The Bikes
On this trip you’ll be riding a customized B&R hybrid with flat bars. We also equip you with a handlebar bag, helmet and water bottle. See Equipment Details
- Type
Private
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
Self-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 4
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.
Your pace, our routes, Italy's pleasures
Explore Pienza and Siena with Carlo, a Tuscan native, and expand your palate with local wine-maker Elisabetta. From tiny Montefollonico to lordly Montepulciano, Tuscany embodies the good life. Revel in a cyclist’s paradise as our friends reveal its many charms.
per person from Based on 4 ppl double occupancy
Request your date for exact pricing 6 Days / 5 Nights
Pienza to Florence Start Planning Share This Trip View Our
SAMPLE ITINERARIES
- 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.
Request your date for exact pricing 6 Days / 5 Nights
Pienza to Florence Start Planning Share This Trip View Our
SAMPLE ITINERARIES
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 for your request. One of our travel experts will reach out shortly to start planning your dream trip.
How do you want to travel?
Go Bespoke
Tuscany Self-Guided Biking Private
Ready-to-Book private tours are designed to be enjoyed off-the-rack, but there is room for minor adjustments to fit the trip to your needs. If the gap is too great, then we’d be happy to tailor-make you a Bespoke trip from scratch. Simply tell us a few details about your group and select your preferred date. One of our Trip Designers will spring into action, confirming the details or exploring alternatives, over the next 48 hours.
Best Time to Visit
| January | April | July | October |
| February | May | August | November |
| March | June | September | December |
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
Meet Carlo, your local guide and Tuscan native who will lead you on an insightful visit of Pienza, a remarkable Renaissance gem. Head out on your bikes for a wonderful loop ride and enjoy dinner tonight at the hotel's vibrant restaurant.
The highlight of today's loop ride is the majestic Montepulciano, a medieval and Renaissance hill town where wine shops line the cobblestone laneways.
Embark on a magnificent pedal to Siena through the beautifully stark crete hills, perhaps Tuscany's most iconic stretch of road. Early this evening you’ll be met by Siena’s leading wine expert for a private wine tasting at his enoteca just steps from your hotel.
Today Carlo will join you again to lead you around Siena to illuminate its medieval wonders. This afternoon ride through the beautiful vineyards and rugged forests of Chianti.
Enjoy a loop ride through the rolling hills, passing through the well-known villages of Gaiole and Radda, both postcard-picturesque. Early evening enjoy an aperitivo on the hotel’s terrace overlooking the vine covered hills in every direction. Dine on the property or at our suggested restaurants just a short walk or taxi away from the hotel. Cin cin!
Linger over breakfast before a private car takes you to Florence city centre or airport.
CLOSE 
Want to see a full
day-by-day breakdown?
Click below
day-by-day breakdown?
Click below
Pedal peacefully.
Hotels
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.View hotel website »
Relais degli Angeli, Siena
Positioned in the heart of beautiful Siena, the Relais degli Angeli is an elegant historic building boasting luxury interiors with painted ceilings and jewel trim. The spacious terrace is the perfect to spend cocktail hour as the sun sets in the background. View hotel website »
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. View hotel website »
Fantastic trip! The organization, accommodations, local experts and logistics were spot on, as I've become accustomed to with B&R.
— Felicia Smith
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 4
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 and one dinner
- A private guided tour of Pienza
- A private guided tour of Siena
- A private wine tasting
- 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 baggage transportation
- Drop-off transportation to Florence
- GPS-enabled device pre-loaded with each day’s route(s)
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.
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