Self-Guided Walking Tours & Biking Tours

Please wait …

Wander through classic Tuscan landscapes of rolling hills, vineyards and olive groves


  • Hike iconic Tuscany and its hilltop towns of Montepulciano, Pienza, Montalcino, plus glorious Siena
  • Savor bold Vino Nobile and sweet Vino Santo within the antique cellars of Montepulciano
  • Listen to the Benedictine monks of Sant ‘Antimo Abbey for blissful, harmonic Gregorian chants
  • Roam the golden grasslands of Val d’Orcia, an inspiration to Renaissance poets, writers and artists
  • Discover the fresco masterpieces of Monte Oliveto and healing thermal baths of Bagno Vignoni

Walk the romantic and off-the-beaten paths of southern Tuscany, discovering the hilltop towns of Montepulciano, Pienza, Bagno Vignoni, Montalcino and the city of Siena, a UNESCO World Heritage Site. Wander through classic Tuscan landscapes of rolling hills, vineyards and olive groves to Renaissance towns and hilltop hamlets.

Explore the fresco masterpieces depicting the life of Saint Benedict at Monte Oliveto and hear the Gregorian chants of white-robed monks in Sant’ Antimo Abbey. Walk the lovely landscapes of southern Tuscany and the lesser known wine regions south of Siena. Unwind in the healing waters of ancient Etruscan hot spring baths or with a glass of wine at restaurants serving only the most authentic, seasonal and gourmet Italian cuisine.

Each evening, enjoy authentic Italian hospitality at its finest, staying in hotels within the pretty streets of Medieval towns or at agriturismos deep within the Tuscan countryside.

Day 1: Arrive Montepulciano

Montepulciano, surrounded by the vast vineyards of Sangiovese, is a quintessential Tuscan town and the perfect start of your Italian hilltop adventure.

Spend the day exploring the Medieval walls, cobblestone streets, and hidden corners of this beautiful Renaissance commune in the Italian province of Siena. Roam the leather shops and Italian bakeries lining the elegant squares, or join a historical tour of the Palazzo del Commune and Cantina del Redi (the official filming sites for the vampire saga “Twilight” series). Stop off at any Enoteca (local wine shop), along the way for tastings of region-famous Montepulciano d’Abruzzo and Vino Nobile; the perfect pairing to local meats, cheeses, breads and olives. 

Overnight: Montepulciano

Day 2: Walk to Pienza

Follow scenic paths from Montepulciano and San Biagio church, to the extraordinarily beautiful and peaceful village of Montichiello. Find a café for a cappuccino or bruschetta snack within this hidden gem, famous for its annual productions of the “Teatro Povero,” before continuing onward to Pienza.

Pienza, a UNESCO World Heritage Site, is an exquisite town of Renaissance architecture, favored and influenced by Pope Pius II. Stop by a local cheese shop for a taste of Pecorino cheese, a regional sheep’s milk cheese named and derived from Pienza and its expansive rolling farmland.

This evening, enjoy a pleasant stroll down the Via Dell’Amore for spectacular views of the Val d’Orcia and its rolling hills of colorful hues that inspired Renaissance poets, writers and artists.

Walk: 9.5 miles / 15 km (+1608/-1781ft.)

Overnight: Pienza

Day 3: Walk to Bagno Vignoni (Thermal Baths)

Wander through the Val d’Orcia to the charming hamlet of Bagno Vignoni. Enjoy walking through pastoral countryside, oak wood forests and cypress tree-lined roads to the restorative waters of Bagno Vignoni, once a main healing and rejuvenating point for pilgrims voyaging to Rome. Soak in the mineral hot spring baths and delight in the same therapeutic qualities as the Etruscans did centuries before you. 

Tonight, relax within the wellness spa of your hotel and dine at the associated Ristorante la Terrazza in commemoration of your pilgrimage from Pienza to Bagno Vignoni.

Walk: 9.5 miles / 15 km (+1024/-1624ft.)

