Day 1 – Welcome to Orvieto! Arrival on your own to Orvieto, one of the most beautiful small towns of Italy dramatically set atop vertical cliffs and surrounded by ancient defensive walls! Relax in this peaceful place
Our group will meet at 4:00 pm for a walking tour to better understand the 3,000 year history of this charming town.
Dinner is included today.

Day 2 – Transfer to Semproniano and a warm-up ride (13.2 miles/22 kilometers)
We will transfer from Orvieto to Semproniano, a little medieval town located in the Maremma region, among the hills of Albegna. The surrounding area is an example of a cultivated countryside covered with vineyards and olive groves.
Once in Semproniano, you’ll enjoy a light lunch at the hotel. We will have a brief introduction to the tour and a gentle warm up ride to get familiar with the bikes.
Breakfast and lunch are included today.

Day 3 – Biking the rolling hills of Tuscany and a cooking class (18.3 miles/30.5 kilometers)
A gentle rolling ride that takes you south to Sovana and Pitigliano, two of the most unique medieval towns in Italy. Enjoy Etruscan and Roman history told through incredible works of art: exquisite frescoes and paintings. Sovana is a jewel of Italy, a treasure chest of art and history, architecture and culture. Pitigliano is a village carved in tufa cliffs with a thousand caves and houses like towers situated on a prominent massive rock that is visible for miles. This charming town embraces and actively promotes its history. A wine and food tasting featuring local produce will complete the tour held in one of the many caves carved in the rock centuries ago.

In the afternoon our friends, Angela and Enrico, will introduce us to the local cuisine and take us through the preparation of a traditional Tuscan dinner using regional ingredients and original techniques. Buon appetito! We will stay in Semproniano again tonight.
Breakfast, lunch and dinner are included today.

Day 4 – To a lovely country hotel close to the medieval town of Scansano (22.86 miles/38.1 kilometers)
Today our destination is the resort hotel called Antico Casale di Scansano which offers a full range of amenities such as jacuzzi, sauna, massages and two outdoor swimming pools. The ride features spectacular views of the valley below where one sees grazing sheep and goats. The vineyards grow the Morellian grape, the local name for the red Sangiovese varietal which is the famous red wine from the Maremma area. Upon arrival at this rural resort Irene will greet us and show us our accomodation for two nights overlooking an equestrian centre and panoramic valley below from our terraces.
Breakfast is included today.

Day 5 – Down hill! (21 miles/35 kilometers)
After breakfast we glide down hill on a curving gradual sloping quiet road for 8 miles. Perhaps the best down hill of our trip. The first village we reach is Magliano in Toscana, surrounded by a wall built between the 13th and 15th centuries and allowing entrance into the village by one of three gates. Today’s ride will vividly demonstrates why we’re here – the superlative rural vistas which seemingly never end.

In the afternoon we will enjoy an olive oil tasting at the hotel hosted by Giorgio, a very expert olive oil producer of the area. A wonderful experience! We will spend another relaxing night at the countryside hotel.
Breakfast and dinner are included today.

Day 6 – Bike toward the sea (37.7 miles/62.8 kilometers)
After the spectacular down hill, a gentle rolling ride will take you toward the sea through the pretty village of Capalbio and ending our ride in a very charming resort of the area.
Breakfast and lunch are included today.

Day 7 – Bike to the beach of Talamone (20.22 miles/33.7 kilometers)
Experience the flat and quite road of the area toward the medieval town of Talamone, standing on a small promontory overlooking the Meditarranean sea. Here a small pretty beach to swim and feel the beauty of the sea. A picnic lunch is arranged for you today with local fresh products of the area.
Overnight in the resort for our farewell dinner together.
Breakfast, lunch, and dinner included today.

Day 8 – Departure Day
After breakfast, end of services and we will say our goodbyes. Ciao!

Actual tour itinerary may vary slightly due to unforeseen circumstances.

Click on any photo to enlarge it.

