Azores Santa Maria & São Miguel

This is a moderate programme: six walks ranging from 6.8 to 13.2 km, around 67 km in total, with some sustained climbs and descents on volcanic terrain. If you hike regularly at home and are comfortable with steep ground for an hour or two at a time, you will be fine. No technical skill or scrambling is involved — but nothing on these islands is flat, and some sections cross loose, slippery stone, so walking poles are well worth packing.

A direct flight of around twenty minutes links Ponta Delgada on São Miguel with Vila do Porto on Santa Maria, and it is included in the price. You fly out on day 3, spend three nights on Santa Maria, and fly back on day 6. Both flights leave in the late afternoon, once the day's walk is finished, so no walking day is lost to travelling. We book them and coordinate everything with your hotels.

Because these two are the least alike in the whole archipelago, and seeing them back to back is the point of the trip. São Miguel is the big, green, volcanic one — calderas, fumaroles, laurel forest and mist. Santa Maria is the oldest island geologically, the furthest south, and by some way the driest and sunniest, with red clay badlands and pale sand beaches that exist nowhere else in the Azores. Twenty minutes in the air takes you from one to the other.

No, and that is one of the main reasons people book this rather than arranging it themselves. Four of the six walks are linear, starting and finishing in different villages, and on Santa Maria public transport barely exists. Every transfer to and from each trailhead is included on both islands, along with your airport transfers on arrival and departure days. Some are substantial: the drive up to the Sete Cidades caldera on day 2 takes the better part of an hour.

Seven nights in two hotels, one on each island, on a bed and breakfast basis: four nights in Ponta Delgada and three in Vila do Porto. Because you stay in the same hotel on each island, you unpack twice in the whole week rather than every night. The standard option uses the Hotel Canadiano in Ponta Delgada and the Hotel Colombo in Vila do Porto; the upgrade option uses the Hotel São Miguel Park and the Charming Blue. The itinerary, the walks and the transfers are identical either way — only the hotel category changes.

Mild and changeable. The Atlantic keeps temperatures moderate all year — rarely above 26°C in summer or below 14°C in winter — but the weather moves fast and rain is possible in any month. May to September gives the longest days and the most settled conditions, and in June and July the hydrangeas lining the lanes are in full bloom. Spring is green and quiet; autumn and winter are perfectly walkable and far less busy, with more cloud on the high ground. Santa Maria is noticeably drier and sunnier than São Miguel year-round, so the two halves of the week often feel like different climates. Bring a proper waterproof whatever the season — it matters more here than sun cream. Whales and dolphins are most often seen between April and October, if you want to add a boat trip to a free afternoon.

Yes. There are no groups and no fixed departure dates, so you choose your own start date and set your own pace. We publish a specific solo traveller rate covering single occupancy in both hotels, and our team is reachable throughout the week if anything needs changing.

Every route follows the Azores' waymarked trail network, and you also get our own app with offline GPS navigation, the GPX tracks for all six walks and a written description of each stage — all of it downloadable before you set off, so it works without mobile signal. On your arrival day we can run through the whole week with you on a video call, and we stay reachable throughout in case anything needs rerouting.

On this trip your suitcase stays with you: you sleep in the same hotel on each island, so it simply stays in the room and you walk with a daypack carrying water, food, sun protection and a waterproof. The only time it moves is on the inter-island flight, when it travels with you. As that is a domestic hop, baggage limits are tighter than on international flights, so a single case is the sensible approach — we send you the exact conditions when your booking is confirmed.