Rolling hills, vineyards, and centuries-old villages surround the timeless place that is Tuscany. Amidst this beauty, Castelfalfi stands out as a destination where nature, history, and contemporary hospitality come together seamlessly. Its restored medieval village—complete with a historic castle and carefully curated boutiques—feels completely immersive. Here, your stay manages to be authentically Italian yet refined. Even the oldest traditions can be observed—from a working agricultural estate producing organic wine and olive oil to wildflower honey from the apiary, each delivering a true taste of the land.

Where is Tuscany?

Located in Central Italy, Tuscany is a region that spans from the Tyrrhenian Sea to the Apennine Mountains. For those arriving via flight, Castelfalfi sits a four-hour drive north of Rome’s Leonardo da Vinci International Airport. Home to world-renowned art-filled cities like Florence and Siena—each just over an hour drive from Castelfalfi—Tuscany has long been celebrated for its extraordinary history, architecture, and cultural heritage.

Tuscany has been a magnet for civil innovation throughout human history.

Smaller towns such as San Gimignano and Volterra are roughly thirty-five minutes from Castelfalfi by car and further enrich the experience with their medieval charm, cobbled streets, and authentic local atmosphere.

Tuscany has been a magnet for civil innovation throughout human history. It was the cradle of the Renaissance movement and a centuries-long stronghold for the artistic and economic development of Europe. Further back in history, the land was home to the Etruscans, a pre-Roman civilization known for its sophisticated architecture, political systems, and art. Now, these vast records of human achievement can be explored through refined, curated, and custom experiences at Castelfalfi.

Where to Stay in Tuscany

Truly distinctive, a stay in Castelfalfi is defined by the richness and diversity of what the property has to offer, all set within a beautifully restored medieval village in the heart of Tuscany. It’s not just a resort—it’s an elevated ecosystem organically blended into a small village, where the castle was once inhabited by Giovanni di Francesco Gaetani and his wife Costanza de Medici in the 15th-century.

This expansive 2,700-acre property is where history, nature, and contemporary hospitality come together to create a destination in and of itself. The architectural identity of Castelfalfi is deeply rooted in its heritage. A centuries-old borgo, or medieval village, and castle was restored to preserve its authentic character while integrating refined, modern design. On the same foundations of the eighth-century village now stands a charming, cobblestoned borgo. And where entire textbooks worth of history once occurred, there’ is now an opulent spread of tennis courts, pools, restaurants, all set into and in reverence of Tuscan’s natural beauty.

These vast records of human achievement can be explored through refined, curated, and custom experiences at Castelfalfi.

This balance extends to the accommodations, which include 146 elegant rooms, suites, and private villas featuring all the modern comforts you crave while embracing materials, textures, and earthy tones inspired by traditional Tuscan style. This thoughtful design all comes together to provide a warm and authentic sense of place. Your SmartFlyer advisor will find the perfect accommodation for your needs, whether you’re looking for a romantic escape for two or a multigenerational family vacation.

Days on the Borgo

Castelfalfi has an extraordinary breadth of experiences available on its grounds, upending expectations for a resort stay. There are over forty bespoke programs at the property that your SmartFlyer advisor can arrange. Try truffle hunting with an expert and guide dogs. Join chef-led pasta-making classes or the art of falconry with an on-site expert. Learn how to properly taste-test olive oil or hike the many trails winding through Castelfalfi’s picturesque woods. For those traveling with children, there’s a Montessori-inspired day club and a perfectly shaded adventure park, complete with swinging ropes and tree houses.

Plan to explore diverse culinary offerings that Tuscany is known for, including traditional Tuscan cuisine and contemporary Italian dishes inspired by local, seasonal ingredients at Olivina and Il Rosmarino. For more variety, Bar Ecrú offers an international menu, still using the same principles of fresh ingredients. Plus, it’s an ideal spot to order a craft cocktail and take in the surrounding cinematic vistas. The estate is also home to a working agricultural farm, allowing guests to connect directly with the land through tastings and immersive experiences led by experts.

Wellness in Tuscany

When you’re not delighting in one of the bespoke offerings, head to Castelfalfi’s spa, created in partnership with Thai brand RAKxa. Located in Castelfalfi’s main building, the 1,600 square foot spa features a sauna, indoor pool, and a steam room, all in a tranquility-inducing design featuring blonde wood and marble. Make time for custom diagnostic treatments—we recommend the Awakening Recovery massage, which is perfect for resetting after a long travel day, or hours spent basking in the Tuscan sun.

Where to Explore in Tuscany

Beyond the boundaries of the resort, Castelfalfi and its borgo are also the perfect, intimate launch point to explore the rest of Tuscany. When you want to venture out, your SmartFlyer advisor can arrange private tours to nearby San Gimignano, and Volterra, each roughly a thirty-five-minute drive away.