Siciclando carefully chooses every aspect of a tour, including the accommodations. Our choices are based on comfort and quality. We often choose hotels that are family-owned and operated because they provide a richer experience and because it is important to us to support the efforts of these individuals. We have developed relationships with many wonderful hotel operators. Here is a sample of the hotels on this tour.

• Semproniano
• Scansano
• Capalbio

Tour accommodations will be based on availability and the time of year. Once you have made your final payment for the tour, we will send you a confirmation letter that includes daily accommodations and contact information.

Level of difficulty: Easy to moderate

The Tuscany Maremma bike routes are among beautiful hills, which means mostly gentle ups and downs. This tour is described as moderate to easy with an average 22 miles per day. Some days there is an optional extension of 18-24 miles for those interested and ready. This flexibility allows different levels of bikers a great tour at their preferred pace.

We will begin the tour with a warm up ride on day 2. Days 3 and 4 are nice loop rides along rolling terrain ending with gentle climbs to hilltop villages and offer extensions for those wanting a longer ride. Day 5 and 6 are gentle rides — note, day 6 is our longest ride of 38 miles and a gentle climb to the town of Magliano in Toscana. Day 7 is nice ride along the coast with an optional extension.

Travel notes

Airport: the trip is based on ROMA Fiumicino

Books

• Under the Tuscan Sun by Frances Mayes (now, also a movie)
  The true story of an American women who buys and restores an abandoned villa in the countryside of Tuscany. Follow along as she discovers the beauty of the simple Italian life.
• Bella Tuscany: The Sweet Life in Italy by Frances Mayes
  A continuation of the New York Times Bestseller Under a Tuscan Sun. Re-enter the world of Tuscany for more beautiful stories of this place and its people.
• In Tuscany by Frances Mayes
  The book begins with “Tuscany is a world; Italy is a universe.” See for yourself the observances of this wonderful place.
• On the Shore of the Mediterranean (Travel Narrative) by Eric Newby
  A sparkling observer and famously entertaining, Newby tackles the Mediterranean in the merry classic account of travels to North Africa, Italy, Greece, Turkey, Cairo, and Jerusalem.
• The Hill Towns of Italy by Richard Kauffman
  An oversize survey of the towns, people, and countryside of Tuscany and Umbria. It covers 13 classic towns in the region including Siena, Cortona, Perugia, Assisi and Orvieto. First published in 1983, the book is a good mix of handsome color photographs and insightful text.
• Central Italy, Tuscany and Umbria by Berrie Kerper
  A quirky, literary guide to the history, food, and landscape of Tuscany and Umbria – as presented in travel essays by writers foreign and local. With an extensive annotated bibliography for each section.
• The Tuscan Year, Tuscan Life and Food in an Italian Valley by Elizabeth Romer 1996
  An intimate portrait of life on a Tuscan farm, as seen primarily through the robust food. Romer captures the goings-on in the countryside, especially in the kitchen.
• A Thousand Days in Tuscany by Marlene de Blasi
  “Filled with warmth and the rich and simple drama of a beautiful life. The evocation of country dishes is mouthwatering, the lyrical beauty irresistible.” Susan Herrmann Loomis, author of Cooking at Home on Rue Tatin

Group tour price

• 4-5 people € 1870 per person
• 6-7 people € 1635 per person
• 8+ people € 1465 per person

Pricing philosophy

Additional options and fees

• Hybrid Bike rental – € 100 which includes 1 bike pannier per bike, helmets and a cycle computer.
• Road bike rental €175.00 which includes 1 bike pannier per bike, helmets and a cycle computer.
• Single occupancy for hotels € 240.00

Included

• 8 day tour
• 7 nights lodging in four comfortable hotels
• 7 breakfasts
• 4 dinners (D1,D3,D5,D7)
• 4 lunches (D2, D3, D6, D7)
• Olive oil tasting
• Walking tour of Orvieto (D1)
• Walking tour of Pitigliano (D3)
• 1 cooking class (D3)
• Wine tasting (D3)
• 1 massage at the spa
• Coordinated transfer IN (from Orvieto to Semproniano)
• Coordinated transfer back to the hotel on day 3
• Coordinated transfer back to the hotel on day 4
• One English speaking tour leader
• Van support throughout the tour

Not included

• Flights and public transportation
• Travel insurance
• Admission fees not mentioned above
• Personal expenses such as drinks, phone calls, etc.
• Gratuity of Tour Leader(s)

Self-guided option

This tour is not available as a self-guided option.

