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Italy Awaits

Luxury journeys ready for spontaneous spirits

Indulge in Italy’s timeless beauty—at a moment’s notice. From sun-soaked Amalfi coastlines to vineyard-lined Tuscan hills, Butterfield & Robinson curates exquisite last-minute journeys with the same seamless service and luxury touches we’re known for. Your spontaneous escape awaits.

Why travel to Italy this fall?

We're glad you asked...

Quieter Coastal Charm

With summer crowds gone, pastel villages and dramatic cliffside roads feel blissfully serene.

Perfect Sea Breezes

Mild autumn days are ideal for soaking up sun-kissed terraces and sparkling Mediterranean views.

Rich Cultural Layers

From ancient ruins to vibrant markets, Sicily’s storied past and lively present shine brighter in the fall calm.

Flavors of the Season

Cooler days bring heartier regional dishes and seasonal specialties that celebrate Sicily's abundance.

Rolling Hills Aglow

Vineyards and cypress-lined roads are bathed in golden light, ideal for unhurried exploration.

Harvest Time Traditions

Autumn is Tuscany at its most authentic, with villages alive in celebration of food, wine, and community.

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Why you should be in Italy this fall

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Harvest Time Traditions

Autumn is Tuscany at its most authentic, with villages alive in celebration of food, wine, and community.


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Quieter Coastal Charm

With summer crowds gone, pastel villages and dramatic cliffside roads feel blissfully serene.


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Rich Cultural Layers

From ancient ruins to vibrant markets, Sicily’s storied past and lively present shine brighter in the fall calm.

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Tuscany Wine Country Biking

Oct 5 - Oct 10, 2025

Tuscany was made for two wheels—rolling hills, vine-draped valleys, and medieval towns that haven’t changed much since knights rode through. Spin from one postcard view to the next, sip and savour with our local friends, and sit down to home-cooked feasts that taste like nonna’s greatest hits. This is Tuscany beyond the guidebook—authentic, delicious, and impossibly scenic.

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Plan your own personal Tuscan dream

Tuscany Bespoke

Step into the rhythm of the Tuscan Hills

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.

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Tuscany Bespoke

Welcome to Butterfield & Robinson, the ne plus ultra of active luxury travel. We bike. We hike. We boat. We’ll even dogsled. Whatever it takes to experience a region up close and in deep. Our insatiable curiosity is matched only by our taste for travelling in style and comfort. Your time is precious. So we make your journey jaw-dropping at every turn.

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