In Deep: A Brief History of Montepulciano

Perched between two of Italy’s most scenic valleys, and&nbsp;a frequent prize for two of Tuscany’s&nbsp;great city-states,&nbsp;the history of Montepulciano is (almost) as rich as the famous wine that bears its name.<h3>Founded While Fleeing</h3>Montepulciano was reputedly founded in the 6thC by the people of Chiusi who were fleeing the Barbarian invasions. The first written accounts of the town refer to the settlement as Mons Politianus — which explains why the townspeople are known as Poliziani.Due to its strategic position overlooking the Val d’Orcia on one side, and the Val di Chiana on the other, the town was constantly being fought over by the Florentines and the Sienese. In 1202, the Poliziani chose Florence as their protectorate (ostensibly because it was farther away and could assert less control over their lives).Over the next 200 years, however, Montepulciano changed hands several times; this flip-flopping of ownership is the reason for the town’s artistic riches, as each ruler sought to out-do the last.<h3>Finally Florentine</h3>The final reversal in ownership happened in 1511, when Montepulciano once again came under the jurisdiction of the Florentines. Florence’s influence on the town is obvious in the style of Montepulciano’s palazzi, which bear the symbols of Florence: the giglio — or Florentine lily — and the marzocco, the heraldic lion.Montepulciano is also the birthplace of one of the Renaissance’s most celebrated lyrical poets, Poliziano (né Angelo Ambrogini), who took the Italian version of his hometown’s ancient name as his own.Today, the town is most famous for its wine: vino nòbile di Montepulciano. Described as the “king of all wines” by a 17thC poet, it was one of the first with an origin guaranteed by the Italian government.Montepulciano wine is a blend of prugnolo gentile (a type of Sangiovese, the predominant varietal in Chianti and Brunello di Montalcino), canaiolo and mammolino grapes.<h3>San Biagio</h3>Standing majestically at the end of a cypress-tree lined drive just outside the Montepulciano town walls, this church is the masterpiece of Florentine architect Antonio da Sangallo the Elder.Built of honey-coloured travertine stone, it was constructed in the form of a Greek cross, with a dome and façade flanked by two bell towers (one of which remains unfinished). The project was Sangallo’s focus for the last 15 years of his life and was one of the most ambitious of its time.

Tales of miracles in Montepulciano span the ages: the Madonna delle Grazie was said to have bled when stabbed by an angry youth in 1514, and bruises were said to have appeared on the remains of the Madonna di San Martino after being hit by an iron chain in 1580. Legend has it that the image of the Virgin appeared on one of San Biagio’s walls on April 23, 1518, opening and closing her eyes.The Virgin’s appearance is said to have returned over several days, as witnessed by most of the town’s residents (accompanied by healing in many cases). In her honour, the people decided to build a temple around the Virgin, funded with donations from far and wide. The inscription over one of the doors is a testament to this project.The church is dedicated to Saint Biagio (Blaise), an Armenian doctor who became a bishop and renounced worldly comforts in favour of a contemplative life in the mountains. He was later imprisoned on a charge of practising magic and was tortured with a sharp instrument used to card wool.His treatment made him the patron saint of carders, which is why he is frequently featured in Tuscan paintings. (The textile industry was at the centre of the region’s medieval wealth.) The saint is also invoked by Italians to remedy sore throats, as he once saved a child choking on a fishbone that had gotten lodged in her throat.&nbsp;Explore the many hilltop towns of <a href="https://www.butterfield.com/places-to-go/europe/italy/tuscany">Tuscany</a> on a <a href="https://www.butterfield.com/trip/small-group/tuscany-wine-country-biking">biking</a>, <a href="https://www.butterfield.com/trip/small-group/tuscany-umbria-walking">walking</a>, or <a href="https://www.butterfield.com/trip/small-group/tuscany-wine-country-womens-multi-active">multi-active trip.</a> Not sure which is for you? Go <a href="https://www.butterfield.com/trip/bespoke/tuscany-bespoke">bespoke</a> and tailor the trip to suit your exact interests and dates.

Explore the history of Montepulciano—from medieval rivalries and Renaissance architecture to its enduring legacy as one of Tuscany’s most celebrated wine regions.

A Brief History of Montepulciano | Tuscany’s Renaissance Town & Wine Heritage

Experience Italy like a local with Butterfield & Robinson

Italy

Why Italy with Butterfield & Robinson

Every detail is handled with precision—so you can arrive, settle in, and simply enjoy Italy as it unfolds.

