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!
- Type
Small Group
XSmall Group
The right number of like-minded travellers to make new friends.
Private
Your dates. Your group. Our expertly-designed itinerary.
Custom
Tailored to your interests, a bespoke travel experience.
- Support
24/7 Guided
XSelf-Guided
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.
Daytime Guided
Throughout the day, a knowledgeable local guide provides insider access and expert tips. At night, you can explore and dine on your own.
24/7 Guided
Our B&R guides are with you throughout, anticipating needs, translating languages, providing advice and—above all—facilitating fun.
- Difficulty Level
Level 3
XLevel 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.
Explore Italy's most exalted region
Savour a feast prepared by our local friends—and enjoyed in their backyard. Take in the evening energy of Siena and join in the laughter radiating from the piazza. Dine under the stars, at a winery, on a meal prepared by our private chef. We don’t just visit Tuscany—we bring its story to life.
Trip designed by Travel Expert Courtney Mundy
View Courtney’s Profile Video: Why We Love Tuscany BikingCLOSE X
per person from
Florence to Florence Share This Trip request a
DETAILED ITINERARY
- AUD
- BRL
- CAD
- EUR
- GBP
- USD
X
Currency Conversion
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.
Single supplement:
Prices vary based on departure season. 6 Days / 5 NightsFlorence to Florence Share This Trip request a
DETAILED ITINERARY
CLOSE
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.
Thank you. Check your email for details on your request.
Select Your Trip Dates
Small Group Dates Go Bespoke
Go with the right number of like-minded travellers to make new friends.
CHOOSE YEAR
Guaranteed Departure Limited Space Adult Family Trips
Limited Space
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.
CHOOSE DATES
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 QUOTEDay 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.
CLOSE 
Want to see a full
day-by-day breakdown?
Click below
day-by-day breakdown?
Click below
Sip and then dip.
Hotels
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 honesty, 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
Level 3
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.
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
- A handlebar-mounted 7” Samsung Galaxy tablet with preloaded GPS bike routes
- B&R biodegradable water bottle
- All transportation from rendezvous to drop-off
- All baggage transportation
- All gratuities for baggage, porters and hotel service
The Bikes
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
Road Bike
Hybrid Bike
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
Your dreams—realized.
Your expectations—exceeded.
And your mind? Totally and utterly blown.
Your expectations—exceeded.
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.
Loading...
B&R: Fuel your Wanderlust. Join more than 70,000 fellow wanderers. Sign up for our newsletter to receive insights and advice from our travel experts.
Slow down to see the world
© 2025 Butterfield & Robinson Inc. All Rights Reserved