Assaggio Toscana Bike Tour

Savor “A Taste of Tuscany” As We Bike Through The Glorious Heart of Italy

*NEW Weekly Departures Every Monday from April 17 – October 16, 2017*

Our six-day Taste of Tuscany bike tour is the perfect introduction to Italy’s much-loved region of sublime landscapes, fine cuisine and even finer wines! Starting on the banks of the Arno in Malva, our Tuscany cycling routes follow delightful, twisting roads, past stone-built hamlets, and through fertile landscapes warmed by the sun. We pedal through the dramatic Pratomagno mountains, famed for their myriad microclimates, passing tiny historic towns as we cruise down byways lined with cypress trees and flanked by ripening vineyards.

On the Sette Ponti (Seven Bridges) road, we’ll cross the Ponte a Buriano, renowned as the rustic backdrop to the Mona Lisa’s enigmatic smile. Along the way you’ll get to savor the best of the region’s cuisine, attend authentic Tuscan wine tastings, and visit ancient Etruscan ruins. Our magical Tuscany cycling adventure ends in Cortona, a hill-top town gifted with spectacular views, which was brought to life in the acclaimed motion picture, “Under the Tuscan Sun!”

A Myriad of Treasures Await You On This Unforgettable Tuscany Cycling Tour

You’ll be immersed in the history, heritage, and mystique of this alluring land, as our Tuscany bike tour wends through the region’s exquisite landscapes. Our biking route takes in medieval Loro Ciuffenna, with its elegant gorge-spanning bridge, the fortified village of Lucignano, and the Renaissance gem that is Arezzo. Known for its many artistic treasures, Arrezzo was the beautiful backdrop for the Oscar Winning Film “La Vita e’ Bella” (Life is Beautiful).

Crossing the border into Umbria, the “Green Heart of Italy,” our cycling adventures take us to the deep-blue waters of Lago Trasimeno, where we’ll see the site of the epic clash of Hannibal and his elephants with the Roman legions. Along the way, we’ll learn how Tuscan vintners create world-class wines and explore Roman ruins, Etruscan tombs, and Renaissance palaces. Each day’s biking in Tuscany will end with wining, dining, and relaxing in specially selected luxury accommodations.

“I loved the extras–mini lessons in Italian language, food, history, culture, the wine tastings, and the way both guides turned chance events and encounters into a little window of life in Italy.”
-Priscilla B. Portland, OR


*Tours available every Monday from April 17 – October 16, 2017. Tours will run with a minimum of 2 guests and a maximum of 18 guests. Tours with 4 or fewer guests will have 1 guide. Reservations open until November 25, 2016.


  • Tuscany cycling routes that pass through numerous vineyards in one of the world’s finest wine regions
  • Cruise through charming rural landscapes flanking the historic Sette Ponti Road
  • Discover the delights of Tuscan olive oil with a special tasting tour
  • Delve into ancient history in the land of the Etruscans
  • Enjoy an 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

Weekly tours every Monday April 17 - Oct 16, 2017

Trip Dates:

  • 04/17/17 - 10/16/17

Make this tour Private or for more information, call:


Day by Day

Welcome to Malva!

Our recently reimagined bike tour of Tuscany will take in picturesque villages, history-steeped towns, soaring castles, and iconic wine terroirs. We will provide a group shuttle for you from San Giovanni Valdarno train station (at 12pm), or you can meet us at the hotel around 1pm. Here we will enjoy a light lunch, introducing you to our guides and plans for your Tuscany cycling adventures.

Then we’ll help you out with bike fitting, before leaving on a warm-up ride to Loro Ciuffenna, home to one of the oldest operational water mills in Tuscany. Those wanting an extra loop can pedal on to le Balze di Piantravigne, with its beautiful views of the Valdarno Superiore. In the evening we will dine in style 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 Castiglione 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

  • Use of custom bicycle fully-equipped with odometer, map case, handlebar, seat bags, and bike pump
  • Informative tour leaders on-hand throughout the Ciclismo Classico tour
  • Ciclismo jersey and water bottle
  • Shuttles at both the beginning and the end of your tour

On The Tour

  • Van support
  • 1 wine tasting
  • 1 olive oil tasting
  • 1 cooking demonstration
  • Walking tours of Arezzo and Cortona

Accommodations & Meals

  • All accommodations
  • All breakfasts
  • 1 light lunch and 1 picnic
  • 4 dinners
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

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