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

On our Tuscany Self guided Walking Tour you will follow timeless walking paths through the landscape that has inspired travelers for centuries. We offer this tour as a Self Guided Walking Tour, and it may also be chartered as a guided tour for groups.

2017 Price: €1150 Euros per person, based on double occupancy

Single Supplement: €250 Euros

Price Includes:
  • 7 nights hotel
  • 7 breakfasts
  • luggage transfers
  • trip information package that includes maps, route descriptions, suggested sights to visit
  • emergency phone numbers for our Italian staff support (shorter itineraries available)
Price does not include:

International flights, lunches, dinners, beverages

“The accommodations on our Tuscany Walking Tour were wonderful….all quiet and lovely. Wonderful breakfasts that fueled us until dinner! The itinerary suggested local dining spots which were all great, moderate, and again local and familial. We met many other independent hikers and bikers along the way that were doing similar trips.
As we have always organized our own trips, backpacking and kayaking, it was a real luxury to have our luggage moved from hotel to hotel. The bags always showed up and often were in our room. The local folks who do the transfers and drop offs were so friendly and real. Never treated us like anything but a friend with advise and tips about local happenings. The trek is so interesting with Etruscan history, beautiful vistas, friendly locals, incredibly fascinating villages, olive orchards, wine and great food. The itinerary really encompasses all that.” ~ Mary M.

Tour Difficulty

You choose your own dates and number of days and we organize the hotels, luggage transfers, route information and provide local support.

  • Difficulty: Easy, travel at your own pace.

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

Tour accommodations are in a splendid assortment of villas and charming country inns that will provide a sense of history and a taste of the local warmth and hospitality. You can look forward to gourmet meals that are characteristic of this region and made with the freshest local ingredients seasoned with tasty olive oil and herbs. You will be able to sample some of Italy’s most famous cheeses and wines from vineyards along our route.

This hiking vacation in Tuscany is more than just a great walk. It is your opportunity to fully experience the delightful countryside and wonderful people of Italy.

This self-guided tour is a fully organized vacation for the independent traveler who wants the freedom to walk at his or her own pace. You’ll have complete support behind the scenes. Our Italy representative will meet you at the beginning of your tour for an orientation. You will receive a packet with detailed route instructions, maps, suggestions for sights to visit along the route and emergency support phone numbers. You can take a spontaneous detour and always feel secure that your hotel room will be waiting for you. You will be able to travel at your own pace without a guide or support vehicle to hurry you along or to slow you down. Your luggage will be transported each day to the next accommodation, which will be reserved and prepaid. You don’t need to worry, as emergency support is just a phone call away.

Tour Map

Tour Video

Day 1 - Acquaviva to Montepulciano (3 hours walking time)

Arrival in Chiusi where you are met by our Italian representative who will spend a short time going over the tour with you answering any question you may have. (The train takes about an hour and a half from Rome and trains operate every 2 hours throughout the day. See travel information below.) Our representative will then drive you to Acquaviva where the trail to Montepulciano starts. Hotel in Montepulicano, 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.

Day 2 - Montepulciano/Pienza (6 hrs walking time)

From the church of San Biagio on the outskirts of town, you will follow an old road through the countryside. Stop at the walled village of Montichiello for lunch or a cappuccino before making your way to Pienza, a small town once called “the pearl of the Renaissance”. Partly redesigned by Pope Pius II, Pienza boasts a splendid Renaissance cathedral and the charming Palazzo Piccolomini. Sample pecorino, a local sheeps’ cheese.

Day 3 - Pienza to Bagno Vignoni (5 hrs walking time)

The walking today crosses a beautiful region of rolling hills, oak woods and lovely villages. Your destination tonight is Bagno Vignoni, a thermal spa town where the main square is a basin of steaming hot water. This is considered by many to be the most charming village in all of Tuscany! Hotel in Bagno Vignoni.

Day 4 - Bagno Vignoni to Sant’Antimo/Montalcino (5 hrs walking time)

Today's walk takes you along dry river beds in a rather wild environment to reach the Abbey of St Antimo. 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. We’ll arrange to have you transported from the Abbey to Montalcino, your home for the night.

Day 5 - Montalcino to Buonconvento – (4 hrs. walking time)

Montalcino is renowned for its ruby-red Brunello wines, so you’ll spend much of the day strolling through vineyards as well as olive groves. Then you’ll enter the primeval landscape of the crete senesi , where shepherds tend the sheep whose milk is used to make pecorino cheese. Spend the next 2 nights at a delightful inn near Buonconvento.

Day 6 - Buonconvento Loop (3 hrs. walking time ONE WAY)

Enjoy a leisurely day relaxing around the pool or follow a hilly path to the 14th-century Benedictine Monte Oliveto Maggiore, one of the most impressive abbeys in Italy. Contemplate the cloister with its magnificent fresco cycle on the life of St. Benedict. The walk to the abbey takes 3 hours and if you prefer not to walk back to your inn, the owner of your accommodation will come and pick you up.

Day 7 - Buonconvento to Siena – (5 hrs walking time)

Walk along a winding dirt road over hills and through oak woods. Pass Murlo, a tiny medieval borgo, the oldest settlement in the area. A ring of houses forms Murlo’s defensive walls. Visit the Museo Etrusco, which commemorates the town’s Etruscan origins. Then on to Radi and Monteroni d’Arbia, where we will arrange a transfer to Siena

Day 8 - Departure

Your tour ends after breakfast, but you will want to enjoy the sights of Siena before your departure. Stroll through Piazza del Campo and to the spectacular Duomo, one of the few full Gothic cathedrals built south of the Alps. There are both train and bus stations in Siena with easy access to both Rome and Florence. You might also choose to spend an additional day in Siena as there is so much to see here.

Who comes on a Nichols Expeditions Walking 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 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 tour.

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.


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.


You do not need to be able to speak Italian, as you will be surprised at how many folks speak English in Italy. However, a good dictionary or a translation application on your phone can be quite helpful.


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).


On the tour: we suggest $125 per guest to cover our local guide and various service people at the lodges during the tour. On your own: most restaurants include a service charge, but an additional 5-10% 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 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

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