Travel deeper, effortlessly

Long-standing local relationships open doors to private tastings, rare moments, and meaningful encounters.

Access you can’t arrange on your own

Walk, cycle, linger—each day balances movement with indulgence, perfectly paced and never rushed.

Designed for how you want to explore

You don’t just visit places; you’re welcomed into them, guided by those who know them best.

Introductions, not itineraries

From handpicked hotels to unforgettable meals, each choice is elevated, thoughtful, and deeply rooted in place.

Beauty in every detail

This is travel shaped by decades of expertise—elegant, intuitive, and effortlessly enriching.

Italy, refined

A visit to Italy conjures images of crystal blue seas and vineyards dappled with sunshine. But let’s not forget the sun-kissed lemon groves and truffle-laced forests. Indulge in the Italy that few others see: once you’re embraced by the goodwill and aromas of all corners of this land, you may just forget to return home.The secret to Italy? Communing with Italians (some of whom work in our Tuscan office). That’s why we don’t just track down the best pasta—we ask our local friends when they’re free, then invite you to a feast on their estate. (Grazie, <a href="https://www.butterfield.com/get-inspired/in-tuscany-home-is-where-the-hospitality-is">Lungarellas</a>!) We don’t merely visit the Statue of David—we host a private dinner party at the Accademia. And we don’t just “see” Italy—we plunge you directly into la dolce vita. Fellini wishes he could do Italy like us.

Discover the heart of history, culture, and romance

Luxury small group and private Italy tours across Tuscany, the Dolomites, Amalfi and more. Award-winning experiences, private estate dinners, and 60 years of local access.

Luxury Biking, Walking & Private Tours in Italy

Hidden Gem

Exclusive Access

Timeless Charm

Umbria is Italy in soft focus—misty mornings, monk-strolled lanes and vineyards that roll on forever. Wander cobblestone towns where time politely hit pause, sip olive oil like it’s fine wine (trust us), and bed down in castles-turned-hotels. With Reschio’s rustic-luxe magic and a soundtrack of Gregorian chants, Umbria invites you to slow down—and stay awhile.

The ‘Green Heart’ of Italy

Hike Umbria's valleys, explore Orvieto's underground city and join exclusive truffle hunts on a tailor-made itinerary. A private Italy journey, entirely yours.

Umbria Bespoke | Butterfield & Robinson

Iconic Italy

Authentic Food

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.

Feel the rhythm of Tuscany

Bike from Florence into Chianti's vineyards on a tailor-made itinerary. Private estate visits, truffle hunts and Tuscan food culture, built entirely for you.

Tuscany Bespoke | Butterfield & Robinson

The Dolomites’ stunning peaks have drawn mountaineers for centuries, yet somehow they remain one of Italy’s best-kept secrets. Explore the two most enchanting corners of the gorgeous Dolomites region: the Alpe di Siusi and Alta Badia. Experience the region’s remarkable people, unforgettable hikes, and sumptuous cuisine. Your taste buds will never forget the gastronomic surprises in store, the perfect reward after an invigorating (and jaw-dropping) alpine hike.

Breathtaking Landscapes

Tranquil Environment

Vibrant Culture

Italy’s Dolomites: outrageously scenic, slightly mysterious, and suspiciously crowd-free (shhh). Wander lush Alpe di Siusi’s larch forests, eye-popping meadows and trails beneath Sassolungo’s iconic peaks. Explore Alta Badia’s valleys, meet locals who proudly cling to Ladin traditions, and refuel with hearty alpine meals. Luxurious spas soothe tired legs—because even intrepid hikers deserve a little pampering.

A spectacular alpine hideaway

The itinerary below is a sample and is subject to slight changes in routes, accommodations and activities. Please download the itinerary for your selected departure for precise details.

Preview the itinerary

Experience Designer

Explore the gorgeous (and little known) Alpe di Siusi. Experience the region’s remarkable people, unforgettable hikes, and sumptuous cuisine. Your taste buds will never, ever forget the gastronomic surprises in store, the perfect reward after an invigorating (and jaw-dropping) alpine hike. B&amp;R Travel Expert Georgia Yuill was named Top Travel Specialist for the Dolomites 2020 by Condé Nast.

Hike a UNESCO World Heritage Dolomite landscape on this small group tour. Flower-filled meadows and mountain rifugios with the Alps' finest pasta.

