, one of those places that seems to come straight out of a dream. Get lost in its medieval alleys, admire the elegant facades of Renaissance palaces, and enjoy a romantic walk to Piazza Grande: from here, the view stretches across the surrounding hills, offering a panorama that warms the heart even on the coldest days. Or, to warm up, you can indulge in a glass of the exquisite Nobile di Montepulciano​ wine, which you can savor at one of the many local bars and restaurants you'll encounter during your stroll, ideally paired with a plate of pici pasta or a meat dish.


2. Romantic walk among the cypresses

No matter the season, the Val d'Orcia always offers breathtaking experiences. If you've chosen Montepulciano as your starting point to explore Tuscany, we highly recommend taking a walk along the paths that weave through the cypress groves, one of the symbols of this region, just a short distance from the village. Choose a short yet stunning walk, like the one leading to the Madonna di Vitaleta Chapel: an iconic and exceptionally beautiful spot.


3. Discover Pienza, the city of love

Did you know that Pienza is known as the "ideal city" of the Renaissance? If the answer is no, let us tell you it's a small gem, perfect for exploring on foot and enjoying a romantic moment. Its streets have evocative names like Via dell'Amore, Via del Bacio, and Via della Fortuna, and not by chance, the poet Giovanni Pascoli wrote that Pienza was “born from a thought of love and a dream of beauty.” But most of all, don't miss the view from the natural terrace overlooking the Val d'Orcia: a living painting that takes on a magical light in every season of the year, offering a glimpse of Mount Amiata. Via del Casello is perhaps the most picturesque viewpoint in Pienza, the perfect place to bring your sweetheart.


4. A day within the walls of San Gimignano

In Tuscany, there are countless villages that seem to come straight out of a fairy tale: San Gimignano, with its towering towers, is one of them. Stroll hand in hand along the medieval walls, visit the artisan shops in the historic center, and stop at one of the local wine bars for a glass of Vernaccia, perhaps paired with a platter of typical local products. Of course, a "climb" to one of the many towers is a must, where you can enjoy a stunning view of the city and the surrounding countryside together.


5. The thermal baths in Tuscany: relaxation and intimacy

Could thermal baths be missing from the list? In Tuscany, they are a must-visit for anyone looking to relax and share wellness moments with their partner. One of the most enchanting destinations is certainly Bagno Vignoni, famous for its square transformed into a unique thermal bath in the world: around the tiny village, you'll find spa resorts and pools where you can soak in hot waters.

If you prefer a more intimate atmosphere, head to the free thermal baths of Saturnia, where the Cascate del Mulino creates a natural corner perfect for relaxing together. Other options include Rapolano Terme, with its cozy spas, and the thermal baths of Montecatini, known for their timeless elegance. Whether you choose a natural spring or a wellness center, Tuscany's thermal baths will offer you moments of pure magic.


6. Volterra and its timeless charm

Volterra is one of the most captivating gems in Tuscany: famous for its Etruscan past, the village welcomes you with its imposing walls and a historic center that has preserved its medieval charm. Start your visit at the majestic Piazza dei Priori, dominated by the eponymous palace, one of the oldest municipal buildings in Tuscany. Then, lose yourself in the narrow streets lined with artisan shops and ancient alabaster workshops, where you can watch skilled craftsmen at work. And finally, don't miss a visit to the Medici Fortress, which offers a spectacular view of the surrounding countryside. One last tip? Stop at the city’s viewpoints during sunset, when the village lights up with a warm and romantic glow, offering a magical view of the “Balze”, the characteristic rocky formations.


7. Lucignano and the Tree of Love

Have you ever thought about promising "eternal love" in front of the Tree of Love? In Lucignano, a small medieval village in the Valdichiana, it's possible. This is a place full of charm and perfect for those seeking a romantic experience, known as the "village of love" because it houses one of the most evocative symbols of eternal affection: the Tree of Love, a masterpiece of goldsmithing preserved in the Municipal Museum. It is said that this golden tree, rich in symbols and decorations, brings good luck to couples who visit it. After admiring this wonder, enjoy a stroll along the village's concentric alleys, designed to create a sort of "architectural embrace".


