Included: An experienced, local hiking guide with extensive knowledge of the area 8-day guided walking holidays in Portugal Accommodation for 7 nights in a charming farmhouse (double rooms) Most meals All breakfasts Welcome regional snack Three dinners (with 2 drinks) — on Day 1, Day 7, and one more day throughout the week All lunches (picnic lunches during daily tours, one lunch in Arraiolos) Transfer during the tour Personal accident insurance for tour days Not included: Transportation to Portugal Airport transfers Tourist tax (€1 to €4 per night, per person) Cooking class — available to add, let us know if you’re interested Guide gratuities — optional Insurance — recommended, available at checkout

How fit do I need to be?

These guided walking holidays in Portugal are beginner-friendly ! Check out the itinerary to learn about day-by-day distances and elevation gains, but in general, you’ll be hiking between 10 to 18 km (6 to 11 miles) per day . All that’s required is a decent level of fitness and you’re good to go!

What do I need to bring?

Here’s a list of the equipment you need to bring: Day pack large enough to carry all the items listed (around a 25-40L bag) Hiking poles — optional Water bottle or hydration bladder (2L capacity) Lightweight hiking boots or shoes Comfortable hiking clothes Spare clothes for layering Waterproof rain jacket Sunhat and sunglasses Swimming suit Toiletries (sunscreen, hand sanitizer, bug spray, toilet paper, etc.) Camera — optional (but recommended) Dress comfortably and for the weather in clothes you can move in. We suggest bringing clothing appropriate for the season. Layers are best and don’t wear jeans.

Group sizes and age requirements

Group sizes and pricing For these guided walking holidays in Portugal, the usual client-to-guide ratio is 14:1. It takes a minimum of 2 people for this tour to operate. The maximum group size is set at 12 adults and 6 children. Guided walking holidays in Portugal can be arranged for larger groups. Contact us to make arrangements. Min. age requirements If you are older than 18, you’re good to go. Minors younger than 18 may be permitted to join the hike, but must be in the presence of a parent or legal guardian. Let us know if you’re traveling with children upon booking.

Getting there and meeting location

To get to Évora, the starting point of your guided walking holidays in Portugal, most people fly into Lisbon Airport (LIS) . You can either rent a car or take public transport (bus and train) to get to Évora, it will take you 1.5-2 hours. Once you get there, head towards Monte Do Serrado De Baixo , your beautiful accommodation for the whole stay. Alternatively, your guides offer Lisbon airport transfers at an additional cost. Let us know if you’re interested upon booking.

Safety measures in Portugal

We highly recommend that you cover all your bases with insurance. To make your booking and traveling experience as carefree as possible, you’ll be offered to simply insure your trip with Redpoint at checkout. Redpoint—the official 57hours insurance partner—tailors protection packages for adventure travel, offering a comprehensive travel program, even in remote locations! Trip cancellation, natural disasters, pandemic coverage, medical evacuation, primary medical expenses—regardless of the travel interruption that may happen, Redpoint will have you covered.

Check out Early bird options for best sellers here

ALENTEJO | PORTUGAL

Relaxing Walking Holidays in Portugal

8 days | Easy | 5.00

From $2,096 ()

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Portugal’s Alentejo region isn’t just easy on the eye—it also has 6,000-year-old monuments, UNESCO World Heritage Sites, and a delicious cuisine. We’ve been making people fall in love with this region since 1994, and these 8-day walking holidays are one of our favorite trips! This adventure is all about slow living, so we’ll take our time exploring the scenic countryside, beautiful historical sites, charming wineries, local cafés, and much more. Our base for the week will be a lovely farmhouse equipped with all modern comforts, a lush garden, and a swimming pool, ideal for sipping on a cocktail at the end of the day. If you’re about sightseeing super popular stuff, this tour isn’t for you—we’ll walk along isolated trails, visit small local businesses, and discover the crowdless Portuguese countryside!

Adventure Highlights

Steeped in history: Megalithic monuments dating back to 4,000 BC, Renaissance aqueducts, impressive medieval castles…
Supporting local businesses: We’ll visit local wineries (Portugal has some of the best wines in the world), a pottery, historic farms, and local cafés
Slow-paced walking holiday: This isn’t about getting to a point as fast as possible—we’ll take our time discovering gorgeous landscapes of Portugal’s Alentejo

Duration

8 days

Season

April through June, September through October

Group size

Up to 14 people

The adventure, day by day

Download itineraries

A fan of relaxing holidays, easy walks, and a ton of cultural heritage? Portugal’s Alentejo region is perfect for you. Over the course of 8 days, we’ll immerse ourselves in the beauty of this region by going on different walks every day, bringing us a mix of varied landscapes and sceneries. We’ll be based in a charming farmhouse for the duration of this trip, just perfect for getting back to after a day of exploring our surroundings. This region of Portugal has delicious authentic cuisine as well as some of the best wine in the world (Alentejo is the wine market leader in Portugal), so we’ll make sure to taste typical products as well. Lodgings are included, as well as most meals, and transfers during the tour. You’ll return from this trip feeling relaxed and refreshed!

