Hill Towns of Tuscany Highlights6 Days & 5 Nights 4.8 Read 16 reviews
- Hike iconic Tuscany and its hilltop towns of Montepulciano, Pienza, and Montalcino
- 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
Self Guided | Go at your own pace on an independent tour.
Inn to Inn Walking | A classic point to point walking trip, staying in a different location each night
This trip is suitable for:
Multi-Generational, Groups > 10
Ideal if you have an interest in:
- Historical Journeys
- Special Occasions
Activity Level & Terrain
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.
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.
Included in this trip are overnights in hand-selected accommodations. We’ve carefully 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.
- Overnights in boutique hotels and country inns
- Breakfasts included
- Private transfers as per the itinerary
- Luggage transfers
- Turn-by-turn route notes
- Detailed information pack
- Macs Adventure Navigation App
- 24/7 Telephone support
- 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)
When To Go
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.
Getting to the Start
By Air: We recommend flying to Pisa, Florence or Rome, and then you can catch the train from the city centre railway station to Montepulciano (usually changing in Chiusi or elsewhere). Approx. journey times to Montepulciano; Pisa 2h50-3h20, Florence 1h50-2h15, Rome 1h50-3h15). Train timetables are available at Trenitalia; www.trenitalia.com
If you wish, from Chiusi you can opt to take a local bus, or taxi the short distance to Montepulciano (25 mins, payable locally).
Getting from the End
At the end of your trip, we transfer you to Buonconvento train station, where you can catch the train to Siena. From Siena you can take the train back to Pisa (2h00-3h15), Florence (2h15-3h15) or Rome (2h15-3h20). Again, please see Trenitalia’s website for timetable planning.
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.
The distances and ascent/descents are approximations of the recommended routes. Please be prepared by packing all necessary items, for example, proper rain gear (jacket and pants), sun hat, sunscreen. Your information pack has a detailed equipment list which includes standard walking gear such as good walking boots or shoes, warm and waterproof clothes for the cooler months and lightweight clothing for summer, and a day pack.
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.
Travel insurance helps protect your travel investment, your belongings and most importantly you, from unforeseen circumstances that may arise before or during your trip.
f 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.
ItineraryDay 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.
Owner Cinzia Caroli offers a warm welcome to all guests coming to her extraordinary charming B&B. Rooms are museum-like, decorated with period Italian antiques and frescoed ceilings while on the other hand you will have just recently renovated bathrooms with modern fittings.
The Hotel Il Marzocco has been operating as a hotel since 1860 and operated by the same family since 1900. It has the welcoming and refined atmosphere of a large country house and is furnished with genuine XIX century furniture.
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.
Recently renovated the Hotel Corsignano is a newly certified a “Green” Hotel. This beautiful 4- star Hotel is beautifully furnished and extremely comfortable, set in the frame of Tuscany's most beautiful and unspoilt area, reaching from Pienza to the Orcia-Valley.
Hotel Residence San Gregorio is situated a few hundred meters away from the ancient walled town of Pienza, in the heart of Tuscany. It offers an ideal exclusive environment to spend a night or a few days immersed in the magical atmosphere of a renaissance town, considered to be an architectural jewel.
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.
Surrounded by the warm steam from the thermal spring, continuing the legend of healthy water, one finds the ancient construction of the Rossellino, home of Pope Pius II Piccolomini, today known as the Hotel "Le Terme". The rooms are decorated in classical style and the restaurant specialises in traditional Tuscan style food where simple ingredients are combined into delicious dishes. All complimented by delicious wines from the surrounding villages.
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).
Located in the medieval old town of Montalcino with magnificent views of the Tuscan Hills. With an emphasis on excellent service this charming small hotel is situated in part of the eighteenth-century “Catasto Leopoldino” in the historic centre of Montalcino. However, there is reason to believe that the building may have been used since the Middle Ages (owing to its location in the vicinity of Porta Burelli) as a shelter for the Sienese people fleeing from the Florentine army.
A charming retreat in the heart of Montalcino, a family-run Hotel in a warm and quiet building, facing a gorgeous landscape over the Tuscan countryside. This is “Il Giglio”. The hotel has just 12 rooms, each one with cast-iron bed frames, painted ceiling and travertine stone bathrooms in a harmonious blend of rustic Tuscan style and classical elegance. The breathtaking panorama through the windows contributes to create an atmosphere that can only be experienced, never described.
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.
Fattoria Pieve a Salti is an agriturismo that has been converted from restored farm ruins into a stunning country hotel complex including a swimming pool and health centre. The rooms are furnished in traditional rustic Tuscan farm style.
Hotel Ghibellino is a modern 23 room three-star hotel in the centre of Buonconvento. It has an excellent reputation and the comfortable air-conditioned rooms are a relaxing haven.
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.
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