Assaggio Toscana

Savor “A Taste of Tuscany” as we Tour the Heart of Italy by Bike!

Our six-day, entry-level assaggio, or “tasting,” of Tuscany cycling tour is the perfect introduction to Italy’s beloved central region! Commencing in the terraced foothills of upper Val d’Arno on the river Arno, our route follows delightful, twisting roads, cooled by breezes in stone villages, and through fertile landscapes warmed by the famous Tuscan sun. We pedal through the dramatic Pratomagno range with their myriad microclimates, and tiny towns along byways lined with fig trees, vegetable gardens and vineyards. On the Sette Ponti (Seven Bridges) Road, we’ll cross the Ponte a Buriano, centerpiece of the background of the Mona Lisa, painted by Leonardo da Vinci. Along the way savor the best of Tuscan cuisine and regional specialties, attend authentic Tuscan wine tastings, visit Etruscan ruins and much more before we conclude our bike trip in the storybook medieval village of Cortona, brought to life in the acclaimed motion picture, “Under the Tuscan Sun!”

Tuscany’s Treasures Await on this Unforgettable Cycling Tour

Immerse yourself in the history, the heritage and the mystique of Tuscany as our bike tour wends through the region’s enchanting landscapes. Our route includes the lovely town of Loro Ciuffenna, the fortified village of Lucignano, and the Renaissance gem of Arezzo with its many artistic treasures, backdrop for the Oscar Winning Film “La Vita e’ Bella” (Life is Beautiful). Crossing the border into the “Green Heart of Italy” – Umbria and the blue waters of Lago Trasimeno – we’ll see where Hannibal and his elephants met Romans legions in epic battle. Along the way we’ll learn how Tuscan vintners combine modern technology with traditional methods to create world-class wines, and explore Roman ruins, Etruscan tombs, and Renaissance palaces, while relaxing at the end of each day in luxury accommodations. This is European bicycle touring at its best!


  • Discover Tuscan olive oil
  • Vineyard views galore!
  • Spin along the delightful Sette Ponti Road
  • Visit the land of the Etruscans
  • Authentic Tuscan wine tasting

Trip Details:

Biking Classics

Price: $3,795

Single Supplement: $600

Length: 6 days / 5 nights

Level: Athletic Beginner

Total Mileage: 125 miles

Daily Average: 25 miles

Terrain: Rolling, some flatland

Start/End Locations: Malva/Cortona

Trip Dates:

  • 05/16/16 - 05/21/16
  • 05/26/16 - 06/03/16
  • 06/06/16 - 06/11/16
  • 06/13/16 - 06/18/16
  • 06/20/16 - 06/25/16
  • 07/12/16 - 07/17/16
  • 09/05/16 - 09/10/16
  • 09/19/16 - 09/24/16
  • 10/04/16 - 10/09/16
  • 10/17/16 - 10/22/16

= Sold Out

Make this tour Private or for more information, call:


Day by Day

New! Malva

Today take our group shuttle at 12 pm in San Giovanni Valdarno train station or meet us at the hotel around 1 pm for a light lunch and introductions. We warm up with a ride to Loro Ciuffenna and visit one of the oldest operational water mills in Tuscany. The extra loopers pedal to le Balze di Piantravigne. Tonight we dine at the elegant Ristorante La Cantinella.

Loop to Reggello

After breakfast we pedal through the dramatic sun-drenched Pratomagno range where micro-climates flourish. We stop and visit Castello dei Bonsi for an olive oil tour and tasting before lunch on your own in Reggello. The extra loopers pedal to le Balze di Piantravigne, and the Parco Carabè for an artisan gelato. The normal loopers will have a delightful, easy ride on “Via dei Sette Ponti”. Tonight before dinner at the fantastic Villa Belpoggio restaurant we’ll have an Italian lesson.

Malva to Arezzo

Ride to the Ponte Buriano, made famous by Leonardo da Vinci‘s background on the Mona Lisa. In the afternoon we’ll have a guided walking tour of the town of Arezzo, the backdrop for the Oscar Winning Film “La Vita e’ Bella” (Life is Beautiful). Tonight is a free night to explore the restaurants and cafes of lively Arezzo on your own.

Arezzo to Cortona

Our destination is Cortona, an exquisite hill town filled with Etruscan treasures. We stop for a delicious picnic lunch and wine tasting at the Santa Vittoria vineyard estate. A late afternoon guided walking tour of Cortona leads us to Roman arches, Etruscan tombs, and Renaissance palaces.

Loop to Castoglione del Lago

Today we take a short ride along a very charming lake and we’ll walk along the Palazzo della Corgna. Just before lunch on your own in Castiglione del Lago, we stop to visit a local bike shop where you can purchase Italian-made cycling gear and souvenirs. After lunch, you can either shuttle back to Cortona or get a few more miles under your belt and bike back to Cortona. In the late afternoon, there’s an optional cooking class on the famous Tuscan cantuccini--take some home for a real Taste of Tuscany!


Why not extend your Tuscan journey for a few extra days to see Florence’s Renaissance treasures? Today, after breakfast, around 9am we will shuttle you to Cortona’s train station and we are happy to assist you with any post tour travel needs, whether you are continuing on to a new city or returning to Florence.

What's Included

Trip Planning

  • Bike rental equipped with odometer, map case, handlebar and seat bags and bike pump.
  • Ciclismo jersey and water bottle
  • Shuttles at beginning and end of tour

On The Tour

  • 1 wine tasting
  • 1 olive oil tasting
  • 1 cooking demonstration
  • Walking tours of Arezzo & Cortona

Accommodations & Meals

  • All accommodations
  • All breakfasts
  • 4 dinners
  • 1 light lunch and 1 picnic
Here’s a sampling of some of the amazing places you’ll stay on your journey.

For a full listing, request a detailed itinerary!

Villa Belpoggio

Relais Villa Belpoggio is a beautiful Tuscan Boutique Hotel, located in the Chianti area right in the middle of the triangle connecting Florence to Arezzo and Siena. All the accommodations are peaceful, comfortable and of great atmosphere.
View their website

Vogue Hotel Arezzo

Located in the heart of the city, Vogue Hotel Arezzo is perfect for conducting business or enjoying the sights of the city. It is also the premier choice among hotels in town. The hotel’s high-impact design and dedication to service creates a one-of-a-kind hotel experience in Arezzo. The hotel offers 26 exceptional rooms, all with a different design and layout that make each experience unique.
View their website

Villa Marsili

Villa Marsili is situated inside the town walls. The villa dates back as far as late '700 and the present owners have restored all original style details and architectural characteristics lost through centuries of previous interventions.
View their website

Meet the Guides