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Ride the hills of quintessential Tuscany, explore Siena, and discover lesser-known villages.

This Magnifica tour visits some of Tuscany’s iconic destinations and is filled with culture and authentic beauty. While Tuscany does not need any presentation, it never disappoints. The area south of Florence, between Siena and Val d’Orcia, will set the stage for our exploration by bike. Remember that you can ride as little or as much as you want, or take the day off altogether. We start in Cortona, the delightful hill town made famous by Frances Mayes in her bestselling novel, Under the Tuscan Sun. We’ll then move to the countryside in the outskirts of Pienza. You will visit medieval hilltop towns, abbeys, and wineries. Siena is the embodiment of a medieval city and it will be our grand finale. In the Chianti region, you will explore part of the production area with a visit to the Brolio Winery (the “inventors” of Chianti). We should also mention that this area has been known since Roman times for its thermal springs and we will take advantage of that.

Not sure if you can do it? Contact us to schedule a call about how demanding the rides are or about reserving and E-bike.


  • Two important wine regions: Chianti and Val d'Orcia
  • UNESCO World Heritage Sites of Val d’Orcia and Siena 
  • Villages of Pienza and Montepulciano
  • Stunning cycling along rolling hills covered with vineyards and quaint medieval villages
  • The thermal spa of Rapolano Terme
  • Some of the best regional food in Italy     
  • Crete Senesi         
  • Cortona, the village featured in “Under the Tuscan Sun”   
  • Private wine tasting at Castello di Brolio

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Private room (single supplement) USD 695


7 days (6 nights)



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Overall, you exceeded my expectations. I was so blown away by this trip. One of the best experiences I have had since doing these types of trips.

Amanda Blackburn Tuscany Cycling Tour

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Day by Day

[fa icon="plus"] Day 1

Cortona - 10 mls - Hilly

Your guides will meet you at the Florence airport for a late morning shuttle. Cortona stands on a hilltop near the border with Umbria and offers fantastic views over Lake Trasimeno and Valdichiana. It is surrounded by vineyards, olive groves and country houses made of stone. Rich in Etruscan relics, Medieval buildings and Renaissance works, it was also a place that many Renaissance artists called home. After the release of Frances Mayes' book, Under the Tuscan Sun (1996), and the movie adaptation of the same name (2003) starring Diane Lane and Sandra Oh, the area became even more famous. A short warm-up ride will swing by Villa Bramasole and through some beautiful farmland. Our hotel features a stunning location atop Cortona. Glass in our hands, we will enjoy the sunset from the garden while the guides describe the week ahead.

[fa icon="plus"] Day 2

Cortona - 33 or 45 mls - Rolling

We leave Cortona and we plunge into fertile farmland covered with vineyards, olive groves, and orchards. While riding panoramic routes that wind through the green countryside around Cortona, we will stop to enjoy the views granted by a magnificent rolling road.

You have now crossed the border into Umbria, the so-called “Green Heart of Italy.” At about midway we’ll find our lunch spot. The way back is through a serene valley with tobacco fields. Climb back to Cortona (or get a ride in the van) and spend the rest of the afternoon wandering the streets to check out the local artisan shops. Tomorrow, we move to Pienza.

[fa icon="plus"] Day 3

Val d'Orcia - Pienza - 40 mls - Hilly

Today you will enter the Val d’Orcia and we make it to its most significant town, Pienza. Pienza is known for Pope Pio II, for its perfectly-preserved medieval center, and for pecorino cheese (ready to taste pecorino cheese gelato?). Its hilltop location also affords a stunning view of the valley.

The ride will touch Montepulciano, Monticchiello, and, finally, Pienza for lunch with a view. All of those villages are easy to spot because of their dominant positions. There will be plenty of photo opportunities!

Free afternoon to relax and to explore the village or your own or follow your guides for a guided walking tour.

