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Tuscany Self-Guided Biking

Self-guided cycling

5 days

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Rating in Italy
Tour details
Destinations: Florence, Siena, Montepulciano
Type of adventure: icon-03.png Self-guided cycling
Guide language: English
Price: min $ 3495
Duration: 5 days
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  • Type


    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.

  • Support


    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.

  • Hotels


    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.

  • Level


    “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.”

    Click here for full details on each activity level »

Your pace, our routes, Italy's pleasures

With lush, rolling hills, medieval towns and meandering roads keeping it all together, Tuscany is a biker’s idyll. There is something eminently peaceful about riding through hilltop towns that have stood watch since the Middle Ages, passing vines tended by generations of winemakers, and savouring traditional cuisine made from the freshest and tastiest local ingredients. This is the region you imagine when you think of Italy; home to olive groves and cypress trees, Roman battlefields, Renaissance churches and charming villages—from tiny Montefollonico to lordly Montepulciano.

Trip designed by Travel Expert Courtney Mundy TRIP DETAILS per person from $3,495 USD
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Based on 4 ppl double occupancy
Request your date for exact pricing 6 Days / 5 Nights
Pienza to Florence request a DETAILED ITINERARY

Day 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.


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 in Siena
  • 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)
All tour descriptions and conditions are given in accordance with the information of Butterfield & Robinson
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Interesting facts
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Do you enjoy sweat breaking out on your forehead and your heart racing like mad as you find yourself half suspended in the air with the few thousand meters beneath your feet? I bet you are an avid climber looking for just another dose of thrill.