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Sailaway Vacations

Greek Islands Sailing

Sail through the cradle of Western civilization, where ancient mythology meets azure waters, traditional white-washed villages, and some of the world’s most beautiful islands.

Ancient Mythology

Cycladic Islands

Apr – Oct

Island Highlights

Mykonos

Cosmopolitan island famous for its windmills, nightlife, and beautiful beaches

Vibrant nightlife

Iconic windmills

Paradise Beach

Santorini

Volcanic island with dramatic cliffs, blue-domed churches, and spectacular sunset

Wine tasting

Caldera views

Oia sunsets

Paros

Traditional Cycladic charm with excellent windsurfing and marble quarries

Traditional villages

Golden Beach

Parikia port

Naxos

Largest Cycladic island with ancient ruins and pristine beaches

Portara monument

Mount Zas

Plaka Beach

7-day Cyclades Island Hopping

Daily Schedule

1

Athens to Kea

Depart Alimos Marina, sail to picturesque Kea island

2

Kea to Syros

Explore the elegant capital of the Cyclades

3

Syros to Mykonos

Famous windmills and cosmopolitan atmosphere

4

Mykonos to Paros

Traditional Cycladic architecture and golden beaches

5

Paros to Naxos

Largest island with ancient Portara monument

6

Naxos to Santorini

Dramatic volcanic cliffs and world-famous sunsets

7

Santorini to Athens

Return via temple of Poseidon at Cape Sounion

Meltemi Winds

Strong northerly winds (Force 4-6) from July-September provide excellent sailing but require experience. Spring and fall offer gentler conditions.

Photography Paradise

Iconic blue-domed churches, white-washed buildings, and dramatic sunsets create endless photo opportunities throughout the islands.

Island Culture

Experience authentic Greek hospitality, traditional tavernas, and ancient sites while enjoying modern amenities and vibrant nightlife.