At B&R we make it incredibly easy for you to journey with your friends, family, colleagues or on your own. Create your own private trip by taking over one of our dates—or we can request a fresh one. Prices are sliding scale to suit the number of travellers. Interested in tweaking the itinerary? We can do that too. Ask us for details!
The right number of like-minded travellers to make new friends.
Your dates. Your group. Our expertly-designed itinerary.
Tailored to your interests, a bespoke travel experience.
Combines the hallmarks of any B&R itinerary (excellent hotels and beautiful routes) with the freedom of pacing each day exactly the way you like.
Throughout the day, a knowledgeable local guide provides insider access and expert tips. At night, you can explore and dine on your own.
Our B&R guides are with you throughout, anticipating needs, translating languages, providing advice and—above all—facilitating fun.
- Difficulty Level
Level 1: Occasional
Biking – 40-50 km (25-30 mi.) a day over relatively flat terrain with a few small hills—all very manageable for people trying their first biking trip.
Walking – 6-10 km (4-6 mi.) a day on country lanes, footpaths and coastal or forest trails, all on relatively flat terrain, perhaps with an occasional hill.
Level 2: Recreational
Biking – 40-50 km (25-30 mi.) a day over terrain that’s relatively flat but will include inclines and the occasional climb or two.
Walking – 8-12 km (5-7 mi.) a day over relatively flat terrain, with occasional steeper climbs.
Level 3: Enthusiast
Biking – 40-50 km (25-30 mi.) a day in gently rolling countryside, with occasional longer climbs to points that are well worth the effort.
Walking – 11-15 km (7-10 mi.) a day over rolling terrain on a variety of surfaces. Most days, one or two steeper climbs to spectacular viewpoints or places of interest.
Level 4: Avid
Biking – Roughly 50 km (30 mi.) a day in consistently rolling countryside, with repeated climbs and longer options available.
Walking – 11-15 km (7-10 mi.) over terrain that varies between rolling and hilly, with a few steeper climbs.
Level 5: Expert
Biking – 50-60 km (30-45 mi.) a day over both level and tougher, hillier terrain with multiple 100 km (62 mi.) options. The routes are designed for avid cyclists and include plenty of chances to push yourself.
Walking – 11-15 km (7-10 mi.) a day over fairly hilly terrain offering lots of challenges. Routes are along high meadow paths and/or well-maintained cliffside or alpine trails, with a few steep ascents to make you feel invigorated.
Experience the Strade Bianche route
While we’ve been travelling to Tuscany for decades, this is the first release in our challenging trip series. We’ve paired famous race trails with the crème de la crème of gravel bikes. The payoff is not just the challenge of riding along gravel with heart-pounding ascents and thrilling descents, but also the unbelievable places it takes you.
See new safety measures and cancellation policies for our Small Group trips here.
Trip designed by Travel Expert Courtney MundyView Courtney’s Profile
Converted from USD based on the latest exchange rate. Final amount and payment will be in USD. Final conversion rate is determined by your bank.
Florence to Siena Share This Trip request a
Ready for Adventure?
Simply fill out this form to view the itinerary. We’ll also email you a copy so you can refer back to it later.
Select Your Trip Dates
Go with the right number of like-minded travellers to make new friends.
This departure is either sold out or almost fully booked. With a deposit, we will request additional rooms from our hotels where possible.
Adult Family Trips
These are departures we have designated as appropriate for families with kids in their late teens and 20s.
Have a custom trip designed exactly to your interests. Like a tailor making a bespoke suit, it will fit you perfectly.
Our Bespoke trip designers are a talented bunch who can craft unforgettable experiences for your specific group—and working within your needs and budget.
Get in touch with a Trip Designer to begin planning your perfect vacation.REQUEST A QUOTE
Day by Day
Out of the city, we travel to the heart of Chianti Classico. Ease into rugged terrain along a famed race trail before sipping on the region's best wine, paired with fresh cuisine. Benvenuto!
Go all-in on gravel today! Blaze through the paths and grind over challenging inclines before slowing down to see a stunning vineyard — a private experience hosted by old friends awaits.
Pedal on flat ancient roads before kicking it up a notch in the rolling valley of Val d'Orcia. Choose your challenge this afternoon before we say 'Salute!' to the mesmerizing landscape.
Deeper into the lush valley our ride leads us up to a famous medieval hilltop town for lunch. Tonight, steep in old stories of Pienza and dine in a magnificent garden.