Overnight: Bagno Vignoni

Day 4: Walk to Sant’ Antimo & Transfer to Montalcino

Delight in a more challenging, but equally rewarding, walk to the secluded abbey of Sant’ Antimo. Once a former Benedictine monastery built in the 12th century, explore this beautiful and secular stone abbey and its importance to King Charles the Great and the monks in study and prayer. Become enchanted by the white robed monks and their Gregorian chants during mass (conducted several times per day).

After exploring the abbey, take a private transfer to your overnight accommodation in Montalcino (approx. 25 min).

Walk: 9 miles / 14 km (+1604/-1558ft.)

Overnight: Montalcino

Day 5: Walk the “Crete Senesi” to Buonconvento

Enjoy a hearty breakfast in preparation for a full days walk within the famous Brunello wine region, passing rows of vineyards and olive groves and through the timeless landscapes of the “Crete Senesi,” to Buonconvento.

Deriving from the Latin word for a “happy, lucky place,” delight in the ethereal beauty of the unchanged village of  Buonconvento and your overnight agriturismo deep within the Tuscan countryside.

Walk: 10.5 miles / 17 km (+899/-1742ft.)

Overnight: Buonconvento

Day 6: Walk Monte Oliveto Maggiore to Buonconvento

Begin this day with an early transfer to the Monte Oliveto Maggiore Monastery, an impressive abbey built of red brick and founded in 1313. Discover this beautiful Benedictine abbey famous for its frescoes displayed in the great cloister. Take a closer look, starting clockwise, to admire the 35 fresco masterpieces depicting the life of Saint Benedict.

Depart the abbey and walk into the spacious, rugged countryside of the Crete Senesi. Walk up-and-down the rolling hillside and back to your agriturismo for an afternoon relaxing in the outdoor swimming pool, spa or comfort of your “camera” (bedroom).  

Walk: 7 miles / 11 km (+1033/-1283ft.)

Overnight: Buonconvento

Day 7: Transfer to Grancia di Cuno Medieval Farm & Walk to Siena

Take a short transfer to the well-preserved Medieval farm at Grancia di Cuno for a lovely walk to Siena (approx. 25 min). Enjoy a final stretch of timeless Tuscan landscape as you walk towards this enchanting city, glistening in the distance ahead.

In Siena, grab a panino or gelato in the Piazza del Campo, admiring the amazing architecture of this shell-shaped city. Famous for its centuries of Palio horse races, Siena remains a city of extraordinary significant and exquisite beauty. 

Walk: 11 miles / 17 km (+778/-381ft.)

Overnight: Siena

Day 8: Onward Travel

Depending on your travel arrangements, join a history tour or roam the city’s monuments and museums before departure, or continue your Italian adventure further with one of our coastal walks of the Cinque Terre or Amalfi Coast.

If you need help planning your onward travel, including a private transfer from your hotel in Siena to the Siena Train Station, please contact us at our office here at Macs Adventure, and we would be more than happy to help.


Included in this trip are 7 nights in hand-selected accommodations. We’ve carefully hand-selected properties to ensure that you enjoy every minute of your stay while in Tuscany.

Single Rooms & Solo Walkers

This trips is based on two people sharing a room. If you’d like separate rooms, a single supplement is required.

If you would like to request a twin room (same room with two separate beds), please notify us at the time of booking so we can request this option.

This trip is also available to solo walkers (a solo supplement is required).


Breakfast is included each morning and consists of a traditional European style breakfast ranging from coffee, tea, yogurt, granola, seasonal fruit, meat, cheese and baked goods. In most cases, a hot dish (eggs and pancakes) will be served a la cart or can be ordered off a menu.

Lunches and dinners are not included in this trip, so you are free to choose from nearby available options. We recommend finding cafés or restaurants located in the towns or along the walking route, or you can purchase snacks and a picnic lunch to bring along with you. Further information can be found within your information pack and route notes.

Additional Nights

You can easily request to add on an extra night at any location during this itinerary. Please notify us at the time of booking should you wish to add extra nights. 




Montepulciano - B&B l'Agnolo

Located in the center of Montepulciano, this once grand home is now a beautiful, boutique bed and breakfast, still displaying original art from its ornate high fresco ceilings. Admire the town of Montepulciano and the surrounding landscape at this lovely B&B, for an enjoyable holiday in comfort, peace and beauty.







