Tempting Tuscany

On this tour you will enjoy visits to the wonderfully unique historical centers of Siena, San Gimignano, Colle Vald’Elsa, Buonconvento, Montalcino, Pienza, Montepulciano; Abbey of St. Antimo and the superb Monastery of Monte Oliveto; exquisite medieval villages, century-old farms and churches; sweeping views over the breathtaking Tuscan landscape, an undulating patchwork of wine groves and olive trees; the barren geometrical cypress-crested mounds of the “Crete” hills; visits to the wine region of Chianti and Brunello; mild climate and delectable Tuscan food; mostly hilly terrain. La Dolce Vita! Life is sweet!

Daily Itinerary

Day 1: Arrival in Poggibonsi. You will be met by one of our representatives at the train station and he will drive you to your accommodations for the night in Villa Lecchi. This is a beautiful villa near Castellina in Chianti and is also known for excellent food. Alternatively, you will sometimes stay in a villa near Staggia Senese if Villa Lecchi is full.

Day 2: Monteriggioni – Colle di Val d’Elsa – San Gimignano – 21 miles (35 km)
Your first day of cycling takes us to charming Monteriggioni, made famous by Dante’s description in his Divine Comedy. It is a peaceful, walled village, perfectly preserved, perched on one of the hilltops near Siena. Its fortress was an important Ghibelline outpost built in the 13th century and it is an ideal place for a short stop. Continue to Colle di Val d’Elsa, where the oldest part of the town is the “colle alta”, the higher part, with a well preserved medieval center. You’ll also have time to visit some of the glass-blowing workshops. Colle di Val d’Elsa is internationally renowned for the production of crystal glassware and art. Then, after lunch, its on to San Gimignano, one of the best-preserved medieval towns in Italy. This spectacularly beautiful hill town is famous for its numerous towers, which make it conspicuous from a great distance and one of the most well recognized views in all of Italy. The entrance to San Gimignano is through the beautiful Porta San Giovanni (1262). Inside the walls we’ll find the important Collegiata Church, consecrated in 1148, near the center square. Its sidewalls are covered with frescoes depicting scenes of the New and Old Testament and are considered some of the greatest works of Italian Gothic painting. There are many art galleries and museums in San Gimignano and in almost every narrow street is an opportunity to win next year’s Kodak prize! Return to Villa Lecchi for a delicious dinner.

Day 3: Villa Lecchi – Chianti – Siena – 24 miles (38 km)
Follow winding roads through the Chianti countryside, past lush vineyards and superb wineries, to Siena, one of the most beautiful cities in Italy. After Florence, Siena, once Florence’s most powerful rival, is by far the most interesting town in Tuscany and offers us many treasures. Highlights are: the dazzling Cathedral and the Palazzo Pubblico, both gorgeous Gothic buildings, and the Piazza del Campo, one of the most remarkable squares in Italy and the site of the yearly “Palio” horse races in July and August. Stroll through the famous Piazza del Campo, enjoy a gelato, and find a charming trattoria for dinner tonight.

Day 4: Siena – Buonconvento – 25 miles (40 km)
Pedal on the Chianti country roads as the landscape changes from lush vineyards to the more linear cypress-crested hills of the “Crete” near Buonconvento. Here shepherds tend the sheep whose milk is used to make the famous pecorino cheese. You will pass through the tiny village of Murlo, the oldest settlement in the area, before arriving at today’s destination, a delightful agriturismo just 3 km from Buonconvento. In the summer you can have a refreshing dip in the pool here and in the autumn a relaxing massage and sauna are possible at their beauty farm.

