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 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 Experiences:
Walk the hidden rooftop terraces of Florence Cathedral, guided along elevated pathways that reveal rare perspectives of the city
Join a family of truffle hunters and their dog, uncovering seasonal treasures in the forest before sharing a home-cooked truffle-based lunch
Meet the farmers of Podere Il Casale on a guided tour, watching cheese take shape and sampling their celebrated wines and produce
Savour a private olive oil tasting with the artisans of Buccia Nera, guided through olive oils produced on their hillside estate
Signature Day: Experience our distinctive Signature Day, choosing between e-biking through olive groves, a Chianti vineyard visit, a private jewellery heritage tour, 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
Included in the Price
- A Signature Stay in a restored medieval village - All breakfasts, five lunches, and six dinners, featuring restaurants that capture the authentic cuisine of Tuscany - Named Signature Guide with outstanding knowledge and guest satisfaction - Gratuities for local support staff so every detail of your journey feels effortless - Comfortable transport, including a private mini coach - Complimentary transfers on arrival and departure, ensuring a smooth journey
Not Included In The Price
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 your Signature Guide for an introduction to the village, tracing stone pathways and ascending the 14th-century tower that once sheltered the great Italian poet, Dante.
As dusk softens the courtyard, we gather at 2 Stone Room in the garden for an aperitif, followed by an intimate dinner.
Day 2 Savour the Tuscan countryside | Join artisans for a private olive oil tasting in a family estate
Signature Experience: Begin at Buccia Nera, a family estate framed by vineyards and olive groves in the hills of Arezzo. Here, we are welcomed for a privately guided tasting and introduced to their extra virgin olive oils.
Continue into the countryside for lunch at Osteria Cuprena, enjoying a seasonal menu of produce from their garden. Later, take a short stroll through Arezzo, moving from modern boulevards into medieval lanes and pausing at the Pieve, Piazza Grande, and lawns of Il Prato.
As evening settles, we gather at Osteria dei Mercanti, where traditional Tuscan hospitality and produce combine for an enchanting meal.
Day 3 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.
After lunch at B-Roof, 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. A private visit to a restoration lab reveals the meticulous work involved in conserving historic tapestries, textiles, and precious objects.
The evening ends at La Ménagère, where a shared aperitivo-style dinner unfolds in a library-like setting of botanical-themed books.
Day 4 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:
Cycle quiet country lanes by e-bike, pausing in an olive grove for bruschetta, honey, and cheeses before returning for a lunch of local produce.
Sip your way through Chianti, visiting a renowned winery for a tasting that uncovers the region’s rich winemaking heritage
Step inside a 14th-century palace in Cortona, joining the DelBrenna family for a private introduction to their jewellery heritage.
Stay within Gargonza for a hands-on cooking class, mastering fresh pasta with the castle’s chef before sitting down to lunch.
Dinner is at leisure at Castello di Gargonza, or your Signature Guide can give alternative recommendations nearby.
Day 5 Follow flavours and ancient crafts | Hunt for truffles with a family of experts
Signature Experience: This morning, meet a renowned truffle-hunting family whose knowledge spans generations. Walk into the woods with their skilled dog, learning how to recognise quality truffles and learn the traditions surrounding them, before settling into a home-cooked truffle-based lunch.
Continue to Volterra for a guided afternoon steeped in ancient craftsmanship. Perched high on a ridge, this Etruscan city reveals layers of history in its Roman theatre, fortified walls, and medieval piazzas overlooking the Tuscan hills. Wander its narrow stone lanes to understand why Volterra has long been a centre of artistry, culminating in an alabaster demonstration that brings this storied craft to life — from raw, milky stone to delicately carved detail.
Return to the hotel for a relaxed dinner of regional cuisine.
Day 6 Discover Renaissance Pienza | A taste of Tuscan tradition
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 Pienza, the ‘ideal city’ envisioned by Pope Pius II and designed around harmony and proportion. Discover its elegant piazzas, warm stone façades, and stunning vistas over the Val d’Orcia - this is Tuscany at it's most beautiful. Continue to Montepulciano for a relaxed walk through its historic centre and end the day in a cantina, where a light dinner is paired with a curated tasting of local wines.
Day 7 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. 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.
Return to Gargonza for our farewell dinner set within a medieval wine cellar and its charming garden terrace. A seasonal three-course menu, thoughtfully prepared by Chef Davide Canella, highlights local and seasonal Tuscan flavours and wine pairings, bringing the journey to a warm close.
Day 8 Say a fond farewell to Tuscany
After breakfast, take a final moment to breathe in the quiet of Gargonza, appreciating its courtyards, its stillness and its gentle sense of place. Those with later flights may wish to linger over one last coffee or enjoy a slow walk through the estate, before returning to Florence.
This chapter may close, but Tuscany’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.
