Hill Towns of Tuscany Highlights
- Explore the famed hill towns of Southern Tuscany on foot
- Scenic walks between Renaissance and medieval towns, vineyards, and olive groves
- Relax and recharge in the thermal baths at Bagno Vignoni
- Time to reflect and listen to the sound of monastic chants in Sant’ Antimo Abbey
- Fantastic cheese, pasta, and wine including Brunello di Montalcino and Nobile di Montepulciano
Gallery
Itinerary
Day 1 Arrive in Montepulciano, transfer to the town centreThis Tuscan walking tour begins in the medieval and Renaissance hill town of Montepulciano. On arrival at Montepulciano Train Station there is an included transfer to the town centre which is a few kilometres away.
The historic centre of Montepulciano is a traffic free zone so it’s a pleasant place to explore on foot. Admire the impressive views over the rolling Tuscan landscape that this tour will further explore over the coming days. The town is packed with elegant Renaissance buildings, ancient churches, and charming squares to sample a glass of local wine in whilst watching the world go by.
Please let us know your arrival train time as soon as possible after booking so your arrival transfer can be booked accordingly.

Our hosts offer a warm welcome to all guests to their extraordinarily charming B&B. Rooms are museum-like, decorated with period Italian antiques and frescoed ceilings while on the other hand there are renovated bathrooms with modern fittings. Each bedroom has a TV, fridge, and air conditioner.

A 10-minute walk from the centre of Montepulciano, this 18th century property is decorated with antique furniture and classical décor in keeping with its historic charm, whilst having modern amenities like WiFi access and air conditioning. This small hotel has a bar and peaceful gardens.
Leave Montepulciano through one of the historic gates before heading out into the surrounding countryside. From the San Biagio Church, follow a quiet trail pass vineyards and olive groves to the peaceful village of Montichiello. Why not pause here for a relaxed lunch or perhaps just a quick cappuccino before continuing to the hilltop town of Pienza.
Pienza is a UNESCO World Heritage Site with unique Renaissance architecture. The town is well known for its delicious pecorino cheese and truffles; this is a great spot to indulge in Tuscan treats!
For anyone wanting to take an easier walk today it’s possible to transfer to Montichello and walk from here to Pienza.
Shorter walk from Montichiello: 6kms/4mi Ascent/Descent: 472m/522m
Walk from Montepulciano: 15kms/9mi Ascent/Descent: 472m/522m

This comfortable and homely hotel is located in the town centre, just off the main square. They have a focus on sustainability and have received green certification. They have a restaurant, bar, Jacuzzis, and terrace. Rooms are equipped with air conditioning, WiFi access and some have a balcony.

Situated just a few hundred metres away from the centre of the ancient walled town of Pienza. This charming hotel is traditionally decorated and is surrounded by a peaceful garden. There’s a restaurant and bar. The comfortable bedrooms have air conditioning and WiFi access.

This small hotel is set in a quiet position, surrounded by a peaceful garden and yet just a few steps from the historic town centre. There is an outdoor swimming pool with sun loungers and deckchairs to relax on. In the warmer months breakfast is served outside on the terrace. There is a wellness centre with Turkish bath, sauna, and treatments available (additional costs apply). There is also a bar and breakfast room. The comfortable bedrooms are equipped with air conditioning.
This is a particularly great walk as most of the time it’s possible to see both where you've been and where you are aiming for. Setting out on the walk from Pienza; admire the views across the valley with its typical Tuscan scenery of cypress trees, rolling farmland, and olive groves. Along the way stop in San Quirico d'Orcia. A walled town with an elegant 12th century church and ornate gardens. It is a great place to spend some time exploring.
Pass through Vignoni with its iconic stone tower before arriving in the spa town of Bagno Vignoni. The thermal baths complex is the perfect location soak up the Tuscan warmth and relax after a day’s walking.
For anyone wanting to take an easier walk today it’s possible to transfer to San Quirico d'Orcia and walk from here to Bagno Vignoni.
Shorter walk from San Quirico d'Orcia: 5kms/3mi Ascent/Descent: 311m/488m
Walk from Pienza: 14kms/9mi Ascent/Descent: 311m/488m

The unique location of this hotel is what truly makes it special. Surrounded by the warm steam from the thermal hot springs located just outside. The hotel has a spa where you can partake in the mineral rich thermal waters. There’s a Roman sauna and treatments are available (additional charges apply). There’s also a bar, restaurant, and terrace. The restaurant specialises in traditional Tuscan cuisine where simple ingredients are combined into delicious dishes. All complimented by wines from the surrounding villages. Bedrooms are decorated in classical style and have air conditioning and WiFi access.

