We Bike Tuscany

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Lonely Planet Florence &
Tuscany travel guides
Tuscany Challenge


The beauty of Tuscany seen from a super-fast carbon frame road bike. If you're a "serious" cyclist looking to challange yourself, you will be rewarded with a biking experience like no other as you discover a magical and very special part of the region that (for now at least) remains somewhat "hidden." This is the Maremma, a biker's paradise, a wine and food-lover's paradise -- and it's where we begin our adventure. Near the coast of southern Tuscany, with the sapphire blue Mediterranean always in view, you'll pedal through gorgeous countryside, perhaps alongside professional cyclists as they train for the Giro d'Italia or Tour de France (this is also international training ground). Of course for us, it's not all work. We'll stop occasionally to visit a winery and sample some of the most reknown reds of Italy, if not the world (optional stops include Ornellaia and Sassicaia). In the evening, dine in our favorite restaurants of the area. On Day 3 you'll rack up the miles as we transfer to the Val d'Orcia. The "Terra di Siena" with its lone cypresses, lunar landscape and golden ochre is classic Tuscany. Not so "hidden" as the Maremma, perhaps, but certainly not to be missed. And our rides will be no less challenging as we we bike one-of-a-kind routes to the enchanting medieval villages of Pienza, Montalcino and Bagno Vignoni, to name just a few. On Day 6 another transfer ride takes us to the lush green countryside of Chianti with its vineyards, olive groves and castles dotting the hills. Winding down for our final day, we pedal a more relaxed pace into Florence, reaching the finish line at Piazzale Michelangelo. The breathtaking view of the city will be the background for our group photo and a congratulatory glass of spumante. You've earned it!


$4980 per person

  • Duration: 7 days/6 nights
  • Distance traveled: 30-50 miles per day
  • Area: Maremma, Val d'Orcia, Chianti
  • Nearest city: Livorno, Siena, Florence
  • Places visited: Bolgheri, Castagneto Carducci, San Galgano, Pienza, Montalcino, Radda in Chianti, Florence
  • Tour type: Road biking
  • Bike type: Road bike
  • Skill level: Advanced
  • Season: April - October
  • Number of participants: 2-8
  • Minimum age: 16
  • Fully guided: yes
  • Support vehicles: yes
  • Transportation to start site: yes


DAY 1 - Warm up ride 14.9 miles

Pick up in Florence, train station or airport and transfer by van to the town of Castagneto Carducci (Maremma). Check in at hotel, light lunch and bike fitting before a warm up ride in the area. Visit the medieval town of Bolgheri and enjoy a private wine/olive oil tasting and winery tour at Castello di Bolgheri in the afternoon.

Dinner at Enoteca Osteria San Guido, night at Hotel Zi Martino - Castagneto Carducci

DAY 2 - Loop ride 51.1 miles

One of the most beautiful rides in Italy. Today we head towards Sassetta and Suvereto, biking on the edge of a neverending gently rolling country road offering spectacular views of the Mediterranian sea.

Dinner at Ristorante Ugo - Castagneto Carducci, night at Hotel Zì Martino.

DAY 3 - Transfer ride 45.3 miles

Transfer ride from Castagneto to the unique and hauntingly beautiful abandoned Abbey of San Galgano.

Dinner at Agriturismo San Galgano, night at Agriturismo San Galgano

DAY 4 - Transfer ride 41.3 miles

Transfer ride from San Galgano to the hilltop Reinassance town of Pienza, recently designated "Worldwide Heritage of Humanity" site by UNESCO. See the land slowly change, turning from green to ochre before arriving at your final destination. Cheese tasting along the way.

Dinner at Trattoria Fiorella - Pienza, night at Relais Il Chiostro di Pienza

DAY 5 - Loop ride 45.3 miles

Loop ride in Val d'Orcia. We head to Montalcino where a Brunello tasting and guided tour at Barbi Winery (one of the area's top producers) awaits. From there, head south towards the Abbey of Sant'Antimo for a brief but unmissable stop. On the way back to Pienza, visit the village of Bagno Vignoni, famous for its Roman thermal baths in the middle of the piazza.

Free night for dinner on your own, night at Relais Il Chiostro di Pienza

DAY 6 - Transfer ride 54.3 miles

From the lunar landscape of the Val d'Orcia, head north to the lush green vegetation of the Chianti. We bike surrounded by vineyards and olive groves to our destination near Radda in Chianti.

Dinner at a favorite local restaurant, night at Hotel Ultimo Mulino - Radda in Chianti

DAY 7 - Transfer ride 40.3 miles

Transfer ride to Florence. Today's itinerary takes us further into the heart of the Chianti Classico region and along the roads of the Eroica, famed Tuscan bike race that takes place every October. You'll pedal through Radda, Castellina, San Donato, Panzano and Greve enroute to one of Italy's greatest and most fascinating cities.

Picnic/wine tasting at Locanda di Pietrafitta


  • Pick up/drop off in Florence or in the surroundings
  • Accommodations at 3-4 star inns, all with pools
  • All breakfasts, one picnic lunch, cold drinks and snacks along the way
  • Five dinners with unrestricted menus (wine not included); one free night for dinner on your own
  • Maps and detailed route directions
  • Van support and baggage transfers
  • Private guided tour at winery and three wine tastings
  • Cheese tasting
  • 20 Speed high quality carbon frame road 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.