Walking in Portugal

Here is our range of walking holidays in Portugal

All our walking holidays in Portugal, Madeira and the Azores are researched in depth, with everything taken care of for you, so that you can just turn up and walk. We offer walking holidays in Portugal, Madeira and the Azores, and every walking holiday that we offer takes you off-the-beaten-track to discover the true culture and atmosphere of these fascinating locations.

Click on the appropriate 'View Holiday' button for further details, take a look at our activities section for further information about how our walking holidays work, or see our Portugal page for further information about our holidays in Portugal, Madeira and the Azores.

Walk the Algarve's Wild West

Cape St Vincent lighthouse, Sagres

From $1287 per person

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A warming winter walking discovery allowing you to see the best of the unspoilt Western Algarve region. The lush flora and diverse fauna of the Algarvian hinterland compliment the dramatic seascape scenery of the Atlantic coastline perfectly. The hotels are a brilliant mix of rustic charm and stylish grandeur, complete with swimming pools and serving the best of local Portuguese cuisine.

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  • 6 nights, hotel-to-hotel
  • All continental breakfast and 3 evening meals included
  • Holidays with gastronomic meals.
  • Holidays with wine-tasting opportunities.
  • Varied routes for nature lovers and botanists.
  • Destinations with bird watching opportunities.
  • Discover stunning historic sites en-route.
  • Lots of swimming opportunities.
  • Eco-friendly holidays.
  • Holidays to enhance your wellbeing.
  • Perfect for couples.
  • Follow stunning coastal routes.

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Marvels of Madeira Walk

From $1542 per person

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Perfect for year-round walking, the floating garden of Madeira is a paradise of tropical flowers, exotic birds and trees, romantic gorges and emerald seas. Luxury 4 and 5 star hotels throughout provide exquisite local cuisine with possibility of sampling the island's famous full-bodied wine.

Departures:
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  • 7 nights, hotel-to-hotel
  • All continental breakfasts, 2 picnics and all evening meals
  • Holidays with wine-tasting opportunities.
  • Varied routes for nature lovers and botanists.
  • Destinations with bird watching opportunities.
  • Lots of swimming opportunities.
  • Great vegetarian meal options.
  • Holidays to enhance your wellbeing.
  • Delightful island holidays.
  • Beautiful lakes and rivers.

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Walking Portugal's Land's End

Clifftop view of beach

From $1608 per person

Explore Portugal's Lands End on our 8 night walking holiday of the Algarve region with a contrast of inland walks and dramatic coastal paths. Each hotel has a pool and we’ve included 3 evening meals for you so you’re also free to sample the region’s superb local restaurants.

Departures:
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  • 8 nights, hotel-to-hotel
  • All continental breakfast and 3 evening meals included
  • Varied routes for nature lovers and botanists.
  • Destinations with bird watching opportunities.
  • Discover stunning historic sites en-route.
  • Lots of swimming opportunities.
  • Great vegetarian meal options.
  • Perfect for couples.
  • Follow stunning coastal routes.

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Contrasts of the Costa Vicentina Walk

Santa Clara lake

From $1732 per person

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With 300+ days of sunshine a year, it's little wonder that this holiday is such a winner with Headwater walkers! But it's not just the weather: Portugal's Alentejo offers wonderfully deserted beaches, tiny white villages, gently rolling hills and colourful fishing harbours - all untouched by tourism.

Departures:
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  • 7 nights, hotel-to-hotel
  • All continental breakfasts, 6 picnic lunches and 7 evening meals
  • Varied routes for nature lovers and botanists.
  • Destinations with bird watching opportunities.
  • Great vegetarian meal options.
  • Eco-friendly holidays.
  • Perfect for couples.
  • Follow stunning coastal routes.
  • Beautiful lakes and rivers.

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Birding in the Alentejo

Hoopoe

From $1782 per person

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Exclusive bird watching week in Alentejo - a region so rich in bird life it has over 120 resident species as well as many migrants passing through. Your week will be hosted and enhanced by local resident and hotelier Frank McClintock, who has built a reputation as one of Portugal's foremost birding guides.

Departures:
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  • 7 nights, single centre
  • Continental breakfast, 6 picnic lunches and all evening meals
  • Destinations with bird watching opportunities.
  • Lots of swimming opportunities.
  • Great vegetarian meal options.
  • Eco-friendly holidays.
  • Expert-led holidays.
  • Holidays to enhance your wellbeing.
  • Perfect for couples.

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Walking the Algarve's South-West

Algarve beach

From $1863 per person

Discover the South-West corner of the Algarve on our self-guided walk following coastal footpaths and inland trails.

Departures:
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  • 10 nights, hotel-to-hotel
  • All continental breakfast and 5 evening meals included
  • Holidays with gastronomic meals.
  • Varied routes for nature lovers and botanists.
  • Destinations with bird watching opportunities.
  • Discover stunning historic sites en-route.
  • Lots of swimming opportunities.
  • Great vegetarian meal options.
  • Perfect for couples.
  • Follow stunning coastal routes.

View holiday

Exploring the Azores Triangle

countryside view over lake in The Azores

From $2004 per person

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A 7-night guided tour of one the the world's most beautiful and diverse archipelagos. Explore the 'black' mountain island of Pico, 'blue' Faial, and the lush 'green' of Sao Miguel.

Departures:
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  • 7 nights, twin centre
  • All continental breakfast and 5 picnic lunches included
  • Varied routes for nature lovers and botanists.
  • Destinations with bird watching opportunities.
  • Great vegetarian meal options.
  • Eco-friendly holidays.
  • Holidays to enhance your wellbeing.
  • Perfect for couples.
  • Follow stunning coastal routes.

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A Walk Through the Algarve

Odeceixe Beach

From $2409 per person

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Join us on this 10 night journey through the unspoilt Algarve following river trails, flora laden paths, stunning coastal walks, and the highest point in the region all accompanied by a vast array of birdlife.

Departures:
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  • 10 nights, hotel-to-hotel
  • All buffet breakfasts, 7 evening meals and 8 lunches
  • Holidays with gastronomic meals.
  • Holidays with wine-tasting opportunities.
  • Varied routes for nature lovers and botanists.
  • Destinations with bird watching opportunities.
  • Discover stunning historic sites en-route.
  • Lots of swimming opportunities.
  • Great vegetarian meal options.
  • Eco-friendly holidays.
  • Especailly good for solo travellers.
  • Perfect for couples.
  • Follow stunning coastal routes.
  • Beautiful lakes and rivers.

View holiday

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Customer ratings

Based on 131 customer reviews, the average satisfaction rating for Walking in Portugal is
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Headwater's Walking in Portugal 4.5801526717557 131
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