Tuscany is on your bucket list and what a better way to experience it than a retreat that celebrates the best of what the region has to offer?


Shared Room: $3,400

Private Room: $3,700

Set in the idyllic UNESCO protected rolling hills of Pienza, Amy works with her Italian friends to provide a unique cycling retreat that celebrates the essence of the incredible surroundings. Your cycling expert, Matt, has carefully planned routes designed to exhilarate the rider. Winding roads through Tuscan villages, cypress lined lanes, and rows of vineyards and olive groves provide the back drop for the rides with stops to appreciate the surroundings. Yoga offers balance in a cycling retreat often fraught with tight hamstrings and the straining of neck and shoulders. The food is celebratory and we learn from the Italian culture to appreciate the art of food as we take in cheese tastings, winery visits, and authentic Tuscan cuisine.

Where We Go

We base out of magnificently restored farmhouses in the hills of Pienza.  While eating an incredible Italian breakfast complete with creamy cappuccinos and the call of the sheep herder in a nearby field, we will discuss the day and bike routes that we will experience.  Take a quick dip in the pool before beginning the adventure.  Our rides are carefully planned and mapped out and each ride is guided.  Our drivers accommodate with bike mechanic knowledge and spare parts. After the morning ride we will explore the villages including Sienna, Montelpulciano, Pienza, and San Gimignano.  Our dinners will consist of a feast to re-fuel both body and soul.

Included in the Package

  • 4 Guided rides with hybrid bikes
  • Yoga classes
  • Accomodations in a beautiful Pienza farmhouse.
  • All transportation and cycling back‚Äďup on the trip
  • Gourmet and hommade Italian breakfasts complete with
  • Americanos or Cappuccinos

  • 5 dinners
  • Rental bicycles and necessary equipment
  • Visits in ancient villages including Sienna, Montepulciano, Pienza,¬†and San Gimignano.
  • 2 wine tastings
  • A cheese and olive oil tasting overlooking the Val D‚Äô Orcia region
  • Average mileage of 20 miles per trip and option to upgrade to a road bike

Agenda Highlights


Take a short mapped bike route through the heart of Pienza stopping in the town itself for a lunch, time to stroll and take in the quaint shops and artisan offerings before a cheese tasting overlooking the hills.  An afternoon break to refresh before an incredible meal at one of the hottest restaurants in Pienza at La Bandita.

# 2

Ride through the hills of Montepulciano early in the morning after breakfast. Our yoga class follows us today for a gentle practice in the park before lunch. This particular route takes us into this famous village where we will visit the ancient wine cellars. Our guided tour into this original Etruscan cave and one time World War bomb shelter is one of the most unique stops in this village.

We will enjoy a wine tasting before returning to a beautiful Italian park for an authentic Italian BBQ.

# 3

A day off from the bikes. See Sienna with our favorite Tuscan guide Stella! A true expert, born in Sienna she walks us through this unique city rich in history and explains the architecture and folklore of this famous city. We will be there as the city bustles with excitement preparing for the world famous Paelio horse races. Free time in the afternoon means a delicious lunch overlooking the Piazza Del Campo or climbing the clock tower of this beautiful city.  Our adventure continues as we visit the Barone di Ricosole Castle, take a guided tour including a private wine tasting and end our experience eating right on the castle grounds.

# 4

A Tour of Monteriggioni and San Gimignano.  Taste the best gelato in the world and and shop the charming ancient alleys of these beautiful villages Dinner in Bagno Vignoni, a quaint village surrounded by roman baths. Enjoy one of those authentic off the grid experiences in this unique village often overlooked by Americans.


Your Retreat Guides


Amy Annis

Amy has been leading yoga retreats for many years on Madeline Island and in June of 2014 she began a yearly retreat to Italy to experience an amazing adventure. Working with some of the best guides and her favorite people, she is looking forward to re-creating a wonderful adventure for another group. Collaborating with Matt on a cycling retreat is a dream come true.


Read more about who we are here. 


Matt Tietz

Matt is a 44 year old business owner and father of two fantastic kids, age 16 and 18.  He has been a friend of Amy and her family for about 15 years living in the same neighborhood, enjoying many laughs, dinners and glasses of wine.  He is a self-proclaimed travel-aholic and serious cyclist who owns a garage full of bikes (1 stashed in Scottsdale, AZ), proudly shaves his legs, and rides over 4,000 miles per year.


An extrovert who tries to bring out the humor in everyday life, Matt is passionate about cycling himself and also about getting others in to cycling.¬†Matt‚Äôs focus in life is to ‚ÄúShare experiences with family and friends that focus on Health, Fitness, Humor and Travel.‚Ä̬† In other words, he was cut out to lead the cycling portion of this retreat.