Tuscany Tuscany & Umbria Bespoke

A region of rejuvenation

If leisure’s what you seek, then head to Tuscany and Umbria and bask in one of its 39+ luxurious spas. A land of natural wonders, Tuscany is renowned for its many thermal springs—legend has it that its sulphurous springs were created when Jupiter’s thunderbolt fell in battle against Saturn—so a dip in its warm waters, and even a stroll through its famed hiking circuits (which offers sights of castles and Romanic churches) is sure to offer an experience that feels out of this world.


Dream ~ what՛s your perfect trip?
Design ~ meet your personal trip designer
Decide ~ collaborate on your custom trip
Depart ~ start packing
The best time of year to visit Tuscany is from May to October.

Trip Ideas

Family Vacation

We’ll arrange everything on this family trip from romantic dinners and guided historical walks through vineyards and olive groves, découpage lessons and medieval games for the kids, and bike rides for the whole family down cypress-lined streets past the family farms and peaceful hilltop villages. Bottom line: everyone has a vacation for the ages, regardless of age.

  • Ride along a portion of the pilgrimage route to Rome, out of Trequanda and over some rolling countryside with views of the Crete Senesi in the distance.
  • Explore the magical town of Cortona, high up on the hills overlooking the Val di Chiana.
  • Take part in a medieval flag-throwing demonstration and learn how to toss Palio flags in Siena from real sbandieratori.

Inspired? Craft a similar Bespoke guided trip starting from $1,000-$2,000 per person per night.

Biking & Walking

As lovely as the Tuscan countryside and cuisine are, they’re at their best when enjoyed in good company. Here, our friends are your friends, and we have great ones. Giovanni brings Cortona to life for us. In Umbria, we’ll ask Mamma Dina to serve up her homemade pasta for us. And before we part, our friends at the Avignonesi winery will send us off in style.

  • Ride to Castello di Brolio, the estate still home to the descendants of the Baron Ricasoli – renowned for being the inventor of the Chianti Classico.
  • Walk past tiny villages that are frozen in time towards our favourite Tuscan cooking school.
  • Join local guide Giovanni, whose family has been here since at least the 14thC, to walk towards the 4thC hilltop town of Cortona.

Inspired? Craft a similar Bespoke guided trip starting from $2,000-$3,000 per person per night.

Tuscany & Umbria Bespoke

Feature Hotels

Casabianca, Asciano

The CasaBianca, a 15thC villa and working farm, has been converted into comfortable apartments in the heart of Tuscany’s most gorgeous countryside. We take full advantage of its extensive grounds while staying there. Our gracious hosts, Alba & Luigi Scaperotta, produce their own wine and olive oil, and give us a pizza-making demo using the villa’s original wood-burning oven. View hotel website »

Relais Borgo Scopeto

This Tuscan 11thC estate has been through the ages renowned as “the” meeting place for scholars and politicians. Since being brought into the modern era in 2005—it is today a place of tranquil and classic Tuscan beauty. You are sure to enjoy the elegance and comfort of the rooms, the superb traditional Tuscan cuisine, beautiful pools and incredible grounds—over 5,000 hectares of Chianti vineyards. View hotel website »

Our Trip Designers are a special breed. Part guru, part collaborator, part mind-reader, they have the full breadth of B&R resources at their fingertips. Extraordinarily well-travelled, they’ve been there, lived there, done it, planned it and eaten it, too. With a combined geographic knowledge that’s nothing short of staggering, they can save you literally years of research. Above all, they’re incredibly good at what they do.

Talk to our design team »


“There were many great moments on our fabulous trip through Tuscany. The fact that everything was so smooth was clearly due to the professional planning of B&R and it’s great team. The views were delightful and the our new friendships are amazing!”

— Fabio Vidigal, Bespoke Tuscany Biking 2011

Tuscany & Umbria Bespoke

Notes from the Road

  • In Deep: SienaDelve deep into this perfect medieval time capsule, where (thanks to enlightened zoning restrictions dating all the way back to 1307) the palaces and churches of Siena have been preserved like nowhere else in Italy. While the resulting wealth of art …
  • Rave Reviews: TuscanyWhether you’ve been working at something for five minutes or five decades, it’s always nice to hear an encouraging word (or two). And thanks to our amazing travellers, we frequently find ourselves feeling very encouraged indeed. Check out what some o …
  • Tuscany Biking: The Tour of a LifetimeButterfield & Robinson is thrilled that one of our trips was once again named to National Geographic Traveler‘s list of the 50 Tours of a Lifetime. Our Tuscany Biking trip was selected as one of the Best Tours in Europe! Read an excerpt of NG Travele …

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