Pienza - Residence San Gregorio

Residence San Gregorio is situated in the ancient walled town of Pienza, the heart of Tuscany. Enjoy this exclusive environment to spend a night (or a few days) immersed in the magical atmosphere of the Val d'Orcia and architectural jewel of Pienza.







Bagno Vignoni - Hotel Le Terme

Surrounded by the warm steam from the thermal springs, constructed by the Rossellino and home of Pope Pius II Piccolomini, lays the Hotel “Le Terme.” Enjoy the healthy waters of the spa, comfortable rooms decorated in classic Tuscan style and dinner at the Ristorante la Terrazza where simple ingredients are combined into delicious dishes complemented by the wines of the surrounding region.







Montalcino - Hotel Dei Capitani

Hotel Dei Capitani is fantastically positioned in the center of the Medieval town of Montalcino. Delight in a warm welcome and the wonderful panoramic views over the Tuscan countryside, including a beautifully designed swimming pool and terrace area.







 Fattoria Pieve a Salti - Buonconvento

Buonconvento - Fattoria Pieve a Salti

Enjoy a night in a traditional Tuscan agriturismo, or country hotel, offering total tranquility and overlooking the incredibly beautiful Tuscan countryside. Delight in a vast array of facilities, including an outdoor swimming pool, spa, horseback riding adventure and restaurant serving home grown food directly from the estate.







Siena - Hotel Chiusarelli

Hotel Chiusarelli, a Neoclassical villa built in the 1860s, is one of the first hotels in Siena. Having been resorted in 2010, while keeping original aesthetics, enjoy the magnificent frescoed halls and dinner at the “Gli Orti di San Domenico”, for a charming atmosphere and flavors from traditional Tuscan cuisine.





This tour is available to start anytime between March and October. 

As Tuscany is a very popular destination, we suggest you book as soon as your plans are finalized to ensure availability for specific dates.

When to Go?

The springs months of April, May and June offer warm sunshine, fewer crowds and pleasant conditions. The autumn months of September and October are also a favorite time of year, boasting cooler weather and a striking landscape made up of a yellow, gold and red pallet.

July and August are also great months to go but can be very hot for walking. If booked during these months, we therefore advise you to start your walk very early in the morning to avoid the midday heat.


While the route is not waymarked (with the exception of some sections), navigating is easy using the Macs Adventure Navigation App.

Your daily walks will be mapped in the app with GPX tracks, including route notes and turn-by-turn directions. All of these resources are available to download for offline use. More information is outlined within your detailed information pack, in addition to 24/7 telephone support from Macs Adventure should you require assistance.

Grade & Terrain

This tour is graded easy to moderate with six days of walking and a maximum distance of 11 miles. Daily walks average around 7-11 miles (9 on average, 4-6 hours) along rolling terrain as you walk to-and-from hilltop towns.

Most of the route follows farm tracks and dirt trails, while on some days you will be walking along minor country roads with minimal traffic. On the fourth and fifth day of this trip, the walking is a bit more challenging due to the rugged ups and downs of the Tuscan region south of Siena. 

You should be in decent physical shape and comfortable walking every day to fully enjoy the walking on this tour.


Our pre-departure information pack has  detailed advice and a packing list on what to bring. This includes warm and cold walking gear, hiking boots, rain gear, day pack and other specifics. 

Luggage Transfer

Your bags will be transferred from your accommodation as per your itinerary and moved onto your next overnight accommodation. We ask you to limit your luggage to one bag of up to 50 lbs. per person.

Travel Insurance

Travel insurance helps protect your travel investment, your belongings and most importantly you, from unforeseen circumstances that may arise before or during your trip. For more information, please visit our travel insurance page by clicking this link.

Getting to Chiusi-Chianciano 

By Air & Train:

Florence, Rome and Pisa all have airports with flights from international and national destinations. 

We recommend flying into Florence and taking a taxi from the airport to the Florence Train Station. On an average weekday, there are 23 trains per day traveling from Florence to Chiusi-Chianciano Terme (approx. 2 hours, 10 euros).

