Overview
An 11 day, self-guided walking holiday on three of the islands of this otherworldly archipelago: São Jorge, Faial and Pico island. The wild volcanic land and seascapes of these Portuguese islands are a magnet for magic, with trails to volcanic craters, along ancient coastal paths and secret waterfalls. Island-hopping between these three islands, they all offer something special: on Pico you walk in the shadow of the highest mountain in Portugal (2,351m); on São Jorge the volcanic plains or fajãs make for wild walking and, on Faial, walk alongside the crater in the heart of the island, formed by the most recently active volcano of the Azores, Capelinhos.
- Pico Island
- São Jorge Island
- Faial Island
- Mount Pico, the highest mountain and volcano in Portugal
- Faial’s Caldeira crater
Itinerary
Day 1: Arrival in Pico Island
You are met and transferred from Pico Airport to the first accommodation. Depending on your arrival time, we recommend exploring Lajes do Pico or relaxing by the pool.
- Accommodation: Pico Terramar & Spa or similar on Pico Island
Day 2: Pico Island: Vineyards trail | 6.5km
Our driver transfers you to the Vineyards trail, where you walk along the eastern coast of the island on a trail that takes you through UNESCO World Heritage vineyards. This route ends in Madalena Harbour. You are transferred back to your hotel.
- Walking for the day: 2.5, 6.5km ↑0m ↓100m
- Accommodation: Pico Terramar & Spa or similar on Pico Island
Day 3: Pico Island: Lagoa do Capitão | 9.1km
Walk the trail from Lagoa do Capitão (Captain’s Lagoon) down to São Roque. Captain’s Lagoon offers one of the best views of Mount Pico, and it’s also a great birding spot. Follow a dirt track through a forest, a demanding descent for those after a challenge. You are met by the driver at the end of the walk, who takes you back to the hotel.
- Walking for the day: 3h, 9.1km ↑100m ↓770m
- Accommodation: Pico Terramar & Spa or similar on Pico Island
Day 4: Pico Island: Caminho dos Burros | 9km
Our driver collects you and heads towards the central plateau of the island. The route follows the Caminho das Lagoas (Path of the Lagoons) to the northern coast, with views of Mount Pico behind you and São Jorge Island in front. This walk follows on a forest trail as far as Baía das Canas (Bay of Canes) which is perfect for a swim, before being met and transferred back to the hotel.
- Walking for the day: 4h, 9km, ↑100m ↓800m
- Accommodation: Pico Terramar & Spa or similar on Pico Island
Day 5: São Jorge Island
In the morning, you are transferred to the harbour for the 1h 40mins ferry crossing to São Jorge Island. Once you arrive, you’re met at the port and transferred to the accommodation, where you have time to relax by the hotel pool.
- Accommodation: Hotel São Jorge Garden or similar on São Jorge Island
Day 6: São Jorge Island: Pico da Esperança to the coast | 17km
Our driver transfers you to Pico da Esperança, the island’s highest point (1,053m). Today’s walk is not short on panoramic views of the four surrounding islands: Pico and Faial in the south and Graciosa and Terceira in the north. The route ends in Fajã do Ouvidor lava fields, where we recommend a visit to the natural blue volcanic pools on the coast. To avoid the last demanding descent, you are met in the previous village to be transferred back to the hotel.
- Walking for the day: approx. 5h, 17km ↑300m ↓1,000m
- Accommodation: Hotel São Jorge Garden or similar on São Jorge Island
Day 7: São Jorge Island: the northern coast | 9.5km
To start today’s coastal walk, we collect and drop you off at Serra do Topo. Follow a trail that’s dotted with Azorean heather and juniper, before descending towards Fajãs de Caldeira do Santo Cristo, a nature reserve on the coast. Being the only fajã (or lava plain) connecting to the sea on the island, it is renowned for shellfish, making it the perfect spot for lunch. Continue on to Fajã dos Cubres, which has some stunning crystal clear lagoons and surrounding green cliffs. On the descent, we suggest a visit to a refreshing waterfall with a view.
- Walking for the day: approx. 3h, 9.5km ↑50m ↓650m
- Accommodation: Hotel São Jorge Garden or similar on São Jorge Island
Day 8: Faial Island
In the morning we take you to the harbour for the 2h 30 mins ferry crossing to Faial Island. Once you arrive, you’re met at the port and transferred to the accommodation. Relax on the beach or by the marina with plenty of restaurants for dinner.
