Sailing Tours & Trips in Aegean Islands

A 54-56ft sailing yacht takes you through Aegean waters from Santorini to pristine coves. The itinerary features swimming at Gaidharos Bay, visits to Amorgos' 11th-century Moni Hozoviotissis monastery, and hands-on sailing between islands. Share authentic maritime life with 11 fellow passengers.

The 57-ft yacht glides through Aegean waters, visiting eight distinct islands over 10 days. Highlights include snorkeling in secluded coves, Homer's tomb on Ios, and Venetian ruins in Paros. From Mykonos' iconic windmills to Sifnos' ceramic workshops, this voyage showcases authentic Greek maritime life at approx. $230 per day.

The bluest Aegean waters carry you from Santorini to Mykonos on a sleek 54ft yacht. Sailing skills improve between Ios's pristine Manganari Beach and Amorgos's rugged coastline. Traditional ports in Koufonisia and sunsets from Syros's hilltop Ano Syros village highlight the journey.

Ferries connect the Aegean Islands, with nights in Mykonos and Naxos before reaching Santorini's dramatic cliffs. The marble Portara gateway stands as remnants of Apollo's 6th-century BC temple, while Little Venice in Mykonos features famous windmills and the Church of Panagia Paraportiani.

A comfortable group cruise takes you through the heart of the Cyclades, visiting the UNESCO-listed Delos archaeological sanctuary and stopping at hidden spots like the Cave of Katafyki in Kythnos and Kolona Beach's striking sand strip. From Piraeus Port, the route goes through crystal-clear Aegean waters to Amorgos, where the cliff-hanging 11th-century Monastery of Panagia Hozoviotissa hangs above the sea. Swimming near the Olympia shipwreck in Liveros Bay offers a unique underwater view. This 8-day sailing adventure welcomes families and travelers ages 8+, with stops in medieval Syros' Ermoupoli, the glamorous shores of Mykonos, and Naxos' hillside kastro. Pottery workshops in Kea and thermal springs in Loutra add variety to the journey.

The 57-ft luxury yacht sails for 8 days between Santorini and Mykonos. Folegandros offers cliff-side exploration, while Sifnos showcases ceramic workshops. Hidden coves provide perfect snorkeling spots, with beach time at Magganari on Ios and stunning sunsets over Hora's whitewashed buildings.

A state-of-the-art 57-ft yacht takes you through the Aegean's azure waters, from Mykonos' Little Venice to Folegandros' clifftop villages. The route passes through Santorini's volcanic caldera, with stops at Ios' Magganari Beach and Naxos' ancient Temple of Dimitra.

A modern yacht carries travelers from Mykonos's Little Venice to Thirasia's volcanic shores. The route includes hands-on sailing through the Small Cyclades, stops at Amorgos's ancient port of Katapola, and visits to Ios's protected Kolitzani Beach. The trip balances sailing adventures with island exploration.

A 44-46ft private catamaran sails through the Sporades archipelago, visiting Skiathos, Skopelos, and Alonnisos over 8 days with an expert skipper. The iconic Agios Ioannis church featured in Mamma Mia sits along the route, then stand-up paddleboarding happens in the National Marine Park of Sporades where Mediterranean monk seals and dolphins swim alongside you. Remote Kyra Panagia island, inhabited only by monks, offers complete disconnection from the world. Anchoring in Planitis Bay provides total isolation and quiet.