Women’s Tuscany Trip: Italian Food, Wine and Cycling 2021 TBA


Location - Tuscany

September 12, 2020 - September 19, 2020

Cycling around Tuscany, Italy

Trip Details

Meet in Chiusi, a main stop on the Florence – Rome railway. Head to our hotel in Pienza where we’ll stay for the next four nights. Settle in and then unwind on the terrace enjoying sweeping views of the Tuscan countryside. Get fitted with high end rental bikes and then we’ll stretch our legs with a short ride. Back at the hotel, enjoy a welcome happy hour with local wine and cheese and then go out for dinner as group.

Each morning starts with a sumptuous buffet breakfast at our hotel. At breakfast preview the day’s ride and excursions. Daily mileage is 30 to 40 miles. The schedule and ride lengths are subject to change due to weather conditions as well as participants’ abilities and desires.

Today’s ride north through Montisi, Trequanda and San Giovanni d’Asso. The area is rich with farms, hamlets and castles. This evening, visit a villa for a cooking class. Learn to cook a traditional Tuscan dinner including pasta from scratch.

Ride to Monticchiello: Cycle through a scenic landscape dotted with vineyards, cypresses and hilltop medieval villages. Stop at a farm for a tour that includes world class artisan cheese making. Enjoy a second cooking class here, making our lunch with farm fresh ingredients. Dinner is on your own tonight.

Ride to Castiglione D’Orcia and explore the ruins of an ancient castle. From the top we have a 360 degree panoramic view of the Val D’Orica. On our return ride stop along the way at Bagno Vignoni, a Roman thermal spa town and soak our feet in the thermal hot spring. Back in Pienza, enjoy a wine and cheese happy hour outside overlooking the valley we just rode through. Out to dinner together tonight.

Ride to Montalcino, a medieval city renowned for its Brunello wines. Our luggage is transferred to our Montalcino hotel. After lunch in the courtyard of our new hotel, we walk to the Padelletti cellar for a tour and wine tasting. Enjoy dinner on your own in one of Montalcino’s many excellent restaurants.

Ride south through the vineyards of Montalcino. Make a stop at the vineyard of Castello Banfi and walk through the glass museum. Next we ride to Ciacci Piccolomini D’Aragona for a tour and a wine tasting in their bicycle museum. Back in Montalcino we enjoy another fun dinner together.

Ride to Mont Oliveto, a 14th century Benedictine Abbey. Magnificent frescoes line the hallways of the abbey. We have a spectacular ride back to Montalcino with fantastic views. Tonight we enjoy our last dinner together celebrating our adventures with our new friends!

After breakfast we’ll taxi to the Chiusi train station to continue your travels or head to the airport.

Ends at 4:00pm

What to Expect

  • Beautiful bike rides through rolling hills
  • 7 nights lodging in 3-star hotels. (4 nights in Pienza, 3 nights in Montalcino.)
  • Double Occupancy Rooms (ask [email protected] about single occupancy options for a surcharge.)
  • 7 breakfasts
  • 5 dinners
  • 2 lunches (included at Podere il Casale farm and on arrival at our hotel in Montalcino)
  • 3 wine and cheese happy hours
  • Bike rental (high end road bikes)
  • Cooking class and farm tour
  • Cooking class at Pienza Villa
  • 2 Vineyard tours and wine tastings
  • Ground transportation from and to Chiusi train station, taxi to evening cooking class
  • Luggage transport between hotels in Pienza and Montalcino
  • Experienced Backcountry Babes trip leaders
  • Camaraderie and fun in a supportive environment
  • Have any questions? Email us at [email protected]

About Your Trip Leader

Lisa Graves rides in Tuscany every fall. She has cycled through all of Europe, including a year long “cycle about.” When not riding her bike she can be found kayaking, rock climbing & skiing throughout rural Maine. This is Lisa’s 7th year leading the Tuscany trip. Over the years she has refined the trip to give us the best of the best!  Italy is a fantastic place to cycle and enjoy great food and wine. We look forward to our 2020 Tuscany cycling adventure and hope that you can join us!

Getting There

Fly to Rome, airfare estimate is about $1000 from many major cities.  From Rome, take the train to Chiusi.  Chiusi is on the main Rome-Florence trainline, and is about 90 minutes and $27.   Leaders will provide detailed information on train schedules and traveling by train.


I can’t even describe the emotions I feel thinking back to the two backcounty ski hut trips I’ve done in Canada with Backcountry Babes. It’s a lot of “Oh my god that was fun!”, but it was also such a confidence builder. I feel like I can hang, I’m a badass, and now I know all these incredible women that I can use as role models.

Amy H,Canada Hut Trip

This trip was one of the most rewarding outdoor experiences I’ve ever had. Great women, fantastic guides, way too much food, and AMAZING skiing! As soon as I got home I was already signed up for next year’s trip.

Lauren S.Canada Hut Trip

My eternal thanks to Backcountry Babes for showing me what the backcountry is all about. The March 2016 trip to Powder Creek Lodge was my first hut trip in BC. We skied the lodge’s spectacular terrain, tracking up perfect virgin fields of white and bootpacking cold couloirs when the vertical got too steep to skin. I disconnected from the world all week (!) and instead connected to 14 women who were strangers to me at the beginning and now are anything but. I left exhausted and worked and spoiled for life. Can’t wait to do it again!

Esme D.Canada Hut Trip

I just returned from my third Backcountry Babes backcountry hut trip, and I can’t wait to go again! It’s not just about the powder, the peaks or the ability to disconnect for a whole week. It’s about these amazing women–babes who are smart, passionate, compassionate AND who know how to shred the gnar! Thanks, Backcountry Babes for the conversation on the skin track, the tips and education, the encouragement and the non-stop laughs.

Jen F.Canada Hut Trip

Our trip to Japan was phenomenal! As the location becomes more exotic, it becomes more important to have a guide who knows the area and knows where to find the goodness; Check. Combined with fantastic organization and a small group, we spent all of our time in the enjoyment zone. Kudos to Emily for getting all the elements just right, and creating a lifetime memory.

Casey S.Sante Fe, NM