In 1997, 92 cyclists pedaled out of Gaiole in Chianti, to protest the paving of Tuscany’s white gravel roads, or strade bianche. Now an annual event, L’Eroica celebrates pure cycling joy and has inspired the development of our third Explorer-style tour among the white roads of Tuscany. Ride romantic and famed winding cypress-lined roads, visit hilltop towns, and immerse yourself in one of the most photographed areas of Italy – the Val d’Orcia, a UNESCO World Heritage designated landscape. Highlights include the Renaissance and Medieval towns of Siena and Cortona plus riding through small, medieval Tuscan villages, or “borgos”, thermal spa towns, and stunning views everywhere you look. Days are longer on Explorer tours since it takes time to ride gravel (but like all Explorer tours, the route is a mix of off pavement and paved). If you are used to riding on gravel, you’ll love these routes. If you are new to gravel, this is a great way to see if you have a taste for it!
Learn more about our Explorer Tour Styles at the webpage at this link!
* We are happy to match solo travelers who would like to share a room with someone of the same gender. If no match exists, due to hotel pricing, we will charge 50% of the private room charge. This charge will be collected at the time of the final payment. If a roommate assignment is available it will be refunded at the conclusion of the tour.
** For information about what your tour status means please see our FAQ page.
Cycle the famed white roads of Tuscany, the vineyards of Montalcino, Siena and its beautiful piazza, the Val d'Orcia - a UNESCO World Heritage Cultural Landscape with its picture perfect vistas, Roman spa towns, hidden villages, winding gravel roads with views for miles from the top.
Keep in Mind: We work hard to maintain consistency across all of our tours, but some trips have unique differences. Here are some things to keep in mind about this tour.
This tour spends time on and off paved roads so support van and aid may not always be readily available. You will have the option to pedal with a guide or pedal on your own, but please be aware that if you are cycling on your own we recommend you are comfortable cycling in remote areas. Learn more about what is included and what to expect on your Explorer tour at the Explorer Tour Style page at this link.
Includes
6 nights, 7 days. All breakfasts, meals as noted in itinerary, use of a hybrid bike or e-bike. Full van support, GPS on your bike for navigation.
Learn more about what is included and what to expect on your Explorer tour at the Explorer Tour Style page.
Consider that around 50% of the ride will be on gravel roads and roads sometimes with rough terrain. Your pace will be slower and the perceived effort will be greater than when you are on pavement.
Highlights: Piazza del Campo, the majestic Duomo, and a maze of medieval tiny alleys
Arrive today in our centrally located hotel and start to explore the city of the Palio: a historical and traditional horse race that brings locals and tourists out alike. Siena, once a fierce rival of Florence, has kept much of its medieval atmosphere. A walk through town cannot miss the main square Piazza del Campo where the Palio is held.
Highlights: Eroica white roads, Crete Senesi hills, cypres iconic views, Buonconvento
Start from Siena and head towards the spectacular "Crete Senesi," or badlands of Tuscany, on the white roads of the famous Eroica race. Pedal through hidden hamlets and medieval Tuscan villages as you cycle the Arbia Valley on your way to the walled village of Buonconvento. 50% unpaved.
DAY 3: Cycle to Monte Oliveto Maggiore and the Asso Valley
Highlights: Iconic Tuscan cypress views of the Val d'Orcia, Montalcino vineyards
Today's loop ride explores the Asso Valley and the imposing Abbey of Monte Oliveto Maggiore. Amazing views open over the Crete hills and their farms as you continue to Torrenieri. Cycle among the Brunello vineyards as we pass at the base of famous hilltop village of Montalcino on our way back to Buonconvento. 30% unpaved.
More Eroica white roads leads us through the vineyards of Brunello di Montalcino. Enjoy the views as we ride through little castles and medieval properties that have been converted into world famous wineries. Our destination today is Pienza, in the heart of the Unesco World Heritage Val d' Orcia. 70% unpaved.
Highlights: Pienza, Bagno Vignoni San Quirico, Vitaleta Chapel
Today is for immersing yourself in the Unesco World Heritage cultural landscape of the Val d'Orcia. You'll ride 'strada bianche' lined with cypresses, explore the town of San Quirico, enjoy stunning Bagno Vignoni with its hot springs, and stop by the most iconic place in Tuscany, Vitaleta Chapel, before returning to Pienza. 54% unpaved.
Highlights: Montefollonico, vineyards of Montepulciano, the Chiana Valley, Cortona
Our final ride takes us beyond Val d'Orcia were our beloved white roads takes us into wooded forests. Sudden fortified hilltop villages delight us with exceptional vistas over the valleys and Montepulciano vineyards. Glide down gentle hills all the way into the Chiana valley and our last night's stay in Cortona. 43% unpaved.
Meeting time 2 p.m. - on Day 1, meet your fellow cyclists and Tour Leaders at the Day 1 Hotel specified on the itinerary.
Note:
As you are planning, remember that the hotels listed in our itineraries are our primary hotels and are - in rare cases - subject to change. Before you make arrangements, check with us if your tour departure is guaranteed. If your tour departure is out further than 6 months, please also check with us as there might be slight changes to the itinerary.
The below information will help you plan your arrival. For more tips or other routes, you might like Rome2Rio.