Tour code

TM

Day 1 – Welcome to Tuscany! – Poggibonsi

You will arrive on your own in Poggibonsi. You will be met by our representative who will drive you to your villa in Staggia near Castellina in Chianti.

Day 2 – Colle Vald’Elsa to San Gimignano (21 miles/35 km)

Departing from Villa Lecchi, first you will encounter the fortified town of Monteriggioni with its distinctive round shape dominating the surrounding plain. On to Colle Val d’ Elsa and its glass blowing artisans, some of which you can visit. Today’s route will also take us to San Gimignano with its beautiful towers. You will want to spend some time here to explore the city and perhaps some of the village shops before starting back to Villa Lecchi.

Day 3 – Castellina in Chianti to Siena (31 miles/52 km)

Enjoy beautiful biking through winding Chianti roads among luscious landscapes with vineyards and superb wineries. Our day will end in Siena where you may enjoy a gelato (ice cream) at one of the most famous squares in Italy, the Piazza del Campo. Overnight in Siena.

Day 4 – Siena to Buonconvento (19 miles/32 km)

As you bike today you will notice lush vineyards give way to the linear cypress-crested hills of the “Crete.” Murlo is a charming little village on your way to the farm where you will spend the night. In summer months you may enjoy a refreshing dip in the swimming pool. There are also relaxing massages and a sauna available for your enjoyment.

Day 5 – Buonconvento to Montalcino (27 miles/46 km)

We start towards Buonconvento, then head for the Monte Oliveto Monastery, an imposing brick building that overlooks a rugged landscape of dry ravines. A soft downhill will take you to the start of a fairly long uphill to reach Montalcino. You will spend the night in a nice hotel in Montalcino, the home land of Brunello wines.

Day 6 – Sant’Antimo abbey loop ride (20 miles/34 km)

Enjoy this fortified town from which you will enjoy stunning views from all directions. The descending trail road will lead you to the beautiful and peaceful church of Sant’Antimo Abbey where you may be able to listen to Gregorian chants. A lovely end to a peaceful day.

Day 7 – Montalcino to Pienza and Montepulciano (27 miles/45 km)

A very full day beginning with Bagno Vignoni and its thermal pool in the center of town. On to Pienza, the renaissance jewel redesigned by the pope Pio the II to become a “liveable” town. It is also an agricultural center well known for pecorino cheese and truffle production. A dirt road will take you to Montichiello, a nice little village immersed in the “Crete.” Here you can stop for a nice lunch or a cappuccino before continuing to Montepulciano known for its “Nobile” wine.

Day 8 – Departure Day

End of our services after breakfast. Ciao!

Actual tour itinerary may vary slightly due to unforeseen circumstances.

Click on any photo to enlarge it.

Siciclando carefully chooses every aspect of a tour, including the accommodations.

Our choices are based on comfort and quality. We often choose hotels that are family-owned and operated because they provide a richer experience and because it is important to us to support the efforts of these individuals. We have developed relationships with many wonderful hotel operators. Here is a sample of the hotels on this tour.

• Siena
• Buonconvento
• Montepulciano

Tour accommodations will be based on availability and the time of year. Once you have made your final payment for the tour, we will send you a confirmation letter that includes daily accommodations and contact information.

Level of difficulty: Moderate

There is no easy way to tour Tuscany. It is a hilly country so with all the ups and downs, the altitude gap at the end of the day is never small. However we tried hard to keep it as smoth as possibile. The toughest day is the third, from Siena to Buonconvento and the longest is the fifth if you have road bikes and have to stay on asphalt roads.

Travel Notes

The reference airports for the tour are Perugia, Pisa, or Rome.

You can also find information about travel by train.