Day 1: Arrival

Make your way to Monte do Serrado de Baixo, a beautiful farmhouse near Évora. Depending on your mode of transport, it’s a 1.5-2-hour ride from Lisbon Airport. You’ll have a trip briefing, talking about the days ahead. Enjoy your first dinner in Portugal and get some rest.

Meals: Dinner
Accommodation: Monte do Serrado de Baixo

Day 2: The Silver Water Aqueduct

We’ll leave the guesthouse towards the 16th-century aqueduct, built to solve the water shortages in the city. This walk will lead to the ancient city of Évora. Along the way, we’ll pass by small farms and aromatic herbs that grow by the aqueduct. To end the day, after a visit to the most relevant historical sites, there is nothing better than a cool drink in Évora center square, where we will be surrounded by age-old buildings and feel the flow of life passing us by.

Meals: Breakfast, picnic lunch
Distance: 12-15 km / 7.5-9 miles
Elevation: +228 m / +750 ft | -236 m / -775 ft
Accommodation: Monte do Serrado de Baixo

Day 3: Megalithic monuments

Today we’ll go on a walk through the beautiful holm oak forest dotted by impressive granite boulders which, 6,000 years ago, were used by our ancestors to build their burial sites and magic cult sites. We’ll take our time exploring these sights and our surroundings. We will visit the Dolmen of Zambujeiro, a megalithic monument from between 4,000 and 3,000 BC, the largest one in Europe! We’ll also visit some other megalithic complexes and structures like Cromlech of Almendres, the Menir of Almendres, and the church of Mitra.

Meals: Breakfast, picnic lunch
Distance: 15-18 km / 9-11 miles
Elevation: +327 m / +1,073 ft | -121 m / -397 ft
Accommodation: Monte do Serrado de Baixo

Day 4: Trip to Arraiolos and Évora or rest day

Today we’ll take a transfer to the Arraiolos village and its surrounding. We will stroll through its quiet streets, visit the castle, and the museum. We’ll go to the lovely Ravasqueira farm and visit the private carriage collection and taste their delicious wine. Then we’ll go to Évora and there will be plenty of time to discover the city on your own! If you prefer to have a rest day, feel free to stay at the accommodation and explore the surroundings on your own.

Meals: Breakfast, lunch
Accommodation: Monte do Serrado de Baixo

Day 5: Castle of Valongo

While we go along the lovely river Degebe, we’ll discover old water mills and try to imagine how they once worked. Then we leave the river side and start walking up to reach a point with wonderful views. Finally a castle starts to take shape on the horizon—the surreal castle of Valongo, built in the middle of nowhere by, some say, the Romans.

Meals: Breakfast, picnic lunch
Distance: 12 km / 7.5 miles
Elevation: +157 m / +515 ft | -139 m / 456- ft
Accommodation: Monte do Serrado de Baixo

Day 6: To the Tower of Évoramonte

We’ll kick off the day by walking along a closed railway through beautiful scenery. If we’re lucky, we will encounter some black pigs, cows, and sheep. Then we climb steep tracks that lead to the castle of Évoramonte. Once there, follow the walls all the way around and take in the beautiful views. You can see Spain from here!

Meals: Breakfast, picnic lunch
Distance: 10 km / 6 miles
Elevation: +366 m / +1,200 ft | -194 m / -636 ft
Accommodation: Monte do Serrado de Baixo

Day 7: Medieval village

Fortified village of Monsaraz in Portugal

The unforgettable village of Monsaraz, built in a castle on top of a hill, is incredible to see. Schist Rock walls will guide the walk around the beautiful fort. The last climb brings you to the top and you’ll enjoy stunning views of a well-kept village and the Alqueva lake. If it’s warm enough, you can even finish with a swim or a canoe trip! On the way back to the farm visit a pottery in São Pedro do Corval.

