Southern Portugal Walking Tour Ocean Beach

Southern Portugal

A unique exploration of Southern Portugal.

A cultural connection of walkers to landscapes and local life.


You choose your departure date!

9 Days - 8 Nights

Priced from:


$500 USD Deposit Due With Registration

per person, double occupancy

Call Us. +1 623.561.0846


Hilltop fortress villages looming over ancient cork oaks and medieval pathways winding through chestnut forests. Roman temples, prehistoric menhirs and untouched fishing villages. From the Spanish border to the rugged coastline of the Costa Vicentina, this unique trip takes you walking through the beautiful, diverse Portuguese province of Alentejo.

To ensure that you get absolutely the most out of your time, you will be met on your first day in Alentejo by one of our local guides, who talks you though the maps, walks and information for the week ahead. They will transfer you between the different areas and are available to give you on-call support and advice throughout your holiday.


This journey of great contrasts starts in the fantastic capital, Lisbon, bursting with a lively cultural scene and historical sites befitting this fascinating country. Explore the gardens and palaces of royal Sintra on the way to the inland of peaceful Alentajo, where you walk ancient paths within the São Mamede Natural Park, linking the beautiful villages such as Castelo de Vide and Marvão. The landscape is of the unique open Mediterranenan forest known as Montado and traditional lifestyles far from the tourist trail, close to the true essence of rural Portugal and its rich cultural heritage.

A relaxing pause from walking in the historic town of Évora prepares you for the second part of the trip, along the Fishermen's Trail of the Rota Vicentina coastal network. This follows high cliffs over the Artlantic Ocean between small fishing villages.

Southern Portugal Highlights


Spend each day and night exploring different parts of the region for a diverse experience.


Walk through unforgettable landscapes and immerse yourself in the culture and community of Southern Portugal.


Exploring Southern Portugal by foot, is an opportunity to create your own unique adventure the whole way. This trip is fully customizable-- tell us how you want to walk. We will help make your dream a reality.

Your Experience

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Level of Activity


This is a walking holiday, so in that sense active, though it should not be terribly challenging for active travelers accustomed to walks of comparable distance. Although the itinerary includes daily walking, you will also have plenty of time to relax in the slower pace of life in Alentejo.


Distances on your walking days average around 15km. Elevation gains/losses are not dramatic by and large. In some cases, particularly at the coast, these can be lengthened and shortened-- your guide can explain these options at your welcome briefing.

Level of Comfort

In keeping with the varied nature of the places you see on this trip, your accommodation is equally mixed.

For most of the first few nights, you stay in local guesthouses, which are friendly, family-run type places. Not overly fancy, but very comfortable, and extremely welcoming.

The first night's accommodation is the most basic/simple; there aren't a great many options in this very remote part of Portugal. It does however give you access to a unique walking route, and a great insight into rural life.

In Marvão, you stay at the Pousada (the Pousadas of Portufal being akin to the Paradores of Spain), which has more in the way of amenities, a smarter restaurant, etc.

Moving west, your hotel at Évora is a delightful place near the city walls, with a lovely terrace and very comfortable rooms. You end the trip with two nights in the charming Herdade do Touril, where you can enjoy great hospitality, delicious food, and a welcoming swimming pool.

Southern Portugal walking hiking tour
Southern Portugal walking hiking tour winery

Level of Culture

One advantage of the slow pace of an inn to inn walk is that it allows you to enjoy not only the nature around you, but also gain a deeper insight into the local life of the area.

This holiday takes you into contrasting areas of Alentejo; from the rural heartland of the world's largest cork-producing area, to the rugged Atlantic coastline. Life in these regions is different in many ways, though in both cases has changed little over the years.

Your pause from walking, between inland Alentejo and the coast, takes in Évora-- the capital of Alentejo. The layers of history here are self evident, from the Roman temple to the imposing cathedral, and the eerie Chapel of Bones to name a few key points. 

This exclusive itinerary has been designed so that you have guided transfers between the coast and inland, which provides a resource to widen your understanding of local life and history. All this ensures that you have a rich cultural experience at each stage of your journey.