Books

• Under the Tuscan Sun by Frances Mayers

Movies

• Il Paziente inglese
• Ballo da sola

Group tour price

• 4-5 people € 1590 per person
• 6-7 people € 1455 per person
• 8+ people € 1280 per person

Pricing philosophy

Additional options

• Private room – € 260
• Hybrid Bike rental – € 100 (€ 18 each additional day), which includes 1 bike pannier per bike, helmets and a cycle computer.
• Road Bike rental – € 175 (€ 27 each additional day), which includes 1 bike pannier per bike, helmets and a cycle computer.
• Cooking class – € 80 per person
• GPS – € 35 Garmin E-Trex Venture HC

Included

• One English-speaking trip leader
• Seven nights in three-star hotels, all rooms with en suite bathroom
• Seven breakfasts and three dinners
• Baggage transportation between hotels
• Detailed route information and maps
• Van support

Not included

• Admission to museums and archaeological sites
• Tickets for trains or any public transportation
• Wine or beverages
• Airfare
• Transfers to the starting point or from the finishing point unless specified; we can assist you in planning and arranging for any necessary shuttles
• Transport of bike case (for guests who bring their own bike)
• Personal expenses (laundry, personal supplies, phone calls, etc.)
• Gratuity

Self-guided option

This tour is also available as a self-guided option at a cost of € 1.130 per person. This option includes:

• Seven nights in three-star hotels, all rooms with en suite bathroom
• Seven breakfasts and two dinners
• Welcome meeting (tour explanation)
• Baggage transportation from between hotels
• Detailed route information and maps
• Telephone assistance

Tour code

TU

Day 1 – Welcome to Assisi, Italy!

Arrival in Assisi and transfer to your hotel. Visit this beautiful town which is within a 10 minute walk from your hotel. Spend time at the stunning Saint Francis Basilica and enjoy the frescos by Giotto. The next morning you are given your information materials: road book, maps, guide book and vouchers. You will have a chance to try your bike and make necessary adjustments.

Day 2 – Loop around Assisi (30 miles/50 km)

Today the ride takes you to Spello a very nice small town, on the Subasio Slopes, with fewer tourists. You will be riding through olive groves with no major uphill except for the final climb back to Assisi. Enjoy another night at the same inn.

Day 3 – Assisi to la Corte del Poggio (36 miles/60 km)

Bike to Trasimeno Lake with a visit to Deruta, famous for its elaborately painted ceramics with techniques developed over centuries. We will also visit Torgiano and Lungarotti wineries for tasting of the region’s unique Montefalco red wine or a stop at the wine museum. You will bike through soft hills and nice villages until you reach la Corte del Poggio. The road is continuously rolling up and down hill. You will be happy to find a nice swimming pool upon arrival at the inn.

Day 4 – Around the lake to Cortona (30 miles/50 km)

Another enjoyable day as we get a nice view of the lake, Monte del Lago, and San Feliciano fishing village from the Montecorognola overlook. Take a boat to Isola Maggiore where old ladies weave their age old laces and where you can taste delicious fish at Sauro’s. Then continue to Cortona where you will spend the night.

Day 5 – Cortona to Montepulciano (27 miles/45 km)

Today you enter Tuscany through the wine country of Montepulciano. Before getting there, you will enjoy a tour of the small Chiusi and Montepulciano Lakes. Once in Montepulciano, tour this beautiful renaissance town. Be sure to visit the superb Cantine del Redi Winery with their vaulted cellars. Enjoy a taste of the “Nobile” at Crociani Winery, a smaller operation, but very friendly.

Day 6 – Montepulciano to Buonconvento (27 miles/45 km)

After a visit to the San Biagio church, head for Pienza, the beautiful Renaissance town, home to Pope Pio the II. On the way discover the incredible “Crete” landscape with barren hills, crowned by rows of cypress trees. Stop in Montichiello, a little medieval borough where you can sip a cappuccino (or a glass of wine) seated at the terrace of the local cafè. Make the detour to visit the thermal town of Bagno Vignoni with its incredible main square. You will spend the night in a nice inn near Buonconvento or in a modern three star hotel in Buonconvento.

