Self-Guided Walking Tours & Biking Tours

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Discover the best hilltop towns of Montepulciano, Pienza, Montalcino and Buonconvento


  • Walk through the glorious landscapes of Southern Tuscany on this self-guided Italian adventure
  • Enjoy an included wine tasting at a Montalcino vineyard to taste the finest Brunello’s
  • Explore the golden grasslands of the Val d’Orcia, a UNESCO World Heritage Site
  • Join a local artisan for a Pecorino cheese tasting within Pienza’s medieval walls
  • Relax in the wellness spas and ancient healing thermal baths of Bagno Vignoni

Our signature walking trip through southern Tuscany to the best hilltop towns of Montepulciano, Pienza, Montalcino and Buonconvento. Eat, drink and walk your way through Tuscany's captivating landscape, relaxing in exquisite hotels and wellness spas, while we take care of everything else.

Set in the hills south of Siena, experience the Vida Dulca (sweet life) of this area, enjoying lovely walks interspersed with lavish lodging, cultural interests and culinary delights. Taste the sharp and salty flavors of Pecorino cheese with a local artisan, savor 100% Sangiovese Brunello's at a wine tasting in Montalcino and enjoy a traditional “Toscana” dinner at the rustic chic restaurant of your tranquil countryside hotel. Unwind in the healing waters of ancient Etruscan hot spring baths and within the pretty streets and brick archways of overnight hamlets.

Stroll along Pienza’s Via Dell’Amore (love way) for picturesque views of the Val d’Orcia, fertile grasslands and iconic cypress tree lined paths.

Day 1: Arrive Montepulciano

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

After a transfer from Chiusi Train Station(approx. 30 minutes), 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.

Overnight: Montepulciano

Day 2: Walk to Pienza & Pecorino Tasting

Follow scenic paths from Montepulcino 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 village of Renaissance architecture, favored and influenced by Pope Pius II. Join a local artisan for an included tasting experience 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.)

Pecorino Tasting & 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. 

Note - a cooking class, with dinner and wine-pairing, can be arranged for you if you desire an additional cultural event this evening. Try your hand at cooking four authentic Italian dishes with the creative guidance of a local chef at “Casa Banchetti” (the hotel owners home). Please let us know at the time of booking if you prefer this option (additional costs apply).

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

Overnight: Bagno Vignoni (Cooking Class)

Day 4: Walk to Sant’ Antimo. Transfer to Montalcino & Wine Tasting

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 with chances to hear the Gregorian chants of white robed monks (conducted during mass, several times per day).

After exploring the abbey, take a private transfer to Montalcino for an exclusive wine tasting of Brunello di Montalcino (approx. 30 minutes).

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

Wine Tasting & 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 meaning a “happy, lucky place,” delight in the ethereal beauty of the unchanged village of  Buonconvento and your overnight agriturismo deep within the Tuscan countryside.

Take a dip in the pool before a special “Toscana” dinner provided by the agriturismo’s associate restaurant, serving only the most seasonal, organic and local genuine products. 

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

Dinner & Overnight: Buonconvento

Day 6: Onward Travel

Depending on your travel arrangements, enjoy a swim or last minute spa before a private transfer to the Buonconvento Train Station.

If you need help planning your onward travel, or would like to add on to your Tuscany adventure with an Almalfi Coast or Cinque Terre walking trip, please contact us at our office here at Macs Adventure, and we would be more than happy to help.


Included in this trip are 5 nights in hand-selected accommodations. We’ve carefully selected properties that are the best in the region to ensure that you enjoy every minute of your stay while in Tuscany.  

We regularly use the following properties but may accommodate you elsewhere if these are unavailable.  

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 is served European style, which consists of 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.

One dinner is included on the last day of this trip and consists of a traditional “Toscana” dinner to ensure a special experience and to feature the best of Tuscan cuisine.

Lunches and all other 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.

