Made famous by the wine of the same name, the Chianti region spells ancient tranquility and adventure in the same breath.


the chianti region of tuscany

Populated by cities and towns including Florence, Siena, and Pisa means there is no end to exploring the far reaches of Western European History. It is easy to get happily lost in such a place. Surrounding these famous bastions are endless rolling hills of green, yellow and lavender, dotted by spectacular Villas, vineyards, and perfectly shaped pines, adorning pathways to the next bend in view. For the person on an outdoor journey, there is no other place possessing such perfection.

As time stops, one has the luxury of cycling through valleys of sunlight, and up the next hill towards any castle or monastery that may be in sight. Some of the hills may be significant, but every view and vista is so divine that any effort is melted to oblivion by the joy of existing in this endless artistic palette, otherwise know as landscape. Reach the top, look over the valley, and you will wonder if you have remained on earth or passed into paradise. The truth is that you have arrived at both. Whether you stay for one week or three, there is an endless variety of routes to follow, for all levels and abilities.

With serious competition only from a few neighboring regions in Tuscany and Piedmont, Chianti is one of Italy's prime wine regions. You will also be able to sample the special Pasta of the Chianti region; with Boar meat! Touring the wineries is an integral part of the Chianti experience, and it goes without saying that we make a point of maintaining this tradition on each tour.

“With Bike Tours Italy you are not a tourist,
you’re family. You don’t tour Italy, you’re immersed in Italy.”
— David Wilkes, Indianapolis
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The Chianti Region – Discovery at every turn


We leave Monteriggioni for a moderate ride in the Tuscan countryside, passing below the fortress of Staggia Senese. We then make our way to the hill-top town of Castellina in Chianti where the small stone church in the center of the village has been restored to its original glory. We will stop here for lunch and enjoy the amazing view across the valley as we sip on a glass or spin the fresh pasta on our forks! As we leave Castellina, we will travel along a road lined with olive trees and "grappoli" of future Chianti Wine, until we arrive in San Leonino, then head back to Monteriggioni.


As we leave Monteriggioni, we head south toward Siena. After 12.42 miles (20 km), we reach the outskirts of Siena and pass through Taverne d'Arbia, continuing on to Crete Senesi where outdoor Italian bars offer freshly squeezed "aranciate". The view from this location is spectacular. These hill top views continue until Vescona Chiesa and Palazzina with ancient stone and brick houses. We take a break under the shady porticos of Ristorante La Mencia, that has a great selection of tasty salamini and seasonal cacciotelle, or you can taste the simple Ciaccino Crudo & Arucola next to the crunchy authentic Pizza Margherita. After sampling the grand collection of local wines like the Chianti Classico, we head to Chiusure, famous for its Artichoke Festival, the mystical Archabbey of Monte Oliveto Maggiore with intricate sun dials, and past the roman walls of Buonconvento. We continue to climb, avoiding the traffic around Siena and arrive back at Monteriggioni. Time for a siesta!


We head west from Monteriggioni following the Strada Provinciale for 3.10 miles (5 km) and we then turn toward Strove, passing by Castel Pietraio. You will be transfixed by the endless fields of vineyards separated by the undulating terrain of Cypress trees surrounding private villas along the way. We make a sharp turn towards the beautiful town of Pievescola. We climb gently up to Osteria del Borgo going as we enter Mensano. This is the perfect place to take a break for lunch. After resting in the sun, we continue north to Casole d'Elsa as it rises out of the landscape. Going through Mensanello we are constantly surrounded by an array of flower beds as we dive down to the intersection with the Estrada Provinciale that brings us back to Monteriggioni. Since the day’s ride has not been too difficult, you might want to sprint your fellow riders to the finish!


The Etruscan ruins and medieval buildings of Valera call as we leave Monteriggioni toward Pian dell’Olmino. This part of the ride is basically flat as the Italian word says is all pretty much flat. Going through Mensanello once more, we follow a zigzag pattern that brings us into Piano. From this point we are headed northwest where the road gently follows an amazing array of gold and green hills for 3.10 miles (5 km) before merging into Strada Regionale that brings into San Gimignano, a beautiful fortress town on the hill, which is a sight to behold. We then head for Strove, climbing hills and passing the hilltop views of Sassi Bianchi, Castagno, and San Vivaldo. We head over to Osteria San Vivaldo for lunch. Here we can load up on proteins with "la fiorentina", a delicious oversized steak! Or you can try Pappardelle with Boar sauce or wild rabbit. A bottle of Chianti might also be calling your name. With new found energy you will be humming down the valley and then leap through the climb to Lano, a beautiful town on the way to Volterra. Once in Volterra, you will be able spend the rest of the day there before being transferred back to our hotel in Monteriggioni.



