Tuscany Bespoke

Bespoke travel lets you take our inspirational cues and craft them into your personalized, private adventure. Collaborate one-on-one with an Experience Designer to put together your tailor-made trip.


"Moving to Florence 20 years ago changed my entire perspective on life. I've learned to step back, slow down and relish in life's simple pleasures. Allow me to open the doors to the deep, authentic relationships I’ve created and show you why Tuscany is such an enchanting place to discover."

—Courtney Mundy, Experience Designer | 2022 Top Travel Specialist, Condé Nast Traveler, Italy

slow down in the tuscan hills


There is something eminently peaceful in meandering through hilltop towns that have stood watch since the Middle Ages, passing vines tended by generations of winemakers and savouring traditional cuisine made from the freshest local ingredients. Tuscany is the region you imagine when you think of Italy: home of olive groves and cypress trees, Roman battlefields and Renaissance churches and a who’s who of charming villages—from Gaiole to Siena to Pienza and more.

Discover the possibilities:


Tuscany on Two Wheels

Ride along quiet roads passing through the medieval villages that put Tuscany on the map. Pedal through the Renaissance idyll of Pienza, savouring some of its famous pecorino cheese. Bask in the energy of Siena and join in the laughter radiating from the piazza. Dine under the stars, in a winery, or at an exclusive chef's table. We don’t just visit Tuscany—we bring its story to life.


Singular Stays: Tuscan Villas

Put down roots in a Tuscan abode and set off on daily excursions to nurture your interests, connect with locals and immerse yourself in the seductive charm of Italian life. Our hand-picked villas exude authenticity and luxury, surrounded by the natural beauty of the Tuscan countryside. Unpack once and settle into the daily rhythms of la bella vita to experience the perfect alchemy of people and place that Tuscany offers. 


Tuscan Food & Wine

Real Tuscan cuisine is the thrill of foraging for fresh, earthy truffles, the silky texture of your own handmade pasta and the oaky, musty scent of centuries-old cellars. Blend your ideal Tuscan red along with an award-winning enologist, select the perfect zucchini blossom on the farm and learn the tricks for creating the creamiest pecorino cheese. Don't just sample Tuscany's acclaimed gastronomy; get to know the artisans behind the products. 


Tuscany with the Kids

Slow down and soak up the Italian passion for la famiglia. Bike cypress-lined roads, meander through olive groves and crash a cooking class in nonna's kitchen. First time to Italy? Embark on a tour of the grand trifecta—Venice, Florence and Rome. Whether it's learning to row in the Grand Canal, climbing Brunelleschi's dome or mastering combat skills with a real-life Gladiator, we'll bring history to life.


Tuscan Cultural Journey

Experience Tuscany through exclusive cultural events with our local experts. Get behind the scenes in Florentine artisan workshops and stroll a rose garden with stunning views of the Renaissance city. Motor through the countryside beneath the Tuscan sun in your vintage Fiat 500. Sip on the Vino Nobile of Montepulciano, enjoy exclusive access to a contrada museum in magnificent Siena and follow your nose on the hunt for fresh truffles


Tuscan Wellness Experiences

Salute the Tuscan sun with our local yoga teacher before exploring the nearby hilltop towns by foot or by bike. Fuel your body with fresh, seasonal farm-to-table ingredients, the hallmark of Tuscan cuisine. Gaze at the stars while soaking in thermal hot springs beloved by the Medici family. Let Tuscany restore your sense of wellbeing and fuel your creative energy as it has for artists and thinkers throughout the centuries. 


Walking in Tuscany

Experience Tuscany's breathtaking landscape and charm, untouched by the passing of the ages. On ancient trails such as the Via Francigena, once walked by pilgrims from Canterbury to Rome, you'll cross paths with locals and witness the intrinsic magic of their rituals: making wine by the rhythms of the moon and tending unruly olive groves just so—to produce the freshest olive oil possible (because store-bought would never do). 

Start the planning process

These highlights are just a sample of what you can do and discover in Tuscany. Mix and match a little bit of everything, add on a few nights and private tours in Rome, Florence and Venice or pair it with another Italian region like Umbria. Connect with your Experience Designer for Tuscany to start piecing together your perfect trip.

Notes From Your Designer:

Ideal trip length: 5 - 8 days

Activity Level: 3

Starting Price: US $1,200 Per Person/Day

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