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    Italy Self Guided Biking / Tuscany & Umbria
  • View Large
    Italy Self Guided Biking / Tuscany & Umbria
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    Italy Self Guided Biking / Tuscany & Umbria
  • View Large
    Italy Self Guided Biking / Tuscany & Umbria
  • View Large
    Italy Self Guided Biking / Tuscany & Umbria
  • View Large
    Italy Self Guided Biking / Tuscany & Umbria
Italy Self Guided Biking / Tuscany & Umbria
Tour Dates: March – October

Charters Tours Available
It’s time to book the Italian Bike Tour of your dreams with exceptional riding, well planned routes and boutique lodgings! We pulled out all the stops on our Tuscany & Umbria bike tour. This unforgettable bicycle tour traverses Tuscany on quiet country roads that pass through vineyards and lead to historic medieval towns where history comes alive.

This tour is available as a Self-Guided, Guided or Charter Tour! We can customize this Tuscany & Umbria Bike Tour with shorter or longer distances and fewer or more days.

2017 Price: €1200 Euros /double occupancy

Single Supplement: €300 Euros

Price Includes:
  • 9 days/8 nights
  • 8 nights hotel
  • 8 breakfasts
  • 1 dinner with cooking class
  • luggage transfer
  • trip information package that includes maps, route descriptions, suggested sights to visit
  • emergency phone numbers for our Italian staff support
  • welcome orientation and bike fitting
Price Does Not Include:

International flights, bike rentals (you may choose to bring your own bike or rent one. Hybrid Bike: €175 Euros / Road Bike €225 Euros), lunches, 7 dinners, beverages.

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

This unforgettable bicycle tour traverses Tuscany and Umbria, two of Italy's most scenic regions where quiet country roads lead to historic medieval cities. Our tour features great riding, fantastic scenery, comfortable lodgings with all breakfasts & dinners included and luggage transfers. Our tour begins in Assisi, Umbria, where the medieval flavor takes you back to the enchantment and mystery of the Middle Ages. The province of Umbria is known as the "Green Heart" of Italy and our route is surrounded by vineyard clad valleys and hillsides covered with olive trees. Ancient walled cities, Etruscan tombs and Renaissance art are a treat for the eye, and Baci, the world-famous chocolate covered hazelnuts from Perugia, are a delicious treat for the palate! The classic charm of Tuscany is picture book perfect. The countryside is an exquisite patchwork of green fields and stately farmhouses silhouetted by Cyprus trees. Extensive vineyards and acres of sunflowers are bathed in pastel sunlight. Our route passes through several renowned wine regions and takes us to some of Tuscany’s most interesting hill top towns. Enjoy strolling centuries old streets that lead to magnificent cathedrals and grand plazas with charming shops and sidewalk cafes. All of the accommodations were specially selected to reflect the warmth and hospitality of the region and provide a real sense of the living history of the region. The scrumptious meals served on the tour are made with local ingredients and seasoned with tasty olive oil and fresh herbs. You will have a chance to sample some of Italy’s best cheeses and most famous wines – the Brunellos from Montalcino and the bold Vino Noble from Montepulciano.

Tour Map

Tour Video

Day 1 - Arrival

Our Italian representative will pick you up at the Assisi train station and transfer you to your first hotel. At that time they will give you a tour orientation and bike fitting. Overnight in Assisi.

Day 2 - Assisi Loop Ride: 45 Km

Enjoy the back-road to Spello, a perfectly preserved town with Roman origins. A visit to Bevagna, another wonderful medieval village. Overnight in Assisi.

Day 3 - Assisi - Poggiolo Ride: 52 Km

Our route through Umbria is highlighted by a visit to Deruta, a town famous for its ceramics. Tonight’s lodging is at Poggiolo, a beautiful old rural villa. Overnight in Poggiolo.

Day 4 - Poggiolo - Cortona Ride: 65 Km

A curvy road will lead us to Lake Trasimeno whose shores teem with migratory birds. You’ll cycle near beautiful olive groves to Cortona, the setting for Francis Mayes’s best seller, Under the Tuscan Sun. Overnight in Cortona.

Day 5 - Cortona - Montepulciano Ride: 50 Km

Today you will enter Tuscany through the magnificent wine country of Montepulciano, one of Tuscany’s highest hilltop towns. Renowned for its Vino Nobile, Montepulciano also boasts a unique blend of Renaissance architecture and is perched on a narrow ridge of volcanic rock. Overnight in Montepulciano.

Day 6 - Montepulciano - Montalcino Ride: 50 Km

Traveling through Pienza, home of Pope Pio II, you’ll find a unique collection of palaces, churches and a charming square. This ride takes you through the Crete landscape, one of the most famous in the world: rolling hills in all shades of brown or green; sturdy brick farmhouses or imposing mansions crowning the hilltops and cypress lined alleys design a perfect scene that inspired painters since the Middle ages. You finish your ride among the vineyards en route to Montalcino, a 13th century paradise and the home of Brunello wine. You will enjoy a two night stay within the walled city. Overnight in Montalcino.

Day 7 - Montalcino Loop Ride: 50 Km

Our loop ride takes you to the gorgeous abbey of Saint Antimo, a well preserved 12th-century church that still echoes with Gregorian chants. There is plenty of time today for shopping and sampling some of the fine Brunello wines. Overnight in Montalcino.

Day 8 - Montalcino - Siena Ride: 53 Km

The road winds through hills and oak woods to Monte Oliveto Maggiore, the most impressive abbey in Italy. Then it’s on to Siena, your final destination. Siena is one of the most beautiful medieval cities in Italy. Its famous Piazza Del Campo is an open-air museum and architectural gem. Overnight in Siena.

Day 9 - Departure

Your tour ends after breakfast. There are both train and bus stations in Siena with easy access to both Rome and Florence.

** 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).


We suggest 10% for exceptional service in restaurants (most restaurants include a service charge) and 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 kilometres (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

Umbria is a region of historic and modern central Italy. It is the only Italian region having neither a coastline nor a border with other countries. It includes the Lake Trasimeno, Cascata delle Marmore, and is crossed by the River Tiber. The regional capital is Perugia. Umbria is known for its landscapes, traditions, history, artistic legacy, and influence on culture.
~ Wikipedia

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