Azores Islands

On the second day, we set course for the island of Graciosa — 44 nautical miles to a land where the wind turns the mills and history speaks at every step. This small island — just 12.5 by 8.5 kilometers — crowned by its Caldeira volcano, welcomes us with the red domes of its windmills, resembling old maritime lanterns. There were once around thirty of them; today only four remain, yet they still turn with the Atlantic winds. In the capital, Santa Cruz da Graciosa, we’ll wander through historic streets lined with elegant 17th–18th century churches, including the 16th-century Church of Santo Cristo and the Baroque Church of Guadalupe — quiet witnesses to centuries of island life.

On the third day, we set our course for São Jorge — 25 nautical miles to the welcoming town of Velas. This island is narrow like a sabre — 53 kilometers long and just 8 kilometers wide. Its highest peak, Mount Esperança, rises proudly to 1,053 meters, while the coastline is scattered with lava-formed fajãs — unique flatlands where the ocean gently embraces the land. In Velas, we’ll stroll through historic streets, sample local delicacies — including the legendary São Jorge cheese — and gather in the evening for our own pirate council under the Atlantic sky.

On the fourth day, we sail to the island of Faial. Here lies one of the most iconic harbors in the Atlantic — a true mecca for sailors setting off on ocean crossings: the legendary Horta Marina. Its walls are covered with hundreds of colorful paintings and graffiti left by yacht crews from all over the world. This tradition has existed for decades. It is believed that leaving a drawing on the harbor wall brings good luck on the next voyage. Every brushstroke tells a story — of a crew, their adventures, and their dreams. And we, too, will leave our mark there.

On the fifth day, we set our course for Pico — the true jewel of our route. A 76-nautical-mile passage awaits us. With favorable weather, we may experience a night crossing, complete with watch rotations and — for those who wish — hands-on training in night navigation. Pico is an island shaped by its volcano. Hidden among its dramatic landscapes are remarkable mountain lakes — Lagoa da Rosada and Lagoa do Paul — places where silence and stillness seem to breathe on their own. Mount Pico rises to 2,351 meters above sea level, while its underwater slopes descend to an astonishing 6,098 meters, earning it a place in the Guinness World Records as one of the tallest mountains measured from ocean floor to summit.

We will spend two days on Pico Island, immersing ourselves in the magic of the volcano and witnessing the mountain in all its raw power.

After fully immersing ourselves in the wild beauty of the Azores, we sail back to our home marina on Terceira Island. It is often at this moment that the realization sets in — how unforgettable and powerful this journey has been, and that “ordinary” vacations will never quite feel the same again. We spend our final night on board, with disembarkation on Saturday by 9:00 AM.