Tempting Tuscany - Self Guided Bike Tour - Van Gogh Tours

Tempting Tuscany

From: $1,550 USD

8 Days / 7 Nights
Type: Self-Guided
Level of Difficulty: Challenging

Imagine Yourself…

  • Biking through a quintessentially Tuscan landscape of vineyard and olive trees
  • Enjoying a gelato as you stroll through the beautiful Piazza del Campo
  • Wandering the historical building of a 14th century Benedictine Monastery
  • Relaxing with a glass of Brunello wine at a charming Italian restaurant


Van Gogh Tours - Tempting Tuscany - Self Guided Cycle TourExplore a wonderfully unique and quintessentially Tuscan landscape on this enchanting guided tour. Travelling through an undulating patchwork of vine groves and olive trees, you’ll discover exquisite medieval villages and century-old churches and farms. You’ll visit the historical centres of classic Tuscan towns like SienaSan Gimignano, Colle Val d’Elsa, Buonconvento, Montalcino, Pienza, and Montepulciano. You’ll wander through the Abbey of St. Antimo and the superb Monastery of Monte Oliveto, and explore the barren geometric mounds of hills topped with cypress trees. The region is home to the famous wines of Chianti and Brunello, and there will be ample opportunity to sample their fare and other delicious, regional cuisine. With beautiful scenery, authentic local food, and a mild climate, cycling is the ideal way to explore the region. 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 for a ride to your accommodations for the night in Villa Lecchi. This is a beautiful villa near Castellina in Chianti. If Villa Lecchi is full, you may instead stay in a lovely villa near Staggia Senese. 

  • DAY 2 - Villa Lecchi - Colle di Val d'Elsa - San Gimignano - Villa Lecchi – 25 miles (40 km)

    Departing from Villa Lecchi, you’ll come to charming Monteriggioni, made famous by Dante’s description in his Divine Comedy. This peaceful walled village, perfectly preserved, is perched on one of the hilltops near Siena. Its fortress was an important Ghibelline outpost built in the 13th century and it’s an ideal place for a short stop before heading to Colle di Val d’Elsa. The oldest part of the town is the “colle alta,” the higher part, with a well-preserved medieval center. Colle di Val d’Elsa is internationally renowned for the production of crystal glassware and art, and you’ll have time to visit some of the glass-blowing workshops. Later, it’s 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 visible 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. Inside the walls you’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! You’ll return to Villa Lecchi for the night.

  • DAY 3 - Villa Lecchi – Chianti – Monteriggioni - Siena – 26 miles (42 km)

    You will follow winding roads through the Chianti countryside, past lush vineyards and superb wineries, towards Siena, one of the most beautiful cities in Italy. After Florence, Siena 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. You can stroll through the famous Piazza del Campo, enjoy a gelato, and find a charming trattoria for your dinner tonight.

  • DAY 4 - Siena - Buonconvento – 25 miles (40 km)

    You’ll pedal on the Chianti country roads as the landscape changes from lush vineyards to more linear cypress-crested hills of the “Crete” near Buonconvento. Here shepherds tend sheep whose milk is used to make the famous pecorino cheese. You’ll 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 is possible at their beauty farm.

  • DAY 5 - Buonconvento - Montalcino – 28 miles (46 km)

    After a steep climb, you’ll 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 with some monks remaining as caretakers. Ancient pines surround the cloister and the walls are decorated with gorgeous frescoes detailing the history of St. Benedetto and the Benedictine Order. After some time here, you’ll 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 later 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 the lofty towers and ramparts that provide sensational views in all directions across the Orcia Valley. You can 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 won’t 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 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, you can return to Montalcino where you’ll spend a second night.

  • DAY 7 - Montalcino – Pienza - Montepulciano – 28 miles (45 km)

    You’ll pedal through many wonderful places today. You can pause at the ancient hot spa of Bagno Vignoni to soak your 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. Then you can 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 at the 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. Continuing along a dirt road you’ll find yourself in Monticchiello, a tiny walled village, and then you’ll head on for beautiful Montepulciano, one of Tuscany’s highest hilltop towns famous for its red Vino Nobile wines.

  • DAY 8 - Tour Ends

    You can stroll around Montepulciano before your departure. You’ll be transferred to the Chiusi train station that has access to Rome, Florence, and Milan.

Dates & Prices

Green = Open | Yellow = Limited | Red = Full




Solo Traveller


$ 1550

$ 1780

$ 1930

  • Prices are per person in US Dollars – inclusive bike rental
  • Choose your own starting date
  • This tour can be guided upon request
  • What's included

    • 7 nights of double occupancy lodging in mostly 3-star, air-conditioned hotels with private facilities each night
    • 21-speed bike rental
    • Daily breakfast 
    • GPX files
    • Luggage transfers
    • All taxes and gratuities for the hotel and restaurant portions of the tour
  • Bikes

    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, and optional bike computer. It’s also possible to replace our pedals with your own “clip on” pedals. Helmets are not included, so please bring your own helmet!

    We have a few bike upgrades available on this tour. Here are the supplemental prices (per tour):

    Bianchi Via Nirone Road Bike: $40
    Wilier Carbon Frame: $96
    Electric Bike: $120

    We advise you only to rent an electric bike if you have first tried one at home. They’re heavier than regular bikes and therefore can be difficult to maneuver. In addition, you can rent children’s bikes, child seats, bike trailers, and tag-alongs.

    Van Gogh Tours - Bike Tours - Guided and Self Guided - Italy Van Gogh Tours - Bike Tours - Guided and Self Guided - Italy

  • Meals

    Included in the tour price you’ll receive daily buffet breakfast. For the buffet breakfasts there’s an assortment of cold meats and cheeses, eggs, bread, jams, cereal, yogurt, fruit, coffee, and tea. For lunches you will be in a town so you can find lunch at a restaurant.  For your dinners you can choose one of many delicious restaurant options within easy walking distance from our hotel. 

  • Not included

    • Airfare
    • Alcoholic and bar beverages
    • Lunches and dinners
    • Transportation other than scheduled transfers
    • Trip cancelation insurance


The accommodations listed below are examples of those usually used on the tour. Depending on availability, you may be booked in a different accommodation of equal quality.

Hotel Villa San Lucchese

Hotel Villa San Lucchese

  • Poggibonsi
  • Restaurant terrace with panoramic views
  • Pool surrounded by lush garden
Hotel Chiusarelli

Hotel Chiusarelli

  • Siena
  • Rooms renovated according to NeoClassical style
  • Walking distance to historical center


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