We Bike Tuscany

Recommended in
Lonely Planet Florence &
Tuscany travel guides
Your Tuscan Sun


This is a great bike tour starting in Greve in Chianti and ending six days later in Rapolano Terme.

You'll bike on back roads reaching the most beautiful spots of the Chianti and the Crete Senesi, with guided tours at the castle of Meleto, Siena, and the Abbey of Monte Oliveto Maggiore.

Van support, top class hotels, wonderful dinners in renowned restaurants, wine tasting, and thermal bath are all included in this unforgettable journey under the Tuscan Sun.


$4580 per person

  • Duration: 6 days/5 nights
  • Distance traveled: 8-25 miles per day.
  • Area: Chianti
  • Nearest city: Florence, Siena
  • Places visited: Tuscany, Italy
  • Tour type: Road touring
  • Skill level: Advanced
  • Season: April - October
  • Number of participants: 2-7
  • Minimum age: 16
  • Fully guided: yes
  • Support vehicles: yes
  • Transportation to start site: yes


Day 1

From Florence you'll be driven for about 20 kms to an ancient Tuscan Villa near the village of Greve in Chianti. Experience a warm up ride through the vineyards and your first taste of the Tuscan hills! In the evening you'll head for Greve. Enjoy the last Tuscan sun of the day as you drink aperitifs in the lovely piazza.
Dinner: On a terrace overlooking the square of Greve
Accommodation: Villa Corte di Valle

Day 2

This is your first full biking day - the Florentine Chianti at its best. You'll enjoy a great ride on back roads and dirt roads. Picnic on a hilltop overlooking Volpaia, a wonderful medieval village. After a visit, you'll head to Gaiole in Chianti where you can enjoy gelato in the piazza! Your second night will be spent at a medieval mill turned into a charming and distinctive inn.
Dinner: At a local restaurant
Accommodation: Ultimo Mulino

Day 3

By now you will be perfectly fit and used to the hills to face this short but tough ride into the very heart of the Chianti Classico region. You will see cypresses, vineyards, olive groves, and castles along the way to Castello d'Ama and Radda in Chianti.
Dinner: Ultimo Mulino
Accommodation: Ultimo Mulino

Day 4

Today is a big day. Traveling south, down to the outskirts of Siena, you'll see the land slowly changing turning from green into ochre. But first a jump into history! An unforgettable guided tour at a castle will make you feel like living in the 13th century. Yes, there's also a wine tasting here! Continue south then head to Brolio to soothe your thirst with another wine tasting (one of the best of the area), and a winery tour. Then a winding downhill will take you to the enchanting village of San Gusmè. After all this work it's time for a reward. In a panorama as far as the eye can see, a long drive of imposing century-old cypress trees leads to a magnificent 17th century villa. This is where you will spend your fourth night in Tuscany.
Dinner: Free night with dinner on your own
Accommodation: Borgo San Felice

Day 5

From Borgo San Felice a beautiful ride (mostly downhill this time!) will lead you to Siena, the capital of this land. A two-hour private guided walking tour is waiting for you here. You'll learn everything about this incredible town and all its secrets. Then you'll have a van transfer back to your Villa.
Dinner: Local restaurant
Accommodation: Borgo San Felice

Day 6

Head further south today into the Crete Senesi, a land where poets and artists of all times have always found inspiration. You'll bike to Monte Sante Marie through one of the most beautiful scenic roads in Tuscany. After a visit to the village of Asciano, we head to Rapolano Terme where a rewarding super-extra relaxing bath in the thermal spring will help you to take off the fatigue of six days of hard work!


  • Pick up/drop off in Florence or in the surroundings
  • Accommodations at the best Tuscan Villas and inns of the region, all with pools
  • All breakfasts, one picnic lunch, cold drinks and snacks along the way
  • Four dinners with unrestricted menus, one free night for dinner on your own
  • Maps and detailed route directions
  • Van support and baggage transfers
  • Guided tour at winery and two wine tastings
  • Private guided walking tour of Siena performed by a local licensed guide
  • 27 Speed high quality hybrid bikes, helmets, water bottles and handlebar bags
  • Small groups for personalized service


Please send us an email if you need more info. We will reply within 48 hours.