- Accommodation:Refugio dos Capelinhos or similar on Faial Island
Day 9: Faial Island: Capelinhos Volcano – Caldeira | 20.3km
Head to the south coast for a short walk to the Capelinhos, the site of a volcanic sea eruption in 1957, which lasted for 13 months. Take a short walk to the Capelinhos Lighthouse and take in the volcanic landscapes. The journey continues along forest roads until you arrive at Cabeço do Fogo viewpoint. Heading to Caldeira, the centre of the island, there are spectacular views over the north and west coast. The trail ends at Ermida de São João just above the caldeira, where you cross the tunnel with a view over the interior of the crater, before you are transferred back to the hotel in the afternoon.
- Walking for the day: 8h, 20.3km ↑654m ↓1490m
- Accommodation: The Plantation Faial or similar on Faial Island
Day 10: Faial Island: Caldeira – Ribeirinha | 17.5km
After a short transfer, arrive at Caldeira do Cabeço Gordo, which is 2km wide and 400m deep. It’s the highest point on Faial Island and provides clear views of Graciosa, São Jorge and Pico Island. The route takes you along the edge of the crater and then downhill along a red dirt track through forest. At the end of the trail transferred back to the hotel in the afternoon.
- Walking for the day: 6h, 17.5km ↑m ↓m
- Accommodation: Internacional Azores Boutique or similar on Faial Island
Day 11: Faial Island and departure
The tour comes to an end after breakfast.
What to expect
Accommodation
Accommodation on this tour includes a mix of mostly small, locally-owned hotels, B&Bs and traditional guesthouses. They have been carefully selected based on a variety of criteria including their location, warm hospitality, fine local food or commitment to natural adventures. All rooms have en-suite or private bathrooms.
Click to view default hotels
- Pico Terramar & Spa (Pico Island)
- Hotel São Jorge Garden (São Jorge Island)
- Refugio dos Capelinhos (Faial Island)
- The Plantation Faial (Faial Island)
- Internacional Azores Boutique (Faial Island)















Hotels are subject to availability. In the event of a particular hotel being fully booked for your chosen dates, we will replace it with a hotel of equal value and quality level. We will provide exact accommodation details to you upon booking confirmation.
Meals
Breakfast is included every day. When no restaurant location is available on route, lunches and snacks should either be bought from local shops, or packed lunch can be pre-ordered from your hotel the night before.
Difficulty and terrain
This walk is graded easy to moderate and includes daily walks of between 10-18km following footpaths, tracks and coastal paths. This tour is suitable for people that are in good physical condition. Although the daily distances are not that far, you should be aware that there are some elevation gains on all walks (read more about difficulty grades). The walks mostly take place on coastal or inland footpaths and, at times, rocky tracks. Some of them are marked. However, please be aware that the trails are often poorly maintained and, after rain can be slippery. It is, therefore, a good idea to bring hiking boots with good grips. You can always call our 24/7 local assistance phone number anytime if you need assistance. More detailed info on route navigation will be included in your holiday information pack.
When to go
This trip is available during the whole year.
The flexibility of self-guided holidays means that there are no fixed dates, and you can start your trip on any date during the season. In terms of the weather, it is typical that the warmest months are July, August, September and October, with average daily temperatures of 22C – 24C during the daytime.
For more information on the area, refer to our blog, Best time to go to Portugal.
Getting there
Click to view travel options
Our recommended airport for this tour is Pico Airport (PIX). Complimentary private transfers from/to Pico Airport are included in your package.
Inclusions
Included
- 10 nights accommodation with breakfast included.
- Luggage transfers between hotels
- Transfers according to the programme, including boat fares
- Detailed digital holiday information pack including GPS-checked and regularly updated route descriptions, road notes and maps. Please note that the info pack is emailed to you prior to departure, and no printed documents are mailed or provided on-site.
- 24/7 phone assistance by our local office/representative
Excluded
- Airfare and transfers not explicitly listed as included in the programme
- Lunches, dinners, drinks and snacks
- Travel insurance (required – get a quote online)
- Personal expenses
- Local tourist taxes and entry fees (payable on-site)
- Any items not explicitly listed as included
- eSIM data for international travel (get an eSIM)
Options, extras and supplements
- If you’re travelling in a group, a supplement applies to group members who would like to have a room of their own
- We regret that this tour is not open to solo travellers.
- Extra nights along the trail are bookable upon request












































