Bespoke
Tuscany Bespoke
Step into the rhythm of the Tuscan hills
Country
Italy
Accommodation Options
Boutique hotels, luxury resorts & private villas
Things to See & Do
Biking, culinary, culture, walking & wine tastings
Best Time To Go
April – June, September – October
Carbon Neutral Trip
In a verdant land of stone villages, sunlit vineyards and landscapes that beg you to slow down, pedal past cypress-lined lanes, sip Chianti where it’s born and wander Renaissance cities that never lost their magic. From Florence’s masterpieces to Pienza’s perfect pace, this is a region built for lingering—and for living very, very well.
Tuscany is famous for a reason: it’s iconic landscapes and quintessential Italian flair make it the perfect place to slow down and explore by bike or on foot.
Take your tastebuds on a journey through the region with farm-to-table meals and lovingly curated wines—while resting your head in idyllic accommodations.
We have a strong presence in the region, and with our Experience Designers living locally, you'll be invited into the Tuscan home where our decades-long history and local connections open the doors to longtime friends, offering exclusive experiences.
Experience Designers
Trip Inspiration
Snapshot of a Day
Pedal through Tuscan vineyards, before stopping at our favourite olive oil producer for a tasting of “liquid gold” and lunch among the olive groves.
Inspiration
Tuscany on Two Wheels
Cycling through Tuscany immerses you in its rich culture and stunning landscapes. Pedal through medieval villages, explore the Renaissance charm of Pienza and savour its famous pecorino cheese. Ride through classic Chianti towns like Radda and Gaiole, home to the Eroica vintage cycling event. Soak in the lively piazza energy in Siena. Join a relaxed cooking class in a private home to learn Tuscan culinary secrets. Marvel at the frescoes of Monte Oliveto Maggiore and dine under the stars at a charming winery or exclusive chef’s table. In Tuscany, we don’t just visit—we bring its story to life.
Recommended Duration: 6-8 days
Best Time To Go: April – June, September – October
Things to See and Do: Visit classic Chianti towns, explore Pienza and Siena, taste world-class wines and take cooking classes.
Don't Miss Out On: Cycling the stark, iconic hills of the Crete Senesi—a bucket-list item for avid cyclists.
Snapshot of a Day
Stroll through the rolling hills of Pienza, passing the iconic Madonna di Vitaleta chapel, before enjoying a cozy lunch at a charming trattoria.
Inspiration
Walk the Trails of Tuscany
Experience Tuscany’s timeless charm on foot. Trace a piece of the pilgrimage trail carved by St. Francis of Assisi, and witness local rituals such as winemaking by the moon and olive oil production. Explore Pienza, the “ideal” Renaissance town, and stroll past the dreamy Madonna di Vitaleta chapel. Walk through the Chianti hills to Brolio Castle, birthplace of Chianti Classico, and join a trifulao for a truffle hunt in the woods. In Siena, enjoy exclusive access to a contrada of the Palio horse race. Enjoy dinner in Bagno Vignoni and a soak in the thermal baths under a starry sky. Every step in Tuscany reveals its enduring story.
Recommended Duration: 5-7 days
Best Time To Go: April – June, September – October
Things to See and Do: Thermal baths at Bagno Vignoni, visit the Chapel of Madonna di Vitaleta, trek through the Chianti hills and go truffle hunting.
Don't Miss Out On: Walking the Via Francigena, an ancient pilgrim trail from Canterbury to Rome.
Snapshot of a Day
Join our local guide for a stroll through San Frediano’s artisan workshops, then marvel at Michelangelo’s David after a delicious lunch.
Inspiration
A Tuscan Cultural Journey
Experience the heart of Tuscany through exclusive cultural events with local experts. In Florence, stroll along the Arno River and explore San Frediano’s artisan workshops, where you’ll learn the secrets of marbled paper, leather goods and fine jewellery. Visit the Uffizi Gallery or marvel at Michelangelo’s David before dining with a view of the Duomo. Motor through the countryside in a vintage Fiat 500, sip Vino Nobile in Montepulciano and hunt for truffles in the Tuscan hills. Walk a stretch of the Via Francigena, then enjoy a wine tasting in an award-winning cellar. In Siena, get special access to a contrada of the famous Palio horse race. Tuscany’s rich culture, from its artisans to its landscapes, will stay with you forever.
Recommended Duration: 8 days
Best Time To Go: April – June, September – October
Things to See and Do: Explore the San Frediano neighbourhood and visit artisan workshops, Uffizi Gallery and Michelangelo’s David in Florence, visit a farmer’s market followed by a hands-on cooking class.
Don't Miss Out On: Exploring Siena with our local guide, with exclusive access to a contrada of the Palio horse race.