Dolomites Hiking Tour | COMO Alpina & Aman Rosa Alpina | Butterfield & Robinson

Our Super Tuscan has been finely crafted for the traveller who delights in truly exquisite accommodation, exceptional wine and wants to suss out the idyllic countryside through a well-structured blend of activity—pedalling past hilltop hamlets, ambling among vines tended by generations of winemakers and (optionally!) rising to salute the famous Tuscan sun on a yoga mat. In between, you’ll savour traditional cuisine made from the freshest ingredients. It’s a robust build. Fancy a taste?B&amp;R Experience Designer Courtney Mundy has been named a Top Travel Specialist by Condé Nast Traveler.

Incredible Rides

One-of-a-kind Hotels

Local Wines

Think of this as the Super Tuscan of trips—bold, balanced, and built to impress. Pedal through olive groves and hilltop hamlets, sip with winemakers whose vines have stories to tell, and savour meals so fresh they practically introduce themselves. With luxe stays and medieval magic around every bend, this ride goes down very, very smoothly.

Embodying the finest of the region

Featured stays

Haven't found the perfect itinerary yet? No journey should be one-size-fits-all. With our bespoke trip planning, you have the freedom to curate a travel experience that fits your unique interests and desires.

Experience Designers

Our Super Tuscan has been finely crafted for the traveller who delights in truly exquisite accommodation, exceptional wine and wants to suss out the idyllic countryside through a well-structured blend of activity—pedaling past hilltop hamlets, ambling among vines tended by generations of winemakers and (optionally!) rising to salute the famous Tuscan sun on a yoga mat. In between you’ll savour traditional cuisine made from the freshest ingredients. It’s a robust build. Fancy a taste?

Spend 5 nights cycling Chianti Classico on this small group tour. Estate tastings, truffle hunts and 1 converted Tuscan monastery as your base.

Super Tuscan Biking | Butterfield & Robinson

Nowhere does slowing down feel more appropriate than Piemonte, the birthplace of 'Slow Food', where epicurean delights await around every corner and verdant vineyards abound. On this trip, you'll indulge in fresh cuisine paired with many of the best vintages (on us, naturally), ride through UNESCO-listed villages and sparkling wine hubs, then kick back at your intimate and gorgeous stay.&nbsp;

Insider Access

In Piemonte, even the hills take their time—rolling gently past vineyards, truffle forests, and villages that seem handpicked by UNESCO. Pedal through sparkling wine country, feast like royalty in the home of Slow Food, and sip Barolo where it’s born. With intimate stays and views that demand lingering, this is biking–and B&amp;R–at its best.

Our little secret in Italy

Savour the pace of Piemonte

Nowhere does the slowing down feel more apropos than Piemonte, the birthplace of Slow Food, where epicurean delights await around every corner and verdant vineyards abound. We pair our meals with many of the best vintages (on us, natch), then kick back at the intimate and gorgeous La Villa.

Spend 5 nights cycling Barolo's Nebbiolo vineyards in a small group. Family cellar visits, truffle hunts and pasta at tables you will not find without a guide.

Piemonte Biking | Butterfield & Robinson

Discover one of the most attractive mountain landscapes in the world as you saddle up on an electric-assisted mountain biking journey through the Dolomite Mountains. Nestled in the north of Italy, this alpine land offers a unique blend of cultures and cuisines, stunning landscapes, always inviting hospitality and endless fun and exploration through its peaks and valleys. Pedalling through two of the region’s corners, the Alta Badia and the Alpe di Siusi, your rides can be as moderate or challenging as you wish, all guaranteed to be backdropped by craggy peaks, tranquil meadows and delightful (and delicious) mountain huts.B&amp;R Experience Designer Georgia Yuill has been named a Top Travel Specialist by Condé Nast Traveler.

Luxurious Stays

The Dolomites are like the Alps’ charismatic cousin. Spin through Alta Badia’s dreamy valleys and Alpe di Siusi’s peaceful pastures, customizing each route to your preferred level of comfort (or bravado). Recharge at rustic mountain huts, savour hearty alpine fare, and soak in views so jaw-dropping you’ll be glad you had an electric assist.

Take on the Dolomites on two wheels

$9,495 based on two travellers. Request a detailed itinerary for pricing for more than 2 people

Spend 5 nights tackling the Dolomites' legendary passes on a small group e-bike tour. Gardena, Sella, Campolongo, with expert guides and the Alps' finest hotel.

Dolomites Self-Guided E-Mountain Biking | Butterfield & Robinson

Prepare to savour some of the best meals of your life. Did we say meals? We meant wines (think Barolos and Barbarescos). Wait – we meant views (think Italian Riviera). Oh, shoot, no. We meant hotels (there’s a reason they call them Splendido).

