When most people think of Mediterranean sailing, they picture the height of summer. Busy harbours, crowded anchorages and soaring temperatures. But some of the best adventures begin after the crowds have gone home.

Each autumn, a beautifully restored brigantine returns to Sicily for a series of extraordinary voyages through the UNESCO-listed Aeolian Islands. These aren’t luxury cruises or sailing holidays where you simply sit back and watch the scenery drift by. They’re authentic hands-on adventures where you’ll become part of the crew, helping to hoist sails, take the helm and navigate one of Europe’s most fascinating coastlines under traditional sail.

The Aeolian Islands are unlike anywhere else in the Mediterranean. Seven volcanic islands rise dramatically from deep blue seas, each with its own character. Wander the whitewashed streets of Lipari, anchor beneath towering cliffs at Salina, swim in crystal-clear bays and experience one of nature’s greatest spectacles as Stromboli’s near-continuous eruptions light up the night sky.

Autumn is arguably the ideal season to experience them. The sea remains warm after summer, daytime temperatures are comfortable for exploring ashore and the prevailing winds often provide excellent sailing conditions. It feels quieter, slower and altogether more authentic.

Whether you’re completely new to traditional sailing or already have offshore miles under your belt, there’s a voyage to suit your ambitions. Some focus on classic island-hopping under sail, while others combine life aboard with guided volcano hikes led by experts who bring the islands’ remarkable geology to life.

More than anything, these are journeys for travellers who value experiences over itineraries. You’ll share watches with your fellow crew, enjoy meals on deck, wake to a different anchorage most mornings and discover just how rewarding it is to travel at the pace of the wind.

Autumn 2026 Departures

Sail to Fire – Aeolian Islands

5–12 September 2026 | 8 days | From €1,380

A classic introduction to the Aeolian Islands, combining hands-on sailing, secluded anchorages, volcanic scenery and unforgettable evenings watching Stromboli erupt.

Sail to Fire – Aeolian Islands

12–19 September 2026 | 8 days | From €1,380

A second departure following the same spectacular route, perfect for those wanting an authentic tall ship adventure in the Mediterranean.

Hike & Sail – Aeolian Islands

19–26 September 2026 | 8 days | From €1,380

Combine traditional sailing with guided hikes across some of Europe’s most dramatic volcanic landscapes.

Hike & Sail with Peter Amann

12–24 October 2026 | 13 days | From €2,275

An extended expedition for nature lovers, combining classic tall ship sailing with expert-led exploration of Sicily and the Aeolian Islands.

Whether you’re looking for your first taste of life aboard a traditional sailing ship or searching for a Mediterranean adventure unlike any other, these autumn departures offer a rare opportunity to experience one of Europe’s most remarkable island groups the way sailors have for centuries—under sail, guided by the wind and immersed in the journey itself.

Oh, and if you need some more inspiration, our Social Media Manager Frankie joined them on board and wrote a wonderful post about her ‘rewilding’ at sea – read it for inspiration!