Set in a restored 16th century horse and carriage station, this small hotel is located on the Via Francigena, where, in centuries past, pilgrims from Northern Europe travelling to Rome regularly sought rest and refreshment. The building has retained its original charm and, at the same time, has all modern comforts. There is a restaurant, bar, terrace, garden, outdoor swimming pool, and massage treatments are available (additional charges apply and advance booking is recommended). Each bedroom is individually furnished in romantic Tuscan country style, and they have air conditioning and WiFi access.
A more challenging but rewarding day’s walking awaits. Follow dry riverbeds through a fairly wild environment. The view initially is dominated by the castle on the hill, Ripa d'Orcia. Ascending into the medieval village of Castelnuovo dell'Abate. There are fine views from here down the valley with its iconic Tuscan scenery and vineyards galore. Reaching Sant’ Antimo, an isolated abbey situated in a pastoral landscape. This large abbey is an impressive example of Romanesque Cistercian architecture. The exterior facade has a menagerie of animals, and the interior frescoes are very intriguing. After time to explore the abbey, there is an included transfer to the accommodation in the charming medieval town of Montalcino.
Ascent/Descent: 486m/472m

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 18th century “Catasto Leopoldino” in the historic town centre. 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). It would have been a shelter for the Sienese people fleeing from the Florentine army. Today the hotel has maintained its historical character whilst offering modern comforts. There is a restaurant, bar, terrace, and a large panoramic garden with an outdoor swimming pool. Bedrooms are decorated in a traditional style and have air conditioning and WiFi access.
Walk through the famous Brunello wine region, passing vineyards and olive groves, before entering the Tuscan landscape of the “Crete Senesi” with its rolling hills and farmland, dotted with patches of woodland and quaint little villages. The walk finishes up at Fattoria Pieve a Salti Agriturismo near Buonconvento. Our characterful accommodation is the ideal spot to relax after a long walk, alternatively why not explore a bit more and visit nearby Buonconvento. This photogenic village is still nearly entirely surrounded by the ancient city walls with only a small section being destroyed in World War II. There’s also a pretty little church and two small museums here - Religious Art Museum of the Val d’Arbia and the Museum of Sharecropping.
Alternatively, there is an easier walking option today, which is slightly shorter and is a gentle downhill route into Buonconvento village. Spend some time exploring here before transferring to Fattoria Pieve a Salti.
Shorter walk to Buonconvento: 12kms/7mi Ascent/Descent: 43m/396m
Walk to Pieve a Salti: 16kms/10mi Ascent/Descent: 277m/522m
Please note that on the rare occasions that the Fattoria Pieve a Salti Agriturismo is fully booked the accommodation will instead be in a small hotel centrally located in Buonconvento. In which case it will be the shorter walking option used today.

This agriturismo has been converted from farm buildings into a stunning country hotel complex including both an indoor and outdoor swimming pool, garden, tennis courts, spa with sauna, steam room and massages available (additional charges apply and advance bookings is recommended). The agriturismo is in a natural truffle zone, famous for its white truffles, so this is often an inclusion on the hotel restaurants menu along with a range of locally produced wines and organic produce grown on the farm. Bedrooms are furnished in traditional rustic Tuscan farm style and have air conditioning.

This small hotel is on Buonconvento's main street, so is ideally located for exploring on foot. Its comfortable bedrooms have been decorated in a clean, modern style but have also highlighted the building historical features. They have air conditioning and WiFi access.