In Tuscany and Umbria, slow down to a gentle pace of life and wander from golden-hued horizons to lush, verdant lands. Your journey begins tracing the hills of Montepulciano and Val d’Orcia, travelling along age-old routes that were carved into the landscape step by step. Pass vines tended by generations of winemakers and travel through Pienza, a picturesque Renaissance town. In Umbria, indulge in local cuisine and crostata made with our friend Agnieska, and spend a day exploring&nbsp;endless olive groves, flowering meadows and forests. At the end of each day, spend time relaxing at your beautiful hotels—from the brand-new Casa Newton to Monastero di Cortona, a converted monastery, and Hotel Castello di Reschio, a thousand-year-old castle.

Great Walks

Walk your way through Tuscany and Umbria, where every trail feels like a love letter to slowing down. Trace ancient paths through Montepulciano and Val d’Orcia, bake crostata with our friend Agnieska, and wander olive groves that roll on forever. With castle stays, Renaissance towns, and a thousand golden horizons, this is Italy at its most soul-soothing.

From the Golden Land to the Green Heart 

Preview the itinerary 

Spend 5 nights hiking between Cortona and Umbria's green valleys on this small group tour. Truffle trails and 1 converted Tuscan estate as your base.

Tuscany & Umbria Walking | Butterfield & Robinson

Discover the true magic of old Italy, surrounded by olive groves and our charming local friends. We make every step count with routes featuring sublime coastal roads, cobbled paths that weave through whitewashed towns and distinctive stone trulli. End your journey with two nights in UNESCO-listed Matera, with its ancient cave dwellings inhabited for thousands of years.

The magic of old Italy

Bask in olive groves and gorgeous whitewashed villages as you stroll along the aquamarine Adriatic in one of Italy’s most blissfully low-traffic corners (we’re the only walkers here!). Back at hotel Sant’Angelo – a B&amp;R exclusive in UNESCO Matera – feast on the freshest seafood you’ve ever had while you quaff luscious local Primitivo.

Savour a feast prepared by our local friends—and enjoy it in their backyard. Take in the evening energy of Siena and join in the laughter radiating from the piazza. Dine under the stars, at a winery, on a meal prepared by our private chef. We don't just visit Tuscany—we bring its story to life.Please note the hotel lineup for 2024:May 5th: Villa di Piazzano, Grand Hotel Continental, Pieve AldinaFor all other departures: Villa di Piazzano, Grand Hotel Continental, Le FontanelleFor information about the hotels assigned to your departure, kindly contact your Travel Advisor. You can also download the detailed itinerary to view the complete hotel lineup.

Exceptional Wines 

Tuscany was made for two wheels. From the vine-striped ridgelines of Chianti Classico to the chalk-pale crete approaching Siena, then south through Montepulciano's hilltop streets and on into Umbria — this is the long version of Tuscany, the one they left out of the guidebook. Ride with friends who have been making biodynamic wine in these valleys for generations. Stay at COMO Castello Del Nero and Villa di Piazzano. Sit down to dinners that happened to be exactly what you'd order if you knew. This is where the word dolce actually means something.

Explore Italy's most exalted region

Savour a feast prepared by our local friends—and enjoyed in their backyard. Take in the evening energy of Sienna and join in the laughter radiating from the piazza. Dine under the stars, at a winery, on a meal prepared by our private chef. We don't just visit Tuscany—we bring its story to life.

Spend 5 nights biking Tuscany's hilltop estates on this small group tour. Cypress lanes, Chianti straight from the cellar and 1 farmhouse that redefines luxury.

Tuscany Wine Country Biking | Butterfield & Robinson

To truly understand Italy’s most enigmatic island, we explore it by sea, setting sail in an exquisite&nbsp;gulet&nbsp;that will serve as our home during our voyage. Biking or hiking off the ship each day, we explore sheep-covered hills, vertiginous limestone cliffs that plunge into the cobalt sea, and the glam of Costa Smeralda. Unforgettable? Cruising to La Maddalena and Corsica.B&amp;R Experience Designer Georgia Yuill has been named a Top Travel Specialist by Condé Nast Traveler.Please Note! This trip offers 12 available spaces, so book early to secure your spots. Or, get in touch with a Travel Advisor to Privatize the departure for an exclusive journey with your crew.

Italian Coastal Wellness

To truly understand Italy’s most enigmatic island, we explore it by sea, setting sail in an exquisite&nbsp;gulet&nbsp;which will serve as our home during our voyage. Biking or hiking off the ship each day, we explore sheep-covered hills, vertiginous limestone cliffs that plunge into the cobalt sea, and the glam of Costa Smeralda. Unforgettable? Cruising to La Maddalena and Corsica.

