Imagine trying to describe to someone the essence of life in Tuscany. The elegant pleasure of riding a bicycle down one of its cypress-lined roads. The exquisite notes of a celebrated, full-bodied red from one of its vineyards. Or how that second serving of Pappardelle al Cinghial tastes just as good as the first.
All without having experienced it yourself.
You see, at Travelive, we believe that exceptional trips begin with firsthand knowledge. Which is why we regularly invest in educational journeys that allow our local teams to explore destinations and properties exactly as our travelers do. And one such journey recently took them to none other than Tuscany.
Investing in Knowledge, Strengthening Partnerships, Creating Better Experiences…in Tuscany
No brochure or photo gallery can quite capture the feeling of waking up in a villa among Tuscany’s rolling hills. Which is precisely what inspired Travelive’s latest cross-department visit to some of Tuscany’s most exceptional villas and estates.
Beyond catching a glimpse of La Dolce Vita, each visit offered a unique opportunity to see these beautiful properties through the eyes of our travelers. What made the journey especially valuable, however, was the range of perspectives brought by team members from across Travelive. Each viewed the properties through the lens of their own expertise, helping the entire group gain better insight into how to match travelers with their ideal stay.
By the end, the journey introduced us to three remarkable Tuscan properties, each offering its own unique interpretation of Tuscan living. And here’s a closer look at what makes them so special.
Viesca Toscana
The Story
Once the private summer residence of Salvatore and Wanda Ferragamo, Viesca Toscana offers a more intimate expression of Tuscan living. Sharing the same ownership and celebrated culinary philosophy as nearby Il Borro, this elegant countryside estate combines the privacy of a luxury villa with the refined service of a boutique retreat, all within easy reach of Florence and the Chianti wine region.
Key Features
- A beautifully restored 16th-century Manor Villa, complemented by 6–7 private villas with their own pools, plus 17–20 elegant suites spread between the manor and the charming Borgo di Pian Rinaldi hamlet
- A large freshwater swimming pool, two tennis courts surrounded by century-old poplar trees, and Spa La Corte, offering hydromassage, sauna, and holistic wellness treatments
- Farm-to-table dining at Il Borro Tuscan Bistro di Viesca under the direction of Executive Chef Andrea Campani
- Yoga, guided meditation, mountain biking, and curated wine and culinary experiences throughout the estate
- An idyllic setting for weddings and celebrations of up to 120 guests, featuring a private chapel, panoramic terrace, and elegant indoor event spaces
Best For
Travelers seeking the privacy of a luxury villa with the comforts of a refined estate. Particularly well suited to multigenerational families, exclusive-use groups, intimate destination weddings, and milestone celebrations.
What Sets It Apart
Rather than feeling like a traditional resort, Viesca Toscana feels like being welcomed into a private Tuscan estate. With guests spread across elegant villas and a peaceful hamlet, every stay feels wonderfully secluded, personal, and effortlessly exclusive.
Il Borro
The Story
Purchased by Ferruccio Ferragamo in 1993 and lovingly restored over three decades, Il Borro is not a recreation of a medieval village but the real thing. Today, this beautifully preserved Relais & Châteaux estate combines nearly a thousand years of history with a thriving organic farm, offering travelers an authentic window into Tuscany's enduring traditions.
Key Features
- Guest rooms and suites scattered throughout the restored medieval borgo in classic albergo diffuso style, alongside private villas and farmhouses, including the impressive ten-bedroom Dimora Il Borro
- A fully organic estate producing award-winning wines, olive oil, and seasonal produce, complemented by cellar tours, tastings, and hands-on cooking experiences
- Artisan workshops, boutique shopping, and an exceptional wine and art gallery featuring works spanning centuries
- Two outstanding dining venues, Osteria del Borro and Il Borro Tuscan Bistro, both overseen by Executive Chef Andrea Campani
- Horseback riding, golf, e-biking, hiking, and countless opportunities to experience the estate's spectacular countryside
Best For
Travelers who value authenticity, history, and cultural immersion. An exceptional choice for luxury FITs, incentive groups, and guests looking to combine outstanding gastronomy, wine, and outdoor experiences with a genuine sense of place.
What Sets It Apart
Il Borro invites guests to become part of a living medieval village. Every stroll through its stone streets, every glass poured from its vineyards, and every meal prepared with ingredients grown on the estate tells another chapter of its remarkable story.
Castelfalfi
The Story
Once a nearly abandoned 800-year-old medieval village, Castelfalfi has been thoughtfully transformed into one of Tuscany's most complete luxury resorts. Spanning more than 2,700 acres, it blends history, wellness, outdoor adventure, and sustainability on a scale unmatched anywhere else in the region.
Key Features
- Two on-site hotels, the five-star Il Castelfalfi and the charming La Tabaccaia, alongside an expanding collection of luxury villas and farmhouses
- Tuscany's largest golf destination, featuring a spectacular 27-hole championship course and dedicated clubhouse
- Four outdoor swimming pools, an adventure park, archery, tennis, truffle hunting, and an extensive private nature reserve
- A beautifully restored medieval borgo filled with boutiques, restaurants, bars, an organic vineyard, and olive groves
- Fully sustainability-certified operations across both the estate and its renowned golf facilities
Best For
Larger groups, golf enthusiasts, and travelers seeking exceptional variety within a single destination. Its scale and flexibility make it particularly well suited to incentive programs, multigenerational family gatherings, and celebrations where every guest can enjoy Tuscany in their own way.
What Sets It Apart
Where Viesca offers intimate villa living and Il Borro immerses guests in medieval Tuscany, Castelfalfi delivers the complete resort experience. It is a destination where championship golf, wellness, fine dining, outdoor adventure, and centuries of history come together within one extraordinary estate.
Tuscany The Way it Should Be
Three remarkable properties. Three distinct ways to experience Tuscany. One shared goal: helping every traveler discover the stay that’s right for them.
At Travelive, every destination visit is an investment in creating better journeys. By experiencing exceptional properties firsthand, our specialists are able to recommend every property with confidence, ensuring every Tuscany itinerary is as thoughtfully curated as the region itself.
So, if you’re ready to craft an unforgettable Tuscan escape for your travelers, contact groups@travelive.com or italy@travelive.com and let our firsthand expertise lead the way.