A small hotel in the centre of Buonconvento. It has a large terrace on the third floor providing a great view over the historic village. The comfortable bedrooms have WiFi access and air conditioning, and some have a balcony.
A short transfer is included to Buonconvento Train Station, where there are trains to Siena. Alternatively, it’s possible to arrange a private transfer to Siena for an additional charge. Please ask our Sales team about this at the time of booking.
From Siena catch the train to Rome, Pisa or Florence airports or perhaps continue to journey further within Italy. Tuscany combines perfectly with our coastal walks of the Cinque Terre and Amalfi Coast or any of the Umbria trips.
Other Information
Is it for me?Perfect for anyone who walks regularly and wants to explore at their own pace. There are plenty of places of historic interest to discover amidst picture-postcard scenery. All coupled with comfortable and welcoming accommodation, and mouth-watering food and wine. There are ascents/descents to the hill towns at the start and end of the walks, due to the nature of the rolling Tuscan scenery. However, most walks can be shortened.
Slower Adventures | Where walking and cycling meet easy-going exploring, our Slower Adventures are the perfect combination. Most days are filled with picturesque journeys with some free time to dive into the destination and experience the people, local food and culture as you go.
Inn to Inn Walking | Walk from place-to-place changing accommodations each night. Generally staying in B&B’s, inns, and guesthouses.
Solo Travellers
As a guide, we would suggest that the minimum age of traveller this holiday would be suitable for is: 12 Years
This trip is graded ‘easy to moderate’ overall, however it should be noted that the terrain is hilly and summer temperatures can be high. Most of the route follows dirt tracks and trails and, minor roads occasionally. On days 2, 4 and 5 the walking is graded more towards the ‘moderate’ side as these are more challenging days. There are options to shorten the walks most days by joining the luggage transfer to get closer to your destination.
Stay in charming small hotels, guesthouses and agriturismos. We carefully select small and friendly accommodation that offers great value, so you enjoy every minute.
Additional Nights
Many of our walkers choose to add extra nights along the walk to sample more of the wonderful walking and attractions available in Tuscany. We would recommend spending extra nights in Pienza, Montalcino and/or Siena. Please notify us at the time of booking should you wish to add extra nights.
Single Rooms & Solo Walkers
This trip is based on double occupancy (two people sharing a room with one bed). If separate rooms are required, then a single supplement is payable. If a twin room is needed (same room with two separate beds), please notify us at the time of booking so we can request this option. This trip is available to solo walkers.
Meals
The delicious Tuscan food and wine is undoubtedly a highlight of this holiday.
Breakfast is included each morning and normally consists of a traditional European style continental breakfast ranging from coffee, tea, yoghurt, granola, meat, cheese, and baked goods. In some cases, a hot dish (eggs, pancakes, etc.) will be served or offered á la carte.
Lunches and dinners are not included in this trip. We recommend finding cafés or restaurants located in the towns or along the walking route, or to purchase snacks and a picnic lunch to bring along on the walks from local supermarkets and markets. Alternatively, most accommodations will be happy to provide a packed lunch on request and this can be booked on arrival. Dinner is available either at your accommodation or nearby restaurants. Further details can be found within your information pack and the Macs Adventure Smartphone App.
The routes are waymarked in some areas, but not in others. However, we provide the Macs Adventure Smartphone App making it simple to follow the route using a smartphone. Rest assured that by downloading the route maps in our app, that this will continue to work even in areas without any mobile or internet reception. For extra reassurance there are turn-by-turn route notes within the app too for the majority of walks.
- Accommodation in en suite rooms in charming hotels, guesthouses and agriturismos on a twin share basis
- Daily breakfasts
- Transfer as per your itinerary
- Door to door baggage transfers as per your itinerary
- Access to maps, GPX tracks and daily route information with the Macs Adventure smartphone navigation app
- All your trip documents including a detailed information pack provided digitally through your online Macs “My Account”
- Telephone support from our offices and local partner in the event of a problem
- Travel insurance (required) and personal equipment
- Lunches, dinners, drinks, and snacks
- Tourist taxes (charged locally at hotels)
- Travel to and from start and finish points
- Any additional transfers or public transport required to shorten the walks or skip a stage
- Additional nights before, during or after the tour
- Private transfers to the start and from the end points of the tour
- Room upgrades
This tour is available to start anytime between April to October, and possibly March, but we will need to check for you that the hotels have opened for the season as several in Tuscany only open at Easter, so it depends when this falls and if they have decided to open sooner.
Peak Season Availability
As Tuscany is a very popular destination, we suggest booking as soon as possible to ensure availability for specific dates.
Time of Year
