Sail Sicily 2027

Step aboard your Aeolian adventure at Marina Portorosa at around 5pm. We set sail northward across the Tyrrhenian Sea as the dramatic volcanic archipelago comes into view.

We arrive at Vulcano, the southernmost of the Aeolian Islands and perhaps the most dramatic. Vulcano is still volcanically active — you can see and smell sulphurous steam drifting from the crater. We'll anchor in a bay close to the town centre and eat alfresco at a friendly local restaurant serving Sicilian specialities and freshly caught seafood. The atmosphere here is relaxed and authentic — Vulcano remains refreshingly unspoiled despite its natural wonders.

The keen among you may want to rise early and climb Vulcano's volcano before breakfast. Then we set sail for Panarea, the smallest and most exclusive of the Aeolian Islands.

By afternoon we arrive, mooring off the main harbour and taking our tender ashore. The island has long been a favourite of Italian high society, and its traffic-free streets are lined with whitewashed houses draped in bougainvillea, chic boutiques, and stylish bars. The main village, San Pietro, is a maze of narrow lanes perfect for wandering. Enjoy sunset drinks at one of the fashionable rooftop bars before choosing from several excellent restaurants — the vibe here is elegant, and the evening passeggiata along the waterfront is a delight.

A chance to test your sailing skills as we head to the outermost of the Aeolian Islands. En route we stop at the enchanting Grotta dell'Amore (Cave of Love) for lunch and a swim in crystal-clear water.

Stromboli is known for having one of the most continuously active volcanoes on earth. Small eruptions occur several times a day, and after dark the glowing lava trails down the Sciara del Fuoco (the "Stream of Fire") are visible from the water. The village itself is charming and unhurried — pale-painted houses and black lava-stone lanes winding down to a working fishing harbour. We moor within easy reach of the village; for those wanting more, there is the opportunity to join a guided hike to the caldera.

Today we sail to Salina, the second-largest island in the archipelago and arguably the most beautiful. Salina is defined by its twin extinct volcanoes which give the island a dramatic, mountainous silhouette. We pause for lunch and a swim beneath the island's stunning coastal cliffs.

By afternoon we berth at a marina at Santa Marina Salina, the island's main port. The waterfront promenade is lined with family-run restaurants, gelaterias, and wine bars. For dinner, you'll find excellent traditional Sicilian cuisine — pasta con le sarde, caponata, and of course the freshest seafood. We mark the midpoint of the trip with a dance party on one of the boats — usually an unmissable event!

This morning we sail around the dramatic northern coast of Salina, treated to breathtaking views of the island's twin volcanic peaks rising nearly 1,000 metres above the sea. Sheer cliffs, hidden coves, and hillsides covered in Mediterranean scrub and vineyard terraces unfold as we go.

Our destination is Spiaggia di Pollara, one of the most photographed locations in the Aeolian Islands. This crescent-shaped beach sits within the remains of an ancient volcanic crater, half-collapsed into the sea to create a natural amphitheatre. We enjoy lunch on board and time for swimming, with its spectacular natural rock arch framing views across to the neighbouring islands. By late afternoon we moor near Rinella — dine at a waterfront taverna as fishing boats return with the day's catch and the sun sets over the Tyrrhenian Sea.

This morning we set sail for Lipari, the largest of the Aeolian Islands. We'll enjoy lunch at one of the bays along the west coast, where wild and dramatic surroundings give way to crystal-clear water for swimming.

By mid-afternoon we dock at Lipari's marina. Lipari has been continuously inhabited for over 6,000 years, and its history is written in layers: Greek fortifications, Roman baths, Norman cathedral, and Spanish ramparts all clustered on the rocky headland. This evening explore the historic centre — perhaps the cathedral or museum — before settling into one of the many excellent restaurants. Lipari offers the widest dining choice in the archipelago, from traditional Sicilian trattorias to contemporary wine bars. The main street, Corso Vittorio Emanuele, comes alive with locals and visitors enjoying the passeggiata and gelato.

It's a short sail to Spiaggia Praia di Vinci, a sheltered cove with some of the clearest water of the week — perfect for one last long lunch at anchor. After lunch we retrace our route south across the Tyrrhenian. We arrive back at Marina Portorosa in time to gather for a final dinner together ashore — a chance to share favourite moments from the week over a bottle of Malvasia delle Lipari.

We need to leave the yachts by 0900. The nearby train station connects easily to Messina, Catania, and Palermo, with onward services across the island. If you're extending your trip, Taormina is just an hour away — perched dramatically above the sea with views of Etna, it's a perfect final flourish before heading home.