From Monteriggioni, we head south. Following endless lines of pine trees and vineyards, we reach Badesse, an ancient walled town with a spectacular view across the city. As we circumvent its walls, we head further south along the Via Uopini, weaving our way through small villages and gentle rolling hills, until we reach the edge of Siena. We set our sights on the famed Cathedral of black and white marble stripes and are surrounded by the scent of olive groves as we roll down the hill towards Il Campo at the heart of Siena. Lunch is in the making, and we stop at a small restaurant near the edge of the city for a break. After soaking up the sunshine and the expansive fields of vineyards and yellow flowers, we head north on our way to Quercegrossa, a beautiful village set in gentle rolling hills and very windy streets. After weaving our way through the local area, and perhaps partaking of the local gelato, we head to Villa Parigini and then on to Monteriggioni.


We leave Monteriggioni early in the morning by van to Siena where we take the direct train to Cinque Terre. The train-car is equipped with a special space dedicated to the bicycles, right next where we will be sitting.  Once arrived in Vernazza we'll climb the road between flower garden terrance and olive trees. Once on the main road connecting the Cinque Terre its time to take an espresso break and enjoy the breathtaking scenery from above.  Following the road we can visit Corniglia or we can head back toward Manarola.  Going south we can then descent to the center of town in time for the train back to Siena.  A glass of wine or beer awaits us at the hotel. Later that evening we'll meet up for our last dinner.  It will be a special one.  So special it will have you singing all the way across the village!

After breakfast transportation to airport will be provided.

RIDE TYPE                                                                                                                              Moderate

PREMIERE HOTELS and INNS                                                                                                     7 Days / 6 Nights


May 18 - 25. 2019

September 22 - 28. 2019


From $3,600 till January 31, 2019 

CALL FOR GROUP RATES                                                                                                             Single / Double Occ.

AIRPORT PICK UP/DROP OFF                                                                                   Bologna/Firenze, Italy                                  


For more info call 703-220-2424



Hotel Monteriggioni

You breathe a timeless air inside the medieval walls of Monteriggioni. Monteriggioni, a small medieval village in the Sienese hills, was originally built in the 13th century as a fortress to defend Siena against the Florentine attacks. A surrounding wall, divided by 14 towers, protects the little group of houses gathered in the square, which has a 14th century parish church and a well in the centre.  Nothing has changed within the walls of Monteriggioni, compared to a crown by the great poet Dante Alighieri in his Divine Comedy.


The only Hotel located inside the medieval Fortress of Monteriggioni. The twelve romantic bedrooms and "La Maison" are drenched in history and near both Siena and Florence.

Guest Rooms

Bedrooms with their own unique style, elegant, and intimate atmospheres which make a holiday in Tuscany truly unforgettable.  Each of the ten double and two single bedrooms of the Hotel Monteriggioni has its own unique style.
Antique furniture, precious textiles, exposed beams and warm Tuscan terracotta tiles emphasize the exclusive nature of this historic residence resting on the Sienese hills.
All of the bedrooms are equipped with air-conditioning, Internet Wi-Fi, direct the phone, satellite TV, a mini-bar and a safety deposit box. Each of the bathrooms offers a complimentary toiletries set, a hairdryer and a direct line telephone.

Superior Rooms

The Superior Rooms look out over the boundry walls of the Fortress of Monteriggioni, between the centuries-old olive trees and the stone swimming pool in the garden.
All of the bedrooms are equipped with air-conditioning, Internet Wi-Fi, direct line phone, satellite TV, a mini-bar and a safety deposit box. Each of the bathrooms offers a complimentary toiletries set, a hairdryer and a direct line telephone.

Facilities & Services

Personal attention in an exclusive and welcoming atmosphere. It's easy to feel at home at the Hotel Monteriggioni.

Breakfast is served either in the main dining room, in the bedroom or, during the summer months, in the garden. The international breakfast at Hotel Monteriggioni offers a rich variety of foods, all made with high quality ingredients: sweet pastries and savoury dishes such as cold cuts and local cheeses, fresh juice and coffee. The Bar is open all day and offers soft drinks, wine, liqueurs and cocktails either by the glass or bottle.

Hotel Monteriggioni is the only place which receives its guests inside the walls of the Fortress of Monteriggioni; guests can get in and out of the private car park in the town centre at any time.

The Hotel Reception is open 24 hours a day. The owners, Michela Gozzi and Luigi Cagnazzo, are always ready to answer any questions about the major Tuscan art cities and the ancient villages of the area. They can give useful advice about local events, city or airport transfers, guided tours and local excursions.

The advantageous position of the hotel’s garden gives it a spectacular view over the enchanting Sienese countryside.

The ancient wall surrounding the medieval village separates the garden from the soft hills which look out towards Siena and Florence.

Between the aged olive trees and the stone swimming pool, guests may find a quiet corner to read, chat or simply relax and enjoy the peace of the garden. In summer time, breakfast, aperitifs and cocktails are served in the garden so that guests may truly savor this magical scene.

Restaurants & Bars

Transform the genuine, simple local ingredients into tasty dishes, learn traditional preparation techniques and ancient recipes which have been passed down through generations, savour typical Sienese products such as cold cuts and cheeses, meat and game, breads and desserts.

Learn about the true flavour and passion of traditional Tuscan cookery on one of the courses organised by the Hotel Monteriggioni.