Meals: Breakfast, picnic lunch, dinner
Distance: 11 km / 7 miles
Elevation: +248 m / +814 ft | -243 m / -797 ft
Accommodation: Monte do Serrado de Baixo

Day 8: Departure

After the final breakfast at the guesthouse, your guided adventure has come to an end. If you’d like to stay longer and explore the area, just ask us for some recommendations!

Meals: Breakfast

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Photo gallery

Monsaraz village within a castle at night

Lodging & food

Farmhouse

Located near Évora, this charming farmhouse nurtures the traditional architecture of the Alentejo region. With its thick walls keeping the house cool in warm weather, this house is the perfect base for summer explorations.

This place will feel like home. There is a lovely lush garden with a swimming pool, so don’t miss out on taking a swim while the only sound you hear is the chirping of birds. Bring a gin & tonic, find your place in the sun or in the shade, and enjoy!

While you take a stroll around the house, you’ll likely come across pets and domestic animals, including dogs, donkeys, sheep, chickens, and lambs. There’s also a Classic Car museum, a unique private collection and an exclusive experience for the guests!

Rooms

Each room has a different theme, inviting you to explore the arts of cork extraction, olive and grape picking, or bread making. Featuring a living room, an honesty bar, books, music, games, and much more, this house has all modern comforts within a rustic and authentic atmosphere.

Food

All breakfasts, picnic lunches, and three dinners are included in the price of this tour.

- Every morning you’ll kick off your day with delicious breakfast made and prepared at the Monte do Serrado de Baixo, the charming farmhouse you’ll be staying at. You can expect a variety of breads, cereals, meats, cheeses, sweet breads, fruit, and eggs.
- For picnic lunches, you will enjoy homemade sandwiches prepared by the guides.
- Dinners are also varied and always focus on the regional concept—black pork, cod, veal, chicken, and much more.

In the dining room, you can enjoy breakfast with a view of orange orchards. You will taste homemade jams, cottage cheese with olive oil and oregano, or with honey and walnuts, homemade bread and cake. There will always be plenty of regional cheeses and chorizos! And, of course, the delicious Alentejo bread. Orange juice will be made from oranges just outside, while fruit and vegetables will be sourced from the farmhouse gardens.

Adventure, packed to go

Relaxing Walking Holidays in Portugal

Adventure Brochure

Adventure brochure

Download to share and explore full itineraries, key info, FAQs, and guide details.

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Meet your guides

Seasoned pros, local legends, and passionate adventurers—your trip is in the best hands.

5.00

Teresa

General manager and guide

Teresa has been the soul of a hiking company and Monte do Serrado de Baixo farmhouse for the last 20 years. The first adventure she recalls was trekking after her father in the mountain of Gerês, when she was 5 yo. She has practiced several outdoor sports and loves to travel by bike. For two years, she was travelling through Australia, New Zealand, Thailand, Laos, India, and Nepal. With endless energy, she will guide a cycling tour as well as a canoeing trip or set up an original outdoor event for a company meeting.

What others say about this adventure

5.00 (4 reviews)

Ruth C.

|May 2025

Interesting hikes paired with visits to historical sites.

Terry_and_Suzanne

Delightful walking tours in and around Evora, Portugal. Our group of 15 was guided on several days of excellent walking tours in the Alentejo region of Portugal. Teresa was our guide, and she was fabulous – informative, fun, and very well prepared. She served us delicious picnic lunches every day. I would definitely hire her again if I go back!

kdtravels17

Had a great walking week with Turaventur in April, 2017. With our guide we visited ancient stone circles, vineyards, old hilltowns and had local experiences that only a guide who lives in the area can provide. This is a jewel waiting to be discovered…so glad we did!

Show all reviews

Ruth C.

|May 2025

Interesting hikes paired with visits to historical sites.

Terry_and_Suzanne

kdtravels17

910sandyd

Theresa was our group guide for 5 days and it was an incredible adventure as we heard all about the history, agricultural life, and life in general around Evora. After a visit to a cheese making farm Theresa lead us to all the stone monoliths in the area as we walked through groves of Cork Trees. We learned about the harvesting and processing of cork and the following day we hiked to a medieval castle surrounded by vineyards. Other days we visited a winery for wine tasting, toured the old city of Evora, walked to a hilltop city, visited a pottery shop, ate at a local restaurant where we made our own bread, and our last day we followed the Aqueduct to her farm where we saw her father’s antique car collection and enjoyed an outstanding lunch at her B & B. Theresa is organized and enthusiastic about making sure you have an outstanding experience in her country. She brought a picnic lunch for all 15 of us each day with local breads, cheeses, vegetables and pastries! You can’t beat this genuine Portugal experience because she is passionate about her job and has the answers to your questions.I’d love to hike with her again in the future.

