• Overview
  • Itinerary
  • Oceania 45 Sailing Map
  • Cost

Date: Choose your dates! (21 nights)
Host: Local Expert Guides
Cost: Pricing varies, ask us!
Trip Type: Top Picks, Cruising – Yacht to Small Ship

Three weeks exploring the stunning Greek, Sicilian and Aeolian islands will leave you breathless. Land in Athens where you’ll witness the grandeur of the Acropolis, Panathenaic Stadium, the National Gardens and Zeus Temple. Then enjoy a seven day sailing adventure visiting uninhabited and busy islands alike. One of such islands, Hydra, was built in the shape of an amphitheatre on a slope overlooking the Argosaronic gulf, and is one of the most romantic destinations in Greece. Here you’ll see 500 donkeys taking the place of public transportation. The south side of another such island, Moni has beautiful caves and cliffs perfect for snorkelling.

With your feet back on solid ground discover Mt. Etna volcano where you can’t miss volcanically grown wine (enjoy a wine tasting at Cottanera Winery). In Milazzo stroll along the ancient Strada Reale and see the Sicilian Romanesque style Cathedral, begun in 1131 and adorned with Byzantine mosaics. Continue to Agrigento to explore the legendary Valley of the Temples, where the remains of seven Doric temples stand in a breathtaking setting of almond groves and olive trees. Finish off your adventure in Syracuse or choose to stay longer and ask us about extension options.


  • 7 days on the areas stunning turquoise waters, sailing between islands
  • Visit the colorful cliffs of Santorini where everything from hotels to restaurants is picture perfectly perched
  • Explore Mt. Etna, Europe’s largest and most active volcano
  • Learn of the Jewish impact on the area’s history and culture today
  • Head to the markets for some famous Palmero street food
  • Visit the catacombs of San Giovanni and crypt of San Marciano In Syracuse

Brief Itinerary

  • Athens (2 nights)
  • Sailing (7 nights)
  • Santorini (2 nights)
  • Taormina (3 nights)
  • Sicily (4 nights)
  • Agrigento (2 nights)
  • Syracuse (1 night)

For details on accommodation, daily activities and more visit our interactive itinerary here. 


Starting Athens/Ending Syracuse

Due to the great fluctuation in the euro currency and variation of pricing based on dates and group sizes, prices for all of our services will be quoted upon request. This policy enables us to provide you with the most competitive and up to date quotes. We invite you to browse our website to select the travel style that meets your needs, our Customs Travel Advisors are only a call/email away ready to provide any assistance in designing your itinerary.