Italy: Bike Tour of Tuscany

Sept. 25-Oct. 2, 2020

We have added a day and night in Florence including a guided walking tour, dinner and accommodations at the delightful Hotel Cellai!

This tour captures the essence of the Italian experience including visits to Florence, Siena, Montalcino, Pienza, Montepulciano and Bagno Vignoni. We have selected absolutely stunning accommodations and include superb meals, wine tastings, and a personalized walking tours of Florence and 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.

We have taken great care to develop a tour that offers you the full pleasures of the enchanting Tuscan countryside as well as visits to a delightful collection of small villages and towns. We travel through vineyards, past olive groves, and along narrow ancient roads lined with cypress. We wander the narrow alleyways of tiny medieval villages like Murlo, Montisi, and Castlemuzio; listen as the monks chant at Sant’Antimo; relive movie scenes from “The English Patient” as we stroll the grounds of Santa Anna in Caprena; delight in a visit to the elegant Castello Banfi Estate and vineyards; and spoil ourselves on our last night at the 5-star spa hotel, Fonteverde.

We are also the fortunate beneficiaries of the Italian obsession with all things culinary. Abundant regional produce, wild game, local mushrooms, olive oil, pecorino cheese, local truffles, and homemade pastas, all complemented with the finest local wines (and a superb wine tasting event!) assures that we will be treated to the finest regional cuisine imaginable.

The hotels are quite exquisite. Each was carefully selected by us not only for its superior quality but also to ensure that you are always staying within the city walls so you can stroll the narrow streets, visit the shops, see the sights at your leisure, and immerse yourself in all the day-to-day Italian experiences that make this a true adventure.

Italy: Bike Tour of Tuscany

DAY ONE  |  Arrival Day  |  Walking Tour  | 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 TWO  |  Walking  Tour  | Hotel Athena
We arrive in Siena to enjoy a walking tour of this spectacular historic city. You are then fitted for your bike. In the evening, we are treated to a great dinner at Osteria Nonna Gina, a popular local restaurant.

DAY THREE  |  Distance: 26 or 34 miles  |  Terrain: Intermediate  | Hotel Vecchia Oliviera
After breakfast, we will have a meeting to discuss the details of the tour, safe cycling, and other issues, and you receive your 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 FOUR  |  Distance: 22 or 34 miles  |  Terrain: Intermediate  |  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 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 FIVE  |  Distance: 24 miles  |  Terrain: Intermediate  |  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 SIX  |  Distance: 30 miles  |  Terrain: Intermediate  |  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 SEVEN  |  Distance: 28 miles  |  Terrain: Intermediate  |  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 EIGHT  |  Departure Day
Departure day. In the morning we will transport you to the train station in Chiusi. Trains to Rome and Florence stop here several times each day. Our leaders will assist you in making all your train reservations for your departure.

Tuscany, Italy Bike Tour


Make your reservation with confidence. Your 2020 tour is completely 100% refundable up to 90 days of the tour date.

reserveSeptember 25-October 2, 2020: $3,495
Reserve with $500 deposit

Final payment due 90 days prior to your tour (personal check, Visa, MasterCard, American Express or Discover)

Single Supplement Fee for Private Room: $498

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

  • If you cancel 90 or more days prior to the start of your tour, there is no cancellation fee.
  • If you cancel between 60 and 89 days prior to the start of your tour, you will forfeit 50% of all tour payments.
  • If you cancel between 0 and 59 days prior to the start of your tour, all tour payments will be forfeited.


logo-scotland-cellaiHotel 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 Athena is located just inside the Porta San Marco,in the beating heart of Siena and close to the historic center.  It offers a magnificent panoramic viewover the hills of the surrounding countryside. Their proximity to the ancient city walls ensures peach and quiet, yet within a 10-minute walk, you’ll reach the Campo, the Duomo and the Baptistery..

logo-scotland-vecchiaThe 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.


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.


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.

What’s Included

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. Airfare is not included.


We are happy to provide you with a bike to use at no charge. Our bikes come equipped with a front handlebar bag, rear carrier, water bottle, mirror and flat pedals. Pedal cages and soft gel seat covers are available on request. We are also happy to put your own clipless pedals (pedals that attach to your biking shoes) and seat on your bike if you wish. Specific details and styles of bikes available in each location are indicated under each photograph below. The make of bikes provided varies by location.

Virtual Tour of Tuscany, Italy