Explore Florence, Chianti, Siena, and the Val d’Orcia on this ten-day tailor-made Tuscany journey, moving from Renaissance art and Chianti Classico estates to Brunello cellars and UNESCO-listed countryside.
10 days
|From $7,500 pp
Explore Florence, Chianti, Siena, and the Val d’Orcia on this ten-day tailor-made Tuscany journey, moving from Renaissance art and Chianti Classico estates to Brunello cellars and UNESCO-listed countryside.
This itinerary moves through Tuscany at the pace the region demands, from the Renaissance streets of Florence through the Chianti wine road into Siena, then south through the UNESCO-listed Val d’Orcia to Montalcino and Pienza.
Each section of the journey is distinct in character. Chianti is rolling hills, family-run estates, and Chianti Classico tasted at the source. Siena is medieval architecture and the kind of civic pride that has not dimmed in seven centuries. The Val d’Orcia is something else entirely, a landscape that has been painted and photographed so many times that arriving in it for the first time still manages to feel like a surprise.
The itinerary is built around staying in the landscape rather than commuting through it. A vineyard estate in Chianti, a working agriturismo in the Val d’Orcia, and a position within walking distance of Montalcino’s wine culture give the journey three distinct bases that each deliver a different version of Tuscany. A private driver connects the sections. Everything else moves at the pace you set.
Most international flights arrive into Florence Airport or Pisa, both within easy reach of the city by private transfer. Your driver meets you on arrival and transfers you to your accommodation. Two days in Florence covers the essential ground without the pressure of a longer stay.
The Uffizi Gallery holds the largest collection of Italian Renaissance art in the world, with Botticelli’s Birth of Venus and Primavera requiring time rather than the thirty-second stop that crowds enforce. A visit timed for before the public opening gives the rooms a quality of quiet that the standard ticket does not provide.
The Oltrarno, Florence’s south bank neighborhood of artisan workshops, antique dealers, and less visited churches, provides the other side of the city. The Boboli Gardens, the Pitti Palace, and the covered market at Sant’Ambrogio are all within walking distance of each other.
A private transfer south from Florence joins the Chiantigiana, the road that winds through the Chianti Classico wine zone between Florence and Siena. Known locally as the SR222, it passes through vineyards and olive groves, stone farmhouses, and cypress-lined driveways for much of its length.
Your base for three nights is a vineyard estate within the Chianti Classico zone, selected for its position on the wine road and access to the estate’s own tastings in the cellar or on the terrace. Greve in Chianti, the informal capital of the wine zone, holds a weekly market, an enoteca with over a thousand local labels, and a butcher’s shop producing finocchiona for generations. Panzano, a few kilometers south, is home to Dario Cecchini, whose butcher’s shop operates as much as a cultural institution as a place to buy meat.
Antinori nel Chianti Classico, built into a Chianti hillside, is one of the most architecturally significant wine buildings in Italy. The underground cellars, the restaurant, and the tasting menu reflect the scale of the Antinori family’s investment in this landscape. A private guide visit can be arranged on request.
A private transfer west from the Chianti estate takes the journey into Siena for a full day before continuing south. Siena was one of Europe’s wealthiest cities in the 13th and 14th centuries, and the Piazza del Campo, the shell-shaped public square at the city’s center, is the most direct evidence of what that wealth produced.
The Palazzo Pubblico on its southern edge holds the Sala del Mappamondo, with Simone Martini’s 1315 Maestà fresco on the wall, and the Sala dei Nove, lined with Ambrogio Lorenzetti’s Allegory of Good and Bad Government, one of the most important civic artworks in Italian history.
The Duomo, a 13th-century cathedral with a striped marble facade and an interior that includes Nicola Pisano’s pulpit and Michelangelo’s St Peter and St Paul, is the other essential stop. The Piccolomini Library within the cathedral is decorated with ten frescoes by Pinturicchio that are consistently overlooked by visitors moving through to the main nave. A private guide covers both in a morning without the pressure of a tour group’s schedule.
Lunch in Siena before the transfer south. The drive to the Val d’Orcia base takes around 45 minutes depending on the exact location.
