Portugal : The Azores

Island Hopping in the Azores

Trip code: W14EC 4.5 (2 reviews)

Self-guided walking

14 nights,

Level: 2

22.0Kg CO2e

Navigation App


  • Island hop across Sao Miguel, Sao Jorge, Pico, Faial & Santa Maria
  • Walk around the crater rim of legendary Sete Cidade on Sao Miguel
  • Discover stunning coastal cliffs on the island of Sao Jorge
  • Explore lava fields and vineyards on Pico with stunning panoramic views from Pico Alto
  • Embrace mother nature as you visit Capelinhos on the island of Faial, location of the last volcanic eruption in the Azores.
  • An authentic and untouched island, Santa Maria is known as the sunny isle due to its drier climate.


  • 14 nights accommodation
  • All breakfasts and 8 evening meals
  • Headwater navigation app
  • Luggage transfers between hotels
  • Internal flights and ferries


It is hard to believe that the Azores are part of Europe. Born from the immensity of the Atlantic Ocean, this lush green archipelago of volcanic islands is a far cry from continental Portugal. The nine Islands of the Azores are Europe's western most point located in the middle of the Atlantic Ocean. The Azores have long been known as one of the most scenically varied areas to explore, each of the nine islands has its own characteristics, from steep craters to abundant wildlife and sites of historical interest. The islands of the Azores are a paradise for walkers and nature lovers with their blue lakes bordered by flowers, dazzling views of the sea from high in the hills and lush green landscapes of ancient volcanic craters.

This 14-night island hopping holiday features the best of the Eastern and Central Islands of the Azores including Sao Miguel, Sao Jorge, Pico, Faial & Santa Maria.

Sao Miguel is famous for its beautiful landscapes and exceptional volcanic lakes. The largest of the Azorean islands it is known as Ilhe Verde - Green Island. A stunning coastline of small bays with black sand and precipitous sea cliffs interspersed with small harbours add further interest. The island features three major calderas (volcanic craters) now with lakes sparkling at the bottom. Sete Citdades even has a village at the bottom of the crater and two lakes one blue and one contrasting green.

Sao Jorge has the most-jagged coastline of the Azores Islands, with coastal cliffs surrounded at sea level by Fajas. These small flat pieces of land are formed by lava flows and are distinctive features of the Azores. Discover spectacular waterfalls, lush ravines and the chance to explore the interesting fishing village of Velas.

Pico is the most volcanic of the Azores Islands, renowned for its almost perfectly coned mountain of Pico Alto standing at 2352m, making it the highest peak in all of Portugal. Enjoy stunning walks through interesting fauna and picturesque villages. The local approach to wine production and vineyard culture has been preserved through the years, making for remarkable scenery of unique vineyards and dark grey basalt.

Faial is known as the Blue Island for the abundance of blue hydrangeas seen all over the island and due to its deep relationship with the sea, with its harbour proving important for many adventurous transatlantic sailors. Famous for its stewed octopus in wine amongst the Azoreans - you should most certainly try some! Faial island offers a contrasting picture of rich and diverse flora and a dry lunar landscape. The walking here takes you to volcanic crater rims with breath-taking views and the opportunity to explore the lighthouse and museum which shows the history of volcanic eruptions.

Santa Maria is the oldest of the Azores Islands and being the most eastern and southern island, its climate is also much drier. Due to its drier climate, Santa Maria offers unique characteristics including fascinating rock formations and stunning fauna (it is a geologists and botanist's paradise). It also features what is considered by many to be the best beach in the Azores, Praia Formosa.


Walks are along dirt tracks (both broad and narrow) and minor roads with tarmac or gravel. Footpaths are marked reasonably well.




Day 1: Arrive in Sao Miguel

Arrive at your hotel in Sao Miguel.

You stay at Selected hotels.

hotel details

Your Hotels, The Azores

On this trip we use a selection of hotels on each of the islands. We use a variety of mostly 3-star hotels and guest houses throughout with en suite facilities. They may be located either in the towns themselves or in the surrounding countryside.

All prices are based on 2 persons sharing, so if there is an odd number of people travelling in your party or you are travelling alone, there will be a compulsory supplement for a single room for the tour duration.

Day 2: Furnas to Lagoa das Furnas (13km/8.1mi)

Take the bus (payable locally) to Furnas and walk to the Lagoa das Furnas. The walk starts and finishes in the attractive village of Furnas, with an optional extra walk round the village at the end. Confirmation of the volcanic origins of São Miguel is nowhere more evident than here. The picturesque Parque Terra Nostra is in the village centre, together with thermal baths.


Day 3: Sete Cidades (15km/9.3mi)

Take the bus (payable locally) to Sete Cidades, set within the volcanic crater containing Lagoa Azul and Lagoa Verde, a must on any visit to Sao Miguel. One route takes you up to the crater rim on the west side of the lakes, finally descending to the small village of Joao Bom.