B&amp;R’s Women’s Only trips are designed by women, for women to experience new regions, cultures and communities from female perspectives. Venture straight to the heart of Italy through the regions of Tuscany and Umbria, laden with history, cuisine and natural beauty. Wander on foot and by bike through the Tuscan landscape across fields of wheat, rolling emerald hills, stretches of sunflowers and sun-drenched vineyards&nbsp;connecting from one picturesque village to the next. Immerse yourself in your peaceful surroundings with&nbsp;morning yoga and step into our friend Margot’s estate to savour exquisite wines. Cross into Umbria via shady wooded paths and hills blanketed in wildflowers to your hands-on&nbsp;crostata&nbsp;cooking class. Retreat to Reschio, Italy’s finest hotel, and explore its enchanting grounds before dining in the castle. By the end of this journey, you’ll feel a deep connection to this serene and magical corner of Italy.

Local Connections

Active Adventure

Cycle, stretch, sip, repeat—this is Italy at its most rejuvenating, reinvigoratinng and remarkable. Pedal through sunflower fields, wander wildflower trails, and find your flow with morning yoga. Bake crostata in the hills, toast fine wines at Margot’s estate, and retreat to dreamy Reschio, one of Italy's best hotels. It’s a multi-active escape with just the right dose of magic (and vino).

Wander through the idyllic countryside

Tuscany & Umbria Women's Multi-Active | Butterfield & Robinson

Savour a feast prepared by our local friends—and enjoyed in their backyard. Take in the evening energy of Sienna and join in the laughter radiating from the piazza. Dine under the stars, at a winery, on a meal prepared by our private chef. We don't just visit Tuscany—we bring its story to life.



“A dream place"—that’s how Steinbeck described Amalfi. And when you take in the Path of the Gods, the hotels (we stay at Le Sirenuse, just like he did), the food and the Limoncello, you’ll understand why. Dream place? More like fantasy land—but who are we to correct a Nobel laureate?B&amp;R Experience Designer Courtney Mundy has been named a Top Travel Specialist by Condé Nast Traveler.

“A dream place"—that’s how Steinbeck described Amalfi. And when you take in the Path of the Gods, the hotels (we stay at Le Sirenuse, just like he did), the food and the Limoncello, you’ll understand why. Dream place? More like fantasy land—but who are we to correct a Nobel laureate?

In the Footsteps of Gods

Spend 5 nights hiking Capri, Ravello and Positano on this small group tour. Path of the Gods clifftop trails, sea cave swims and views that justify every step.

Amalfi Coast Walking Tour | Capri, Positano & Le Sirenuse | Butterfield & Robinson

Crowning Italy’s northern border, the Dolomites are widely regarded as one of the most attractive mountain landscapes in the world. Trails wind between massive peaks, offering new vistas at every turn and charming rifugi (mountain huts) that welcome hikers and bikers alike.&nbsp;Evenings are a delightful mixture of South Tyrolean and Ladin cultures, where you can dine on distinctive culinary specialties and savour the region's fine wines.

The Dolomites are where alpine drama meets Italian flair. Hike jagged peaks, cycle storybook valleys and fuel up on pasta with a side of strudel. With luxe lodges, a dash of Austrian charm and views that redefine “breathtaking,” this UNESCO gem is mountain magic—served with a glass of Südtirol’s finest.

Experience the Italian Alps 

experience the italian alps

Explore the towering peaks of the Dolomites

Bespoke travel lets you to 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.

Whether you arrive for powder or peaks, experience the Dolomites on a tailor-made itinerary. Ski touring, rock climbing and Italy's finest mountain food.

Dolomites Bespoke | Butterfield & Robinson

Vineyards, grottos, and whitewashed villages set against the Adriatic: myriad landscapes await you in Puglia, the historic hunting grounds of marauding royalty and occupying forces (who clearly come for the nosh). Foodies, get ready to swoon for fresh, local ingredients and rich wines in Puglia and Basilicata, the gardens of Italy.

Ride through southern Italy where ancient history meets Adriatic eye candy. Spin past olive groves, stone Trulli, and sun-bleached villages that look plucked from a dream (or a very trippy postcard). Explore fortified farms, feast like a local, and cruise serene coastal roads. Matera to Puglia delivers the rarest form of la dolce vita—one that's blissfully free of crowds.

