Explorer: White Roads of Tuscany

Explorer: White Roads of Tuscany

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!

Tour Dates & Prices

Date
Price
Private Room Fee
Note
May 7-13, 2023
USD$2995
USD$450
 Departure confirmed!
Aug 27-Sep 2, 2023
USD$2995
USD$450
 
Oct 1-7, 2023
USD$2995
USD$450
 

* 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.

Tour Style: Explorer Hold A Space Request Private Departure Download Itinerary Tour Map
  • Trip At-A-Glance
  • Tour Summary
  • Daily Itinerary
  • Travel Information
  • Map
  • Reviews
  • Similar Tours
Trip At-A-Glance

Trip At-A-Glance

  • Length / 7 Days
  • Total Distance / 230km (140 miles)
  • Avg. Distance / 45km (28 miles) per riding day
  • Tour Level & Tour Style / 3.0 Explorer
  • Countries / Italy
  • Begin/End / Siena/Cortona
  • Price / From USD$2995
More Photos
Tour Summary

Tour Summary

  • Highlights
    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, 3 dinners, 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.
  • Arrive / Depart
    Florence (FLR) Peretola or Pisa (PSA)/ Rome (FCO)
  • Overall Tour Level
    3.0 difficulty level 3.0

    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.

  • Daily Ride Summary

    Day

    Distance/Gain
    mi/ftkm/m

    Terrain

    Day Level

    Notes

    1
    Test ride
    2
    43km / 526m
    Hilly
    difficulty level 2.5
    3
    42km / 649m
    Hilly
    difficulty level 3.0
    4
    40km / 880m
    Hilly
    difficulty level 3.0
    5
    42km / 700m
    Hilly
    difficulty level 3.0
    6
    63km / 697m
    Hilly
    difficulty level 3.5
    7
    Last day

Terrain Legend

Gentle Gentle

Rolling hills Rolling hills

Hilly Hilly

Very hilly Very hilly

Mountainous Mountainous

Daily Itinerary
Download Itinerary

DAY 1: Welcome to Siena

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.

DAY 2: Cycling the Crete Senesi

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.

  • Distance: 43km (27mi)
  • Gain: 526m (1725ft)
  • Terrain: Hilly
  • Day Level: difficulty level 2.5
  • Meals: Breakfast, Dinner
  • Lodging:

DAY 3: Cycle to Monte Oliveto Maggiore and the Asso Valley

Highlights: Iconic Tuscan cypress views of the Val d'Orcia, Montalcino vineyards, Pienza

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.

DAY 4: Buonconvento to Pienza

Highlights: Iconic Tuscan cypress views of Valdorcia, Montalcino vineyards, Lucignano d'Asso, Eroica roads, Pienza

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.

DAY 5: Loop ride in Val d'Orcia

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.

DAY 6: Cycle Pienza to Cortona

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.

  • Distance: 63km (39mi)
  • Gain: 697m (2286ft)
  • Terrain: Hilly
  • Day Level: difficulty level 3.5
  • Meals: Breakfast, Dinner
  • Lodging:

DAY 7: End of the tour in Cortona

Highlights: Medieval town center, the Etruscans Museum

The tour ends in Cortona. This town offers more gems to be discovered! Stay on, explore more of Tuscany, or head to Rome.

  • Meals: Breakfast
Travel Information

Travel Information

Day 1: Arrival Information

Welcome to Siena

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)

  1. 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.
  2. 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!

6 to 3 Months Prior to Tour Start Date

  • 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.

6 to 2 Weeks Prior to Tour Start Date

  • Start reading one of the books or watching one of the movies from our Reading and Movie Lists: https://www.experienceplus.com/blog/travel-planning/
  • Plan what you are going to pack and start packing! Refer to the Packing Lists on our website at https://www.experienceplus.com/blog/travel-planning/packing/.
  • 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.

Map

Map

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