• Wander Castelfalfi’s borgo: The heart of the estate, Castelfalfi’s restored medieval village, offers a unique atmosphere where history comes to life. With its castle, food, curated boutiques, and magical landscape, it’s perfect for a leisurely stroll immersed in authentic Tuscan charm.
• Explore the Castelfalfi Wine Shop & Garden: Set within the borgo, the wine shop and garden provide a relaxed yet refined setting to discover the estate’s organic wines and olive oils. Tastings here are both educational and immersive, offering a direct connection to the land.
• Lounge like an Italian movie star at Alpemare Beach Club: For a slower pace, Alpemare Beach Club is a sophisticated seaside escape with rows of perfectly neat lounge chairs and cabanas. Since the 1960s, Italy’s most fashionable have been flocking to the Tuscan beach town of Forte dei Marmi, which offers upscale shopping, vibrant nightlife, and sandy shores touching cerulean waters. Through Castelfalfi’s partnership with Alpemare Beach Club, guests can enjoy an exclusive beach visit combining relaxation, privacy, and refined service. Just over an hour away by car, your SmartFlyer advisor can handle all the logistics of getting you there and back.
• Take a private tour of San Gimignano: Famous for its medieval towers, San Gimignano is a UNESCO World Heritage Site that feels untouched by time. A private tour allows guests to explore its history, artisan shops, and panoramic views in a more intimate way. With a skyline of fourteen preserved Medieval towers and 13th century walls, it still retains unique feudal attributes hard to find elsewhere.
• Go back in time in Volterra: Known for its Etruscan origins and alabaster craftsmanship, Volterra delivers a more authentic and less crowded Tuscan experience than more well known villages in the region. It’s so quaint that the entire town is almost completely car and traffic-free. The dramatic setting—high walls, a central bell tower, a Roman theatre—and rich history make it a fascinating destination to explore with a private guide.

The Perfect Day at Castelfalfi

The perfect day at Castelfalfi depends entirely on your personal preferences. You can embark on an exclusive wine tasting tour with a sommelier, take an afternoon to learn about centuries-old traditions of vineyards and olive groves, or learn archery in the ancient forests. To spark your imagination, we’ve put together one ideal day, the SmartFlyer way.

• Wake up in the La Pergola Villa. One of five villas in Castelfalfi, La Pergola is tucked into the borgo, and the three-bedroom accommodation is replete with a private, heated pool. Over breakfast prepared by a private chef in your villa, take in the rolling Tuscan hills from the panoramic terrace.
• Move your body. As you take in birdsong, the soft rustling of leaves, and the gentle wilderness surrounding Castelfalfi, warm your body up with a restorative yoga session led by a private instructor. As one of several fitness offerings available on the property, the special yoga in the wood program is a perfect way to connect physically with the environment and kick off your day.
• Spend the afternoon exploring Tuscany’s wilderness. Take advantage of the extensive programming and embark on a truffle hunt with an expert guide and specially trained “truffle dogs.” After you find the treasured ingredient, complete the excursion with a truffle-inspired lunch prepared for you.
• Take in the sunset with a drink. After a day spent exploring one of the nearby city centers, unwind with an aperitivo at Bar Ecrù, Castelfalfi’s bar and terrace. With dreamlike views as the sun sets and the stars come out, it’s the perfect spot to indulge in la dolce vita. We love ordering the “Spring in Tuscany,” a fragrant, citrusy cocktail made with rosemary-infused gin.
• End the evening with a hearty Tuscan meal. Finish your day with an authentic farm-to-table dining experience at Olivina. Expect straightforward and elegant dishes made with the freshest and most high-quality ingredients. We recommend starting with the seafood tagliolini and getting the seabass to share.

Where to eat at Castelfalfi

Castelfalfi offers five unique dining outlets on property in addition to its in-room or in-villa dining, ensuring a completely relaxing stay.

• Alimentari: Located in the heart of the borgo, Alimentari is a charming deli-style spot perfect for a casual bite. Guests can enjoy local cheeses, cured meats, schiacciate (traditional Italian flatbread), and regional wines in an authentic village setting.
• Bar Ecrù: Set on a panoramic terrace, Ecrù is the perfect spot for signature cocktails, combining refined flavors with sweeping views over the Tuscan hills.
• Il Rosmarino: A relaxed and welcoming trattoria, Il Rosmarino is your go-to for classic Tuscan dishes and artisanal pizzas. Its informal atmosphere makes it ideal for enjoying traditional flavors in a more casual setting. This spot is perfect for lunch or an easy dinner after a long day out in the sun.
• Latte e Menta: The on-property relaxed bar and gelateria is ideal for a light break during the day. Known for its artisanal gelato and refreshing drinks, it’s a favorite for both families and those looking for a simple indulgence.
• Olivina: Olivina celebrates Italian cuisine with a strong focus on locally sourced, seasonal ingredients, serving an authentic farm-to-table experience within the estate. Under Florence-born Chef Matteo Cervini, the fine details of Italian cuisine are brought to life with expert skill.

Where to eat in Tuscany

• Casa Masi: Less than a twenty-minute drive from Castelfalfi in nearby Montaione, Casa Masi gives a refined take on Tuscan cuisine in an intimate setting. The focus on high-quality ingredients and elegant presentation makes it a standout in the area.
• Il Caminetto: A more rustic and traditional option just twenty minutes from Castelfalfi in Montaione, Il Caminetto is loved for its hearty, home-style Tuscan cooking. The atmosphere is warm and unpretentious, offering a genuine local dining experience.
• Linfa: Located about thirty minutes away from Castelfalfi in San Gimignano, Linfa is a Michelin-starred restaurant that delivers a creative and contemporary culinary journey. The tasting menu highlights innovation while maintaining a strong connection to the region.
• Arnolfo: Approximately forty minutes from Castelfalfi, Arnolfo is a two-Michelin-starred destination known for its exceptional fine dining. Located in the tiny town of Colle di Val d’Elsa, the cuisine here is highly refined, combining techniques, creativity, and outstanding ingredients in an exceptional setting. Glass walls showcase the quaint hillsides; the sharp design of the space sits in perfect contrast with the soft landscape that surrounds it.

Enjoy a side of Italy you haven’t experienced yet. Whether you’re looking to bask in Tuscan nature with an immersive wellness reset or to enjoy a balanced itinerary of art, culture, and relaxation, Castelfalfi has something unique for you.

Ready to get planning your Tuscan Escape? Contact your SmartFlyer travel advisor.