Day 5: Buonconvento – Montalcino – 28 miles (46 km)
After a steep climb, pedal through the spectacular eroded hills of “Crete” and then through thick cypress and olive groves as you approach the 14th-century Benedictine monastery of Monte Oliveto Maggiore, one of the best known Benedictine monasteries in Tuscany. The monastery was founded for hermits in 1313 and was suppressed by Napoleon in 1810. After restoration it was made a national monument though some monks remain as caretakers. Century old pines surround the cloister and the walls are decorated with gorgeous, well-preserved frescoes, detailing the history of St. Benedetto and the Benedictine Order. Contemplate the cloister with its magnificent fresco cycle on the life of St. Benedict. Then continue to Montalcino, the capital of Brunello wine. From Montalcino you’ll have a magnificent view over the mountains of Umbria and on a clear day even the islands of Elba and Corsica! Montalcino has a rich cultural and political history. The area was already inhabited in the Paleolithic Era and Etruscan and Roman settlements developed here. In the Middle Ages Montalcino was a flourishing, independent town, but it was repeatedly attacked by Sienna and Florence and in 1559 it became part of the Grand Duchy of Tuscany. Montalcino has numerous medieval houses with gardens, orchards and streets that climb up and down, offering picturesque vistas. You can visit Montalcino’s 14th century Siennese fortress with impressive ramparts built by Cosimo I. There are steps up to the lofty towers and ramparts that provide sensational views in all directions across the Orcia Valley. Sample and purchase some of the outstanding Brunello wines in one of the many wine stores sprinkled throughout this charming town.

Day 6: Montalcino – Sant’ Antimo – Montalcino – 12 miles (20 km)
You will not be changing hotels tonight so you can decide to relax in beautiful Montalcino and stroll around the town. Or you can follow the trail to the inspiring Benedictine Abbey of Sant’ Antimo. Few of the monastic buildings remain, but the 12th-century church is well preserved and is an outstanding example of the Italian Romanesque style. With luck, you’ll visit at a time when the monks celebrate mass and the church echoes with Gregorian chants. Then return to Montalcino where you spend a second night.

Day 7: Montalcino – Montepulciano – 28 miles (45 km)
You pedal through many wonderful places today. Pause at the hot sulfurous ancient spa of Bagno Vignoni. Here we can soak our feet in the warm sulphurous waters, appreciated since Roman times, that bubble up into a large pool constructed by the Medici family in the picturesque Piazza and then continue on to the perfect Renaissance town of Pienza, an architectural jewel famous also for its cheese, the pecorino di Pienza. Pienza was planned and built from 1459 – 1462 by the famous Florentine architect Gambarelli by request of Pope Pius II. Walking through the narrow streets of this walled city is a photographer’s delight; the cathedral and the Pope’s residence are well worth a visit. Continue on a dirt road that will take you to Montichiello, a tiny walled village, and then head for beautiful Montepulciano, one of Tuscany’s highest hilltop towns and famous for its red Vino Nobile wines.

Day 8: Stroll around Montepulciano before departure. You will be transferred to the Chiusi train station that has access to Rome, Florence or Milan.

Getting There

We will meet in the afternoon at the train station in Poggibonsi a good hour away by train from Florence. Please let us know the arrival time of your train at least one week before your trip! For train schedules visit the website of the Italian Railways, www.trenitalia.com or www.raileurope.com.


Daily breakfast and two dinners are included

Prices and Dates

Check out “Italy Tours” in our GUIDED Tour Calendar

Tour Length

8 days/7 nights

      – 7 nights of double occupancy lodging in mostly 3-star, air- conditioned, hotels with private facilities each night
      – Daily breakfast and 2 dinners
      – 21 or 24-speed hybrid bicycle
      – Van support OR cycle guide
      – Daily route directions for individual departures in the morning
      – Luggage transfers
    – All taxes and gratuities for the hotel and restaurant portions of the tour

21 or 24-speed hybrid bikes are included in the price of the tour. Bicycles come equipped with: grip shifters, handlebar bag, bell, cage and water bottle, optional bike computer. It is also possible to replace our pedals with your own “clip on” pedals. Helmets are not included; please bring your own helmet!


For this tour, your group can choose between a cycle guide OR van support. If you choose a bilingual Italian cycle guide, they will bike with you and guide you on the routes and around the towns. There is no van following you! If you choose van support, this is done by a bilingual Italian support driver who transfers the luggage, goes over the route notes and checks on the bikers during the day. They would not bike with you. You have to follow the directions on your own.

The level of difficulty is moderate to challenging, as the daily routes are on mostly hilly terrain. Good cycling experience is recommended to deal with up and down hills and periodically busy Italian traffic.


– Airfare
– Alcoholic and bar beverages
– Airfare
– Lunches and five dinners
– Transportation other than scheduled transfers


Average daytime temperatures in Italy in April and May are 55-75. June, July, and August range from 65-85, and September and October from 60-75. It rains about 7 days per month, with more rain in September and October and less rain in July and August.

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