Walking in the Azores — Self-Launched Island Hopping

Fly into João Paulo II Airport (PDL) and take the local bus or a short taxi (~€8) into the centre. Check into a central guesthouse or hostel private room and spend the evening on the harbour-front promenade. Wander past the 16th-century Forte de São Brás and the Convent and Chapel of Nossa Senhora da Esperança, then eat at a tasca near the marina. Do a supermarket run for trail snacks and picnic supplies — self-catering breakfasts will save you a lot over two weeks.

🚌Local bus or taxi from PDL airport; walk everywhere in town

🛏Guesthouse/hostel private room in Ponta Delgada centre (~£45/night for a double)

• →Harbour-front promenade stroll
• →Forte de São Brás (exterior)
• →Convent and Chapel of Nossa Senhora da Esperança
• →Supermarket provisioning

Catch the early bus or a shared transfer toward Sete Cidades (buses are infrequent — check schedules the day before; a shared taxi/transfer is ~€15-20pp each way). Start at the Vista do Rei viewpoint for the classic twin-lake view of Lagoa Verde and Lagoa Azul, then walk the crater rim path down to the Várzea parking area and into the village (roughly 8-10 km, 2.5-3 hrs, easy-moderate). Return to Ponta Delgada in the afternoon. Waymarking is good but bring the Maps.me/Outdooractive GPS track.

🚌Public bus or shared transfer to Sete Cidades (~£15-20pp return)

🛏Guesthouse/hostel private room in Ponta Delgada centre

• →Vista do Rei viewpoint
• →Crater rim walk to Várzea
• →Lagoa Verde and Lagoa Azul

Take the bus or a shared transfer to Furnas via the Gorreana tea factory (the oldest tea plantation in Europe — free entry, cheap tasting). Walk the lakeside loop around Lagoa das Furnas (~4 km, 1.5 hrs) and watch cozido lunches being lifted from the volcanic fumeroles. Order your own cozido at a local restaurant (~€18-22pp, book ahead in high season), then spend the afternoon at Terra Nostra botanical gardens with its iron-rich thermal pool — bring old dark swimwear or you'll stain it orange. Return to Ponta Delgada in the evening.

🚌Public bus/shared transfer to Furnas (~£15pp return)

🛏Guesthouse/hostel private room in Ponta Delgada centre

• →Gorreana tea factory visit
• →Lagoa das Furnas lakeside walk
• →Volcanic fumeroles
• →Terra Nostra gardens and thermal pool (€10 entry)

Your free day. Options: the Serra Devassa circular walk (~5 km) around the Seven Cities massif, the more demanding Salto do Cabrito waterfall trail (~8 km) on the north coast, or a whale-and-dolphin watching boat trip from Ponta Delgada harbour (~€55pp, book through GetYourGuide or directly with a licensed operator — choose one with a 'vigia' spotter ashore and a no-sighting policy). Evening in Ponta Delgada's tascas.

🚌Local bus or shared transfer for trailheads; walk to harbour for boats

🛏Guesthouse/hostel private room in Ponta Delgada centre

• →Serra Devassa circular walk (optional)
• →Salto do Cabrito waterfall walk (optional)
• →Whale watching trip (~€55pp, optional)

Take a morning SATA/Azores Airlines flight from Ponta Delgada to São Jorge (SJZ) — roughly 40 minutes, ~€70-100pp one way if booked early (book direct on the airline site; prices rise sharply close to departure). Settle into a guesthouse in Velas and in the afternoon walk out to Miradouro do Morro das Velas, the old whale-watching tower on a volcanic crater rim (~4.5 km, 2 hrs), for views across to Pico.

🚌SATA/Azores Airlines flight PDL–SJZ (~£70-100pp)

🛏Guesthouse/guesthouse-hotel in Velas (~£45/night for a double)

• →Flight to São Jorge
• →Miradouro do Morro das Velas walk
• →Velas old town

The signature São Jorge hike. Arrange a taxi or shared transfer from Velas to the Caldeira de Cima trailhead (~€20-25pp each way, or hire a car for the day). Walk down the gorge to the coast and along the rocky shoreline to Fajã dos Cubres, with views over the Caldeira de Santo Cristo lake — roughly 10-12 km, 4 hrs, moderate with some steep, potentially slippery sections. Return by taxi from Fajã dos Cubres or pre-book a transfer. Back in Velas for dinner.

🚌Taxi/shared transfer to trailhead and back (~£40-50pp total)

🛏Guesthouse/guesthouse-hotel in Velas

• →Caldeira de Cima gorge walk
• →Coastal walk to Fajã dos Cubres
• →Caldeira de Santo Cristo lake viewpoint

Pick your own long walk: the central ridge at Pico da Esperança (~20 km, ~5 hrs, the island's high point with views to Pico, Faial, Graciosa and Terceira) or a south-coast fajã walk through the island's traditional cliff-edge farming villages (~20 km). Both need a taxi transfer or hire car to the trailhead. Note São Jorge has few marked trails — download GPX tracks in advance and carry water, food and rain gear.