See Puglia at your pace

Experience designer

$5,395 based on two travellers. $4,995 based on four travellers. $4,595 based on six travellers.

Spend 5 nights cycling Puglia's Adriatic coast on a tailor-made itinerary. Cave-dwelling Matera, whitewashed Ostuni and Monopoli's harbour, just for you.

Puglia Biking Bespoke | Butterfield & Robinson

Explore Pienza and Siena with Carlo, a Tuscan native, and expand your palate with local wine-maker Elisabetta. From tiny Montefollonico to lordly Montepulciano, Tuscany embodies the good life. Revel in a cyclist’s paradise as our friends reveal its many charms.B&amp;R Experience Designer Courtney Mundy has been named a Top Travel Specialist by Condé Nast Traveler.

Tuscany’s calling—and this self-guided spin lets you answer at your own pace. Cycle past cypress-lined hills to storybook towns like Pienza and Montepulciano, sip from sun-soaked vineyards, and feast at trattorie that know their way around a wild boar ragu. With local tips for living la dolce vita, Tuscany never felt so personal.

Your pace, our routes, Italy's pleasures

$6,395 based on two travellers. $5,995 based on four travellers. $5,795 based on six travellers.

Visit Pienza to Siena on a tailor-made itinerary. Chianti estates, hilltop towns and 1 converted Tuscan monastery as your private base.

Tuscany Biking Bespoke | Butterfield & Robinson

Natural Beauty

Time Travel

Puglia is sun-soaked, salt-kissed and straight-up irresistible. Ride through olive groves, past whitewashed towns and cone-roofed trulli, then feast on seafood and sip wine under the stars. Pair it with neighbouring Matera in Basilicata, with its ancient stone beauty, and you’ve got Italy at its most soulful. History, flavour and southern charm—served with extra olive oil, of course.

Experience old-world Italy in the heel of the boot

In Puglia, the spirit of old-world Italy comes to life

Bike Baroque Lecce, hike ancient Matera and eat at trulli restaurants most visitors miss on a custom itinerary. Southern Italy, privately guided for you.

Puglia Bespoke | Butterfield & Robinson

Travel beyond as we're the only ones who will take you to both the crystalline waters of Lake Como and over to the stunning Swiss side, wandering through charming Lugano and Ticino. Soak in the incredible views from the water on not one, two, but three separate boat cruises.Please note the 2025 hotel lineup: Grand Hotel Victoria, Grand Hotel Villa Castagnola &amp; Grand Hotel Des Iles Borromees &amp; Spa

Unforgettable Experiences

Italy’s lakes: where nature shamelessly shows off, truffles beg to be found, and villa-hopping by speedboat feels totally reasonable. Wander Lake Como’s garden-lined shores, scale castles with postcard views, and savour lakeside meals with Alice, our favourite local foodie. Swim crystal-clear Mergozzo, hunt for truffles with a seasoned tartufaio (and his adorable dog), and unwind each night in style.

Where grandeur and elegance go to relax

Go beyond the crystalline waters of Lake Como as we’re the only ones who pop over to the stunning Swiss side, wandering through charming Lugano and Ticino. Soak in the incredible views from the water on not one, two, but three separate boat cruises.

Spend 5 nights hiking Lakes Como, Lugano and Maggiore in a small group. Lakeside trails, clifftop gardens and private villa access you cannot arrange alone.

Italian Lakes Walking & Hiking | Butterfield & Robinson

With no shortage of pristine wineries and charming landscapes punctuated by UNESCO-listed vineyards, the Prosecco hills are a wine lover’s dream. Although known as the place where Italy’s most famous DOCG wine grapes grow, you’ll soon discover this region has so much more to offer. Pedal through medieval towns, learn how to make pasta from scratch and savour the gastronomic delights around every corner. Here, the culinary adventures are as extraordinary as the scenery!

Great Rides

Art and History

In the Prosecco Hills, the bubbles are just the beginning. Ride through rolling vineyards, sip Grappa (slowly) where it was born, and wander medieval towns where even the artwork feels tipsy on beauty. With DOCG vines, Michelin-worthy meals, and landscapes that practically toast you back, this region pairs perfectly with every kind of adventure.

Epicurean escapades along ancient paths

Spend 5 nights biking the Prosecco Road on this small group trip. Steep vine terraces, Palladian villas and Asolo's medieval lanes. Northern Italy's finest.