Please note that the details of this itinerary are subject to change. Many of the planned activities are organized according to availability, events or seasonal dates, appropriate weather conditions or the discretion of our guides. We make every effort to provide the experience described in the itinerary with the understanding that some things may change.

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Arrive in Lisbon, where this afternoon you have a private walking tour of the eclectic neighborhoods. The evening is spent enjoying a live Fado music show with dinner.

Meals included: Dinner

Accommodation: Avenida Liberdade Heritage Hotel

On arrival in Lisbon, make your way to the hotel and settle in before your guide collects you this afternoon for your walking tour of the Portuguese capital. The bairros (neighborhoods) of Lisbon are as intriguing as they are diverse, from the labyrinthine alleyways of Alfama to the chic boutiques and galleries of Baixo and Chiado.

Stroll downhill to a lookout point to admire the sweep of tiled roofs that add a distinct character and charm to the Old City. Continue past the impressive Sé (Cathedral) and the city's numerous fado bars and restaurants. Your walk continues into the modern district and the Praça do Comércio, the city's main plaza facing the Tagus, long known as the 'Gateway to Portugal.' This evening you participate in a cherished Portuguese tradition: a fado show with dinner.


The Clube de Fado in the heart of Alfama is a great place to experience the strains of a tradiitional 12-stringed guitar and the sultry voices of the city's best fadistas.

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Today you start the day with a visit to the gardens and palaces of Sintra before your transfer east to the beautiful Alentejo countryside to start your walk.

Meals included: Breakfast

Accommodation: Tapada da Rabela

You are picked up early today to travel the short distance to the town of Sintra for a guided stroll in its beautiful gardens and some in town for lunch at leisure. In the afternoon, a private two-hour road transfer will take you east to the quiet of Alentajo's montado (countryside).

On arrival, your local representative will give you a welcome briefing to provide you with maps and go over the journey ahead. They then remain on call for any assistance you may need throughout your trip.

This afternoon, you can take a stroll around the village or along the rural paths around Beira before enjoying the truly local cuisine of the village's only restaurant, which specializes in the black pig pork so prevalent in the area.

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Start walking today along the rolling terrain of the Alentejo, discovering its rich montado forest of cork oaks and evergreen oaks.

Walk Distance: 15km

                     (340m ascent/170m descent)

Meals included: Breakfast, Lunch, Dinner

AccommodationCasas do Contrabando

On the way, you will pass the small town of Santo Antonio das Areias, where you can stop for lunch or buy supplies for a picnic. The second half of the day will take you along ancient walled paths crossing the Sever River into the picturesque village of Galegos, right on the border with Spain.

This area is also known for its history of smuggling between Portugal and Spain, especially in the years of the Spanish Civil War when coffee was a luxury product that gave wealth to an otherwise poor region. This historic past gives name to your guest house, a cozy shelter where your friendly hosts will treat you to some of their vegetarian cuisine-- a hopefully welcome exception to an otherwise meat-based week!

Take your time this afternoon or early in the morning to visit the historic olive oil mill in Galegos, home to a unique olive oil of exceptional quality.

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Hike toward the hilltop village of Marvão along ancient paths surrounded by giant cork oak fields.

Walk Distance: 12km

                     (450m ascent/150m descent)

Meals included: Breakfast, Lunch, Dinner

Accommodation: Pousada de Marvão

The views of Marvão guide your way in this great walk to a unique town. Part of your first hour of walking today you will be retracing yesterday's walk, but being one of the most beautiful sections and doing it in reverse at a different time of day, we are sure you won't regret it!

Perched on a ridge overlooking the Tejo River valley, Marvão has been a site of strategic importance from the earliest times, something you can fully understand when you climb the ancient cobbled path and enter the castle to discover the vast views around you. From here, armies controlled a vast section of the border with Spain. More poetically, the Portuguese Nobel winner, Jose Saramago, said "From Marvão, you can see the entire earth..."

Take time to visit the local museum and castle and explore the narrow streets before dinner at your Pousada with an expansive view over Spain.

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Castelo de Vide

Descend from the hilltop fortress of Marvão along a centuries-old path through the forest before you reach the flatter approach to Castelo de Vide. 