🚌Hire car (~£35-45/day split) or taxi transfer to trailhead

🛏Guesthouse/guesthouse-hotel in Velas

• →Pico da Esperança ridge walk
• →South coast fajã walk
• →Fajã village visit

Take the Atlânticoline ferry from Velas to São Roque do Pico (~1 hr, ~€12-15pp one way; check the seasonal timetable at atlanticoline.pt as sailings vary by day — book online in summer). Stop in São Roque for the Captain's Lagoon pools, then work along the north coast to see the Cachorro rock formation at Bandeiras on the way to Madalena. In the afternoon visit a small family vineyard in the UNESCO Criação Velha landscape for a tour and tasting (~€15-20pp, book direct). Overnight in Madalena or São Roque.

🚌Atlânticoline ferry Velas–São Roque do Pico (~£13pp); local bus or taxi for Bandeiras/Madalena

🛏Guesthouse in Madalena/São Roque do Pico (~£45/night for a double)

• →Captain's Lagoon, São Roque
• →Cachorro rock formation, Bandeiras
• →Vineyard tour and tasting (~€18pp)

Walk the coastal UNESCO World Heritage vineyard landscape from Porto do Calhau through Candelária village to Madalena — easy going, roughly 10 km, with basalt-walled currais on one side and Faial across the channel on the other. Optional add-ons if you want to spend money: a whale-watching trip from Madalena harbour (€49-65pp depending on season, book direct with the operator) or a guided Pico volcano ascent (very strenuous, 6-7 hrs, ~€95-110pp for a small group — book a certified mountain guide in advance, never go alone).

🚌Local bus or taxi to Porto do Calhau trailhead; walk back to Madalena

🛏Guesthouse in Madalena, Pico

• →Porto do Calhau to Madalena vineyard walk
• →Candelária village
• →Whale watching from Madalena (optional)
• →Pico volcano ascent with guide (optional)

Head to the south coast and walk the Mistérios do Sul coastal trail across the Mistério de São João and Mistério da Silveira lava flows — geologically dramatic, easy-moderate, 8-12 km depending on how far you go. Pass the Ponta Rasa windmill and Silveira village, and finish at the Cheese Museum in São João, which tells the story of the island's cheese-making since 1948 and sells São João cheese and other local delicacies. Get the local bus back or pre-arrange a taxi.

🚌Local bus (~£4-6pp) or shared taxi to trailhead and back

🛏Guesthouse in Madalena, Pico

• →Mistérios do Sul coastal trail
• →Mistério de São João and Mistério da Silveira
• →Ponta Rasa windmill
• →Cheese Museum, São João (cheese tasting)

Short Atlânticoline hop from Madalena to Horta (~30-40 min, ~€10pp; book online). Drop your bags at a guesthouse near the harbour and do the circular walk out onto the Monte da Guia headland (~4.5 km, 2 hrs) — volcanic cones, a tiny chapel and Atlantic views back to Pico. Spend the evening in Horta's famous sailors' bar, Peter Café Sport, and wander the painted marina walls.

🚌Atlânticoline ferry Madalena–Horta (~£10pp)

🛏Guesthouse/guesthouse-hotel in Horta (~£45-55/night for a double)

• →Monte da Guia headland walk
• →Horta marina and Peter Café Sport

Either join a small-group island tour by minivan (~€50-65pp through GetYourGuide/local operators) or hire a car (~£35-45/day split) and drive it yourself. Walk the Caldeira crater rim for views into the forested caldera, then continue west to the Capelinhos volcano, where the 1957-58 eruption added new land to the island — the interpretation centre is worth the €10 entry. Stop at the lighthouse and the black-sand coast on the way back.

🚌Hired car split (£35-45/day) or small-group island tour (~£55pp)

🛏Guesthouse/guesthouse-hotel in Horta

• →Caldeira crater rim walk
• →Capelinhos volcano
• →Capelinhos Interpretation Centre (€10)
• →North coast viewpoints

Take the local bus or a taxi to the north-coast Praia do Norte parish and walk the cliff paths down to Fajã da Praia do Norte through laurel forest, visiting the Chapel of Nossa Senhora da Penha de França. The circuit is roughly 6-8 km with significant descent and climb; bus and taxi services here are limited, so confirm return times before you set off. Last evening in Horta — seafood dinner near the marina.

🚌Local bus or taxi to Praia do Norte (~£15-20pp return)

🛏Guesthouse/guesthouse-hotel in Horta

• →Praia do Norte fajã walk
• →Laurel forest cliff paths
• →Chapel of Nossa Senhora da Penha de França
• →Praia do Norte beach

Breakfast and a short taxi to Horta Airport (HOR) for your onward flight. Direct flights from Horta are limited — most travellers connect via Ponta Delgada, Terceira or Lisbon on SATA/Azores Airlines. If you have a late departure, the Horta museum and marina make for a relaxed final morning. Costs today cover only local transport to the airport.

🚌Taxi to Horta Airport (~£10-15)

🛏—

• →Horta museum (optional)
• →Marina walk