Prosecco Self-Guided Biking | Butterfield & Robinson

Venture to the vine covered slopes of the South Tyrol wine country to the heights of the Italian Alps and discover the Dolomites—a breathtaking mountain range often regarded as the most beautiful in the world. Surrounded by dramatic peaks, verdant valleys, and picturesque alpine villages, the Dolomites beckon to be explored on two wheels. On your e-mountain bike, begin your journey in the charming town of Bolzano, pedalling through the Adige Valley toward the prestigious vineyards of Lake Caldaro. Immerse yourself in the beautiful Alpe di Siusi, reached by cable car whisking you to the peaceful high alpine meadows. Witness the charms of mountain life as you bike through the enchanting village of Ortisei, and hike along the Fassa and Duron Valleys, where an incredible backdrop of the Sassolungo and Sassopiatto peaks accompanies you. After a day of adventure, retreat to luxurious hotels and rejuvenating spas, where you’ll quickly feel the serenity of this beautiful pocket of Italy.&nbsp;This trip is capped at 14 travellers.&nbsp;

Exceptional Wines

In Italy’s Dolomites, every ride and hike feels like a dream. Pedal through vineyard-covered valleys, soar by cable car to high alpine meadows, and spin past storybook villages framed by towering peaks. Hike along a panoramic ridge overlooking the Fassa and Duron Valleys, then unwind in luxurious hotels and soothing spas surrounded by serene beauty.

Cycle peaks and valleys 

Spend 5 nights biking and hiking the Dolomites on this small group adventure. Cycling climbs, alpine meadow trails and Italy's finest UNESCO landscape.

Dolomites Multi-Active | Butterfield & Robinson

Authentic Cuisine

Tuscany is where vineyard-laced hills meet timeless towns and every meal tells a story. Ride through Chianti’s golden landscapes, walk through vineyards guided by passionate female winemakers, and linger over long lunches with women who’ve perfected the art of Italian hospitality. From homemade pizza in the vines to private tastings in storied cellars, this is Italy at its most soulful.

Spend 5 nights biking and hiking Val d'Orcia on this small group women's tour. Cypress hill roads and 1 Tuscan farmhouse where la dolce vita is no cliche.

Tuscany Wine Country Women's Multi-Active | Butterfield & Robinson

Here, sweeping mountain vistas and the spectacularly placed Caesar Augustus (your Relais &amp;&nbsp;Châteaux away from home) conspire to make the sirens sing. Go at your own pace—with local guides at your beck and call—as you traverse the glittering coast (on foot and by private boat), and take in Amalfi’s idyllic mix of luxury and rustic charm.B&amp;R Experience Designer Courtney Mundy has been named a Top Travel Specialist by Condé Nast Traveler.

Unique Gastronomy

Experience By Sea

Amalfi’s beauty runs deeper than postcard-perfect vistas (though they’re delightful, too). Wander at your leisure along cliffside trails, discover why lemons grow as big as your head, and eavesdrop on goats gossiping hillside secrets. From glittering coastlines to charming mountain paths, experience the luxurious-yet-rustic rhythm of life that inspired Steinbeck, and still beckons the Sirens to sing.

Amalfi's stunning coastline

$11,995 based on two travellers. $11,595 based on four travellers. $11,095 based on six travellers.

Spend 5 luxurious nights hiking Capri, Ravello and Positano on this small group tour. The Path of the Gods, hidden grottos and clifftop tables above Italy's finest coast.

Amalfi Coast Self-Guided Walking | Butterfield & Robinson

While we’ve been travelling to Tuscany for decades, this is the first release in our challenging trip series. We’ve paired famous race trails with the&nbsp;crème de la crème&nbsp;of gravel bikes. The payoff is not just the challenge of riding along gravel with heart-pounding ascents and thrilling descents, but also the unbelievable places it takes you.

Poetic Discovery

Sicily is Italy turned up to eleven—grittier, tastier, sunnier and somehow even more charming. Hike through ancient ruins, lunch by sparkling salt pans and toast under the stars with volcanic wine that tells a thousand-year story. With layered history, knockout landscapes and the warmest welcome in the Med, Sicily doesn’t just charm—it conquers.

Sicily’s charm seduces all who visit 

Bespoke travel lets you to 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.

Bike, hike and eat your way across Sicily on a tailor-made itinerary. Baroque Noto, ancient Taormina and Palermo's street food markets. Built for you alone.