Walk Distance: 12km

                     (300m ascent/500m descent)

Meals included: Breakfast

Accommodation: Casa Amarela

Your path leaves Marvão along an ancient medieval road, traversing a chestnut tree forest on the northern side of the hill. After traversing another beautiful forest of Pyrenean oak trees, the path approaches the hill top village of Castelo de Vide, still an untouched gem with layers of history for you to discover.

After settling into your comfortable accommodation on the main square, stroll around the Jewish quarter and up to the castle for fantastic views over the surrounding landscapes, and the trail towards the distant Marvão castle.

If you are feeling energetic in the afternoon, you could do the short steep climb to the Nossa Senhora da Penha chapel to enjoy wide views over Castelo and the Alentejo plains to the North. Enjoy dinner at leisure, perhaps in a local restaurant where, besides the regional pork specialties, you can find tasty game-based dishes.

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Take a break from walking today to drive to Évora, where your private guide unlocks some of the fascinating history of Alentajo's capital.

Meals included: Breakfast

Accommodation: Albergaria do Calvario

You are collected this morning for the drive to the beautiful town of Évora. Along the way, you'll make a stop to explore some of the layers of history, looking at how life has unfolded here over the centuries.

There are a couple of possibilities, depending on the day of the week, but it might be a visit to Roman ruins or a dive into the significance of cork as a crop in this part of the world-- home to 60% of the world's cork production.

On arrival in Évora, you'll have time free for lunch before you enjoy a guided tour of the city in the afternoon. The town is most famous for its striking Roman temple, one of the finest Roman remains on the Iberian Peninsula. There is also the Capela dos Ossos-- a chapel lined with the bones and skulls of thousands of townspeople. It also has a huge and seemingly incongruous 16th Century aqueduct which stands proud above the streets.

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Transfer to the coast to start walking once more, enjoying wonderful views over the rugged coastline and pretty beaches of the Costa Vicentina.

Walk Distance: 16km

                     (150m ascent/175m descent)

Meals included: Breakfast, Lunch, Dinner

Accommodation: Herdade do Touril

Today's walk is a strikingly beautiful cliff-top path established by the fishermen. After a short transfer (2.5 hour drive) from Évora, you will start walking from the wild beach of Almograve following the Fisherman's Trail of the Rota Vicentina.

Along the way you will come across deserted beaches with almost no means of access, in fact, to get to some of them, fishermen used hanging ropes to clamber down and gather shellfish. Half way through today's walk you will pass by Cabo Sardão Lighthouse, where you can see the only sea cliff stork nests in the world.

Arriving to the wild Tonel Beach, turn inland to arrive at your beautiful accommodation in the Costa Vicentina, the tranquil Herdade do Touril. Here you can enjoy a dip in the lovely pool before a delicious dinner, perhaps on the terrace if the weather is kind.

portugal-alentejo-costa-vicentina-sardao hiking walking tour beach ocean

Complete your week of walking with some of the best coastal views anywhere in Portugal, as you walk from Odeceixe to Zambujeira do Mar.

Walk Distance: 17km

                     (200m ascent/200m descent)

Meals included: Breakfast, Lunch, Dinner

Accommodation: Herdade do Touril

After a short transfer from your hotel, start today's walk with one of the most outstanding views in the entire territory: Odeceixe beach seen from the majestic Ponta em Branco.

In fact, today the route passes any number of beautiful beaches: Alteirinhos, Machados, Amália and Carvalhal-- the last being probably the nicest for a swim in the cold Atlantic waters.

Towards the end, you arrive in the welcoming fishing village of Zambujeira do Mar, where you can enjoy a drink before convering the last 5km along the coast to arrive back at the Tonel beach and onward to your hotel. Equally, if you prefer to linger in Zambujeira, it's a quick 10-minute ride back to your comfortable retreat.

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Travel back to Lisbon for departure today, or extend your trip in Portugal's lively capital.

Meals included: Breakfast

It's around 2.5 hours up to Lisbon this morning, so set off with your private driver in time to get to the airport for your flight home.

Alternatively, spend a couple days discovering the buzzing city's mix of great restaurants, historic shops and beautiful architecture.

