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.
We use premium hotels that are unique expressions of the region. Often they’ve had a previous life as a monastery or a castle, but in every case they offer an exceptionally comfortable stay.
These are stylish 4-star properties that offer a casual and comfortable stay. Often without a 24-hour concierge or room service, they tend to be smaller family-run hotels that are perfect for the region.
“I can’t say I really ‘work out,’ but I’m in good shape and am relatively active.”
“I enjoy a good walk or ride, and feel comfortable while on the move.”
“I get moving at least once a week, and don’t mind a little sweat.”
“I get moving a few times per week and enjoy some exertion.”
“I want to feel invigorated each day and going hard is how I like to do that.”
Explore Italy's most exalted region
One of Italy’s most beautiful and beloved regions, Tuscany has earned every accolade and exaltation bestowed upon it. While some come for the sun and to be seen, we’ve got better plans: sumptuous spreads laid out by close friends, behind-the-scenes tours of medieval towns, wine tastings with award-winning oenologists, and spectacular biking through picturesque hills. As much as we appreciate the comfort of its fine hotels, it’s the rustic charms that capture our imagination. Tuscany is magical. Believe the hype.
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Florence to Florence request a DETAILED ITINERARY
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Go with the right number of like-minded travellers to make new friends.
Limited Space / Waitlist
This departure is either sold out or almost fully booked but with deposit we will request additional rooms from our hotels where possible.
Tuscany BikingBOOK NOW
Your private Tuscany Biking trip
FROM (USD) †
|† Double occupancy|
* Trip elements may be adjusted on smaller group sizes.
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
Ride to Montisi and Pienza, with lunch at olive guru Signor Bindi’s estate. Take in the sunset with a glass of prosecco in a romantic courtyard.
Spin across the Val di Chiana countryside to a very special lunch at Casa Lungarella. Tonight, we regroup for an informative tasting of Tuscan reds before head to the neighbouring town of Bettole for dinner at Chef Walter’s villa.
Ride the quintessential Tuscan road through the crete leading northwest to Siena. Enjoy an evening guided city walk followed by a night on your own to explore the town.
Pedal out into the vine-covered hills of Chianti and try its namesake wine in the place it was invented. Enjoy a lazy afternoon relaxing in the hotel’s two swimming pools before dinner.
Spend the morning winding through iconic Tuscan villages such as Radda and Gaiole-in-Chianti. Finish off with a visit to a private wine estate for a tasting and dinner prepared by an exclusive chef.
Enjoy a farewell breakfast at the hotel in Chianti, then arrivederci in Florence.
Sip and then dip.Request a Detailed ItineraryTuscany Biking
Locanda dell'Amorosa, Sinalunga
When Carlo Citterio set out to restore the property that has been in his family for centuries, his first step was to convert the stables into a superb restaurant. Soon other buildings were refurbished: your bedroom may well have been a clock tower or the hunting lodge. Literally translated as “lodging of romance,” the Locanda exudes just that, and has long been a favourite B&R retreat. View hotel website »
Grand Hotel Continental, Siena
Located in the heart of historical and vibrant Siena, the luxurious five-star Grand Hotel Continental is a converted 17thC palazzo, originally designed by the baroque architect Giovanni Fontana. Ponder the history of this majestic, beautifully frescoed building as you sip prosecco in the courtyard or take advantage of its location by heading out to explore Siena’s bustling scene. View hotel website »
Hotel Le Fontanelle, Pianella
Carefully restored over the course of a decade, Hotel Le Fontanelle blends classic medieval Tuscan architecture with thoroughly modern amenities and exceptional service. The guestrooms are comfortable and spacious, and downtime options at the hotel include a full spa and tranquil indoor and outdoor pools, all of which afford scenic and splendid views of the Chianti hills. View hotel website »
The guides, Sarah and Giacomo, were extraordinary. Fantastic people, very warm yet very professional. Most memorable moment was cycling in the rain and feeling completely secure. In all honestly, this experience was probably one of the best my husband and I have ever had.— Marina Piller
Cycle past the rolling vineyards of Chianti and up the crete—clay hills—on the approach to Siena on this luxurious biking tour through Tuscany’s legendary landscape.National Geographic Traveler
We never wanted to be the biggest travel company in the world, just the best.
— George Butterfield
We cover hilly terrain, but we’ve kept the average daily distance to a moderate 38 km (24 miles). As much as possible, we avoid the steepest climbs, but please be aware that Tuscany is hilly.
“I bike about once a week at home.”
Gently rolling countryside, with occasional longer climbs to points that are well worth the effort. Layover days accommodate varying preferences.Read more on our Activity Levels
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.
- All hotel accommodation
- All breakfasts, three lunches, four dinners, including wine
- Services of B&R guide(s) and support van
- All special events, private tours, guest experts and entrance fees
- Use of a customized hybrid or a racing bike with drop bars, equipped with handlebar bag and helmet
- Detailed maps, route suggestions and water bottle
- All transportation from rendezvous to drop-off
- All baggage transportation
- All gratuities for baggage, porters and hotel service
You can’t enjoy a great biking trip without a really great bike. On this trip you’ll be riding a customized hybrid. We also equip you with handlebar bag, helmet and water bottle. Check out our bikes
Notes from the road, on the B&R blog.
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
Insider’s Guide: Florence Hotels
Insider’s Guide: Things to Do in Florence
In Deep: Siena
Rave Reviews: Tuscany
Tuscany Biking: The Tour of a Lifetime
Video: Three Minutes in Tuscany
An Enchanting Encounter at Villa La Foce
A Few Lessons in Family Travel
Dinner with (the Woefully Underdressed, if Impressively Sculpted) David
Vines 101: Chianti Wine
Cuisine 101: An Introduction to the Cuisine of Tuscany
Immersion Kit: What You Need to Know About Tuscany
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