If flying into Rome, take the Leonardo Express train from the airport to Rome Termini (Main Train Station). Trains to Chiusi-Chianciano Terme from Rome depart several times per day (approx. 1.5 hours, 10 euros). 

If flying into Pisa, take the tram from the airport to the Pisa Centrale Train Station. On an average weekday, there are 28 trains per day traveling from Pisa to Chiusi-Chianciano Terme (approx. 3.5 hours, 18 euros).

Prices, ticketing and more information can be found within your pre-departure information pack. For additional information, please check the Trenitalia website for updated timetables.

Getting to Montepulciano

Upon arrival to Chisui-Chianciano Terme Train Station, take a local bus or call a taxi (typically lined up
outside the train station) for transport to Montepulciano (payable

A private transfer from the Chiusi-Chianciano Terme Train Station to Montepulciano can be included in this trip (approx. 30 minutes). Please let us know at the time of booking if you desire to add this option (additional costs apply).

Getting from Siena

From Siena, you can take the train to Florence, Pisa, Rome or any desired onward travel destination. Please see the Trenitalia website for timetable planning.


  • 7 Nights in boutique hotels and country inns
  • 7 Breakfasts
  • Private transfers to the starting or ending points of the day’s walk per the itinerary (Day 4, 6 & 7)
  • Luggage transfers
  • Turn-by-turn route notes
  • Detailed information pack
  • Macs Adventure Navigation App
  • 24/7 Telephone support


  • Flights
  • Travel to Chiusi Train Station
  • Private Transfer from Chiusi Train Station to Montepulciano (arrival)
  • Travel from Siena (onward travel)
  • Travel insurance
  • Lunches, dinners, drinks and snacks
  • Personal equipment


  • Additional nights before, during or after the trip
  • Private Transfer from Chiusi Train Station to Montepulciano (arrival)
  • Travel from hotel to Siena Train Station (onward travel)
  • Single room supplement (if required)
  • Solo supplement (if required)

We are often asked the following questions and we hope that you will find the answers useful. Please do not hesitate to contact us if you have any other questions (or for more advice), from our team here at Macs Adventure.

How fit do I need to be?

This walking trip is graded easy to moderate and involves 4-6 hours of walking each day, so you should enjoy an active lifestyle to get the most from your time in Tuscany. 

How far in advance do I need to book?

As Tuscany is a very popular destination, we suggest you book as soon as your plans are finalized to ensure availability for specific dates.

How does the luggage transfers work?

Your bags will be transferred from your accommodation as per your itinerary and moved onto your next overnight accommodation. We ask you to limit your luggage to one bag of up to 50 lbs. per person.

Which is the best airport?

Florence, Pisa or Rome are convenient airports to fly into both nationally and internationally. Most destinations within Italy have a central train station in which to arrive and depart. 

What happens if I become ill or can’t walk a stage?

If you are not up for walking the entire route, you can stop at any town along the way and call a taxi, or one of our local representatives, from the contact information found within your pre-departure information pack. If you become ill or want to avoid walking an entire day, that's Ok. Due to being a high tourist destination, local taxis and car services are available to call from your hotel, or you can catch a ride with the morning luggage transfer (when applicable). Specifics and contacts numbers can be found within your pre-departure information pack, or you can ask the host of your overnight hotel for assistance. If you need medical services, please seek immediate assistance at your hotel or nearby hospital.

As always, 24/7 support from Macs Adventure is only a phone call away.


Inquire Now

Get adventure news, trail guides, new trip updates and destination inspiration by signing up to receive our regular emails. We only send these by email, and we never pass data to third parties for marketing purposes. Please confirm if you are happy to receive this travel inspiration & advice into your email inbox.

Our full data & privacy policy

Book self-guided walking tours and biking tours with Macs Adventure. Explore Europe, the UK and the rest of the world on our walking tours and biking tours, and find out why thousands of people trust us to arrange their perfect self-guided adventure.

Get In Touch

lf you require more information before booking, please contact us on

+44 (0)141 530 5464

+1 -844-858-0740


© 2019

Macs Adventure - US Office: 3200 Carbon Place Suite 102, Boulder, CO 80301