Back on gravel country roads explore iconic hilltop towns boasting unparalleled views and regional cuisine. Tonight, we celebrate conquering the first B&R Challenge Experience!
After a relaxing breakfast, it's onward to Chiusi Chianciano Terme train station where we'll part ways. Arrivederci!
Iconic tour, incredible bikes.
La Bandita Townhouse, Pienza
La Bandita Townhouse is a boutique hotel tucked inside the historic center of Pienza, a tiny Renaissance village in southern Tuscany. Its 12 guest rooms blend contemporary design with wood beam ceilings, parquet floors and exposed stone walls that are centuries old. A perfect perch to enjoy the local rhythms of life in a Tuscan hilltop town.
Castello di Spaltenna, Gaiole in Chianti
A sophisticated manor, Castello di Spaltenna offers an exclusive atmosphere amidst a unique landscape. Located in the heart of the Chianti Classico wine region, the manor’s luxurious guestrooms offer any possible comfort along with wonderful views over the valley. From the grassy terraces, guests can enjoy the calm of the countryside and beauty of the surrounding landscape.
Our guide was awesome and we loved everything about our trip, especially the hotels included in our tour. #BestVacationEver— Scott
The riding on this trip is aimed at the confident and strong rider who likes to climb! Some of the hills can be avoided with the occasional transfer, and we will be riding a mixture of gravel and paved roads. The bikes are superb on both surfaces but if you bring your own pedals then MTB shoes are the best option in case you need to walk a section.
What’s included? Everything you need. Plus everything you’d
want. Plus a few things you never knew you wanted ‘til you got them.
In a word: everything. In ninety words? Signature B&R guides; local experts; unique, unforgettable biking and walking routes; private tours; authentic local cuisine; lessons and demonstrations; local artisanal wines; wine tastings; all victuals and libations; all the endorphins you can handle; new insight; interesting, fun and like-minded travel companions; a feeling of total freedom. In short: an extraordinary, hassle-free journey of discovery.
- Five nights hotel accommodation
- Meals included as indicated on itinerary
- Gratuities for porters, hotel and restaurant service
- All special events, private tours, guest experts and entrance fees
- Use of a 3T Exploro full aero gravel bike equipped with 650B wheels
- Detailed routes and directions on a dedicated bike computer
- Nutritious and energy packed snacks for riding and electrolyte supplements
- All transportation from rendezvous to drop-off
- All baggage transportation
This particular gravel bike has taken design to the next level. Each curve and detail contributes to making the Exploro 3T an exceptional full-aero bike. Why does full-aero matter? Well, as our expert friends say at 3T, it helps you go slow faster. The sleek, aerodynamic frame helps you cut through the air making for an incredible ride. The geometry and tire size ensures the ride’s as comfortable on gravel as it is on asphalt. Of course, we’ll also equip you with a helmet, bike computer, and water bottle.
Sometimes your B&R trip simply isn’t long enough! Extend your stay for the best vacation possible. If you wish to spend a few days in region either before or after your official B&R trip, and need assistance making those plans, your B&R Travel Advisor can help.
Call us to create an independent travel experience that fits your needs—we can also arrange for a local guide.
Spend more time in Florence
Florence is one of the world’s cultural and historic capitals and merits a day’s visit at the very least. We’ll happily book your choice of Florence's multitude of hotel options, or recommend a city guide if you want an insider’s tour of the city.
More Trip Inspiration
And your mind? Totally and utterly blown.
We craft extraordinary experiences, tailor made to meet
your every need, with every stitch of every day crafted
just the way you want it. Learn more about Bespoke
Notes from the road, on the B&R blog.
Gravel Biking in Tuscany: Q&A with Edoardo Bausani
A Walking Tour of Florence
The 19 Best Shops in Florence
8 of Our Absolute Favourite Tuscan Wines
5 Secrets to Enjoying Tuscany
Reading for the Road: Books About Tuscany
The 7 Most Charming Towns in Tuscany & Umbria
The Best Way To Experience Tuscany: By Bike
A Florentine Staycation: Exploring Florence’s Oltrarno Neighbourhood
Whoooooa Nelly! The Drama, Majesty and Excitement of Siena’s Palio
In Deep: A Brief History of Montepulciano
In Tuscany, Home is Where the Hospitality Is
Travel Two Ways
In Tuscany, A Resplendent Reward
The Best Hotels in Florence (2020)
What to See and Do in Florence According to a Local
In Deep: Siena
© 2021 Butterfield & Robinson Inc. All Rights Reserved