Sailing the Greek islands is a quintessential Greek experience. On this 11-day tour you'll explore many islands of the Greek Cyclades group by private charter yacht. Spend your days exploring little villages on islands with only a few hundred inhabitants, or relaxing on beaches, and your nights listening to the waves and Aegean winds. Culture and history lovers are also in luck, as this tour also spends some time in Athens and makes a day trip to Delphi, one of ancient Greece's most important sites.


  • Explore the museums and ancient ruins of Athens, the Greek capital
  • Experience the luxury of sailing around in a private yacht
  • Visit tiny islands with traditional life, such as Paros, Naxos, Heraklia, and more

Brief Itinerary

Day Highlights Overnight
Day 1 Arrive in Athens Athens
Day 2 Ancient Greek Mythology Tour & Acropolis Museum Athens
Day 3 Day Trip to Delphi Athens
Day 4 Meet Your Charter Yacht in Mykonos Mykonos
Day 5 Naxos Naxos
Day 6 Heraklia (Irakleia) Irakleia
Day 7 Schinoussa Island (Small Cyclades) Schinoussa
Day 8 Antiparos Paros
Day 9 Paros Paros
Day 10 Mykonos Mykonos
Day 11 Trip End  

Detailed Itinerary

Day 1: Arrive in Athens

Monastiraki Square and the Acropolis
Monastiraki Square and the Acropolis

Welcome to Greece! You'll begin your trip in Athens, home to the iconic Acropolis and so much more. The mythology of this spectacular city precedes it, with towering temples to Classical deities, the ruins of ancient marketplaces rubbing shoulders with lively nightlife, crowded flea markets, and contemporary cuisine. After checking in to your hotel, take a rest or make the most of your time in the city at some of these spots:

  • Check out the views of the unmissable Parthenon. (Pro tip: The Parthenon is the temple, the Acropolis is the hill.) This temple to Athena has enchanted visitors since its construction was completed in 438 B.C.E. 
  • Stop at the sprawling National Museum for a crash course in ancient iconography. Don't miss the room housing the Antikythera mechanism, essentially an ancient astronomical computer.
  • Visit a smaller archaeological site at the Tower of the Winds, then stroll down neighboring pedestrian Aiolou Street to stop at shops and cafes. 
  • Find your perfect souvenir or sun hat in the busy stalls of the Monastiraki Flea Market.
  • Hit the ground running with a night out in the up-and-coming Pangrati neighborhood, or amid the nightlife and mezze of the Psyrri district.

Day 2: Ancient Greek Mythology Tour & Acropolis Museum

The Acropolis
The Acropolis

Today, delve into Athens' centuries of history. Experience the ancient stories surrounding you on a guided mythology tour. Meet your archaeologist guide at Syntagma Square, then head to landmarks around the city, including the Acropolis and the Herodion Theatre. Hear stories about Zeus, Athena, Poseidon, Dionysus, and more, all adding resonance to the archaeological ruins you'll visit on this four-hour tour.

Later, take another guided tour at the Acropolis Museum. Named one of the 10-best museums in the world by National Geographic, this modern museum houses a multitude of artifacts removed from the hill of the Acropolis for safekeeping. You'll learn all about ancient religious practices and daily life. From the museum cafe there are great views of the former hilltop home of the museum's collection.

Day 3: Day Trip to Delphi

The Treasury of the Athenians at Delphi
The Treasury of the Athenians at Delphi

Today you'll seek out the oracle during a day trip to the ruins of Delphi, about 2.5 hours' drive from Athens. This essential ancient site was once home to the priestesses of Apollo, who ancient Greeks believed could predict the future. You'll take a guided tour through this sprawling archaeological site, with stops at the Treasury of the Athenians, the Temple of Apollo, and an expansive theater from the 4th century B.C.E.

After exploring the ruins, you can venture up an ancient footpath once used by worshippers of the god Pan, who started from the temples of Delphi and proceeded to the Corycean Grotto for their religious rites. Following in their footsteps, you’ll make your way through a valley of olive trees and be rewarded with views of the Corinthian Gulf and peaks of the Peloponnese along the way. 

