If you’ve ever had the dream of spending an entire week in a luxury Italian villa while you rode to your heart’s content through the postcard-perfect landscape of Tuscany while savoring homemade meals complete with Classico Chianti or Brunello wines, then we would like to invite you to join us in 2020 on our exclusive Tuscan Villa Vacation! Designed for cyclists and their families, you will only to have to unpack one time as you enjoy spending a relaxing week in the heart of Tuscany’s most picturesque region, the Crete Senesi, in a four-star luxury villa that overlooks the magical landscape with its ancient hilltop villas, cypress trees, wheat fields, and olive groves. During your week, you’ll discover the very best roads as you ride to such famed hilltop towns as Pienza, Siena, Montalcino, Montepulciano, and through the stunning Val d’Orcia!

Following your day in the countryside, you can look forward to returning to our private villa to relax in the pool before enjoying our chef-prepared meals that will keep you fueled for the next day’s adventure. Along with the daily cycling, other optional activities include cooking classes, truffle hunting, yoga, wine tasting, horseback riding, and history tours. So make your plans today to join us in Tuscany where you’ll create a new legend to call your own!


Dates: October 5-10, 2020; October 13-18, 2020
Length: 6 days / 5 nights
Price: $5,299.00 pp in double occupancy
Single Supplement: $999.00
Meeting Point: Florence, Italy
Drop-Off Point: Florence, Italy


Day One: Welcome to Tuscany!
Following our meeting at 10 am at our Florence Airport hotel, we will transfer you to our four-star luxury villa in the Tuscan countryside. Upon arrival and check-in, we will enjoy our chef’s prepared lunch before assembling our bikes and venturing out for a ride in the nearby countryside. We will explore the Renaissance village of Trequanda before our dinner tonight overlooking the Tuscan hills!

Day Two: Montalcino and the Brunello Vineyards.
Our first full-day in Tuscany will feature riding to one of Tuscany’s most beautiful hilltop villages, Montalcino, where we will learn about the famed Brunello vineyards! Following the climb into town, admire the views that go on forever before settling into lunch at our favorite “trattoria!” Afterwards, we’ll ride to a local vineyard to learn about the Brunello wines while tasting some of the local vintages. This evening, we’ll enjoy our chef’s prepared dinner for us at the villa.

Day Three: Crete Senesi.
When one thinks of Tuscany with it’s cypress-lined serpentine roads and hilltop villas, that is the Crete Senesi! Today, you’ll discover the best roads in this picturesque region that feels like Disneyland on the bike! Enjoy lunch and a cappuccino in Buonconvento before visiting the Abbaye in Monte Oliveto Maggiore with its beautiful Renaissance frescoes. Following our return to the villa, relax poolside with a glass of wine before our group dinner this evening!

Day Four: Siena and the Chianti Classico.
Today’s “dream ride” towards Siena is one of the most spectacular of the entire week as we enter into the countryside of the Chianti Classico! We’ll enjoy lunch in Castelnuovo Berardenga before finishing our loop back to the villa. Later this afternoon, we’ll venture into Siena so you have plenty of time to explore the shops and restaurants for dinner on your own before relaxing with a cappuccino or some gelato in the Piazza del Campo! Perfecto!

Day Five: Montepulciano, Pienza and the Val d’Orcia!
We think we’ve saved the best for last! Get ready to ride some of the most dramatic landscapes of the entire week as you venture into the Val d’Orcia with it’s stunning landscapes and beautiful hilltop towns that have been the setting for many blockbuster movies such as “Gladiator!” Today’s route will include such charming villages as Montepulciano, Pienza, San Quirico d’Orcia, and Castiglione d’Orcia. Following our return to the villa, we’ll enjoy a festive “Farewell Dinner” courtesy of our chef!

Day Six: Departures.
Enjoy a final spin through the Crete Senesi before morning transfers to Florence. Estimated time of arrival is 12 noon.

*Please note that this trip can be customized a great deal depending on the needs of the group. Thus, please let us know what you would like to include and we will do our best to make it happen.


  • Five nights of luxury accommodations in our Tuscan private villa.

  • Four group dinners.

  • All breakfasts.

  • Four group lunches.

  • All transfers during the course of the trip for you, your bike and luggage.

  • Daily cycling routes with options, guides, and van support.

  • Experienced staff.

  • Professional mechanical assistance.

  • Non-cycling activities that include wine tasting, cooking classes, yoga, history tours, olive oil tasting, truffle hunting, and more. Please let us know what you are looking for so we can customize it for you.

  • Entrance fees for any planned activities.

  • Pre-Tour Info Packet to assist with your trip preparations.


  • Transportation to our pre-Tour hotel in Florence. We will provide you with all of the details of how to arrive there following your arrival into Italy.

  • Lodging before or after the trip.

  • Alcohol. We have a budget for included cocktails, wine and beer. Outside of that, you will be responsible for any additional drinks.

  • Personal souvenirs and incidentals.

  • Optional activities not covered in the original trip planning that you wish to do on your own.

  • Gratuities for Velo Echappe’ Staff.

Please contact us with any questions you may have regarding this trip via the form below. If you would like to reserve space, then please go to our Reservation Page. Thanks!

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Tuscany Villa Vacation