Coed Tuscany Gravel Bike Retreat

Come join us in Tuscany, home to some of the best gravel riding on the planet.  

While gravel riding has been around since the advent of bicycles, there is no question the Italians have perfected the art form.  Tuscany is filled with thousands of miles of gravel roads, or strade bianche (white roads) that thread their way through the rich and welcoming land of postcard and calendar photos, and movie landscapes.

And we’ll be staying in the middle of it all, in Pienza, a UNESCO World Heritage site and the center of this gravel heaven.  Pienza is a beautiful postcard town with phenomenal rides heading out in all directions.  You may know Pienza from THAT scene in Gladiator where Russell Crowe dreams of home in the endless wheat fields.  Yep, that’s Pienza.  It’s also a stone’s throw from the most famous cypress lined winding road in Tuscany featured in just about every Italian based Rom-Com of late.  

We’ll spend seven nights in our home base with six ride days.  But we’ll also have an optional off day adventure to either Siena or nearby hot springs. 

What’s Included?

Our adventure includes: 

• 7 nights lodging at a four star hotel
• 7 big buffet breakfasts
• 6 fabulous dinners (one dinner on your own)
• Guided riding
• An optional off the bike day in either Siena or local hot spring (TBD)
• Wine tasting at a local enoteca
• Cheese tasting at the best pecorino shop in town

What’s not included:

Airfare, transportation to Pienza (although we may be arranging for a transfer from Florence), lunches (which will be on your own during the rides), bike rentals (however, we will arrange them – including e-bike options!)

What Will the Riding Be Like?

In a word – heaven.  We’ll be riding on the storied gravel roads of the Val d’Orcia, also a UNESCO World Heritage site and home to the famous L’Eroica old school Grand Fondo, the professional spring classic Strade Bianche and recent gravel segments of the Giro d’Italia.  

We will be riding between 25 miles and 50 miles a day (it’s gravel so it takes longer) and climbing around 1,000’ per 10 miles.  The riding will be a mix of paved and gravel, with an emphasis on gravel, with rolling hills interspersed with some short punchy climbs and a couple of longer sustained efforts.  

Some of the towns we’ll ride through include Montalcino, Montepulciano, Montechiello, San Quirico, Buonconvento, and Bagno Vignoni  (the only town with a hot springs pool as its town square.)  We’ll ride by the Monastero Sant’Anna in Carpena (the setting for The English Patient) and Crete Sienese (the Sienese clay formations)

You do need to be comfortable riding gravel.  While most of the gravel roads are hard packed there are some softer sections and some washboards from time to time that can sneak up on you.  We really emphasize to everyone to “stay in the boat” and ride well within your comfort window.  Afterall, we are here to soak in the Tuscan landscape, absorb the history of the Strade Bianche and immerse ourselves in La Dolce Vita of Tuscany.

The rolling hillsides through which we’ll ride are a mixture of vineyards (likely lush with grapes ready for the harvest), olive groves (heavy with olives undergoing their last growth spurt before harvest in early November) and newly cultivated hillsides.    

All rides will be guided and we’ll likely split up into two groups so everyone can ride at their comfortable pace.  We’ll also provide GPS links of the routes so you can ride solo or with a friend if you’d like to soak in the Tuscan countryside in a smaller setting.

Where Will We Be Staying? 

We’ll be staying at Hotel Corsignano, a comfortable four star hotel in Pienza with a great breakfast buffet.  Pienza has been around since at least the 9^th century, however, in the 15^th century Pope Pius II (who was from Pienza and whose surname was Corsignano – the original name of the town) decided to rebuild Pienza as the ideal Renaissance town, which became the city plan for many other Renaissance towns throughout Italy.

Pienza sits between the two famous wine towns of Montalcino and Montepulciano, both of which we will be riding through.  While Montalcino is famous for Brunello di Montalcino and Montepulciano for Vino Nobile di Montepulciano, Pienza is famous for its sheep cheese, pecorino di Pienza, which we’ll be tasting and enjoying all week.

