Our walking holidays in Portugal

The jewel in Portugal’s crown is the rural heartlands dotted with villages and vineyards, linked by a superb network of walking routes. Our Portugal walking holidays roam the Algarve, Alentejo, Madeira, the Azores, Sintra, and Peneda Geres National Park. Whether walking as part of a sociable small group led by a local guide, or on a self-guided trip that gives you greater freedom over your route, these holidays are designed to show you lesser-seen aspects of Portugal. Staying in welcoming, family-run accommodations in what are often remote communities that see little tourism, your holiday also helps traditional ways of life to thrive.

Our top Walking holidays in Portugal

Portuguese Coastal Way walking holiday

From €825 to €975
8 days ex flights
The scenic alternative to the classic Portuguese Way
Tailor made

Madeira walking holiday

From £865 to £1200
8 days ex flights
Small group walking tour of Madeira
Small group2024: 20 Jan, 10 Feb, 17 Feb, 2 Mar, 9 Mar, 16 Mar, 30 Mar, 6 Apr, 13 Apr, 20 Apr, 11 May, 18 May, 25 May, 1 Jun, 8 Jun, 15 Jun, 22 Jun, 29 Jun, 13 Jul, 20 Jul, 3 Aug, 31 Aug, 7 Sep, 14 Sep, 21 Sep, 28 Sep, 5 Oct, 12 Oct, 19 Oct, 26 Oct, 2 Nov, 9 Nov, 20 Dec, 28 Dec

Alentejo & Algarve self guided walking holiday, Portugal

From €567
8 days ex flights
Independent coastal walking holidays in the Alentejo Coast

Portugal walking tour

From €1029 to €2229
8 days ex flights
Self guided walking tour in Portuguese Schist Villages

Walk Názaré to Fátima, Portugal

From €649 to €849
6 days ex flights
Walk the famed Nazaré Way
Tailor made

Walking holiday in Madeira

From £1449 to £1749
8 days inc UK flights
Walk through the wild and varied scenery of Madeira
Small group2024: 6 Jan, 3 Feb, 10 Feb, 24 Feb, 2 Mar, 9 Mar, 16 Mar, 30 Mar, 13 Apr, 4 May, 11 May, 18 May, 1 Jun, 15 Jun, 6 Jul, 31 Aug, 14 Sep, 21 Sep, 5 Oct, 12 Oct, 19 Oct, 2 Nov, 16 Nov

Madeira hiking holiday, self guided

From €890 to €1290
8 days ex flights
Explore Western Madeira's paradise for hiking enthusiasts

Azores walking holiday, Portugal

From £2779 to £3149
8 days inc UK flights
Walk to Cete Cidades and the Fire Lakes
Small group2024: 11 May, 1 Jun, 15 Jun, 20 Jul, 10 Aug, 7 Sep, 2025: 10 May, 31 May, 14 Jun, 5 Jul, 19 Jul, 9 Aug, 6 Sep

Coastal walking holiday in Portugal

From £1949 to £2699
8 days inc UK flights
The very best walks from the 125km selection of coastal trails
Small group2024: 9 Mar, 6 Apr, 20 Apr, 11 May, 15 Jun, 14 Sep, 12 Oct, 2 Nov, 2025: 8 Mar, 5 Apr, 19 Apr, 10 May, 14 Jun, 13 Sep, 27 Sep, 11 Oct, 1 Nov

More about our walking holidays in Portugal

Self guided or small group?

For Madeira and the Azores, you’ll definitely benefit from joining a small group walking tour, as these islands have some quite challenging terrain. A local guide will ensure you enjoy the views while someone else handles the directions. Plus, you’ll get to know a great band of like-minded walkers as you go along. In mainland Portugal however, there are many superb walking routes that are well-marked, so you can confidently head out on your own. These trips are ideal for those who like to take things at their own pace, adding a rest day or an extra challenge whenever they fancy it.

Alentejo walking holidays in Portugal

If it’s solitude you seek, you’ll find it in Portugal’s agricultural heartland. Bordering the much better-known Algarve region, and sometimes combined with it, in Alentejo you can very quickly find complete peace and quiet on the trail. The pastoral landscapes are magnificent, fragrant pine groves give way to coastline made up of beaches, sea stacks and picturesque fishing villages, and plains studded with cork oaks, grapevines, olive trees and eucalyptus, all framed against brilliant blue skies. Alentejo walking holidays are usually tailor made, self guided trips, and often follow parts of the Rota Vicentina like the Fishermen’s Trail.

Azores walking holidays in Portugal

Revered as one of the world’s top places for whale watching, the Atlantic archipelago of the Azores has a growing reputation for walking holidays. Best explored on a small group trip, the main islands of Pico, Faial, São Jorge and São Miguel offer routes between UNESCO-protected vineyards, tea plantations, blackened lava fields and dramatic coast where you could see whales breaching the waves. While walking poles are recommended, daily routes are fairly short, leaving plenty of time for boat tours, wine tasting or taking a shower beneath a waterfall. Come in spring for your best chance of seeing blue whales.

Madeira walking holidays in Portugal

Walking holidays are unquestionably the best way to explore this volcanic Portuguese island and the man-made levadas that carry water (and walkers) through mountainous peaks and laurel forest. Typical Madeira walking holidays are week-long small group trips led by expert local guides, and you’ll cover much of the island during that time. Certainly, you will be able to tackle highlights including the São Lourenco Peninsula, the Caldeirão Verde waterfall, and perhaps even the summit of Pico Ruivo, Madeira’s highest mountain. The terrain is challenging much of the time; some hill-walking practise before departure will not be a wasted effort.

The Portugal Way walking holidays in Portugal

A classic Camino de Santiago, the Portugal Way has evolved over the centuries so that there are actually two possible routes. The original route takes you inland from Lisbon to Santiago de Compostela, 616km north, through magnificent Portuguese and Spanish pastoral landscapes. But you can also veer off at Porto, onto a route that follows the Atlantic and Galician coastline before the two routes rejoin over the Spanish border in Redondela. With Portugal Way walking holidays you can take your pick of scenery, and either hearty rural fare or fresh seafood for dinner every evening.
Travel Team
If you'd like to chat about Portugal walking or need help finding a holiday to suit you we're very happy to help.
[Self guided or small group?: Guillaume Baviere] [Alentejo: Justraveling.com] [Azores: Guillaume Baviere] [Madeira: Colin Gregory] [The Portugal Way: Fresco Tours]
Photo credits: [Page banner: aldorado10] [Cycling holidays : Marien van Os] [Walking holidays: VinceTraveller] [Family holidays: Ollie Harding] [Flight free holidays : Ricardo Resende] [Types of holidays : Web Summit] [Where to go in Portugal : Mario Cruz]