Day 4: Praia to Lagoa do Fogo (14km/8.7mi)

Take the bus (payable locally) to Praia. This walk takes you from almost sea level, steeply uphill across meadows, through dense woodland, alongside a levada (water channel), and finally over heather covered mountainside to arrive at the remote shore of Lagoa do Fogo, the highest lake of Sao Miguel.


Day 5: Sao Jorge

Explore historic Ponta Delgada before departing Sao Miguel and flying to Sao Jorge, one of the greenest of the islands.

Day 6: Serra do Topo to Faja dos Cubres (9km/5.6mi)

A real ‘must do’ walk with great variety from misty hills, lush ravines and waterfalls to high cliffs and an insight to life on the Fajas. Plenty of places to linger by the sea for a picnic so be generous with your time in arranging return transport.


Day 7: Parque Sete Fontes to Ponta de Rosais (11km/6.8mi)

An easy walk, through meadowlands to the lighthouse at the far end of São Jorge, the views from the cliffs are spectacular. Sit here for a picnic and feel the real remoteness of these islands, with possible sightings of dolphins and whales.


Day 8: Pico (11km/6.8mi)

Take the ferry over to Pico and, time-permitting, enjoy an easy walk down the lower slopes of Mount Pico with interesting lava tunnels at the start and superb views over to Faial. Or you can opt for a more adventurous walk to the top of Mount Pico (2351m) guide compulsory, best arranged in advance.


Day 9: Lagao do Capitao to Sao Roque (9km/5.6mi)

Take a half day whale watching (optional extra) or take the following walk. This is a stunning walk but with mostly descents down to sea level. The first section is very easy amongst wild scenery contrasting with the second half which is mainly down through interesting vegetation and forest leading to the picturesque village of Sao Roque. This could be a superb full day walk using your extra time to explore Sao Roque, visiting its Whaling Museum and maybe having a swim in the sea.


Day 10: Horta to Rocha da Faja (6km/3.7mi)

Transfer to the port of Madalana for the ferry across to Horta on Faial, check in to your hotel and take one of our walks to Rocha da Faja. This short walk is ideal as an introduction to the Fajas of the Azores.


Day 11: Caldera to Parque Florestal do Capelo (13km/8.1mi)

In good weather this is the highlight of walking on Faial. Walk around the rim of a volcano (dormant), the Caldeira crater, it is breathtaking along with views over Faial and to the ocean and islands in the distance.


Day 12: Capelo to Capelinhos (7km/4.3mi)

This walk is superb with stunning views and an opportunity to explore two crater rims, ending at the Museum in Capelinhos showing the history of the Capelinhos eruption, which only happened just over 60 years ago. Then take an afternoon or evening flight to Santa Maria.


Day 13: Vila to Praia (7km/4.3mi)

Today is an exhilarating walk, first along the cliffs then the sea edge for the last section of the walk. It is a dream for amateur geologists and botanists with the fascinating rock formations and the profusion of plants, beautiful flowers and butterflies.


Day 14: Pico Alto to Anjos (11km/6.8mi)

Your final walk goes along the western end of the north coast and goes through lovely woodland and past the Desert, almost 8 sq km of red clay caused by pyroclastic activity. You can visit viewpoints and a picturesque isolated bay, go through fields, round a headland and along cliff tops, finally emerging into the pretty little town of Anjos where there is an imposing statue of Columbus who returned here, having discovered the New World.


Day 15: Depart Santa Maria

Extending your holiday

If you'd like to extend your trip with extra hotel nights we recommend: Hotel Lisboa Plaza, Lisbon.

hotel details


Hotel Lisboa Plaza, Lisbon


Cash machine

Owned by the same family since 1953, the 4 star Hotel Lisboa Plaza is an imaginatively designed hotel, just off the famous Avenida da Liberdade. All rooms have en-suite marble floored bathrooms, air conditioning, satellite television, direct dial telephones, hairdryers and mini-bar. The public rooms are elegantly furnished and there is a pleasant bar and dining room.



These tour only prices are based on two people sharing. Single supplement from $819.

These flight inclusive prices are based on two people sharing. Single supplement from $819.


Call now to speak to our specialist team at 0044 1606 720199 or email us at sales@headwater.com for enquiries or to book your trip.


Holiday was fantastic. Lost more time transferring than I had realised. Though this is the first time I have done this type of holiday. Have only done inn to inn before. Overall the islands were amazing, the people friendly and helpful and would love to go back .

Lesley Garner, 11 Sep 2023


This was a fabulous holiday to a beautiful destination, generally a high standard of accommodation and efficient travel arrangements given number of flights/transfers/ferries. (As per more detailed feedback provided ) - One or two tweaks would reduce some of the airport waiting time. Great variety of walks, and of course freedom to choose to follow plan or not. Would be good to suggest walks directly from accommodation/town locations - as part of joining Information. local tourist offices can do this but then you have the extra time to find out/plan etc when only 1-3 days available per place. Will definitely plan to return to the Azores and explore some of the other islands too.

Joan Macleod, 11 Sep 2023


Self-guided walking

14 nights,

Level: 2

22.0Kg CO2e

Navigation App

14 nights from $3200


Call: +44 1606 720199