Stride climate

Trip Type : Group Tour
Italy: Bike Tour of Tuscany tour

Italy: Bike Tour of Tuscany

Discovery Bicycle Tours
5.0 . Excellent
Travel Style: You will have solid amounts of both free time and structured time with some activities and meals included. Mixed
Physical Level: Regular walking or cycling over moderately long, hilly, or bumpy distances. Some public transport or utility vehicles such as safari jeeps. Moderate
Lodging Level: Mid-range budget with accommodations ranging from comfortable lodges, guesthouses, and homestays to three star hotels. Value - 3 star
10 days
From: $ 3,395 $ 340 / day
Checking price



  • Explore Florence
  • Visit the spectacular Castello Banfi
  • Enjoy wine tasting at the famous Villa Barbi vineyard
  • Visit to an exquisite small 13th century church

Short Description

This tour captures the essence of the Italian experience including visits to Siena, Montalcino, Pienza, Montepulciano and Bagno Vignoni. We have selected absolutely stunning accommodations and include superb meals, wine tastings, and a personalized walking tour of Siena. You will be led by talented, engaging, and very experienced bilingual Italian guides, whose intimate knowledge of love of all things, places, and people Italian will assure that your vacation is a visual, culinary, and cultural delight.

Groups are between 25-60 people, typically ~30-40. Usually there will be many opportunities to split off and enjoy meals and excursions in smaller groups. This is the most economical way to travel, saving up to 40% versus booking the same itinerary yourself.
Trip Type Group Tour
Spend most of the time outdoors. Common trip themes and activities include cycling, hiking, kayaking, whitewater rafting.
Itinerary Focus Active
Mid-range budget with accommodations ranging from comfortable lodges, guesthouses, and homestays to three star hotels.
Lodging Level Value - 3 star
Flights & Transport Only ground transport
Start City Florence
End City Chiusi

Trip Includes

  • Guided walking tour of Florence
  • Guided walking tour of Siena
  • Brunello wine tasting in Montalcino, entry fees
  • Transfers during the tour
  • 7 nights lodging, 7 breakfasts, 5 dinners (you are on your own for dinner one night in Montalcino and one night in Pienza)
  • All gratuities for accommodations and meals
  • Detailed maps and itineraries
  • Experienced Italian guides
  • Full van support, bicycle and helmet
  • Coach transfer from Florence to Siena
  • Facilitation of transfers to Rome or Florence at end of tour

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Day 1: Arrival Day  |  Distance: Walking

Accommodation: Hotel Cellai

We have added a day and night in Florence including a guided walking tour, dinner and accommodations at the delightful Hotel Cellai! The next morning you are on your own to explore Florence before we transfer to Siena.

Day 2 Distance: Walking  |  Terrain: Intermediate

Accommodation: Hotel Palazzo Ravizza

Around 3:30-4:00 pm, we will take a walking tour of Siena. The tour will end in time for everyone to be fitted to their bikes, and to then enjoy a great dinner at a local restaurant.

Day 3 Distance: 26 or 34 miles  |  Terrain: Intermediate

Accommodation: Hotel Vecchia Oliviera

After breakfast, we will have a meeting to discuss the details of the tour, safe cycling, and other issues, and be given our tour maps and directions. You will then be transported outside of the city to a quiet location on the road to Ville di Corsano where your cycling begins. Lunch (included) is at a beautiful villa overlooking the ancient village of Murlo.

We have designated two good places to end the day’s ride. The first is in Buonconvento. Here you can enjoy a stroll on Via Roma and visit a café before taking the 15 minute van shuttle up to Montalcino. You can also cycle a bit further (but avoid the final short but steep climb into Montalcino)… and we will shuttle you the last few kilometers. You also have the option to cycle up to Montalcino. Dinner is at Re di Macchia, an excellent restaurant that specializes in local cuisine, including their renowned Florentine steak.

Day 4: Distance: 22 or 34 miles  |  Terrain: Intermediate

Accommodation: Hotel Vecchia Oliviera

Today we ride through some of Montalcino’s finest vineyards, home to the famous Brunello di Montalcino and Rosso di Montalcino, and we visit the spectacular Castello Banfi. We then ride (or take a short 10 minute shuttle) up to San Angelo in Colle where we can select from three fine trattorias for lunch. After lunch we ride down to the lovely Abbey at Sant’Antimo in Castelnuovo dell’Abate…and with luck we will arrive in time to listen to the monks chanting inside this picture perfect Romanesque church. We then enjoy a tour and wine tasting at the famous Villa Barbi vineyard before cycling back to Montalcino, You are on your own for dinner this evening and we will give you a variety of superb suggestions as to where to dine.

