Lucca, Banner AS.jpeg


October 15th - 21st  •  7 days 6 nights  •  4 days of bicycling the country side  •  Breakfast and dinners as listed  •  Wine tour  •   Olive harvest & pressing  •  Cooking lesson  •  Guided tour by van to the ancient walled cities of Siena & Volterra  •  Sun Rise Salutations  •  An adventure of a life time  •



You are invited to be one of ten women for this irresistible bicycling and cultural experience. Whether you’re a bike novice, or advanced rider, you will be encouraged at every turn.

There’s nothing quite as breathtaking as Italy from your bike. The unobstructed view provides an intimate experience with the rolling hills, ancient buildings, and oh-so charming culture. You’ll see endless sights along the way, and what you might be surprised to find is yourself!

Bell Tower
Sun Rise
Sun Dial

The villa B&B La Rocca is located in a historical Tuscan Villa dated XVI-XVI century and is recognized by the province administration of historical interest. 


  • Historical living room with ancient billiard table, library, wi-fi, and games
  • 5 rooms in rustic/romantic style (3 double bedrooms and 2 family size rooms)
  • 2 bathrooms
  • Tower and terrace with magnificent views of garden with olive groves overlooking Florence
  • Farmyard animals
  • Artwork covers the walls from Isabella’s grandfather. He was inspired by the Villa and surrounding area to paint some beautiful pieces
  • Local Toti family are present and available on site

The Villa is over 500 years old and has been lovingly cared for. Do not expect luxury but an authentic and romantic/rustic experience. This tour is an intimate experience and will only have room for ten women. There will be no availability of a single room due to space.

Please read tips on what to expect in Italy.

You will be staying at a cozy 500-year-old villa owned and operated by the Toti family. Isabella Toti will be giving our group Italian cooking lessons and sharing other delights of the Tuscan culture. You’ll have time for daily reflection; wine sipping, and a day off the bike for sightseeing. You will also take part in the harvest of the olive by picking and bringing to press the “green gold” to experience a cultural treasure.  

You will find yourself waking up to the crisp morning air as the echo of the local birds chirping and the chime of the bell tower draw you to the vast landscape that directs your gaze toward Florence. 

Arising knowing you lay foot on ancient ground and just steps away from the rich history of the medieval tower above. Realizing you share this experience with a family that has opened their home and way of living with you. 

Along the bicycling route, you will experience the challenge of rolling through the wine region whilst on your way to visit historic sites such as, the birthplace of Leonardo da Vinci and the intact Renaissance era city of Lucca. You will also find yourself naturally interacting with locals as you stop for a caffé or lunch along the way.


  • Airfare
  • Transportation to and from airport (outside of set times)
  • Lunches
  • Helmet and cycling shoes (specify pedal preference at sign-up)
  • Extra activities (guided tour of Florence and night of October 14th)
  • Travel insurance (Check out our recommendation under travel resources. Strongly recommended! It covers medical, travel disruption, damage to belongings, and more. We never travel without it. 



  • Lodging October 15th-21st 2017 
  • Continental breakfast
  • All Dinners listed
  • Road bike (provide measurements at sign-up)
  • Local guide on rides 4 rides total - Intermediate level (guides will evaluate group ability and will determine length and difficulty of rides to suit the group needs)
  • Support vehicle
  • Italian cooking lesson
  • Wine tour and tasting
  • Guided tour of the walled cities Siena and Volterra Italy!
  • Transportation to/from airport-scheduled times. (30 euro each way - outside of set times) 


  • Closest airport is Florence Italy (FLR)
  • Destination Carmignano, Italy (province of Prato) Approximately 15 miles by car


October 14th 

  • Extra day option
  • Tour of Florence (125€ to be paid at the time of service to guide)
  • We can assist with lodging if needed (50€ to be paid when you arrive at the Villa)
  • No meals are included in extra day

October 15th

  • Arrival day
  • Meeting by 5:00pm at the Villa 
  • Bike set-up and snacks
  • Welcome dinner at the Villa 7:30pm

October 16th 

  • Continental breakfast
  • Ride 9:00am (Vinci to visit the birthplace of Leonardo da Vinci)
  • Afternoon olive harvest 
  • Dinner at Villa

October 17th 

  • Continental breakfast
  • Ride 9:00am  (Lucca)
  • Cooking lesson with Isabella

October 18th

  • Continental breakfast
  • Guided tour by van to the ancient walled cities of Siena and Volterra
  • Dinner at Villa

October 19th 

  • Continental breakfast 
  • Ride 9:00am (San Gimingnano) 
  • Wine tour 
  • Dinner at Villa

October 20th 

  • Continental breakfast
  • Ride 9:00am (Greve in chianti and surrounding area)
  • Olive press and tasting
  • Dinner at Villa

October 21st

  • Continental breakfast
  • Departure day