Biking, Hiking, Sea Kayaking, Wildlife Tours
Italy Self Guided Biking / Tuscany
Tour Dates: Mid-March through Mid-November

Tuscany is a charmed land of rounded hilltops covered with vineyards and acres of sunflowers bathed in pastel sunlight.

Tuscany Bike Tours are available as Self-Guided Bike Tours or Charter Tours. Check out the sample itinerary below. We can customize this Tuscany Bike Tour with shorter or longer distances and fewer or more days. Check out our guided tour of Tuscany & Umbria and this is also available as a self-guided tour.

2017 Price: €1200 Euros /double occupancy

Single Supplement: €250 Euros

Price Includes:
  • 8 days/7 nights hotel
  • 7 breakfasts
  • 4 dinners
  • luggage transfer
  • trip information package that includes maps, route descriptions, suggested sights to visit
  • emergency phone numbers for our Italian staff support
Price Does Not Include:

International flights, bike rentals, (hybrid bikes / €145 Euros, road Bikes / €180 Euros, Electric bikes / €250 Euros), lunches, 3 dinners.

“Our trip through Tuscany was great! Hotels were very nice and support people were all very pleasant and professional. Ebikes definitely the way to go!” ~ Mike H. (Self-Guided Bike Tour of Tuscany, Italy)

Tour Difficulty

This is a moderately hilly bike tour that fit riders of all abilities will enjoy. Our routes follow winding secondary roads and average 45 – 65 kilometers per day, with more riding available for the hearty.

  • Difficulty: Moderately Hilly
  • Road Conditions: Smooth & Paved
  • Recommended Bike: Hybrid or Road

Tour Highlights

  • Ancient walled cities
  • Hillsides covered with olive trees
  • Etruscan tombs and Renaissance art
  • renowned wine regions
  • Tuscany’s most interesting hill top towns

Tour Overview

Distant farm houses silhouetted by stately cypress trees form an age old backdrop for classic bike touring in this uncrowded region. Medieval cities with narrow winding streets beckon to be explored. There you’ll find cathedrals, grand plazas and real espresso at a sidewalk cafe nestled between 13th century sculptures. Our routes follow winding secondary roads with very little traffic. Tuscany also offers a great diversity of landscapes, from the vineyard-covered hills of Chianti and Brunello to the barren geometrical cypress-crested moulds of the “Crete”. Such incredible varieties in so short a time!

Tour Map

Tour Video

Day 1 - Arrival in Poggibonsi

You will be met by our Italian representative who will drive you to your accommodations for the night,Villa Lecchi. This is a beautiful villa near Castellina in Chianti and is also known for excellent food.

Day 2 - Monteriggioni/Colle Vald’Elsa/San Gimignano – 35 Km

Your first day of cycling takes you to Monteriggioni, a perfect fortress town built in the 13th century and totally encircled by high walls with 14 heavily fortified watchtowers. Continue to Colle de Val d’Elsa, take time to visit some of the glass-blowing workshops. Then it’s on to San Gimignano, the “city of beautiful towers” and one of the best-preserved medieval towns in Italy before you head back to Villa Lecchi.

Day 3 - Villa Lecchi/Castellina in Chianti/Siena – 60 Km

Follow winding roads through the Chianti countryside, past lush vineyards and superb wineries, to Siena, one of the most beautiful cities in Italy. Stroll through the famous Piazza del Campo, enjoy a gelato, and find a charming trattoria for dinner. (Dinner on your own tonight.)

Day 4 - Siena/Buonconvento – 35 Km

Winding on the Chianti country roads is quite dramatic as the landscape changes from the 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 pecorino cheese. You will pass through the tiny borgo of Murlo, the oldest settlement in the area, before arriving at today’s destination, a delightful agriturismo just 3 km from Buonconvento.

Day 5 - Buonconvento/Montalcino – 46 Km

After a steep climb, pedal through the spectacular eroded hills of “Crete” and then through thick cypresses and olive groves as you approach the 14th-century Benedictine monastery of Monte Oliveto Maggiore. Contemplate the cloister with its magnificent fresco cycle on the life of St. Benedict. Then continue to Montalcino, a classic Tuscan hilltown renowned for its ruby-red Brunello wines, considered by some to be the finest in Italy.

Day 6 - Montalcino/Sant’Antimo/Montalcino (your choice of mileage for the day as you will not be changing hotels tonight)

Stroll around the town before following the trail to the abbey of Sant’Antimo, 10 km away. Few of the monastic buildings remain, but the 12th-century church is well preserved and is an outstanding example of the Italian Romanesque. 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. (Dinner is on your own tonight and you might choose a gourmet dinner and wine tasting at the Fattoria dei Barbi.)