Southern Portugal walking hiking tour

Where We Sleep


Quaint village luxury. The accommodations on this Portuguese walking tour were carefully selected by Jo Ann Taylor and are in the style she has created and the Walking Connection has become known for. The lodges. With gracious amenities and unique local flavor, you will rest comfortably night after night. Your luggage will be transferred between locations and be waiting for you upon arrival.

Herdade do Touril Southern Portugal walking hiking tours

Herdade do Touril


This friendly hotel is set in 5 whitewashed farm buildings built in 1826. A 15-minute walk from Tonel Beach on the Atlantic Ocean, it lies within the Parque Natural do Sudoeste Alentejano de Costa Vicentina.

A perfect place to walk to and from.

Hapada da Rabela

In the tranquility of the rural world and inserted in the Natural Park of Serra de São Mamede, in the village of Beirã, municipality of Marvão, Tapada da Rabela is a space aimed at nature lovers and oriented towards the conservation of natural values.

The Tapada da Rabela building consists of two floors. On the ground floor is located the Reception and the common Living Room, equipped with TV, blu-ray player, sound system, air conditioning, central heating and fireplace. It is on this floor that breakfast and occasional meals are served.


Pousada de Marvão

The Pousada do Marvão is located in the village of Marvão in the region of Alentejo. It is distributed among four small, traditional cottages, and the nearest city is Portalegre, just 21 km away. The village sits at an altitude of 860 metres, which offers fantastic views of Spain and the Alentejo plains.

Enjoy the restaurant, with a cozy atmosphere and rustic ambiance and the best panoramic views in the region, as well as the bar. The rooms afford magnificent views of the mountains or the picturesque village, and all feature televisions and free Wi-Fi.

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"Sitting here numbering my GREAT photos of Portugal! Memories of a WONDERFUL time. THANK YOU, THANK YOU, for a great vacation, AGAIN! Everything was perfect, as always. You have me spoiled on trips!" "                                                                     - Dorothy T  

"I had the most amazing time! Way beyond my expectations! Beyond words!"

- Brenda C                                

"Its the places you go and the people I meet, that's why I have traveled with you for the last 30 years."

- Larry D., Arizona

Southern Portugal walking hiking tour ocean beach

Space is limited on This EXCLUSIVE Adventure with

Jo Ann Taylor, Co-founder & President of The Walking Connetion.



Great! We love talking about walking in Portugal! Give our FAQs below a quick look. You might find answers there. Or email us: or call us at +1 (623) 561.0846 to speak with a team member. Either way, we are at your service, so please don't hesitate to reach out!

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•Unique itinerary designed by Walking Connection co-founder, Jo Ann Taylor in partnership with our local team in Portugal •Expert local driving guide for transfers and on-call assistance for daily walks •8 nights lodging at boutique hotels, as indicated in itinerary •Daily meals, as indicated in itinerary •Complimentary local wines with dinner •Ground transfers throughout •Transportation of luggage each day •All activities detailed in itinerary •Detailed Know Before You Go information, including recommended website, reading lists, packing list, and weather forecast

portugal-alentejo-marvao-cork-oak-hiking walking tour


•Local guide gratuities •All international and domestic airfares with tax (not listed in the above inclusions) •Airport transfers at beginning and end of trip •All items of a personal nature, including beverages and shopping •All passport and visa application fees, vaccination and medical consulting fees •All international departure taxes collected at airport of departure •Additional hotel stay pre- or post- scheduled itinerary •Early check-in or late check-out of rooms •Optional tours  •Photographs or phone calls •Discounts/Refunds on any unused portion of the tour •Travel Insurance •Anything that is not expressly stated in the itinerary or on the inclusion list above

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Updated Covid Policy: Should you have to cancel your tour the following terms will apply: A full refund of your deposit will be given if we are notified 6 months prior to this trip. If your deposit was a credit from a previous trip postponement, the amount can only be used as a future credit. At the 6 month pre tour point we will evaluate the world situation as it pertains to Covid-19 and will inform you of any changes in our policy. For more information on this trip, please contact our office. 1 800 295-9255 or email

portugal-alentejo-evora-herdade-do-freix walking hiking tour wine tasting

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