Sicily Bespoke | Butterfield & Robinson

Our decades-long love affair with the Amalfi Coast has us feeling like members of the Amalfitano family, so don’t be surprised if the barmen or concierge greet you like old friends. Here, nature forces life to slow down. Grapes are harvested by hand on terraced plots, then shuttled by mule along trails that connect colourful fishing ports. Boats cruise to Capri only when the Mediterranean is calm enough to allow it. And pizzas are garnished with hand-picked, wild herbs. If superb accommodation, challenging walks and ocean views are what you seek, then a bespoke trip to the Amalfi Coast is for you.&nbsp;

La Dolce Vita in Amalfi

Scenic Walks, Stunning Views

Exclusive Local Experiences

The Amalfi Coast doesn’t rush—so neither should you. Hike cliffside trails where grapes ride mules, boats only sail when the Med says so, and pizzas come topped with wild herbs and sea air. From family adventures to romantic honeymoons, limoncello to luxe lodgings, Amalfi is a love letter to slowing down in luxurious, spectacular style.

The allure of southern Italy's colourful coastline, Amalfi   

immerse yourself in the elegance of amalfi

Hike the Path of the Gods, boat sea caves and dine on clifftop terraces on a custom Amalfi itinerary. Italy's most photographed coast, privately guided.

Amalfi Coast Bespoke | Butterfield & Robinson

Head to Veneto—where the prosecco is local, the pasta is rolled fresh, and the sun-drenched hills go on for miles. On this journey, cycle from the UNESCO landscape of the Prosecco hills, through charming villages and historic towns to the shimmering Lago di Garda. Dine with the Count of Vidor in their abbey, savour the taste of Grappa in its homeplace and indulge in the art of cooking authentic ravioli with our friend Serena. Along the way, you’ll be immersed in Veneto’s rich history—in Asolo, one of Italy's most charming historic centres, in Piave River and Salò, important WWI and WWII landmarks, and the Museum Gipsoteca Antonio Canova, where you'll witness the stunning works of the renowned Neoclassical sculptor.&nbsp;

Veneto serves up sun-soaked hills, fresh pasta, and more postcard moments than your camera can handle. Pedal from the bubbly beauty of the Prosecco hills to sparkling Lake Garda, dine with a real Count in his abbey, and roll ravioli with our friend Serena. History, hospitality, and a whole lot of dolce vita? Yes, please.

From the hills to the shores

Featured Stays

Some of the best things in life are enjoyed slowly, which is how we approach our exploration of the Veneto; a region that encompasses the area just south of the central Alps and Dolomites. We begin in timeless Venice, amid the palaces of a bygone era, with the renowned city of canals mere minutes from the start of our first ride. From here, we head west through the Po River valley along an ancient trade and military route—the Roman Road—via Postumia. The Veneto is the breadbasket of Italy, and naturally, the gustatory adventures here are unrivalled: the Prosecco is local, vegetables come straight from the field and pasta has been rolled the morning of. Salute!

Spend 5 nights cycling the Prosecco Hills to Lake Garda in a small group. Vine terraces, Palladian villas and 1 of Italy's most beautiful cycling routes.

Prosecco to Lake Garda Biking | Butterfield & Robinson

La Dolce Vita

Pastel villages cling to cliffs along the Cinque Terre coast, while Portofino glows with dolce vita glamour and superyacht sheen—the Italian Riviera is a masterclass in effortless elegance. Hike ancient mule tracks through terraced vineyards, where winemaking is more art than agriculture. Wander seaside towns washed in gelato tones, where every faded shutter and baroque balcony tells a story. Plunge into pools as blue as the Ligurian Sea, letting the Riviera wash over you.&nbsp;

Hike Cinque Terre's 5 coastal villages, boat between headlands and swim hidden coves on a tailor-made itinerary. Liguria at its finest, built for you alone.

Italian Riviera Bespoke | Butterfield & Robinson

Glorious mountaintops wreathed in mists. Fairytale villages with overflowing flower boxes. The bulbous domes of Baroque churches. In the Dolomite mountains, you'll find breathtaking beauty and rustic charm around every corner. Hike to the highest peak, spend the day indulging in culture, or savour the cuisine—here, you can’t make a wrong turn.B&amp;R Experience Designer Georgia Yuill has been named a Top Travel Specialist by Condé Nast Traveler.

If Mother Nature had favourites, the Dolomites might top her list—misty peaks, absurdly pretty villages, and trails ranging from blissfully lackadaisical to ambitiously sweaty. On this self-guided adventure, hike at your leisure, savour rustic culinary delights, and mingle with locals who practically invented hospitality. Warning: real life feels alarmingly dull after this.

Have the Italian Alps all to yourself

Spend 5 nights hiking the Dolomites on this small group trip. Meadow trails, UNESCO mountain peaks and rifugio lunches above the clouds. Done properly.