The springs months of April, May and June offer warm sunshine, fewer crowds, and pleasant walking conditions. May is when most wildflowers are coming into bloom. The autumn months of September and October are also a favourable time of year, boasting cooler weather and a striking landscape made up of autumnal colours. July and August are good months to go but can be very hot for walking and therefore aren’t best suited for everyone. You will have to start early to miss the heat of the day and carry a lot of water (additional weight) with you. Although the towns and villages are buzzing at this time of year which is great to see.
We recommend flying to Florence, Rome, or Pisa and catching the train from the city centre railway station to Montepulciano (usually changing in Chiusi).
If landing at Florence Airport, there’s a shuttlebus into the centre of Florence (taking around 25 minutes). It stops beside the main railway station of Santa Maria Novella.
If arriving at Pisa from the airport take the PisaMover to the main train station (takes 5 minutes). Turn left when exiting arrivals and the PisaMover is at the end of the airport.
Rome has two airports. From Fiumicino Airport take a train to the central station Roma Termini (taking about 30 minutes). From Ciampino Airport there’s a bus to Roma Termini.
Montepulciano is on a minor rail line and the station is a few kilometres outside of town. We have included a transfer from the train station to the town centre. We need you to advise us as soon as possible after booking as to which train you will be arriving on in order for the transfer to be arranged accordingly.
Alternatively, if you’d rather not use the included transfer from Montepulciano Train Station then rather than getting off the train in Montepulciano there are buses that run from Chiusi Train Station to Montepulciano Bus Station or you can take a taxi. The journey is about 25 minutes. Please let us know if you don’t require the transfer.
Approx. journey times to Montepulciano are:
From Florence 1hr50 - 2hr15
From Rome 1hr50 - 3hr15
From Pisa 2hr50 - 3hr20
Train timetables are available at Trenitalia. Please note that not all buses run on a Sunday or they may have a reduced timetable.
A private transfer can be requested. Please let us know at the time of booking if you would like to add this option (additional costs apply).
From the agriturismo a private transfer is included to Buonconvento Train Station, where there are trains to Siena. Alternatively, a transfer to Siena can be arranged for an additional charge. Please ask our Sales team for details.
From Siena take the train back to Florence, Rome, or Pisa. Once again it will be necessary to travel from the central stations in these cities back to the airports (see ‘Getting to the Start’ for further information about this). Please see Trenitalia’s website for timetables.
Approx. total journey times from Siena are:
To Florence 2hr15 - 3hr15
To Rome 2hr15 - 3hr20
To Pisa 2hr00 - 3hr15
Siena Train Station is in the valley below the city centre and there are escalators between the two or there are local buses.
To Florence Santa Maria Novella there is usually a direct train that goes via Empoli and takes around 1 hour 30.
To Roma Termini in Rome it’s normally necessary to change trains in Chiusi-Chianciano Terme.
To Pisa there is usually a direct train that goes via Empoli and takes around 1 hour 40.
One bag of up to 20kg per person will be transferred from each accommodation to the next.
At Macs Adventure, we work in partnership with many luggage transfer providers who set a limit on how many bags/suitcases they will transfer per person, and also the weight of the bag/suitcase. Your booking includes transfer of 1 bag per person. It is very important that you read the luggage information specific to your tour before departure. If you do not adhere to these limits, there is a great possibility that you will be charged locally both for extra bags or if they are too heavy. This limitation can be a challenge, especially as airlines generally have limits that are higher. However, our luggage providers have reasons for these limits (usually due to the Health and Safety of their employees), which we must respect.
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.
The tour information pack has a detailed equipment list which includes standard walking gear such as good walking boots or shoes, warm and waterproof clothes, and a day pack.
It is a requirement of booking this tour with Macs Adventure that you have suitable travel insurance which covers you for the activity and emergency evacuation and hospital care.
To get the most from this trip you should be in good physical shape and comfortable walking on undulating terrain with many ascents and descents. Please read the ‘Is it for me?’ section of the web page and the itinerary for further information in order to ensure this trip is the right fit for you.
As Tuscany is a very popular destination, we suggest you book as soon as your plans are finalised to ensure availability for specific dates especially in travelling during July/August.
You will need good walking shoes/boots, comfortable walking clothes, a day pack, and dependent on when you are travelling; waterproof jacket and trousers, and hats/gloves etc. Our information pack has a list of all equipment to bring on your trip.
You can use public transport or local taxis to continue to your next overnight stop.
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WalkingHow fit do you need to be to climb Kilimanjaro?Read More2 Min Read15 September 2011
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Walking4 Alternative Walks to the West Highland WayRead More3 Min Read10 February 2011
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West Highland WayWhat to Pack for the West Highland Way?Read More4 Min Read13 January 2011
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West Highland WaySkipping a Section on the West Highland WayRead More4 Min Read13 January 2011
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TrekkingKilimanjaro Climb Diary - Summit DayRead More3 Min Read30 January 2010
