Tuscany Tuscany Self-Guided Biking

Tuscany Bike Tour

Structured Independence in B&R Style

This Tuscany bike tour combines three hallmarks of any B&R itinerary—excellent hotels, beautiful riding routes and superb custom-fitted bicycles—we provide the freedom of pacing each day just the way you like. We arrange some can’t-miss meals and events, transfer your bags and equip you with all the information you’ll need to craft the trip you desire. A picnic of panini or a gourmet lunch, a walking tour of historic Siena or a dip in the pool—the choices are yours.

Trip Details

Sinalunga to Florence
6 Days / 5 Nights

Price per person from: $3,295
Single supplement: $1,000
Request your date for exact pricing

Best Time to Visit

  • Jan
  • Feb
  • Mar
  • Apr
  • May
  • Jun
  • Jul
  • Aug
  • Sep
  • Oct
  • Nov
  • Dec

Day by Day

Pedal a warm-up loop through the farmland of the Val di Chiana and take in an optional ride to picturesque Lucignano before dinner at the intimate Locanda dell’Amorosa.

In the heart of the stunning crete hills, visit tiny Renaissance town Pienza for lunch before looping back via Montepulciano’s vino nóbile vineyards and Trequanda’s shimery olive groves.

Ride the SP438 road to Siena, with an optional detour to the historic monastery at Monte Oliveto Maggiore. Enjoy a lesson in Tuscan reds before dining in any of the city’s wonderful establishments.

Start the morning with a guided walking tour of the Duomo and Piazza del Campo. Pedal into the Chianti hills before arriving at your castle away from home, just steps from Gaiole-in-Chianti.

Loop through quintessential hill towns like Radda-in-Chianti. Spend the afternoon lounging in one of the hotel’s two pools with its picture-perfect views of the Chianti countryside.

Linger over breakfast before a private car takes you to Florence city centre or airport.


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 »

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 »

Activity Level


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.


The Bikes

You can't enjoy a great biking trip without a really great bike. On this trip you'll be riding a customized hybrid or a racing bike with drop bars. We also equip you with handlebar bag, helmet and water bottle.

What's Included

  • All hotel accommodation
  • All breakfasts and one dinner, including wine
  • 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
  • Transportation to drop-off in Florence

At Your Service

We take pride in choosing guides who are not only exceptional travelling companions, but who’ll go far beyond the call of duty to ensure an unforgettable experience.

Learn more about our guides »


“Fantastic trip! The organization, accommodations, local experts and logistics were spot on, as I've become accustomed to with B&R.”

— Felicia Smith,
Tuscany Self-Guided Biking 2011

Tuscany Self-Guided Biking

Notes from the Road

Insider’s Guide: Florence Hotels

Much like the Accademia does for David, a slew of well-appointed Florence hotels will make you feel like a masterpiece during your stay.
more »

Insider’s Guide: Things to Do in Florence

Whether you've got a few hours or a full day, there are plenty of things to do in Florence, home to some of the world's greatest pieces of art.
more »

In Deep: Siena

A perfect medieval time capsule, enlightened zoning restrictions have helped preserve the palaces and churches of Siena like nowhere else in Italy.
more »

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