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7 Days Cycling and Yoga Retreat in Tuscany, Italy

Wine Tasting and Yoga Retreat Italy

For trail-blazers and yogis alike, Travel Well Yoga Retreats invites you to experience the best of adventure of cycling and yoga. Set in the idyllic protected rolling hills of Pienza, Amy works with her Italian friends to provide a unique cycling retreat that celebrates with carefully planned routes by cycling expert Matt. All bike adventures are followed up with gentle yoga stretches, adventure by foot, and the best of Italian meals and wine to relax and immerse you in the Italian culture.

Meet the instructors

Amy & Matt
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  • Yoga classes
  • Rental bicycles and necessary equipment
  • Wine tastings and guided rides with hybrid bikes
  • Visits to ancient villages of Sienna, Montepulciano, Pienza, and San Gimignano
  • Cheese and olive oil tasting overlooking the Val D’ Orcia region
  • All transportation and cycling back-up on the trip
  • Daily Italian breakfast and five dinners
  • 6 nights accommodation


5 days with instruction in English
Spoken languages: English
The maximum participants in the group is 15
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During this retreat, you will be staying in a luxury villa. Just six kilometers from the Renaissance masterpiece town of Pienza, yet light years away from the stresses of modern living, this luxury eight-bedroom farm conversion is the perfect escape for this yoga retreat. It has a lovely oak floored dining room, with high ceilings and huge oak and glass windows, sitting room with light flooding in, and huge sofas and armchairs to sink into for a glass of wine after an amazing day.

Upstairs, you will find beautifully decorated double bedrooms, with antique and reinvented bedsteads, marshmallow duvet, stunning views, and all the perfect details you would like to have in your own house. All rooms have lovely en-suite bathrooms, fully equipped with stylish stone tiles and baths or showers.

Every comfort has been considered in the design of this stunning farmhouse. Outside, there are uninterrupted views, a private garden, as well as lovely garden furniture and a barbecue in the summer.


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. You will enjoy an afternoon break to refresh before an incredible meal at one of the hottest restaurants in Pienza at La Bandita.

Ride through the hills of Montepulciano early in the morning after breakfast, followed by a yoga class for a gentle practice in the park before lunch. This particular route takes you into this famous village, where you will visit the ancient wine cellars. A guided tour into this original Etruscan cave and one time World War bomb shelter is one of the most unique stops in this village. You will enjoy a wine tasting before returning to a beautiful Italian park for an authentic Italian barbecue.

You will also have a day off from the bikes. See Sienna with the favorite Tuscan guide, Stella! A true expert born in Sienna, she will walk you through this unique city rich in history and explains the architecture and folklore of this famous city. You 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. Your adventure continues as you visit the Barone di Ricosole Castle. You will take a guided tour including a private wine tasting and end your experience eating right on the castle grounds.

You will also be brought for a tour around Monteriggioni and San Gimignano. Taste the best gelato in the world and and shop in 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, which often overlooked by Americans.

Included excursions

Included in the total cost of this retreat are visits in ancient villages including Sienna, Montepulciano, Pienza, and San Gimignano and a cheese and olive oil tasting overlooking the Val D’ Orcia region.


Amy Annis
As a registered yoga teacher, Amy has experienced working with both new and experienced practitioners. Her love for Madeline Island and the corresponding outdoor activities has led her to develop specific yoga trainings geared towards the performance athlete and outdoor enthusiast. As a survivor, Amy has also developed a gentle teaching style to encourage other women with health battles to reclaim their bodies and their own inner strength. For this reason, all levels of yoginis are welcomed with a lifted heart to embark on these yoga adventures.
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-a-holic and serious cyclist who owns a garage full of bikes (one stashed in Scottsdale, Arizona), 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 into cycling.


This retreat will take place in Pienza, Tuscany, Italy.

Nearby places

  • Pienza - 6 kilometers



  • Cycling
  • Wine tasting


  • Barbecue facilities
  • Dining room
  • Garden


Daily gourmet and homemade Italian breakfasts complete with Americanos or cappuccinos and five dinners are included in the retreat price. Travel Well Yoga Retreats will find the best meals to strive to eat like a local and experience the amazing opportunities for fresh and local meals.

In Tuscany, you will eat fabulous pastas, vegetables, and meats. You will also have the opportunity to visit wineries with cheese and olive oil tastings. Alcohol is optional and available at group meals, at your own expense.

The following meals are included:

  • Breakfast
  • Dinner

The following dietary requirement(s) are served and/or catered for:

  • Organic
  • Regular (typically includes meat and fish)
  • Other dietary requirements on request
If you have special dietary requirements it's a good idea to communicate it to the organiser when making a reservation

What's included

  • 2 wine tastings
  • 4 guided rides with hybrid bikes
  • 5 dinners
  • 6 nights accomodations
  • A cheese and olive oil tasting overlooking the Val D’ Orcia region
  • All transportation and cycling back-up on the trip
  • Average mileage of 20 miles per trip and option to upgrade to a road bike
  • Daily Italian breakfasts
  • Rental bicycles and necessary equipment
  • Visits in ancient villages including Sienna, Montepulciano, Pienza, and San Gimignano
  • Yoga classes

What's not included

  • Additional activities
  • Airfare
  • Airport transfers
  • Alcoholic beverages
  • Lunches
  • Personal expenses
  • Trip insurance

How to get there

Arrival by airplane

Please book your flight to arrive at Florence Airport, Peretola (FLR).

Cancellation Policy

  • A reservation requires a deposit of 30% of the total price.
  • The deposit is non-refundable, if the booking is cancelled.
  • The rest of the payment should be paid 60 days before arrival.
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