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WalkingA Safari Less Travelled - ScotlandRead More5 Min Read09 July 2019
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WalkingExperience The Magic Of Skye In Style With The ExpertsRead More2 Min Read25 July 2019
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WalkingAdventure Of The Week: The Arran Coastal WayRead More3 Min Read10 July 2019
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West Highland WayOne "Appy" Macs Customer!Read More4 Min Read01 July 2019
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WalkingAdventure Of The Week: The West Highland WaheyRead More6 Min Read07 August 2019
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Adventure of the Week: Queen Charlotte TrackRead More2 Min Read24 July 2019
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TrekkingA Safari Less Travelled - England's South West CoastRead More7 Min Read05 August 2019
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Walking40 Miles In One Day For Glasgow Children's HospitalRead More3 Min Read26 July 2019
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Adventure of the Week: Great Glen EscapeRead More1 Min Read31 July 2019
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WalkingAdventure of the Week: Nakasendo Trail, Tokyo, Kyoto, Mount Koya & NaraRead More4 Min Read14 August 2019
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Hiking in Style - You're Worth it!Read More3 Min Read26 August 2019
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How To Avoid The Perils Associated With Ticks?Read More3 Min Read30 August 2019
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WalkingThe Safari Less Travelled – A Rare Find?Read More6 Min Read09 September 2019
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WalkingGreat Glen Escape - Monster Hunting on FootRead More4 Min Read16 September 2019
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Adventure of The Week: Bavarian Alps: Hiking the Salt TrailRead More3 Min Read04 September 2019
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Active Travel in Portugal - Where Should I Go?Read More3 Min Read10 January 2020
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WalkingHidden Gems - The Town of Three LiesRead More3 Min Read06 February 2020
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WalkingSao Miguel: Azores Green Island - Europe's Best Kept Secret?Read More3 Min Read12 February 2020
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WalkingSeven Reasons to Visit the Basque CountryRead More3 Min Read27 February 2020
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WalkingEverything You Need to Know About Walking The Rota VicentinaRead More4 Min Read05 March 2020
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WalkingHistorical Highlights of the Northumberland Coastal PathRead More2 Min Read26 June 2020
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WalkingTop Reasons to Walk the Northumberland Coastal PathRead More2 Min Read19 August 2020
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WalkingFrequently Asked Questions about walking the Northumberland CoastRead More2 Min Read19 August 2020
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Walking4 Reasons to Walk the Pembrokeshire Coast PathRead More2 Min Read25 September 2020
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How Difficult is the Pembrokeshire Coast Path?Read More2 Min Read25 September 2020
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Famous Welsh WritersRead More2 Min Read15 October 2020
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TrekkingTour Of The Matterhorn – 5 Top TipsRead More2 Min Read17 December 2020
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WalkingTop 5 highlights from the Great Ocean WalkRead More3 Min Read09 February 2021
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The Ultimate Walking Boots Guide for BeginnersRead More7 Min Read10 November 2021
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Tips & AdviceEssential Phrases for SpainRead More1 Min Read17 January 2022
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WalkingWhich part of Spain is right for me?Read More2 Min Read18 January 2022
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Walking5 reasons I loved the Sierra de Aracena!Read More1 Min Read18 January 2022
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French Culture and Why I Love ItRead More1 Min Read19 January 2022
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5 Must-See Salvador Dalí sites in CataloniaRead More1 Min Read26 January 2022
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Tips & Advice10 dishes you have to try in Andalucia!Read More1 Min Read14 February 2022
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8 Postcards from the Pueblos Blancos!Read More0 Min Read15 February 2022
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Top 8 Beaches of the Balearic IslandsRead More1 Min Read22 February 2022
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Balearic Islands 101: A Guide to MenorcaRead More3 Min Read01 March 2022
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Tips & AdviceWalk Your Way to WellnessRead More3 Min Read09 January 2023
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Meeting the people behind the scenery - Minna & Classic RoutesRead More2 Min Read01 February 2023
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Walking6 reasons to visit West SwedenRead More3 Min Read02 February 2023
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Walking the Fishermen’s Coast – Where a Forgotten Portugal Meets the AtlanticRead More3 Min Read02 March 2020
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Tips & AdviceCoast to Coast West: A Culinary Trip through the Lake DistrictRead More2 Min Read07 August 2022