The closest airport to the tour start is Florence (FLR)
Frequent train connections are available from Firenze Rifredi (close to the Florence airport), and from Firenze Santa Maria Novella (in Florence center). The train ride takes about 1.5 hours by direct connection from either station. The route is served by regional trains and tickets need not be pre-booked.
Look up Italian train schedules at Trenitalia.com. Questions? See our information on taking trains in Europe here.
Happy planning!
Day 7: Departure Information
End of the tour in Cortona
Your tour ends on the final day after breakfast.
The closest airport to the tour end is Rome Fiumicino (FCO)
Taxi from the ending hotel to Carmucia-Cortona train station (10 min/EUR 15). There is also a bus connection from Cortona Centro station available. Combined bus/train tickets available.
Train from Carmucia-Cortona to Rome (regional trains, no pre-booking necessary, 2.5 hours/EUR 12.80)
Look up Italian train schedules and purchase tickets at Trenitalia.com or Trainline.com. Questions? See our information on taking trains in Europe here.
For more tips or other routes, you might like Rome2Rio.
Keep in Mind
We work hard to maintain consistency across all of our tours, but some trips have unique differences. Here are some things to keep in mind about this tour.
This tour spends time on and off paved roads so support van and aid may not always be readily available. You will have the option to pedal with a guide or pedal on your own, but please be aware that if you are cycling on your own we recommend you are comfortable cycling in remote areas. Learn more about what is included and what to expect on your Explorer tour at the Explorer Tour Style page at this link.
Pre-Trip Planning Checklist
To do right after you booked!
Read through your Reservation Confirmation and After you Book Information (link sent to you by e-mail), it has important information to help you plan your trip!
Check the date on your passport. The expiration date should extend three months past your date of return to your home country.
Refer to your Tour Packet/Itinerary to see step-by-step arrival and departure information for your tour, meeting place and time, if a reservation on a complimentary ExperiencePlus! Shuttle (if applicable) is required, and other important information to help you plan your arrival and departure.
Reserve your flights after you know you have a confirmed tour departure. Please check with our office if you do not know if your trip is confirmed.
Book your pre and post-tour hotel nights.
Begin your chosen training program.
Final payment is due 90 days (120 days for Bike &Barge/Boat tours) prior to the tour start. Please refer to your Invoice and the Final Payment Reminder e-mail we send 10 days prior to the due date for detailed instructions.
We'll email you your access code to Digital Daysheets, Hotel Itinerary, Participant Roster, names and contact information of your Tour Leaders, emergency phone numbers, and other important departure information about 2 weeks prior to your tour start date. All this will be provided to you via a feature called Experiences via the RideWithGPS App (tracks available but not necessary for navigation on Classic, Expedition and Bike & Boat tours).
Day of Your Flight
Get as much sleep on the plane as you can. Pack your one day of cycling gear in your carry-on. See you soon!
What to Expect on Tour
Explorer Tour Style
Learn more about what is included and what to expect on your Explorer tour at the Explorer page.
Gentle terrain includes mostly undulating/flat sections and a rare longer climb (less than 3 km - 2 miles) with an average grade less than 3%.
Rolling Hills
Rolling hills featuring multiple gentle slopes (average grade of 3-4%) usually less than 3 km (2 miles). There may also be an occasional shorter (less than 2 km -1 mile) but steeper climb. Or a longer climb where the average grade is less than 3%.
Hilly
Hilly terrain has climbs up to 3 km (2 miles) with an average grade between 4% and 6%. There may also be climbs longer than 3 km (2 miles), but with an average grade less than 4%.
Very Hilly
Very hilly terrain includes one or more climbs, some of which maintain an average grade (meaning you will have short sections both steeper and less steep in the same climb) of 7% and 8% for no more than 3 km (2 miles). There will also be some longer climbs, but with a lower average grade.
Mountainous
Mountainous terrain includes one or more climbs with an average grade over 8%. Mountainous rides can also include longer climbs (more than 5 km - 3 miles) with an average grade up to 6%.
Level 1 - 1.5
For those desiring gentle rides with a limited amount of climbing.
Level 5, also known as our Expeditions, are multi-week tours designed for strong riders looking for the challenge of riding across countries or continents.
Gentle terrain includes mostly undulating/flat sections and a rare longer climb (less than 3 km - 2 miles) with an average grade less than 3%.
Hilly
Hilly terrain has climbs up to 3 km (2 miles) with an average grade between 4% and 6%. There may also be climbs longer than 3 km (2 miles), but with an average grade less than 4%.
Very Hilly
Very hilly terrain includes one or more climbs, some of which maintain an average grade (meaning you will have short sections both steeper and less steep in the same climb) of 7% and 8% for no more than 3 km (2 miles). There will also be some longer climbs, but with a lower average grade.
Mountainous
Mountainous terrain includes one or more climbs with an average grade over 8%. Mountainous rides can also include longer climbs (more than 5 km - 3 miles) with an average grade up to 6%.
Tour Levels
Level 1 - 1.5
For those desiring gentle rides with a limited amount of climbing.
Level 5, also known as our Expeditions, are multi-week tours designed for strong riders looking for the challenge of riding across countries or continents.
Gentle
Rolling hills
Very hilly
Mountainous
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