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.
“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.”
Embodying the finest of the region
Our Super Tuscan has been finely crafted for the traveller who delights in truly exquisite accommodation, exceptional wine and wants to suss out the idyllic countryside through a well-structured blend of activity—pedaling past hilltop hamlets, ambling among vines tended by generations of winemakers and (optionally!) rising to salute the famous Tuscan sun on a yoga mat. In between you’ll savour traditional cuisine made from the freshest ingredients. It’s a robust build. Fancy a taste?
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 Florence 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.
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.
Families with Adult Children
These are departures we have designated as appropriate for families with adult children.
Super TuscanBOOK NOW
Your private Super Tuscan trip
* 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
Meet your B&R guides in Florence and then head straight to the heart of the Chianti Classico region! Ride through gently rolling hills and breathtaking scenery arriving to a stunning lunch.
Join an optional sunrise yoga class before a morning walk through finely curated vineyards arriving to an intimate farm and winery tucked into the hills. The in-house chef teaches us a few tricks of the Italian pizza-making trade.
Consider morning yoga or initiate the day by bike leaving directly from the hotel and down toward the open countryside. Tonight, an energetic historian gives us an overview of Tuscany's historical significance, with a splash of politics.
Leave directly from the hotel pedaling through the crete, part of the expansive Val d'Orcia and one of the most stunning rides on the trip. Pause for a gourmet picnic courtesy of a local friend then return to the hotel to take advantage of the exceptional spa.
Today's walk is pure heaven as you cruise through the Sienese countryside. On return, an al fresco feast awaits. This evening you'll explore an exclusive winery on a hillside overlooking Montalcino. Salute!
Enjoy a final breakfast at the hotel before the drive to the Florence train station. Buon Viaggo!
Slip into Tuscan scenes
COMO Castello del Nero Hotel & Spa, Tavarnelle Val di Pesa
With 740-acres shored up around it, Castello del Nero is an enchanting vestige of the 12thC recently refreshed to perfectly suit the au courant travel set. Featuring 50 intimate rooms and suites, a Michelin-starred restaurant, an extensive wine cellar and numerous amenities—you’ll experience the best of antiquity and modernity. View hotel website »
Belmond Castello di Casole, Casole d'Elsa
Like a postcard from another time, Belmond’s Castello di Casole places you in the heart of rural Italy. With delightful interior detailing—wood-beamed ceilings, reclaimed antiques, stone walls—the hotel artfully blends comfort with historic charm. Arriving to the main building via the grand cypress-lined lane re-enforces the message; this hotel is timeless. View hotel website »
Rosewood Castiglion del Bosco, Montalcino
Simply stunning and overlooking a quiet corner of Tuscany’s Montalcino area, the beautifully restored 800-year old Tuscan estate boasts a Brunello di Montalcino winery, two restaurants, a spa and more on its 4,000-plus acres. The stylish touch of Massimo Ferragamo and his wife Chiara is apparent in all aspects of the design and layout of the property ensuring an elegant yet authentically Tuscan experience. 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 honesty, this experience was probably one of the best my husband and I have ever had.— Marina Piller
You will cover hilly terrain, but we’ve kept the average daily distance to a moderate 40 km (25 miles). As much as possible, our recommended routes avoid the steepest climbs, but please be aware that Tuscany is hilly!
“I go on a long walk once a week, and I don’t mind a little sweat.”
Rolling terrain on a variety of surfaces. Most days, one or two steeper climbs to spectacular viewpoints or places of interest.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, 5 lunches and 4 dinners, including local wine
- Services of a B&R guide(s)
- Detailed maps, route suggestions and water bottle and walking sticks
- All special events and private tours
- All indicated transportation from rendezvous to drop-off
- All baggage transportation
You can’t enjoy a great biking trip without a really great bike. On this trip you’ll be riding a customized hybrid or a racing bike with drop bars. We also equip you with handlebar bag, helmet and water bottle.
Check out our bikes
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