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Small Group

Super Tuscan Biking

Savouring the finest of the region, from Chianti to Val d'Orcia

6 Days, 5 Nights

Maximum Group Size

16

Activity Level:

B&R Activity Levels

Priced per person from

$9,695 USD

Single Supplement: $3,000 USD

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

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Carbon Neutral Trip

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.

Incredible Rides
Pedal through two iconic regions: the lush forest hills of Chianti and the undulating postcard landscape of Val d’Orcia.

One-of-a-kind Hotels
Rewarding rides are met with equally rewarding stays in Tuscany’s finest hotels, with plenty of time to enjoy the spas.

Local Wines
Taste some of the region’s best wines and unlock special access to incredible cellars.
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Preview the itinerary

No two trips are ever the same, but this will give you a taste of what your journey will be like.

Day 1

Meet your B&R Guides in Florence and head to the heart of the Chianti Classico region. Ride through gently rolling hills and breathtaking scenery culminating at a stunning lunch. This evening, trade stories of your day over Tuscan cuisine and perfectly paired bottles of local wine. 

Activity:

42 km (26 mi.) bike ride from Castellina to San Felice via Lecchi | Elevation gain: 704 m (2,309 ft.) 

Optional ride | 47 km (29 mi.) | Elevation gain: 785 m (2,575 ft.) 

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Day 2

Ride through two of Chianti's most picturesque villages, stopping for espresso and pasta along the way. Those interested in more cycling can take us up on our Century Ride. Tonight we'll visit a nearby estate and sample some of their famous reds while enjoying dinner in the vineyards. 

Activity:

50 km (31 mi.) San Felice loop ride via Gaiole | Elevation gain: 986 m (3,235 ft.)

Optional Century Ride | 108 km (67 mi.) | Elevation gain: 2,074 m (6,804 ft.)  

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Day 3

We'll hop on our bikes directly from the hotel and into the open countryside dotted with castles. Tonight, we'll stroll the cinematic streets of Siena with our local guide, marvel at one of the most beautiful cathedrals in Italy and enjoy "locals-only" access to a Palio contrada

Activity:

34 km (21 mi.) bike ride through Castelnuovo Berardenga | Elevation gain: 464 m (1,522 ft.) 

Optional ride | 47 km (29 mi.) | Elevation gain: 675 m (2,214 ft.) 

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Day 4

Leave directly from the hotel for one of the most impressive rides of the trip through the crete senesi in the expansive Val di Merse. Pause for lunch in a private home with panoramic views before continuing to the hotel for spa time and a Michelin-starred dinner. 

Activity:

62 km (39 mi.) bike ride from San Felice to Buonconvento via Asciano | Elevation gain: 925 m (3,034 ft.) 

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Day 5

Today's ride is pure heaven as you cruise through the Sienese countryside’s vineyards and olive groves, en-route to an al fresco feast by our friends Mattia and Sara. This evening you'll explore an exclusive winery on a hillside overlooking Montalcino. Salute

Activity:

50 km (31 mi.) loop ride through Bibbiano | Elevation gain: 897 m (2,942 ft.) 

Optional ride | 32 km (20 mi.) | Elevation gain: 659 m (2,162 ft.) 

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Day 6

Enjoy a final breakfast at the hotel before the drive to the Florence train station. Buon Viaggio. 

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Rendezvous

Airport City: Rome

Trip Start: The St. Regis Florence

Time: 9:00am

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Farewell

Airport City: Rome

Trip End: Florence Train Station, Santa Maria Novella

Time: 12:00pm

* Itineraries are subject to change. Please confirm exact Trip Start and Trip End locations upon booking.

Featured stays

Itinerary

Borgo San Felice

Location: Chianti, Italy

Itinerary

Rosewood Castiglion del Bosco

Location: Montalcino, Italy

Dates & availability

Dates
Price

per person, double occupancy

+$NaN USD single supplement

Join

Join a group of up to 16 like-minded travellers.

Privatize

8+ people

Pricing depends on group size

Detailed Itinerary

Uniquely tailored for each date

Can't find your dates?
Get in touch to craft a Bespoke itinerary or request an additional date to Privatize.

What's included

Accommodation & dining

All breakfasts, lunches and dinners as indicated on the itinerary.

All accommodation as indicated on the itinerary.

Thoughtfully selected local wines, beers, cocktails or non-alcoholic beverages with all meals.

Active essentials 

Choice of bike as appropriate for terrain (see below), equipped with handlebar bag and helmet.

A biodegradable B&R water bottle.

Use of a smartphone with downloaded GPS routes provided via RideWithGPS.

Guided services & gratuities

Services of B&R guide(s).

All special events, private tours, guest experts and entrance fees.

All gratuities for baggage, porters and hotel services.

Transportation & logistics

Transportation from pick up to drop off.

Baggage transportation.

Access to the B&R support van every step of the way.

What's Not Included: International flights, travel protection, gratuity for your B&R guides.

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This trip is carbon neutral. Learn more about our Sustainability commitment.

Our meals were exceptional, and our guides really made the trip!

It's hard to go wrong in Tuscany, and Butterfield & Robinson trips are our favourite kind of low-stress, active trips. Our meals were exceptional, and our guides really made the trip!

— Sarah W; Seattle, WA

Experience Designer

Good to know

Rides
Rides

Our daily routes include plenty of challenging up and downhills. For non-avid cyclists, consider an e-bike for extra support.

Wine
Wine

Given the emphasis on wine, this trip is perfect for those who enjoy savouring fine drinks.

Packing
Packing

Tuscany can have variable weather throughout the day in October. We recommend packing a Gore-Tex raincoat to stay comfortable and dry.

Food
Food

October in Tuscany offers the region’s most delicious seasonal treasures, like porcini mushrooms, truffles, and squash.

Why choose a Small Group 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 all the planning is taken care of for you. All you need to do is enjoy.


Active Exploration

From emerging destinations to iconic sights, B&R trips show you the world in a new way on our expertly developed cycling, walking and hiking routes. Travelling through historic villages and romantic vineyards and up to striking viewpoints, our routes offer a variety of challenges for every activity level.


Friends for Life

Your fellow travellers are as passionate and curious about the world as you are, which means the conversations and laughs will be as free flowing as your drink of choice. Don't be surprised if your group starts planning a reunion before the trip is done.


Room for Surprises

We love a plan, but we adore a spontaneous moment even more. Whether it’s an impromptu al fresco meal or a moon-lit musical performance, our advice is to expect the unexpected.

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