Small Group
Tuscany Wine Country Biking
A Renaissance escape
6 Days, 5 Nights
Maximum Group Size
16
Activity Level:
B&R Activity Levels
Priced per person from
$6,995 USD
Single Supplement: $2,000 USD
Jan
Feb
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Oct
Nov
Dec
Carbon Neutral Trip
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.
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
Our first ride will immerse us in the heart and beauty of the Chianti Classico region. Pedal through gently rolling hills and breathtaking landscapes, stopping at a cozy restaurant for lunch. Challenge yourself to a longer afternoon ride, or head back to the gorgeous hotel to relax. This evening, indulge in our first dinner together at the hotel.
Activity:
38 km (24 mi.) bike ride through the heart of the Chianti Classico | Elevation gain: 522 m (1,712 ft.)
Optional ride | 46 km (29 mi.) | Elevation gain: 742 m (2,435 ft.)
Day 2
Pedal along country roads, through vineyards and silvery olive groves to a local trattoria for lunch. Tonight, we’re off to a family-run farm and winery where Marta, the owner, will host us. Nestled in the vineyards, we'll enjoy pizza and biodynamic wines.
Activity:
40 km (25 mi.) loop ride through finely curated vineyards and silvery olive groves | Elevation gain: 490 m (1,609 ft.)
Day 3
Today’s ride is one of the most beautiful of the week-we'll pedal through the crete leading to Siena, with the option to make this a Century Ride (100 km, 62 mi.). We’ll pedal into the villa of our old friends who will share their love-story with Tuscany over an unforgettable lunch.
Activity:
42 km (26 mi.) challenging ride through the crete senesi with scenery that justifies the effort | Elevation gain: 700 m (2,300 ft.)
Optional Century Ride | 100 km (62 mi.)
Day 4
We'll on our bikes this morning and pedal through the foothills below Montepulciano, with picturesque views of the temple of San Biagio in the distance. After one final hill, set off to explore Cortona’s winding streets and shops. Sit back by the pool before a relaxing evening dining at the hotel.
Activity:
41 km (25 mi.) ride through the Val di Chiana countryside
Day 5
Set out on a quiet ride through Umbria’s Valle del Niccone, eventually pushing back uphill for lunch in an agriturismo with our friend Francesco. Savour delicacies made with the freshest ingredients before hopping back on the bikes. This evening, we have been invited to a private tasting and dinner in one of the region’s top wineries for a perfect end to our week.
Activity:
54 km (35 mi) loop from Piazzano | Elevation 963 m (3,160 ft.)
Day 6
After one final breakfast at the hotel, we’ll bring you to the train station in Florence for onward travels.
Rendezvous
Airport City: Rome
Trip Start: Grand Hotel Minerva
Time: 8:30am
Farewell
Airport City: Rome
Trip End: Santa Maria Novella train station
Time: 12:00pm
* Itineraries are subject to change. Please confirm exact Trip Start and Trip End locations upon booking.
Featured stays
COMO Castello Del Nero
Location: Chianti, Italy
Casa Newton
Location: Tuscany, Italy
Villa di Piazzano
Location: Cortona, 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.
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.
Food
October in Tuscany offers the region’s most delicious seasonal treasures, like porcini mushrooms, truffles, and squash.
Packing
Tuscany can have variable weather throughout the day in October. We recommend packing a Gore-Tex raincoat to stay comfortable and dry.
Pre and Post trip
This trip drops off at Florence’s train station, a central location that makes it easy to extend your trip in other Italian regions.
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.
