Group or Custom Journeys

Starting at $7,500 Per Person

One of Italy’s most beautiful and beloved regions, Tuscany has earned every accolade and exaltation bestowed upon it. While some come for the sun and to be seen, we’ve got better plans: sumptuous spreads laid out by close friends, behind-the-scenes tours of medieval towns, wine tastings with award-winning oenologists, and spectacular biking through picturesque hills. As much as we appreciate the comfort of its fine hotels, it’s the rustic charms that capture our imagination. Tuscany is magical. Believe the hype.


Trip Highlights

  • Enjoy gourmet picnics in the Tuscan countryside midway through your rides.

  • Learn about the history of Italian wine in places such as private estates and Chianti vineyards.

  • Cycle through tiny villages such as Radda and Gaiole in Chianti.



DAY 1: 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.


DAY 2: 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 heading to the neighboring town of Bettole for dinner at Chef Walter’s villa.


DAY 3: 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.


DAY 4: 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.

DAY 5: 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.

DAY 6: Enjoy a farewell breakfast at the hotel in Chianti, then arrivederci in Florence.


Locanda Dell'Amorosa, Sinalunga

Castel Monastero

Hotel le Fontanelle, Pianella



Pricing starts at $4,995 per person, double occupancy.  Single supplement: $800.  Price varies based on date of journey.


  • All hotel accommodations

  • All breakfasts, four lunches and four dinners, including wine

  • Services of B&R guide(s) and support van

  • 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 special events, private tours, guest experts and entrance fees

  • All transportation from rendezvous to drop-off

  • All baggage transportation

  • All gratuities for baggage, porters, hotel service and local support

Tuscany Biking- Group Journey

Butterfield & Robinson

Learn More