[fa icon="plus"] Day 4

Val D'Orcia - Sant'Anna in Camprena -  31 mls - Hilly

Today’s ride covers another area of Val d’Orcia and it goes by Petroio, and Sant’Anna in Camprena.While these places might not ring a bell, they have been featured in some important movie blockbusters: The Gladiator had a dreamy scene among wheat fields over these hills, and Sant’Anna in Camprena set the stage for some of the scenes in the English Patient. Your guides will be able to point out those locations; use your imagination and enjoy the peaceful landscape chosen by the movie directors. Have you have ridden in a movie setting? Now, you have!

We’ll reach our charming agriturismo stay in time to enjoy aperitivo and sunset.

[fa icon="plus"] Day 5

Chianti loop - 38 mls - Rolling hills

Today’s ride is a roller coaster journey along beautiful ridges and gentle hills through yet more stunning countryside. We are in the Chianti Classico production area. After Castelnuovo Berardenga we reach the Arbia River Valley and we head north. A panoramic road that runs through a forest will lead to a Chianti producer, actually the inventors of Chianti themselves. We will pay a visit to Castello di Brolio of the Ricasoli family. Ricasoli is one of the oldest companies in the world, among the first Italian winemakers, and has been owned by the same family for 32 generations. A unique private visit includes a tasting of the most important Cru wines produced by Barone Ricasoli, right where it all started. After a guided tour of the Ricasoli Collection, the gardens and the apartment of the Ricasoli family (closed to the public), you will be seated in the ancient Armory, where a guide-sommelier will lead you through a tasting.

[fa icon="plus"] Day 6

Siena - 32 mls - Hilly

Your Tuscany trip also features Siena (UNESCO site), where a medieval air lingers amidst the twisting streets of warm, brown brick. Strolling Siena’s narrow maze of cobblestone walkways is an amazing architectural journey. The whole city of Siena, built around the Piazza del Campo, was devised as a work of art that blends into the surrounding landscape. You’ll have a beautiful ride that will take you into Siena via the Crete senesi landscape. Crete senesi are literally “Senese clays,” and the distinctive grey coloration of the soil gives the landscape an appearance often described as lunar. With Siena in sight, you must stop to admire the spectacular countryside with the town as the backdrop. Once in Siena, we take a walking tour with a local guide to learn about this special place and its obsession with the “palio.” Dinner at an authentic trattoria will be the perfect farewell to Tuscany.

[fa icon="plus"] Day 7
Florence airport transfer
Group transfer to the Florence airport after breakfast unless you are extending your stay in Siena.


What's Included

Bianchi Intenso Ultegra-105

Bianchi Via Nirone SBianchi Via Nirone S

 • Two professional tour guides throughout the program

• All accommodations in 4-star hotels (one 5-star)

• All breakfasts, all lunches, and all dinners

• Wine and beer with meals, coffee, cappuccino, and gelato stops

• Tastings of wine and local specialties

• Entrance to thermal spa

• Logistical support during the tour and luggage transfer

• Guided tour of Siena

• Shuttle at the beginning and at the end of the tour

• All activities mentioned in the day-by-day description

• Bianchi bike rental 

• GPS navigation and maps (digital)


• Airfare
• Pre-tour hotel stays and post-tour hotel stays
• Personal expenses such as laundry and cell phone
• Guide gratuity
• Optional tour extension


Villa Marsili






More Info

Food and Wine

It's often pointed that Tuscan cooking has its roots in "cucina povera" - peasant cooking. In truth, though, that can be said of most Italian cuisines. It's true, though, that Tuscan cooking is a simple one. There are no reductions, no fancy sauces, no elaborate creations, no heavy complicated seasoning. Throughout Tuscany, olive groves and wild herbs are everywhere. Many of the best olive oils produced in Tuscany are reserved for use as a condiment at the table, rather than as an ingredient in cooking in the kitchen. Some of the best Italian reds are produced in Tuscany: Chianti, Brunello, Nobile di Montepulciano, not to mention the super-tuscans.


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