An alternative on this day can be a visit to Montalcino and then onto Buonconvento.

Day 7 – Buonconvento to Siena (30 miles/50 km)

The road to Monte Oliveto Maggiore Monastery is a gentle climb from Buonconvento. Stop and visit the abbey before continuing to Asciano, a small town in the heart of the Crete. From there continue on to Sienna. The landscape is more rugged today with plenty of ups and downs, but the landscape is superb and worth the ride. Spend the night in Sienna in a centrally-located three star hotel.

Day 8 – Siena – Departure Day

Free time in Sienna to visit the town before your departure. Ciao!

Actual tour itinerary may vary slightly due to unforeseen circumstances.

Click on a photo to enlarge it.

Siciclando carefully chooses every aspect of a tour, including the accommodations.

Our choices are based on comfort and quality. We often choose hotels that are family-owned and operated because they provide a richer experience and because it is important to us to support the efforts of these individuals. We have developed relationships with many wonderful hotel operators. Here is a sample of the hotels on this tour.

• Cortona
• Corte del Poggio
• Siena

Tour accommodations will be based on availability and the time of year. Once you have made your final payment for the tour, we will send you a confirmation letter that includes daily accommodations and contact information.

Level of difficulty: Moderate

Tuscany and Umbria are no easy regions as the most interesting places are on top of a hill. However we have chosen the smoothest slopes to reach the top and the easiest routes. The toughest day are the fifth with the climb to Cortona and the last, going to Siena.

Travel notes

The reference airports for the tour are Perugia, Pisa, or Rome.

You can also find information about travel by train.

Books

• Under the Tuscan Sun by Frances Mayers

Movies

• Il Paziente inglese
• Ballo da sola

Group tour price

• 4-5 people € 1620 per person
• 6-7 people € 1450 per person
• 8+ people € 1265 per person

Pricing philosophy

Additional options

• Private room – € 265
• Hybrid Bike rental – € 100 (€ 18 each additional day), which includes 1 bike pannier per bike, helmets and a cycle computer.
• Road Bike rental – € 175 (€ 27 each additional day), which includes 1 bike pannier per bike, helmets and a cycle computer.
• Cooking class – € 80 per person

Included

• One English-speaking trip leader
• Seven nights in three-star hotels, all rooms with en suite bathroom
• Seven breakfasts and three dinners
• Baggage transportation between hotels
• Detailed route information and maps
• Van support

Not included

• Admission to museums and archaeological sites
• Tickets for trains or any public transportation
• Wine or beverages
• Airfare
• Transfers to the starting point or from the finishing point unless specified; we can assist you in planning and arranging for any necessary shuttles
• Transport of bike case (for guests who bring their own bike)
• Personal expenses (laundry, personal supplies, phone calls, etc.)
• Gratuity

Self-guided option

This tour is also available as a self-guided option at a cost of € 1.145 per person. This option includes:

• 7 Nights in 3 star hotels, all rooms with en suite bathroom
• 7 Breakfasts
• 2 Dinner
• Welcome meeting (tour explanation and bike fitting)
• Baggage transportation from hotel to hotel
• Detailed road book and maps
• 7 day telephone assistance

Tour code

UT

Day 1 – Welcome to Tuscany!

Arrive on your own in Siena. The hotel is centrally located and will make it easy to visit this very famous town and its superb square: Piazza del Campo.

Day 2 – Siena to Buonconvento (19 miles/32 km)

Today’s bike ride will take you through winding Tuscan roads. Luscious vineyards give way to the more linear cypress-crested hills of the “Crete.” Murlo is a nice little village on your way to the farm where you will spend the night. Summer months allow you to take a refreshing dip in the swimming pool. You may also enjoy a relaxing massage and a sauna.

Day 3 – Buonconvento Loop Ride (23 miles/38 km)

Today, a nice loop ride will allow a visit of one of the most imposing monasterys of central Italy : Monte Oliveto Maggiore with its frescoes by Luca Signorelli. Spend the night at the same farmhouse.

