Island Hopping in the Western Azores

Your Sailing Area

Terceira to Faial, The Azores 

The voyage begins in the archipelago of the Azores, from the port of Praia da Vitória on Terceira island, where there is time to settle aboard Cherokee before sailing the first leg to Graciosa.

This first leg is a passage of around 50 nautical miles. Graciosa is one of the smallest and least visited islands in the Azores, with a harbour that reflects a slower rhythm of life. An additional day here allows time to descend into the island’s Caldeira, an ancient volcanic crater with warm geothermal vents still active below the surface. After a walk and a picnic overlooking the ocean, there is the option to unwind in a local thermal pool or take a quiet swim from the shore.

From Graciosa, the route continues west on an overnight passage of approximately 160 nautical miles to Flores. This is one of the most remote islands in the archipelago, positioned on the very edge of the North Atlantic. The passage will follow a simple watch system, with guests free to join in or rest as they prefer. Dolphins are frequently encountered in this part of the ocean, and the night sky far from land is exceptionally clear. In summer, conditions are often shaped by the stable Azores High, which provides calm, steady sailing. The harbour on Flores has been storm-damaged, so anchoring may be necessary depending on the weather and swell.

If conditions allow for onshore exploration, there will be time to walk inland to the waterfalls and steep, forested valleys that characterise Poço Ribeira do Ferreiro. This is a wild and diverse landscape shaped by high rainfall and volcanic uplift.

The next leg continues east to São Jorge, another overnight passage of around 145 nautical miles. São Jorge is long and narrow, with high ridges running along its spine and small settlements along the narrow coastal plains. A full day ashore provides the opportunity to walk part of the island’s coastal trail, swim in a natural rock pool formed by basalt columns, and visit Café Nunes, which serves beans grown at Europe’s only coffee plantation. In the evenings, Cory’s Shearwaters return to nest, filling the harbour of Velas with their distinctive calls.

The final sail leads to Horta on Faial, a harbour long associated with Atlantic crossings. Breakwaters here are covered in painted plaques left by visiting crews, and the Peter Café Sport is a longstanding meeting point for sailors from around the world. The voyage ends here with a shared dinner ashore.

As with all sailing in the Azores, wind and weather will shape the route. The skipper will adjust timings and anchorages as needed to ensure safe and comfortable sailing.

Please note that the above schedule is subject to weather, wind, and tide. 

Things to note

Sailing vs Shore time

Night-watches

Travel insurance notes

As this is an active adventure holiday, we advise that everyone has the appropriate personal accident travel insurance whilst onboard in addition to standard travel insurance which would cover you in the time between making your booking and departing for your adventure. These policies can sometimes be combined so please check with your travel insurance provider.

Please read more information on our Insurance guidelines page.

This voyage will be more than 12 miles offshore.