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
Walking holiday in Madeira
From
£1549 to £2449
8 days
inc UK flights
Walk through the wild and varied scenery of Madeira
Small group2024: 21 Sep, 5 Oct, 2 Nov, 2025: 4 Jan, 1 Feb, 8 Feb, 22 Feb, 1 Mar, 8 Mar, 15 Mar, 29 Mar, 5 Apr, 12 Apr, 10 May, 17 May, 7 Jun, 14 Jun, 5 Jul, 30 Aug, 13 Sep, 20 Sep, 27 Sep, 4 Oct, 18 Oct, 1 Nov, 15 Nov, 27 Dec
Coastal walking holiday in Portugal
From
£2199 to £2349
8 days
inc UK flights
The very best walks from the 125km selection of coastal trails
Small group2024: 28 Sep, 12 Oct, 2 Nov
Portuguese Coastal Way walking holiday
From
€895 to €1050
8 days
ex flights
The scenic alternative to the classic Portuguese Way
Tailor made
Walking and wine tour of Portugal
From
£2999 to £3149
8 days
inc UK flights
Walking and wine tours through the very best of Portugal
Small group2024: 22 Sep, 29 Sep, 13 Oct
Small group2024: 21 Sep, 19 Oct, 26 Oct, 2 Nov, 9 Nov, 20 Dec, 2025: 18 Jan, 25 Jan, 15 Feb, 22 Feb, 1 Mar, 8 Mar, 15 Mar, 22 Mar, 29 Mar, 5 Apr, 12 Apr, 19 Apr, 10 May, 17 May, 24 May, 31 May, 7 Jun, 14 Jun, 21 Jun, 28 Jun, 5 Jul, 12 Jul, 19 Jul, 2 Aug, 30 Aug, 6 Sep, 13 Sep, 20 Sep, 27 Sep, 4 Oct, 11 Oct, 18 Oct, 25 Oct, 1 Nov, 8 Nov, 29 Nov, 20 Dec, 27 Dec
Alentejo & Algarve self guided walking holiday, Portugal
From
€567
8 days
ex flights
Independent coastal walking holidays in the Alentejo Coast
Tailor made
Island hopping in the Azores, small group
From
£2315 to £2799
14 days
ex flights
An easy walking holiday on the Azores
Small group2024: 22 Sep, 10 Oct, 2025: 12 Apr, 3 May, 17 May, 31 May, 5 Jul, 19 Jul, 2 Aug, 16 Aug, 6 Sep, 18 Oct
Rota Vicentina walking holiday in Portugal
From
€690 to €1490
8 days
ex flights
Self guided walking tour in Rota Vicentina
Tailor made
Hiking holiday in the Azores with thermal hotsprings
From
€900 to €1170
7 days
ex flights
Hike your way through the Green Island and relax in nature
Tailor made
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.
Contact Us
Call us for a chat about our holidays. We are happy to discuss your holiday and help in any way we can. No bots, queues or awful hold music.
01273 823 700
Call us until 6pm
Calling from outside the UK
[Self guided or small group?: Guillaume Baviere]
[Alentejo: Justraveling.com]
[Azores: Guillaume Baviere]
[Madeira: Colin Gregory]
[The Portugal Way: Fresco Tours]
