Island hopping in the Azores

With nine islands spread across 650km of wild, whale-friendly Atlantic Ocean, island hopping holidays in the Azores are the only way to get a full understanding of this archipelago. Each hop reveals unique volcanic origin stories and tiny towns and industries, from tea plantations to whale watching, that have developed because of the fertile lands and ocean.

“All the islands are different,” says Vicky Leach, who manages the walking and trekking holidays at our partner Explore. “Some of the craters are symmetrical and quite perfect, while others are falling away so you can still see a bit of the volcano. You’ve also got the greenery and the flora – there’s so much variety on the islands because of where they’re located and the weather conditions, and the lack of big cities and industry. You get a real mixture; you’re not just exploring tracks with nothing to see.”

There’s one key to unlocking the best insights: local guides. “Our tour leader, Tanya, was born on the Azores. It’s much, much more interesting walking with her,” says Vicky. “If you’re with a local guide then they can point things out and explain why the landscape looks how it does. They’re really good at the flora in the Azores because it’s so unique.”

Leaving the navigation of ferry and plane schedules to the experts simply makes sense. Your tour guide will know from plenty of past experience whether a flight might be delayed because of the weather forecast or what time to leave for the once-daily ferry.

Best for: a full overview of the Azores

This route is mapped out in our most popular island hopping holiday in the Azores. Take two weeks to enjoy this itinerary without rushing. It starts on the biggest island, São Miguel, before moving on to focus on lesser-visited islands like Flores and São Jorge.

“I really like São Miguel because it’s the most diverse of the islands,” says Vicky. “It’s got massive volcanic landscapes that you can walk around, with craters and lakes and waterfalls. It’s more immersive than the other islands.”

“The São Miguel crater walk at Furnas is also fab,” she adds. “It’s a famous one – the pictures are used everywhere because it has really amazing colours, and you get views all across the island as you walk down past the water into the crater at the bottom.”

After three days of exploring, take an 80-minute direct propellor plane flight to Flores – way over in the western island group of the Azores. Many of the visitors here are hikers and canyoning connoisseurs out to explore boulder-strewn forests and waterfalls. The island is known for its abundant flowers – hence the name. While on Flores, you might get the chance to take a boat over to neighbouring Corvo, the smallest and most northerly island in the Azores.

Terceira – a one-hour flight away (sometimes via Horta on Faial) – is popular with cyclists and hikers. Coastal paths and quiet roads lead between harbour towns, volcanic rock pools, hilltop viewpoints and green patchwork fields. “The volcanoes are extinct so it’s quite fertile,” says Vicky. “They make the most out of the land.”

São Jorge is a long, lanky island created from an old volcano chain. You’ll get there by a 6.5-hour ferry ride or 30-minute flight from Terceira. This strange, inhospitable landscape is home to tiny seaside towns and rural hamlets tucked between a craggy coastline, and the ridges and gorges of volcanic calderas and lakes like the Caldeira de Cima.

Faial, just a two-hour ferry journey from São Jorge, is a livelier finale. This central island was at the centre of the local whaling industry in the 19th and 20th centuries; these days, you’ll see more yachts than blubber-laden tall ships. Faial is easy to travel around, so tours will use public buses or a minibus to explore the caldera walks, whaling museum and grey-gold beaches. Travel in midsummer (late July-early August) to catch the bright blue hydrangeas blooming all over the island.

Best for: less-explored islands and flight free island hopping

This island hopping route in the Azores is unusual because it misses out São Miguel entirely. Instead, it takes advantage of the international airport on Faial, using it as a launch pad to focus in on the “Triangle Group” of Faial, São Jorge and Pico. These islands form a close triangle – hence the name – so you can easily travel by ferry between islands. This circuit is particularly popular with hikers, who appreciate the wild landscapes and peaceful trails.

Start off on Faial. Here, you can climb up the volcanic caldera that overlooks neighbouring Pico and scale the bleak octagonal lighthouse at Ponta dos Capelinhos to admire the fresh (geologically speaking, anyway) lavascapes from the 1957 volcanic eruption.

The even wilder landscapes of São Jorge are a two-hour ferry ride away via Pico. You’ll soon see why canyoners head here to rappel down waterfalls and splash through rocky rivers. Or you can get back out on the Atlantic Ocean, watching out for dolphins on their level by sea kayak. São Miguel might have the only commercial tea factory in Europe, but São Jorge lays down its own ace – Europe’s only commercial coffee plantation at Faja de Vimes.

After about three days of exploring São Jorge, you’ll take the ferry to Pico; it’s about 80 minutes away. Relax with vineyard and wine tasting tours at Criação Velha, a region UNESCO awarded with World Heritage Site status. Climb cloud-wreathed Mount Pico, tour the ancient volcanic caves, or head out onto the ocean on a whale watching tour.

You’ll take the 30-minute ferry journey back to Faial in time for your flight home. Thanks to the island views and chance of spying whales, you won’t want to prise yourself from the deck.