Day 4 – Buonconvento to Montalcino (19 miles/32 km)

Your route today takes you towards San Quirico d’Orcia, a lovely small town with many old churches. On to Bagno Vignoni, an ancient thermal town where the main square is a steaming pool. You will spend the night in a nice hotel in Montalcino, the home land of Brunello wine.

Day 5 – Sant’Antimo Abbey Loop Ride (20 miles/34 km)

Enjoy this fortified town where you will enjoy stunning views from all directions. The descending road leads you to the beautiful and peaceful church of Sant’Antimo Abbey where you may be able to listen to Gregorian chants. Come back to Montalcino by a different road.

Day 6 – Montalcino to Pienza and Montepulciano (27 miles/45 km)

A very full day beginning with a visit to Pienza, the renaissance jewel redesigned by Pope Pio the II to become a “liveable” town. This is also an agricultural center well known for pecorino cheese and truffle production. A dirt road will take you to Montichiello a nice little village immersed in the “Crete.” You can stop there for a nice lunch or just for a cappuccino before continuing to Montepulciano known for its “Nobile” wine.

Day 7 – Montepulciano to Cortona (25.4 miles/40.7 km)

Today’s route meanders through vineyards and cypress crowned hills then passes the Farneta Abbey before climbing to Cortona. It is more challenging at the end of the day, but it is worth it. This little town is full of charm.

Day 8 – Departure Day

End of the tour. Ciao!

Actual tour itinerary may vary slightly due to unforeseen circumstances.

Click on any photo to enlarge it.

Siciclando carefully chooses every aspect of a tour, including the accommodations.

Our choices are based on comfort and quality. We often choose hotels that are family-owned and operated because they provide a richer experience and because it is important to us to support the efforts of these individuals. We have developed relationships with many wonderful hotel operators. Here is a sample of the hotels on this tour.

• Montalcino
• Siena
• Cortona

Tour accommodations will be based on availability and the time of year. Once you have made your final payment for the tour, we will send you a confirmation letter that includes daily accommodations and contact information.

Level of difficulty: Easy

This tour is an easy one not only because of the total distance you’ll cover along the week (ony 87 miles!), but also because of the rest days you’ll enjoy on day 4 (option ride is available anyway) and day 6. Besides: the rest day more at the beginning of the tour allows you the possibility to have a gentle beginning of your holiday. The mix with the railway is another point which gives you an opportunity to have relaxing stops from the cycling and more opportunities to share your experience with the local people.

Travel Notes

The reference airports for the tour are Perugia, Pisa, or Rome.

You can also find information about travel by train.

Books

• Under the Tuscan Sun by Frances Mayers

Movies

• Il Paziente inglese
• Ballo da sola

Group tour price

• 4-5 people € 1620 per person
• 6-7 people € 1450 per person
• 8+ people € 1265 per person

Pricing philosophy

Additional options

• Private room – € 275
• Hybrid Bike rental – € 100 (€ 18 each additional day), which includes 1 bike pannier per bike, helmets and a cycle computer.
• Road Bike rental – € 175 (€ 27 each additional day), which includes 1 bike pannier per bike, helmets and a cycle computer.
• Cooking class – € 80 per person
• GPS – € 35 Garmin E-Trex Venture HC

Included

• One English-speaking trip leader
• Seven nights in three-star hotels
• Seven breakfasts and three dinners
• Baggage transportation from hotel to hotel
• Detailed route information and maps
• Van support

Not included

• Admission to museums and archaeological sites
• Tickets for trains or any public transportation
• Wine or beverages
• Airfare
• Transfers to the starting point or from the finishing point unless specified; we can assist you in planning and arranging for any necessary shuttles
• Transport of bike case (for guests who bring their own bike)
• Personal expenses (laundry, personal supplies, phone calls, etc.)
• Gratuity

Self-guided option

This tour is also available as a self-guided option at a cost of € 1125 per person. This option includes:

• Seven nights in three-star hotels
• Seven breakfasts and two dinners
• Welcome meeting (tour explanation)
• Baggage transportation from between hotels
• Detailed route information and maps
• Telephone assistance

Tour code

TE