Tentative Ride Plan

Day One 

Bagno Vignoni – 40K and 3,000’ of climbing

Warm up ride down from Pienza and on to our first gravel segment.  Pop back on to pavement and wind our way up to San Quirico, a charming medieval town, after which we’re back on gravel on the famous Francigena (a 2,000 km pilgrimage route from Canterbury, England to just outside of Rome) where we drop into Bagno Vignoni.  Bagno Vignoni is the only town in Tuscany with a hot springs as its town square.  We can’t get in but there are some delightful restaurants in this picturesque small village for lunch.  After lunch, we’re on flat pavement and then back on rolling gravel to just below Pienza and a quick climb to our home

Day Two

Montpulciano and the Wiggle Road – 44K and 3,200’ of climbing

We start off to the south and down to the bottom of the hill on which Pienza sits.  We pick up a beautiful stretch of gravel and wind our way to San Biagio (a Renaissance Greek cross design church from the early 1500’s) and up to Montepulciano.  A quick walk through town and we’re back on the pavement to the famous Wiggle Road, ok, our term for a beautiful descent with cypress trees at the corners.  From here we’ll pop into Montechiello and back on gravel to Pienza.

Day Three

Montalcino – 82K and 5,700’ of climbing

Our longest ride of the trip starts downhill after which we pick up a long stretch of gravel to Buonconvento.  From Buonconvento we’re on pavement for a bit as we climb out of town, descend and pick up the famous gravel of Castelione del Bosco, which is a sustained climb to just outside of Montalcino.  We’ll drop into Montalcino for lunch, after which we have a long descent where we pick up two fantastic gravel sections and eventually climb back up to Pienza.

Day Four

Siena, Hot Springs or TBD Ride

For those who would like a day off of the bike we can either head to the spectacular medieval town of Siena for the day or head off to the local hots springs for a well-deserved soak.  We’ll have a ride option for those who want to pack in as much riding as is possible.  

Day Five

La Foce – 50K and 3,500’ of climbing

We head back to Montepulciano but the back way, then back towards the Wiggle Road but jump on some gravel instead and head south to La Foce (the estate and gardens of Contessa Iris Rodrigo – unfortunately we can’t go in) and wind our way along a number of gravel roads back to the base of Pienza and a quick climb back up to our home.

Day Six

Val d’Orcia Grand Tour – 65K and 4,600’ of climbing

Today’s ride is a mix of gravel and pavement but we cover some spectacular landscapes.  We’ll head down from Pienza and pick up some beautiful gravel over to Montefollonico after which we pick up some pavement and then back on gravel to Montisi.  A short climb from Montisi to a gravel shortcut and then a winding, paved stretch along beautiful Tuscan ridgelines after which we pick up a long gravel road to the base of Pienza and a short climb back home.

Payment Policy

To secure your spot on a retreat, a non-refundable deposit is required:

• $500 for domestic retreats
• $1,000 for international retreats

Single room reservations may require an additional $200 deposit. Reservations cannot be held without a deposit.

Full payment is due 90 days prior to the retreat. If payment is not received by this deadline, you may lose your reservation. For bookings made within 90 days of the retreat, payment in full is required at the time of registration.

Payment Options:

• Avoid fees by paying via check or Zelle.  
• Payments via PayPal or Stripe incur a 4% processing fee.  

Cancellation Policy

• 91+ days before the retreat: Refund of payments (minus your deposit).
• 90 or fewer days before the retreat: Payments are non-refundable.

Women’s Quest reserves the right to cancel retreats with insufficient participant interest. In such cases, all payments will be refunded; however, Women’s Quest is not responsible for personal expenses, such as airline tickets, due to schedule changes or cancellations.

Travel Insurance

We highly recommend purchasing travel insurance to protect your investment in case unforeseen circumstances prevent you from attending or completing the retreat.

Travel insurance is particularly important in the event you:

• Need to cancel due to illness or injury (including testing positive for COVID-19).
• Require medical care during the retreat.
• Face trip interruptions, delays, or unexpected quarantine requirements.

We suggest a policy that covers:

• Trip cancellation and interruption
• Medical expenses
• Quarantine costs

For maximum flexibility, consider a “Cancel For Any Reason” (CFAR) policy, which provides additional peace of mind. While this type of coverage is more expensive, it offers the most protection for unforeseen changes.

To compare and purchase travel insurance, we recommend using Squaremouth, a trusted platform to find the best policy for your needs. https://www.squaremouth.com/22393

Before purchasing any policy, consult a travel insurance agent to ensure it meets your coverage expectations.