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Island Hopping in the Azores

0044 1606 720199

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  • Holiday code
  • Holiday type
    Self-guided walking
  • Duration
    14 nights
  • Accommodation
  • Activity level
  • Call usfor dates and prices
  • NEW FOR 2023  
  • Departures
    Selected Departures from 10 Jun '23 to 28 Oct '24
  • What your holiday price includes
  • 14 nights hotel-to-hotel accommodation
  • All breakfasts and 8 evening meals
  • Management by your local Headwater-appointed agent
  • Comprehensive route directions
  • Luggage transfers between hotels
  • Internal flights and ferries
  • Optional Upgrades
  • Suitable for
  • Solo travellers
  • Couples
  • Excellent choice for
  • Wine lovers, flora & fauna, bird spotting opportunities, swimming opportunities, coastal routes, high peaks, island exploring, lake & river routes

Portugal: The Azores

Island Hopping in the Azores

  • 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.

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.

We're here to help

If you have any questions about this holiday call our sales team on 0044 1606 720199, use our live webchat or email sales@headwater.com

Day-by-day itinerary

Walking information

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

We're here to help

If you've any questions about this holiday call our sales team on 0044 1606 720199 , or email sales@headwater.com

Day 1: Arrive in Sao Miguel

Arrive at your hotel in Sao Miguel.

Day 2: Furnas to Lagoa das Furnas 14KM/7 MI/3 HRS

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 14KM/9 MI/4 HRS

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 São 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: Povocao to Lagoa do Fogo 13 KM/8 MI/4 HRS

Take the bus (payable locally) to Povocao. 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 São Miguel.

Day 5: Nine Windows Wall 11 KM/7 MI/3 HRS

An early start if you wish to get a walk in before your flight to Sao Jorge. Take a short taxi ride (payable locally) to Nine Windows Wall where the route takes you around the east and north sides of the crater rim of the twin lakes of Sete Cidades. After only a short climb the track undulates along the ridge, affording splendid views on both sides. An option exists to extend the walk to cover the west rim as well as far as Vista do Rei, and then descend past Lagoa Verde to the village. Transfer to the airport to take an afternoon flight to Sao Jorge (50 minutes), then transfer to your hotel to relax for the evening.

Day 6: Serra do Topo to Faja dos Cubres 9 KM/6 MI/4 HRS

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 10 KM/6.5 MI/3 HRS

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: Mount Pico 11 KM/7 MI/ 3 HRS (excluding the top of Mount Pico).

Take the ferry over to Pico and 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 9 KM/6 MI/4 HRS

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 6 KM/4 MI/3 HRS

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 16 KM/10 MI/5 HRS

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 7 KM/4.5 MI/3 HRS

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 evening flight to Santa Maria.

Day 13: Vila to Praia 6 KM/4 MI/3 HRS OR 9 KM/6 MI/4 HRS

Today’s walk is the first section of the round island GR walk and can be done alone or combined with the next section. It 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. The second section, if you wish to continue today, takes you through sleepy hamlets, past a whale observation point and close to some impressive hexagonal basalt formations like those found on the Giant’s Causeway.

Day 14: Santa Maria 27 KM/17 MI/ 11 HRS

This fantastic walk could be done as one very long day's walk, but can also be tackled in sections, or a variety of combinations of sections from east to west. It starts at the beautiful Sao Laurenco Bay on the east coast and immediately climbs up a dramatic cliff, thereafter, undulating through picturesque countryside and gradually ascending into forest to the highest point of the island where you are rewarded with spectacular views all around. A delightful, easy descent through pleasant woodland brings you back to follow the path along the north coast past the island's tiny 'desert' and along stunning cliffs with spectacular views to the sea below and ahead towards the plain. The walk finishes in Anjos, where you can see the chapel where Columbus went to Mass on his return from the New World.

Stage1: 6 KM/4 MI/3 HRS

Stage 2: 8 KM/5 MI/4 HRS

Stage 3: 5 KM/3 MI/2 HRS

Stage 4: 8 KM/5 MI/4 HRS

Stages 1-4 combined: 27 KM/17 MI/ 11 HRS

Day 15: Depart Santa Maria

Where you stay

During your holiday you stay at the following hotels. If you'd like to extend your time at any of these or, if you'd like to enhance your stay with an upgraded room, just let us know at the time of booking.

To find out more call our sales team on 0044 1606 720199, use our live webchat or email sales@headwater.com

Hotels, Island Hopping

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.

Extending your stay

If you'd like to extend your trip with extra nights at the start or end, or if you'd like to arrange a stop off point en-route, then we recommend the following hotels.

Find out more on the hotel website.
Read customer reviews on Tripadvisor.

Hotel Lisboa Plaza, Lisbon

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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.


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.


Here at Headwater we thrive on feedback from our customers. It's the only way we can continue to develop, and where necessary improve, our services and ensure our holidays continue to be the best they can be. However, as this is a relatively new holiday, we don't yet have any customer reviews available.

Dates and prices

You can be confident that our pricing includes all the standard requirements of your holiday and many additional extras. Always ensure that you are comparing like for like when booking your holiday.

This 14 night self-guided walking holiday includes:

Hotel-to-hotel accommodation

All breakfasts and 8 evening meals

Management by your local Headwater-appointed agent

Comprehensive route directions provided prior to departure

Luggage transfers between hotels

Internal flights and ferries

How to book:

To book this holidays speak to our sales team on 0044 1606 720199 or click on the appropriate 'book now' or 'check availability' button below.

To book this holiday call our sales team on 0044 1606 720199 or click on the appropriate 'Book now' or 'check availability' button below.

Please call for prices

We do not currently have departure dates and prices available on-line. The season may have ended for this tour, or we are still in the process of adding these details to our website. Please contact us for further details.

Holiday details

Solo travellers
Please call for details and prices

Please contact us for child prices.

Holiday type
Self-guided walking Managed locally by Headwater appointed agent.


All breakfasts and 8 evening meals

Tailor-made travel

This holiday does not include any flights or rail.

How to book

To book this holidays speak to our sales team on 0044 1606 720199 or click on the appropriate 'book now' button above.

If you need further information before you book simply complete our Holiday Enquiry Form and a member of our sales team will get back to you.

To book this holiday call our sales team on 0044 1606 720199 or click on the appropriate 'Book now' or 'Check availability' button below.