Sail the stunning sun-drenched Cyclades Isles and take dip in the azure Aegean Sea while you explore an enticing blend of modern seafaring and cultural history aboard a privately chartered yacht.

Starting at: $6,995 Ask Us A Question or Call 855-330-1542
 <i>Running on Waves</i> at sunset  The port area on Mykonos  Traditional houses on Mykonos  View of church domes from cliff-top Fira on Santorini  View from cliff-top Oia on Santorini  The view from cliff-top Oia on Santorini

Voyage to the Greek Isles

A Sailing Cruise of the Cyclades

10 days from $6,995

Sail the stunning sun-drenched Cyclades Isles and take dip in the azure Aegean Sea while you explore an enticing blend of modern seafaring and cultural history aboard a privately chartered yacht.

or Call 855-330-1542


Immerse yourself in Cycladic culture amid this stunning string of legendary islands. You’ll visit the site where the Venus de Milo was discovered, sample regional foods and wines, swim in crystal-clear waters off pristine beaches, and enjoy the thrill of sailing aboard your own private yacht.

Highlights Include:

  • Athens: Tour the private Goulandris Museum of Cylcadic Art, the ideal introduction to this cruise.
  • Syros: Explore the historic center of Ermoupolis and meet a local family as you dine in a private home.
  • Delos and Mykonos: Walk amid the sacred landscape of Delos, birthplace of Apollo, and enjoy time at leisure on lively Mykonos.
  • Naxos: See the Kouros statue in Melanes and savor locally produced wines and cheeses.
  • Santorini: Sail into the dramatic crater of Santorini and ascend to the island’s hilltop towns to explore the Minoan Bronze Age settlement of Akrotiri and admire frescoes in the Museum of Prehistoric Thira.
  • Milos: See the ancient theater where the Venus de Milo was unearthed.
  • Sifnos: Travel to the Mycenaean citadel at Agios Andreas and Kastro. 
  • Sailing aboard Running on WavesEnjoy the pleasures of sailing aboard your own privately chartered yacht, a three-masted sailing vessel with contemporary design and state-of-the-art facilities. *

To see itinerary, please click on an option below.


Days 1 & 2 — Depart U.S. / Arrive in Athens

Arrive in Athens and transfer to your hotel, centrally situated in the historic Plaka District, at the foot of the Acropolis. Gather this evening for a welcome orientation and rooftop reception. (R)

Day 3 — Athens / Embark

This morning, gain a deeper understanding of our island destinations at the private Goulandris Museum of Cycladic Art. Enjoy lunch at leisure and free time in the Plaka District before boarding Running on Waves, your elegant home for the next seven nights. This evening, gather for the Captain’s welcome reception and dinner. (B,D)

Day 4 — At Sea / Syros

Enjoy the morning at sea with sails unfurled en route to Syros. On arrival at the superb natural port of  Ermoupolis, “the city of Hermes”, stroll past the ornate churches and neo-classical mansions of the historic center  before being hosted for dinner at a private home. (B,L,D)

Day 5 — Delos / Mykonos

Explore the World Heritage-designated island of Delos, spiritual sanctuary and mythical birthplace of Apollo and Artemis. Today it is a trove of marbles and mosaics among the most extensive archaeological excavations in the Mediterranean region. This afternoon, enjoy the amenities of Running on Waves: perhaps a short swim off the stern marina, a dip in the hot tub, a spa treatment, or simply a quiet interlude on the shaded deck. When evening approaches, disembark for independent exploration of the bougainvillea draped alleyways of cosmopolitan Mykonos and dinner on your own. (B,L)

Day 6 — Naxos

Naxos is the largest and most fertile island of the Cyclades chain, noted for its citrus orchards and olive groves as well as rugged mountains and lush green valleys. Walk the marble-paved streets of Apeiranthos, a village in the island’s mountainous center, and see the 6th century 20-ft marble Kouros statue in nearby Melanes. Continue to Naxos town where Nikos Kazantzakis, author of Zorba the Greek, was schooled, and sample wines and artisan cheeses produced on the island while enjoying a folkloric dance performance. (B,L,D)

Day 7 — Paros

Across the channel in Paros, beautiful white and translucent marble has been extracted since the 6th century BC. See the city of Parikia, built upon the ruins of the ancient capital city of Paros, and its unique archaeological museum. Then, visit a marble quarry before exploring the neighboring islet of Despotiko, where ongoing excavations are turning up exciting new artifacts. (B,L,D)

Day 8 — Santorini

The much photographed half-moon-shaped island was created by a great volcanic eruption around 1500 BC. Widely believed to be the lost kingdom of Atlantis, it was colonized by the Minoans. Visit the Akrotiri archaeological site, a Minoan Bronze Age settlement that was preserved in volcanic ash until its discovery and excavation in the early 20th century. Get a glimpse of ancient Cycladic life at the Museum of Prehistoric Thira and continue to the dramatic cliff-side village of Oia to take in postcard-perfect views of whitewashed houses, blue domed churches, and the sweeping caldera. (B,L,D)

Day 9 — Milos

Milos is the most dramatic of the Cyclades with extraordinary rock formations, hot springs, and white villages perched on multicolored cliffs. See its iconic windmills and whitewashed buildings during a morning stroll of Plaka, the island’s main town. In nearby Tripiti, the Venus de Milo statue was discovered by a farmer in 1820. Purchased as a gift for Louis XVIII, the statue now prominently resides at the Louvre Museum in Paris. In the afternoon, sail around the island to observe its other-worldly mineral and rock formations and stop for a swim.  This evening, gather for the Captain’s farewell reception and dinner on board. (B,L,D)

Day 10 — Athens (Disembark) Return to the U.S.

Bid farewell this morning and transfer to the airport for flights home. (B)

*Please note that this ship requires certain physical demands as noted on the Ship Information page.