Tuscany and the Enchanting Island of Elba


From the Renaissance city of Florence to the pristine beaches of Elba, Tuscany’s cultural wealth and natural beauty are incredibly rich and varied.

We begin south-east of Florence cycling on the Setteponti Road for a couple of days among infinite olive groves. From there we’ll pedal through the vineyards of the hilltowns of Chianti, and through the twisting streets of Siena. Strolling Siena’s narrow maze of cobblestone walkways is an amazing architectural journey, and the view from Siena’s famous tower will make your head spin!

From Siena we travel through dramatic landscapes to Volterra. Our tour finishes on the enchanting island of Elba. One of the most beautiful islands in Italy, Elba has been recognized for centuries for its elusive beaches, warm crystal waters, mountain vistas, and tranquil villages. We’ll park our bikes, dive into the warm blue waters, and discover why Napoleon chose to exile to this humble paradise.


  • Ride through Toscana from mountains to sea with Top Guide Marcello Bonini (2014 Outdoor magazine award) and Ciclismo Classico’s founder and CEO Lauren Hefferon
  • This is our 30th anniversary edition of one of our first tours!
  • Visit Siena and Volterra and learn about Etruscans
  • Visit the famous wine villages of Greve, Panzano, Radda, and Gaiole in Chianti and learn all about Sangiovese grapes
  • Experience an all you can eat gelato diet every day

Trip Details

Single Supplement
9 days / 8 nights
Total Mileage
Daily Average
Rolling to hilly
Start/End Locations
Malva, Italy/Elba, Italy
Trip Dates
06/08/19 - 06/16/19
06/22/19 - 06/30/19
10/12/19 - 10/20/19

Make this tour Private or for more information, call:




We have a rolling ride to Reggello among the hundreds of olive trees on the ancient Setteponti road. A short spin to get acquainted with your bicicletta and your intro “warm-up” to riding in Italy on the gentle rhythm of the Tuscan landscape. For those feeling strong, you can also try the climb to the Benedictine Abbey called Vallombrosa.

Il Borro Loop

Today’s ride explores an often overlooked but intriguing part of Tuscany; following the Setteponti road towards Arezzo we visit the village of Il Borro, a former medieval hamlet turned into a high end resort by the Family Ferragamo.


Today’s ride takes us through the heart of Tuscany weaving through the the famous wine villages of Greve, Panzano, Radda, and Gaiole in Chianti. For centuries these vineyards, olive groves, and oak forests have been the perfect background for Renaissance artists, which come alive with their depiction of colorful wildflowers among lushing forests.

Siena - Rest Day

Siena is the crowning city of central Toscana, to which the region owes its wealth and prosperity. We’ll stroll down memory lane for the Middle Ages as we visit the ancient hospital of Santa Maria della Scala and through its fresco hallway known as “Pilgrims’ Hall’.

This is the official rest day of the trip, but you can still opt for a 28 or 40 mile hilly loop ride out to Monteriggioni or Asciano.

We will have an afternoon walking tour with our fascinating local Siena guide and a wine tasting at an enoteca (a repository for wines).


Today’s ride offers an entirely different and unique side of the Tuscan landscape. Known as the Volterrana, the road carved out in the landscape around Volterra is vast and open, offering views for miles. We begin with gentle rolling hills, passing grazing horse and sheep, acres of farmland with the rich, terra cottasoil. Pass several horse farms as well as pasture land where sheep graze. Once up to the Volterrana, our view bursts open to Le Colline Metallifiere,literally meaning “hills rich in minerals.” On a clear day you you can spot puffs of steam arising from the distant hills to the West as the is famous for its geothermal plants. In the next valley huge pipes pump energy out of the earth.

S. Gimignano Loop

This morning we embark on a lovely loop ride to San Gimignano, one of Tuscany’s best-preserved medieval cities. With 15 remaining towers looming over the beautiful streets, churches, galleries, shops and bars there is plenty to explore by foot. We recommend taking a climb up to the Rocca (fortress), which dates back to the 1350s or check out the entirely frescoed Cathedral. We’ll enjoy an afternoon walking tour of Volterra with our local guide. There are numerous archaeological sites to explore.

Baia Ottone, Elba

We begin with a glorious descent from the heights of Volterra; if it’s a clear
day - you can see Elba! The landscape is an open moonscape of cascading hills that are green in the spring, golden in the summer and soft, crusty brown in the fall. Today we are heading to area of Tuscany called Bolgheri known for it’s “Super Tuscans.” After a stopover in the village famous for the description of the famous Italian poet Carducci we’ll end the day with a relaxing winery visit. Afternoon shuttle and ferry ride to Portoferraio, Elba, overlooking a peaceful bay. On the island we’ll be immersed in true Mediterranean climate and foliage; warmer temperatures, cactus, palm trees and tropical flowers.

Baia Ottone, Elba

The entire loop is about 38 miles and fairly challenging but spectacular. You will be seeing two distinct faces of Elba: one linked to the island’s maritime tourism and the other reflecting its long history of iron mining. Today we cycle through bustling popular Porto Azzurro towards the northern mining town on called Cavo. The scenery as we pass near the mountain ridge “ Volterraio” is dotted with flowering yellow broom offering an arid, yet Mediterranean feel and craggy red cliffs - due to the soil’s high iron content. As we climb out of Rio Marina, we will see the somewhat eerie remains of mining operations, now in various stages of disrepair and oxidation – a spectral tribute to a mining history dating back to Etruscan times.


After breakfast, group shuttle to the port in Portoferraio to catch the ferry back to the mainland. Those departing later will need to arrange a cab. Please allow 3-6 hours to get to your post-tour destination.

What's Included

Trip Planning

  • Carbon bike rental equipped with Garmin Edge GPS
  • Informative tour leaders throughout the program
  • Ciclismo jersey and water bottle
  • Post-tour group ferry

On The Tour

  • 2 cultural visits with local guides
  • 2 wine tastings
  • 1 olive oil producer visit
  • All-you-can-eat gelato

Accomodations & Meals

  • All accommodations
  • All breakfasts, 4 lunches, and 6 dinners

Meet the Guides