Snapshot of a Day
Head into the woods with a local trifulao and his trusty dogs to unearth fragrant black truffles, followed by a hands-on cooking class.
Inspiration
A Taste of Tuscany: Food & Wine
Food and wine in Tuscany are not just about tasting—it’s the thrill of foraging and experiencing the land and its traditions. Hunt for fragrant black truffles with a local trifulao and his dogs, then enjoy a truffle-themed lunch in a hands-on cooking class. Learn to make silky, homemade pasta and discover the secrets of selecting the freshest EVOO and the perfect zucchini blossom. Blend your ideal Tuscan red with an award-winning enologist and explore centuries-old cellars. Take a wine safari in a vintage Land Rover and visit a cheese farm to uncover the secrets of making the creamiest pecorino. You won’t just taste Tuscany's acclaimed gastronomy—you’ll be immersed in it.
Recommended Duration: 6-8 days
Best Time To Go: April – June, September – October
Things to See and Do: Wine safari through vineyards, cooking classes and truffle hunting.
Don't Miss Out On: A private gourmet feast at one of the region’s top wineries, offering million-euro views of the landscape.
Snapshot of a Day
Unwind by the pool at your private Tuscan villa, where luxury meets the breathtaking beauty of the countryside.
Inspiration
Family Time in a Tuscan Villa
Settle into a private Tuscan villa and soak up the Italian passion for la famiglia. Our hand-picked villas exude luxury, surrounded by the natural beauty of the Tuscan countryside. Pedal down cypress-lined roads, through olive groves, to a nearby farmhouse, where you’ll step into Nonna’s kitchen for a hands-on cooking class. Adults can relax by the pool while the kids challenge their B&R guide to a friendly game of bocce. Nearby, enjoy a scavenger hunt through a charming town before sitting down to dinner in the lively piazza. Explore storybook cities like Siena, Pienza and Florence, and meet the sheep at a local cheese farm for an authentic "km 0" pizza lunch. Unpack once and settle into the rhythms of la bella vita.
Recommended Duration: 8 days
Best Time To Go: April – June, September – October
Things to See and Do: Explore Siena, Pienza and Florence, visit a cheese farm, biking and cooking classes, scavenger hunts and bocce.
Don't Miss Out On: The pecorino, fig, and walnut gelato at one of our favourite gelaterias in Pienza.
Featured stays
Hotel Lungarno
Location: Florence, Italy
Villa di Piazzano
Location: Cortona, Italy
Rosewood Castiglion del Bosco
Location: Montalcino, Italy
Borgo San Felice
Location: Chianti, Italy
COMO Castello Del Nero
Location: Chianti, Italy
Process
Step 1
Let's connect
Whether you have a specific trip in mind or are looking for inspiration, get in touch with your travel preferences, and one of our Experience Designers will kick off the planning.
Step 2
Detailed Brief
After a conversation to learn more about your trip, you’ll receive details on an adventure with us, including activities and accommodation options in the destinations. An initial Trip Development Fee is made before moving to the next stage.
Step 3
Customized Itinerary and Confirmation
Your Experience Designer will share a tailored trip plan and will collaborate to adjust and finalize the itinerary. A per-person trip deposit is requested to confirm your trip, with full payment made 95 days* before departure.
Step 4
Support, Start to Finish
Before your trip, you’ll receive details on every step of your journey. You’ll have dedicated support while on trip, and when you return, our Traveller Relationship team will be ready to welcome your feedback and explore ideas for your next B&R adventure!
* Final payment terms may vary based on destination and type of trip.
Good to know
Biking
Tuscany offers diverse terrain which includes some steep hills and challenging up and downhills. We recommend choosing an e-bike if you don't ride hills regularly.
Food
While vegan dining options in Tuscany are available, they can be limited. If vegan meals are essential during your trip, please let your Experience Designer know.
Walking
Tuscany offers diverse terrain, including asphalt and dirt roads and paths with some up and downhills. We recommend familiarity with walking in these conditions.
Why choose a Bespoke trip?
An Effortless Journey
Our expert Experience Designers are perfectionists, using first-hand knowledge of routes, restaurants and hotels to create an unforgettable experience. This means you’re in the best hands to plan your dream trip.
Lifelong Memories
Our Bespoke trips are often described as lifechanging. When every detail and magical moment is planned just for you and your group – you'll get exactly what you’re after, and more. The perfect addition to the memory book.
Years of Local Friendships
We’ve been at this since 1966, and our Experience Designers have been planting seeds and building friendships around the world since day one. The loyalty we share with our connections is invaluable and is what allows us to give access exclusive to B&R.
Creativity and Spontaneity
From our office to our guides on the road, every person who touches your trip pours their passion and creativity into it. When you travel Bespoke, you’ll work closely with passionate planners to create the perfect fit for you and your travelling companions.
