The essence of Tuscany unfolds in the Renaissance splendour of Florence and the timeless elegance of Siena, where art, architecture, and history shape every view. From the cobbled streets to soaring domes, these cities tell stories of creativity and culture that echo through the hills. Led by your handpicked Signature Guide, and primarily based in a privately owned medieval village, you’ll journey through a land defined by beauty and craft, where flavours and traditions reflect centuries of refinement. This is the story of Tuscany: revealed in every piazza, every masterpiece, every glass raised in celebration.
Venture to the very heart of each destination on our Signature Collection, where every journey is shaped by our unrivalled local connections and insider expertise. Step beyond the ordinary with private invitations, rare encounters, and experiences few will ever share. So when someone says, “I’ve been there,” you’ll simply smile, knowing you’ve experienced it differently.
Signature Day: Experience our distinctive Signature Day, choosing between immersive optional activities such as a forest walk and bocce game, a Chianti vineyard visit, a heritage tour in Cortona, or a hands-on Tuscan cooking class
Signature Stay: Stay at Castello di Gargonza, a fortified medieval village restored into a characterful countryside retreat
Signature Guide: Let your hand-picked Signature guide lead you to the region's soul — sharing their home, heritage, and heart
Activity Areas
Culture
Region & Country & City
Europe: Italy, Tuscany
Included in the Price
Elegant, hand-picked accommodation (2 Premium nights, 5 Superior Comfort nights). Signature Stay in a restored medieval village - All breakfasts, four lunches, and four dinners, featuring restaurants that capture the authentic cuisine of Tuscany - Signature Guide with outstanding knowledge and guest satisfaction - Complimentary transfers on arrival and departure, plus comfortable transport throughout (private mini coach) - Gratuities for local support staff so every detail of your journey feels effortless
Not Included In The Price
Request a single room if required, purchase travel insurance and arrange any visas and vaccinations. On this trip, local taxes (approximately €14) are not included.
Map
Itinerary
Day 1 Settle into the rhythms of Tuscany | Welcome reception at 2 Stone Room
After a transfer from Florence, a warm welcome awaits at our Signature Stay, Castello di Gargonza, a privately owned medieval village nestled in the Tuscan countryside. Perched on a quiet hill overlooking the iconic Val di Chiana, it appears almost suspended in time.
Before our welcome reception, join Neri, our host at Castello di Gargonza for an introduction to the village, tracing stone pathways and ascending the 14th-century tower that once sheltered Italian poet Dante.
As dusk softens the courtyard, we gather at 2 Stone Room in the garden for a welcome drink, followed by an intimate dinner.
Day 2 Follow flavours and ancient crafts | Hunt for truffles with a family of experts
Signature Experience: Step into the heart of the Tuscan countryside for an authentic truffle-hunting experience with a local family whose passion for the land has been passed through generations. Accompanied by their expertly trained dog, venture into the wooded hills surrounding their home as you learn about Tuscany's prized truffles, their seasonal varieties and the traditions that have shaped this unique culinary heritage.
The experience concludes at the family's home, where you'll gather around the table for a memorable farm-to-table lunch showcasing freshly prepared regional specialities and truffle-inspired dishes. Paired with local wines, it is a celebration of the authentic flavours, traditions and warm hospitality that define rural Tuscany.
We return to our hotel with time to freshen-up and relax before venturing out this evening to the nearby village of Monte San Savino for dinner.
Day 3 Peel back Siena’s history and heritage | Enjoy a private lunch in the medieval Torre di Roccabruna
An expert-led walk brings Siena to life, revealing its character in layers, from the curve of Piazza del Campo to the cathedral’s intricate marble.
Signature Experience: For lunch, we have a private invitation to dine in the medieval Torre di Roccabruna, once one of Siena’s tallest towers. Our four-course meal is served high above Siena with privileged views across the city and surrounding hills. Dinner is at leisure at Castello di Gargonza.
Day 4 Taste your way through Tuscan traditions | Discover Montepulciano
Signature Experience: Travel to the family-run farm of Podere Il Casale, where a guided walk reveals farm life from stable to dairy. Discover the craft behind their celebrated pecorino cheeses and estate wines, followed by a seasonal lunch.
This afternoon, stroll through Montepulciano’s historic centre and end the day in a cantina, where a light dinner is paired with a curated tasting of local wines.
Day 5 Signature Day | Follow your curiosity through craft, cuisine, and Tuscan landscapes
Today is your Signature Day, where you can select an authentic, curated experience to connect deeply with Tuscan culture. You could:
Sip your way through Chianti, visiting a renowned winery for a tasting that uncovers the region’s rich winemaking heritage (lunch included, 9am-3pm). Alternatively, for those wanting a more relaxed start to the day, why not join Castello di Gargonza’s charismatic sommelier for a tasting of three distinctive Tuscan wines? (4pm-5pm)
Wander through the rewilded woodlands surrounding Castello di Gargonza on a guided nature walk before joining a traditional game of bocce, a cherished local pastime that has brought the village community together for generations (10am-11.30am)
Stay within Gargonza for a hands-on cooking class, mastering fresh pasta with the castle’s chef before sitting down to lunch (10.30am-1.30pm)
Explore the timeless streets of Cortona on a guided walking tour, discovering its medieval landmarks, hidden alleyways and sweeping Tuscan vistas before enjoying a prosecco toast and private visit to the historic DelBrenna family showroom, where centuries of local history and traditional jewellery craftsmanship are brought to life (2pm-6pm)
Dinner is at leisure at Castello di Gargonza.
Day 6 Savour the Tuscan countryside | Join artisans for a private olive oil tasting in a family estate
Depart Castello di Gargonza this morning and journey towards Florence, stopping en route to discover one of Tuscany's most celebrated culinary traditions. Immerse yourself in a guided tasting of locally produced extra virgin olive oils, learning about the region's olive-growing heritage while savouring the distinctive flavours and aromas that make Tuscan olive oil renowned around the world.
Later, we arrive at Plaza Hotel Lucchesi, centrally located in Florence overlooking the river.
Signature Experience: The day ends with a private visit to a restoration lab, which reveals the meticulous work involved in conserving historic tapestries, textiles, and precious objects.
Day 7 Discover the splendour of Florence | Gaze over the cityscape from the cathedral terraces
Signature Experience: Enjoy privileged access to the roof terraces of Florence Cathedral, guided by an expert who brings the city’s history into focus. From this rarely visited vantage point, the city unfolds in layers — red-tiled rooftops, narrow streets, and the soft rise of surrounding hills — revealing Florence’s enduring dialogue between craft, ambition, and landscape.
We continue on a guided walk through Florence, a city that feels suspended in time, a place where every stone holds a fragment of history and every street tells stories of centuries filled with art and culture.
We break for lunch at leisure and an afternoon to explore the streets and architectural wonder of Florence independently.
Gathering again this evening, we head for our farewell dinner at Angel Rooftop, where the city stretches out below the terrace, step into the streets that shaped the Renaissance, from cathedrals and civic palaces to workshops that nurtured generations of artists.
Day 8 Say a fond farewell to Florence
After breakfast, take a final moment to breathe in the Renaissance streets and buildings of Florence. Those with later flights may wish to linger over one last coffee or enjoy a slow walk by the river, before transferring to Florence Airport.
This chapter may close, but Italy’s spirit is one that stays with you long after departure.
Alternatively, open a new chapter of discovery by speaking to your Signature Collection travel expert about extending your stay.