Things to know

Included:
- - An experienced, local hiking guide with extensive knowledge of the area
  - 8-day guided walking holidays in Portugal
  - Accommodation for 7 nights in a charming farmhouse (double rooms)
  - Most meals
    
    All breakfasts
    
    Welcome regional snack
    
    Three dinners (with 2 drinks) — on Day 1, Day 7, and one more day throughout the week
    
    All lunches (picnic lunches during daily tours, one lunch in Arraiolos)
  - Transfer during the tour
  - Personal accident insurance for tour days
Not included:
- - Transportation to Portugal
  - Airport transfers
  - Tourist tax (€1 to €4 per night, per person)
  - Cooking class — available to add, let us know if you’re interested
  - Guide gratuities — optional
  - Insurance — recommended, available at checkout
These guided walking holidays in Portugal are beginner-friendly! Check out the itinerary to learn about day-by-day distances and elevation gains, but in general, you’ll be hiking between 10 to 18 km (6 to 11 miles) per day. All that’s required is a decent level of fitness and you’re good to go!
Here’s a list of the equipment you need to bring:
- - Day pack large enough to carry all the items listed (around a 25-40L bag)
  - Hiking poles — optional
  - Water bottle or hydration bladder (2L capacity)
  - Lightweight hiking boots or shoes
  - Comfortable hiking clothes
  - Spare clothes for layering
  - Waterproof rain jacket
  - Sunhat and sunglasses
  - Swimming suit
  - Toiletries (sunscreen, hand sanitizer, bug spray, toilet paper, etc.)
  - Camera — optional (but recommended)
Dress comfortably and for the weather in clothes you can move in. We suggest bringing clothing appropriate for the season. Layers are best and don’t wear jeans.

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Group sizes and pricing
- - For these guided walking holidays in Portugal, the usual client-to-guide ratio is 14:1.
  - It takes a minimum of 2 people for this tour to operate. The maximum group size is set at 12 adults and 6 children.
Guided walking holidays in Portugal can be arranged for larger groups. Contact us to make arrangements.

Min. age requirements
- - If you are older than 18, you’re good to go.
  - Minors younger than 18 may be permitted to join the hike, but must be in the presence of a parent or legal guardian.
  - Let us know if you’re traveling with children upon booking.
To get to Évora, the starting point of your guided walking holidays in Portugal, most people fly into Lisbon Airport (LIS). You can either rent a car or take public transport (bus and train) to get to Évora, it will take you 1.5-2 hours.

Once you get there, head towards Monte Do Serrado De Baixo, your beautiful accommodation for the whole stay.

Alternatively, your guides offer Lisbon airport transfers at an additional cost. Let us know if you’re interested upon booking.
We highly recommend that you cover all your bases with insurance. To make your booking and traveling experience as carefree as possible, you’ll be offered to simply insure your trip with Redpoint at checkout.

Redpoint—the official 57hours insurance partner—tailors protection packages for adventure travel, offering a comprehensive travel program, even in remote locations! Trip cancellation, natural disasters, pandemic coverage, medical evacuation, primary medical expenses—regardless of the travel interruption that may happen, Redpoint will have you covered.
Deposits

Secure your spot with a 30% deposit upon booking! The remaining 70% of the trip price must be paid 90 days prior to departure at the latest. If booking within 90 days of departure, the full amount is required at the time of booking.

Cancellations

Booking fees are non-refundable after a 48-hour grace period. During checkout, however, you can choose one of 57hours’ flexibility options—Basic, Flexible, or Super Flexible. Depending on which one you choose, a different cancellation policy will apply to your booking.

Basic
- - If cancelled within 48 hours of booking, a full refund will be issued.
  - If cancelled 60 or more days before departure, a 70% refund of the total trip price will be issued.
  - If cancelled within 59 days of departure, no refund will be issued.
Flexible
- - If cancelled within 48 hours of booking, a full refund will be issued.
  - If cancelled 60 or more days before departure, a full refund of the total trip price will be issued.
  - If cancelled 30-59 days before departure, a 50% refund of the total trip price will be issued.
  - If cancelled within 29 days of departure, no refund will be issued.
Super Flexible
- - If cancelled within 48 hours of booking, a full refund will be issued.
  - If cancelled 30 or more days before departure, a full refund of the total trip price will be issued.
  - If cancelled within 29 days of departure, a 50% refund of the total trip price will be issued.

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