8. Maremma: nature, villages, and breathtaking landscapes

Maremma, with its wild and authentic beauty, is another ideal destination for a romantic weekend in Tuscany. Start your journey with a visit to Pitigliano, the "village of tuff," with its houses carved into the rock and its charming narrow streets. Continue on to Sovana, a stunning medieval village, or Scansano, famous for its Morellino wine, perfect for a wine tasting for two.

If you love nature, the Maremma Natural Park offers panoramic trails leading to secluded beaches, perfect even during the colder seasons for a hand-in-hand walk. Don’t forget Capalbio, with its ancient village and the Tarot Garden, a surreal and fascinating place that adds an artistic touch to your romantic escape.


9. Livorno and the Mascagni Terrace: a poetic corner by the sea

Livorno, with its maritime spirit, offers a surprising alternative for a romantic weekend in Tuscany. One of the most evocative spots in the city is undoubtedly the Mascagni Terrace, a vast square overlooking the sea, characterized by an elegant checkerboard floor. Strolling hand in hand along the terrace, especially at sunset, provides an unforgettable experience, with the sky turning golden and the sound of the waves creating the perfect backdrop. Livorno is not just about the sea: visit the Venice district, with its canals and small trattorias where you can taste local specialties like cacciucco. The city will surprise you with its mix of authenticity and beauty, making it an ideal destination for a romantic getaway that blends sea, culture, and gastronomy.


10. Experiences to do together: wine tasting and cooking class

A romantic weekend in Tuscany wouldn't be complete without a culinary experience to share. Take part in a wine tasting at a winery to discover the secrets of Tuscan wines, some of which are world-renowned for their excellence, or try your hand at a cooking class to learn how to prepare traditional dishes to recreate at home. Both experiences not only "delight" the palate but, most importantly, strengthen the bond between you, creating unforgettable memories and special connections with your partner to take home once the weekend is over.


​Romantic weekend in Tuscany: an unforgettable stay at a farmhouse with Tenute del Cerro

Whatever your destination for a romantic getaway, Tenute del Cerro offers everything you need to make your weekend special: farmhouses nestled in nature, fine wine tastings, and the opportunity to enjoy authentic experiences.

Fattoria del Cerro, located in Acquaviva, is ready to host you at the elegant Relais di Villa Grazianella, with a view of the beautiful Sienese hills and its vineyards. The Villa offers 11 rooms and a restaurant, L’Antica Chiusina, where you can taste the delights of Tuscan cuisine expertly reinterpreted by Chef Stefano Azzi. Moreover, guests who book a stay will receive a card for entrance and wellness paths at the nearby and renowned Terme di Chianciano. For those looking for experiences to enjoy with their partner during the romantic weekend, Fattorie del Cerro offers a wide range of options, including cooking lessons, tastings with winery tours, and vineyard tours by e-bike or off-road vehicle.


At the Poderina, located near the beautiful Montalcino, you can take the opportunity to join guided tastings and explore the vineyards where one of the most prestigious and appreciated Italian wines in the world, Brunello di Montalcino, is born. Two 50 sqm apartments, comfortably equipped with all the amenities to make your stay live up to expectations, will be ready to welcome you.


If for your romantic weekend in Tuscany you choose the Pisa area as your destination, in Monteverdi Marittimo, not far from Pisa, you can find the Tenuta di Monterufoli, a gem nestled within a nature reserve. With rooms, suites, independent apartments with views of the valley, and the restaurant La Miniera, it's the ideal starting point for those looking for an experience that combines romance with a touch of adventure. You can explore the woods of the beautiful Natural Park, discover the mines, all while enjoying a tasting of the estate's wines.


A romantic weekend in Tuscany is the perfect opportunity to rediscover connection, while being enveloped by beauty. Whatever your idea of romance may be, this land will give you unforgettable moments: all that's left to do is pack your bags and live your Tuscan dream!

 

 

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