Day 7 - Montalcino/Montepulciano – 46 Km

You pass through many wonderful places today. Pause at the hot sulfurous pool in the piazza at Bagno Vignoni, then continue to Pienza, a Renaissance jewel and birthplace of Aeneas Sylvius Piccolomini who completely redesigned its center after he became Pope Pius II. Relax over a cappuccino in Montichello, 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. Today you will be transferred to the Chiusi train station that has access to Rome, Florence or Milan.

** Shorter itineraries available.

Who comes on a Nichols Expeditions bike tour?

Folks who enjoy our tours are a spirited mix of singles and couples of ALL ages from all corners of the US, Canada and a few international locations as well. Many have accompanied us on numerous tours in the past. Most folks are recreational riders and all seem to share the common bond of an active lifestyle, an appreciation for the outdoors and a love for fun. We will gladly supply references if you wish to speak with someone who has recently been on this trip.

Can I charter this tour?

Yes! You bring the people and we will take care of all the details! This tour can be chartered as either a Guided Tour or Self Guided Tour. Call us for details and availability, 800-648-8488.

The Food

This region has earned its reputation of having the best cuisine and wine in all of Italy. You will be staying in hotels and inns that serve gourmet meals with enough variety to please everyone. As per the itinerary, breakfasts and 7 dinners are included and lunches are on your own. Vegetarian and other dietary restrictions can usually be accommodated with advanced notice.


Weather can be changeable, so be prepared for riding in both sun and showers. Daytime temperatures are 60º to 85º F. and nights are 50º to 70º F. There is always the chance of rain, so to ensure your personal comfort please make sure you have a good quality rain jacket with a hood and rain pants, too. For the sunny days, we recommend using SPF 30 sunscreen and lip screen. If you are really sun sensitive, we suggest sun-blocking clothing.

Camera Gear

Whether you shoot a digital or film camera, bring more media storage cards or film than you think you need! A portable hard drive may be the answer for digital storage. Other useful items are plenty of extra batteries, lens cleaner, lens tissue, lens brush, a mini tabletop tripod and a clean toothbrush to remove grit from your camera.


You do not need to be able to speak Italian, but it can be lots of fun, and our Italian guide can always help you with the finer points of the language. A small dictionary and some creative sign language are helpful, and many people at airports and hotels speak English.


The currency of Italy is the Euro. You will need Euros for beverages, shopping, snacks, and tips for hotel staff. We suggest exchanging a minimum of €200 EUR (more if you like to shop and sample the local wine and ice cream).


Some restaurants include a service charge, but an additional 10% for exceptional service is always appreciated. We suggest a small amount for baggage and taxi service.

Cash & Credit Cards

US CASH: bring only NEW bills with NO tears. You can exchange money at the airport and in major towns. CREDIT CARDS: bring 2 or more Visa or Master Cards in case you have trouble with one. There are ATMs in most of the towns on the tour. To use your Credit Card to get Euros at an ATM, each Credit Card will need a PIN#. Be sure to activate the PIN# and check that it works BEFORE you begin your travels. We also suggest contacting your credit card company prior to your trip to inform them of the countries where you will be traveling and the dates. We do not recommend bringing Travelers Checks because some places do not accept them, exchange rates vary widely and they require a bank to exchange them.


U.S. citizens must have a current Passport to enter Italy. Make sure your PASSPORT DOES NOT EXPIRE WITHIN 6 MONTHS OF THE COMPLETION OF YOUR TOUR. These requirements do vary from country to country, but just to be safe, we recommend going by the 6 month standard, because it’s definitely better to be safe than sorry when it comes to international travel!

Make copies of your passport! We recommend making 2 photocopies of your passport’s photo page and any other valuable documents you might carry with you on the tour. Travel with one copy stored separately from your passport. Leave the other copy at home with a relative or friend (ideally the same person you gave as your emergency contact). In the event that any of your documents are lost or stolen, this will greatly assist the process of replacement.

Travel Delays

Nichols Expeditions is not responsible for any costs you may incur due to delays with transportation (airline or other), weather, road conditions, government intervention, sickness or other contingencies we are unable to control. For international flights, arrive at least 2-3 hours prior to departure (check with your air carrier for their requirements) and allow ample time between connecting flights. If you miss your flight and you need a special shuttle to meet up with the group, you will be responsible for the cost.

Travel Insurance

To protect yourself against life’s uncertainties, we highly recommend purchasing a travel insurance policy!

Learn more about the Travel Insurance.

About Tuscany

Tuscany (Italian: Toscana, pronounced [tosˈkaːna]) is a region in central Italy with an area of about 23,000 square kilometers (8,900 sq mi) and a population of about 3.8 million inhabitants. The regional capital is Florence.

Tuscany is known for its landscapes, traditions, history, artistic legacy and its influence on high culture.
~ Wikipedia

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