Tuscan Traverse | Private Tour

May 23 - 31

  • $USD/person


  • Tour Days


  • Daily Miles


  • Total Miles


  • Shuttle (To/From)


  • Difficulty

This is a giro-style private tour is designed for a group of friends to explore the hiking trails and out-of-the way cycling routes of Tuscany. Our journey will take us to three unique Tuscan locations; roaming from the historical rich lands of Val d’Orcia, the wild Mediterranean cliffs of Elba, and the vineyard lined slopes of the Maremma.


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Where we Stay

Our first and last two nights will be in our home village of Castagneto Carducci. We will kick the tour off with an afternoon hike and ride. Our next day will take us to the island of Elba for two nights. Here the hiking will include trails along the rugged coastline and upper forests of the island. Our riding will take us all over the island, including past the famed rock outcropping known as Napoleon’s chair.  Our second transfer day will take us to Montalcino, at the heart of Tuscany’s interior, where we will spend our days exploring the abundant roads, trails, wine and food. We will end the tour with two nights back in Castagneto Carducci on our local routes in the chestnut forests and along the sparkling Mediterranean. 


Geared For

This is a four pig tour specially designed to incorporate more off- the-beaten-path routes, including gravel sections to ride. Hikes will include old roads used by Napoleon along the coast, trails through the mediterranean macchia, and the forests of Monte Amiata. Depending on interests there are roman artifacts to visit on Elba, and plenty of villages to refresh in along the routes. 

Tour Highlights

We’ve been rediscovering Tuscany and look forward to spending time cycling & hiking throughout these three distinct areas over the course of the week. Our rides will take us on some of Tuscany’s most spectacularly abandoned roads, our wines will be local and draw from the designated wine areas of Bolgheri, Val d’Orcia, Montalcino, and Elba.

Montalcino is a beautifully restored village in the province of Siena. With a rich history throughout the Etruscan and Roman times, there is plenty to explore by foot between the churches, museums, and gardens. The strategic location is ideal for cyclists, allowing fabulous loop rides through some of Tuscany’s most famous countryside. 

We have visited Elba often with our tours over the years, and love the water and beaches, and the ancient Etruscan and Roman history. The island offers a unique flora & fauna which reflects its position in the warm Mediterranean. Late May is when flowers are in bloom, yet before most tourists are in swing. 

Castagneto Carducci is saturated with cycling history; many champions have come from here, trained here, and still live here. Andy has been coming here since his early cycling days with team Motorola and can’t seem to leave. The terrain is quiet, rolling, and varied with vineyards, olive groves, and forests. 

Travel Details

This tour begins and ends with transportation to Pisa airport (PSA)
Pick-up: 10:00 Monday, May 23, 2022
Drop off: Tuesday, May 31 with a shuttle offered to accommodate the 6:00/7:15 a.m. departures. We will also provide drop-offs at the local train station in Castagneto Carducci for guests who want to travel on in Italy.

Included in Tour

  • Airport and local train station transportation 
  • Accommodation for 8 days, 8 nights, travel on the 9th day
  • 8 breakfasts, 7 lunches, 7 dinners with wine included
  • Fully supported riding, mechanic support, follow vehicle
  • Guided hiking for up to 11 guests 
  • Food and drinks on rides. Hikes will stop in cafes when possible
  • Transportation and admission to scheduled tastings, sightseeing & special events

Tour Details

  • Riding days: 8
  • Single Room Supplement of $600 extra, please indicate on booking form
  • A $2,000 non-refundable deposit is due at the time of booking (per our private tour policy)
  • $2,100 ($2,700 single supplement) is due by Feb 23, 2022.
  • Single rooms are limited
  • Weather: 70’s – mid 80’s, with cool evenings
  • Bike rentals available
  • Install low gears and bring 28mm tires, ’cause there is gravel to be found and shortcuts are never easier

Tuscan Traverse | Private Tour

Tuscany | May 23 - 31

  • $4,100

  • 9

    Tour Days
  • 35-80

    Daily Miles
  • 390

    Total Miles

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