After lunch, take a short downhill walk to the museum. Wander through its halls to find the bronze Charioteer of Delphi, marble Sphinx of Naxos, and what may be the first recorded notation of a melody once inscribed on the walls of the Athenian Treasury.

You'll be transferred back to Athens in the late afternoon to rest up or spend the evening out and about in the city.

Day 4: Meet Your Charter Yacht in Mykonos

Windmills of Mykonos

Transfer to Mykonos by ferry or airplane, and from the port or airport travel by taxi to the marina. Your charter yacht will be docked there, and your crew waiting to welcome you on board.

Welcome to Mykonos, an idyllic getaway for cosmopolitan fun lovers. A magnet to the world’s most glamorous personalities since the 1970s, Mykonos today also attracts nature lovers, foodies, and athletes. In Mykonos you will discover remarkable beaches, adrenaline-inducing water sports, a refined local cuisine, and an unprecedented bar scene, all among picturesque architecture, breathtaking views, iconic windmills, and maze-like streets.

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Day 5: Naxos


Today, sail to Naxos, where you can enjoy a free day to explore as you wish. In the active main town you can shop and admire the Venetian architecture and castle area. There are also opportunities for both laid-back relaxation, and water or land activities.

Day 6: Heraklia (Irakleia)


Head to Heraklia today, a diamond-shaped island south of Naxos, and close to Ios island. With just over 150 inhabitants, the permanent tranquility and beauty of Heraklia is evident all around. When you arrive at the charming port of Agios Georgios, you may feel like you've traveled back in time.

Day 7: Schinoussa Island (Small Cyclades)


Today sail to to Schinoussa (the Island of the Sun), one of the most beautiful small islands of the Aegean. It belongs to the Small Cyclades complex, and is close to Naxos, Irakleia, Koufonisia, and Keros. It's home to many endemic plants, and is an important migratory station for many birds.

There are two villages on the small island, Chora and Messaria, with about 256 inhabitants. Schinoussa owes its name to the mastic tree shrub that grows all over the island. The port, Mersini, is considered one of the best shelters for small boats in the Aegean. Its inhabitants are involved in agriculture, farming, fishing, and tourism.

Day 8: Antiparos


Today, arrive in Antiparos, a small island that has stood its ground as an alternative offshoot to neighboring, tourism-oriented Paros, with its fancy nightlife.

Significant archeological findings have been made on Despotiko, an uninhabited island west of Antiparos, as well as at two other neighboring virgin islands, Tsimintiri and Stroggylo. The oldest Cycladic settlement was discovered on Saliagos, an islet off Antiparos. There's a lot to explore while traveling around these islands on your yacht.

Day 9: Paros

Santa Maria Beach
Santa Maria Beach

Explore the small island of Paros, which is frequently overlooked in favor of its more famous Cycladic neighbors. You'll quickly learn that Paros has a special charm of its own, and it's quite traditional in nature. Highlights include the 4th-century Panagia Ekatontapiliani Church, and beautiful beaches with sheltered swimming areas made from rock formations.

Day 10: Mykonos


Feel the famous Aegean winds while relaxing on one of Mykonos' stunning beaches for the day.

Later, take a sunset sailing tour to the nearby island of Delos, where you'll enrich your knowledge of ancient Greek history. The Cyclades islands (kyklos means circle) got their name from the fact that they encircle the sacred island of Delos. The island is a UNESCO World Heritage Site and one of the most important archaeological sites in Greece, plus it's said to be the birthplace of Apollo and Artemis.

Day 11: Trip End

Farewell Greece!

All too soon, the trip has come to an end. Transfer from Mykonos to Athens by ferry or air to connect with an evening flight from Athens back home. If you take the ferry, it may be necessary to stay in Athens an extra night, depending on the time of your flight home. 


Map of Sail the Greek Islands: Athens, Delphi, the Cyclades & More - 11 Days
Map of Sail the Greek Islands: Athens, Delphi, the Cyclades & More - 11 Days