7 Days Sailing by Private Charter in the Greek Islands

We departed Naoussa Port for the short 30-minute crossing to Antiparos, a charming island just off Paros. After anchoring in a quiet bay or near the small port, we enjoyed a refreshing late-afternoon swim before heading ashore to wander the village’s whitewashed alleys. Dinner in town is a perfect first night ashore—consider a reservation at The Rooster, a favorite for its beautiful setting and elevated Greek flavors. Order the slow-roasted lamb or their fresh grilled fish with local vegetables, paired with a crisp Greek wine.

Sail south to Folegandros, a peaceful and stunning island known for its rugged cliffs and dramatic landscapes. Because it sits largely off the main ferry circuit, Folegandros feels quieter and more authentic than many of the Cyclades. Anchor in Karavostasis or a nearby cove for a swim before heading inland.

Spend the evening wandering the island’s beautiful Chora—perched high on the cliffs and considered one of the most memorable villages in the Cyclades. For dinner, try a traditional taverna such as Pounta, and order the slow-cooked lamb or local Tiropita, both classic island favorites.

Cruise from Folegandros to the lively island of Ios, a beautiful passage across the deep blue Aegean. Arrive at Manganari Bay or the main port for a swim in the island’s clear turquoise water before heading ashore.

While Ios is famous for its nightlife, it also offers charming whitewashed streets and sweeping sunset views from the hilltop Chora. Spend some time wandering the narrow lanes, visiting the windmills, or watching the sunset from the church of Panagia Gremiotissa.

As night falls, Ios comes alive. For cocktails and late-night energy, head to FarOut Beach Club for a lively beach scene, enjoy creative cocktails at Pathos Lounge with its dramatic cliffside views, or finish the night dancing at the iconic Scorpion Club in Chora.

Sail north to Naxos, the largest and most fertile island of the Cyclades. Moor in Naxos Town, where Venetian walls and the Portara gateway rise over the harbor. Spend the evening wandering the old town’s maze of lanes and sampling local specialties.

On day five cruise to Delos, the sacred island and archaeological jewel of the Cyclades. Anchor nearby and spend the day exploring the temples, mosaics, and ancient streets of this UNESCO World Heritage site. Stay overnight at anchor off Delos, allowing for a rare and magical evening in the shadow of its history.

On day six, we ended our sailing in Mykonos to spend a few days on the beautiful beaches, enjoying the nightlife and stayed a nice resort close to town. We wandered the narrow lanes of Mykonos Old Town, visited the iconic windmills for sunset views, and enjoyed dinner by the water. Mykonos has an international airport, which allows you to bypass the Athens Airport and fly directly to other parts of Europe.