Day 5: Distance: 24 miles  |  Terrain: Intermediate

Accommodation: Hotel Relais Il Chiostro de Pienza

Today we ride through Torrenieri and then continue with easy cycling along the River Asso to the beautiful medieval villages of Montisi and Castlemuzio where we have lunch. We then ride to the lovely medieval monastery at Sant’Anna in Camprena (made famous by the movie “The English Patient”). From Sant’Anna we ride into the walled Renaissance “city” of Pienza. In the evening we enjoy dinner and local wine at a delightful local trattoria (Buca delle Fatte).

Day 6: Distance: 30 miles  |  Terrain: Intermediate

Accommodation: Hotel Relais Il Chiostro de Pienza

Today’s ride takes us from Pienza to the beautiful walled hill town of Montepulciano. Here we wind our way through narrow cobbled streets and past magnificent palaces to Piazza Grande with its 13th century tower. Perhaps stop here for a leisurely lunch with a glass of the world famous Vino Nobile, and visit the many boutiques and shops. We leave Montepulciano, passing the picturesque Temple of San Biagio, and then cycle to the charming and unpretentious village of Montichiello where a short stroll will reward you with great views over the country side, a visit to an exquisite small 13th century church, and a pleasant sense of rural Italian life. Another highlight of the day is our ride to Bagno Vignoni. This magnificent small resort town is known for its curative hot springs and for the huge ancient pool in the central square which is surrounded by picturesque medieval buildings (most having been built by the Medicis). Dinner this evening is on your own in Pienza. We will give you a variety of superb suggestions as to where to dine.

Day 7: Distance: 28 miles  |  Terrain: Intermediate

Accommodation: Fonteverde Natural Spa Resort

Today we ride on a long gentle downhill, passing huge pinola trees that arch over the road, followed by some modest climbs through beautiful Tuscan countryside to San Casciano dei Bagni. The town is small and attractive and the area is known for its local olives, cheeses, and wines. However the fame of the town rests on the numerous nearby thermal spas and we take full advantage of this opportunity by staying our last night as guests at the luxurious Five Star Fonteverde Hotel, a spectacular property beautifully situated around a Medici villa and ancient thermal baths. Dinner is at Fonteverde.

Day 8: Departure Day

Departure day. In the morning we will transport you to the train station in Chiusi. Trains to Rome, Florence, Venice and Milan stop here several times each day. Our leaders will assist you in making all your train reservations for your departure.


Checking price
Price From $ 3,395
Price Per Day: $ 340 per day
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  • Deposit Price: $ 300
  • Single Supplement (Single Occupancy): $ 498

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Flights & Transport

Only ground transport

Group Size:

Intimate Group - 12 max


Hotel Cellai

Hotel Cellai is located in the heart of the historic center of Florence, surrounded by monuments, churches and buildings of extraordinary beauty. All the most interesting and evocative city sites are within a short walking distance, passing through little streets full of charm and mystery.

Hotel Palazzo Ravizza

Historical significance, spectacular aesthetics and great service have made Palazzo Ravizza one of the standard-bearers among Siena hotels in Italy

Hotel Vecchia Oliviera

Hotel Vecchia Oliviera is situated at the gates of Montalcino in the province of Siena. A town of a noble traditions, Montalcino lies at the heart of the Val D’orcia, and is the home of Brunello the prestigious wine known all over the world for its excellent quality.

Hotel Relais Il Chiostro de Pienza

This elegant hotel located in the heart of the walled Renaissance town of Pienza was once a 15th Century Franciscan monastery. It now offers wonderful rooms with views over red tiled roofs and beyond into the valley.

Fonteverde Natural Spa Resort

The exclusive resort was built in the 17th century by the Grand Duke Ferdinando I de’ Medici amid precious hot springs whose therapeutic properties were known since ancient times. This is the premier spa center in Europe and the resort includes extensive spa facilities,  natural thermal hot waters, seven swimming therapeutic pools, a holistic center and beauty center as well as one of the areas’ finest restaurants.

Cancellation Policy:


If you cancel your tour reservation, your cancellation fee will be determined as follows:

If you cancel 60 or more days prior to the start of your tour, there is no cancellation fee.

If you cancel between 45 and 59 days prior to the start of your tour, you will forfeit 50% of all tour payments.

If you cancel between 0 and 44 days prior to the start of your tour, all tour payments will be forfeited.

Trip ID#:


Trip Excludes

Airfare is not included

Meals Included:

7 Breakfasts and 5 Dinners

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