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
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.
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.)
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.)
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.)
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.)
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.)
Day 6
Enjoy a final breakfast at the hotel before the drive to the Florence train station. Buon Viaggio.
Rendezvous
Airport City: Rome
Trip Start: The St. Regis Florence
Time: 9:00am
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
Borgo San Felice
Location: Chianti, Italy
Rosewood Castiglion del Bosco
Location: Montalcino, Italy
Dates & availability
Dates
Price
per person, double occupancy
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.
This trip is carbon neutral. Learn more about our Sustainability commitment.
Experience Designer
Good to know
Rides
Our daily routes include plenty of challenging up and downhills. For non-avid cyclists, consider an e-bike for extra support.
Wine
Given the emphasis on wine, this trip is perfect for those who enjoy savouring fine drinks.
Packing
Tuscany can have variable weather throughout the day in October. We recommend packing a Gore-Tex raincoat to stay comfortable and dry.
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.
Speak to an Expert