Pecorino Tasting & Wine Tour

A Pecorino tasting is included on the second day of this trip while exploring Pienza. Join a local fromager (cheese expert) in town for the chance to taste flavorful and aromatic sheep milk cheeses native to the area, ranging from fresco (young), semi-stagionato (semi-hard) to stagionato (aged).  

A wine tasting is included on the fourth day of this trip and is held at a local winery in the valley below the town of Montalcino. Enjoy tasting 100% Sangiovese Brunello’s and other famed Tuscan grapes with the expertise of a local wine connoisseur.

Optional Cooking Class

An exclusive cooking class is available during your stay at Hotel Terme in Bagno Vignoni, and held within the hotel owner’s home. Try your hand at cooking authentic Italian dishes for dinner with the creative guidance of a local chef and ingredients from the Val d’Orcia. The class includes cooking an antipasti, primi piatti (first course), secondi piatti (main course) and dessert. Note - Cooking class includes cooking lesson, dinner and wine-pairing. Please inform of at the time of booking if you would like to add on this optional cultural experience. For more information about the cooking class check the Hotel Terme website.

Times and further descriptions will be found within your pre-departure information pack. Please let us know at the time of booking if you have any preferences, intolerances or food allergies so that we may personalize the cultural experiences for you in advance.

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 - Il Tosco

Located in the heart of Montepulciano, experience Tuscan family hospitality unlike any other. Enjoy the grounds of this intimate antique mansion, the unique rooms cared for in every detail and a scrumptious breakfast made from love and tradition of Momma Clori.







Pienza - Il Chiostro

The Relais Il Chiostro di Pienza is a former Franciscan convent dating back to the 13th century, located in the center of the magnificent hamlet of Pienza and heart of the Val d'Orcia. Enjoy a retreat of elegance and tranquility within the spacious rooms, botanical gardens or upon the panoramic terrace with views of the romantic Sienese hills.







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 - Vecchia Oliviera

Hotel Vecchia Oliviera is situated at the gates of Montalcino in the province of Siena. Once an old olive oil mill that has been carefully renovated, delight in Italian hospitality, rooms individually decorated and relaxing in the surrounding landscapes untouched by time.







 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.


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 available 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 being walks 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

We have created this “signature” itinerary to showcase the best walks and to create the perfect balance of sightseeing and cultural experiences.

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

Most of the route follows farms 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 Montepulciano

Included in this trip is a private transfer from the Chiusi-Chianciano Terme Train Station to Montepulciano (approx. 30 minutes).

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 from Buonconvento

Included in this tour is a private transfer from your agriturismo to the Buonconvento Train Station, where you can catch a train to Siena, Florence or any desired onward travel destination. Please see the Trenitalia website for timetable planning and notify us at the time of booking if you prefer a morning or afternoon transfer.

Important Note

This itinerary is designed to allow you a flexible, yet hassle free arrival and departure in and around Tuscany. If desired, a private transfer directly from Siena to Montepulciano (arrival) and a private transfer directly from Buonconvento to Siena (onward travel) can be included in this itinerary instead (additional costs apply). Please inform us at the time of booking if you prefer these options.


  • 5 Nights in deluxe hotels and country inns
  • 5 Breakfasts
  • Traditional “Toscana” dinner (Day 5)
  • Pecorino cheese tasting
  • Wine tasting
  • Private transfer from Chiusi Train Station to Montepulciano (arrival)
  • Private transfer from Sant’ Antimo to Montalcino (Day 4)
  • Private transfer to Buonconvento Train Station (onward travel)
  • Luggage transfers
  • Turn-by-turn route notes
  • Detailed information pack
  • Macs Adventure Navigation App
  • 24/7 Telephone support


  • Flights
  • Travel insurance
  • Travel to Chiusi
  • Travel from Buonconvento
  • Lunches & 4 Dinners
  • Drinks and snacks
  • Personal equipment


  • Private transfer from Siena to Montepulciano (direct)
  • Private transfer from Buonconvento to Siena (direct)
  • Additional nights before, during or after the trip
  • 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.


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