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.
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
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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.
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* Trip elements may be adjusted on smaller group sizes.
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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 di Merse 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
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. When tasked with restoring the property the overarching theme was clear: honour the natural wonders of the hotel and the iconic countryside. Arriving to the main building via the grand cypress-lined lane re-enforces the message; this hotel is timeless.
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.
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.
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!
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
On this trip, you can choose between a customized hybrid with flat bars or a road bike with drop bars. We also equip you with a handlebar bag, helmet and water bottle. See Equipment Details
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.
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
Insider’s Guide: Florence Hotels
Insider’s Guide: Things to Do in Florence
In Deep: Siena
Rave Reviews: Tuscany
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