The Val d’Orcia is a UNESCO World Heritage Site, recognized as one of the landscapes that most fully represents the Renaissance ideal of the relationship between humanity and the natural world. The hills between Siena and Monte Amiata, planted with vineyards and wheat and divided by cypress-lined roads, were painted by the Sienese school in the 14th and 15th centuries and look, from the right angle, almost exactly as they did then.
Your base for three nights sits between Montalcino and Pienza, chosen for its position at the center of the southern Val d’Orcia and its access to the estate’s own wine, olive oil, and produce, with breakfast and dinner drawing on what the farm and surrounding area produce.
Montalcino sits to the west, shaped almost entirely by Brunello di Montalcino. A private cellar visit covers the production method, the aging requirements, and the difference between the Brunello and the Rosso di Montalcino. Lunch at the winery follows. Pienza, 15 kilometers to the east, was built in the 1460s by Pope Pius II as a model Renaissance city and is a UNESCO site in its own right, known for Pecorino di Pienza sold along the main street in wheels from fresh to aged.
Bagno Vignoni, built around a thermal pool fed by volcanic springs in use since Roman times, provides a different kind of afternoon. The hot water streams allow guests to sit with feet in the thermal water while looking out over the Val d’Orcia hills.
A private transfer connects to Florence Airport or Pisa Airport for onward international flights, with the routing dependent on flight connections. The journey from the Val d’Orcia to either airport takes between one and a half and two hours by private car, with the drive back through the Chianti hills providing a final view of the landscape before departure.
The itinerary can be extended with additional nights in the Val d’Orcia, a connection south to Rome, or a side trip to the thermal baths at Saturnia in the Maremma.
Experience the Vatican as few ever do — in the calm of evening, guided by those who know its secrets best. This exclusive after-hours visit reveals the artistry and emotion behind the world’s most famous collection, offering time to pause, reflect, and truly see.
Step into Trastevere — the Rome locals keep for themselves. Wander ivy-lined streets with a private historian, meet artisans still shaping the city by hand, and pause for an unhurried meal in a hidden courtyard. A Do Not Disturb experience revealing the soul of Rome through ease and access.
Experience Rome’s culinary artistry in complete ease. From private gardens to hidden terraces, Roman Dining in Style is a Do Not Disturb moment where food, setting, and connection come together in perfect harmony.
Step beyond Rome’s busy streets into its quietest spaces. From Trastevere’s hidden courtyards to the grand gardens of Tivoli, The Roman Garden Escape is a Do Not Disturb experience designed for stillness, beauty, and time shared with those who matter most.
Step inside Rome’s greatest monument in rare quiet. The Colosseum, Unveiled is a Do Not Disturb experience that reveals the arena’s hidden layers — from its underground chambers to its silent grandeur — guided by those who know its stories best.
Step through the ruins that shaped the modern world. Walking Through Time: The Roman Forum Reimagined is a Do Not Disturb experience revealing where power, philosophy, and architecture first met — and how the story of civilization still echoes between these stones.
Step into Rome’s most enduring masterpiece. The Pantheon is a Do Not Disturb experience revealing the harmony between light, structure, and spirit — an encounter with timeless design that continues to define the modern world.
Step into the light and shadow of Caravaggio’s Rome. From hidden chapels to private collections, Caravaggio’s Rome is a Do Not Disturb experience that reveals the artist’s genius as it was meant to be seen — intimately, quietly, and in place.
See Rome through a modern lens. Modern Rome: Art, Design & Aperitivo is a Do Not Disturb experience revealing the city’s evolving creative spirit — from hidden studios and private galleries to an aperitivo shared above the skyline.
A private visit to Leonardo’s Last Supper offers a rare chance to see one of the Renaissance’s most important works in near silence. This moment reveals the mural’s true scale, its fragile beauty and the architectural harmony of Santa Maria delle Grazie, all without the rush of standard viewing slots.
A private tour of the Duomo di Milano reveals the cathedral’s immense architecture, centuries of craftsmanship and the quiet beauty of its terraces, all without the pace and crowds of standard visits. This is Milan’s most iconic landmark experienced with time, clarity and space to appreciate its details.
Experience a private gondola ride in Venice through peaceful canals. Avoid the crowds with a romantic, tailor-made tour led by expert gondoliers.
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