Channel the spirit of some of Greece's most famous tales as you sail through the Aegean on this nine-day itinerary. Start off by paying the proper tribute at the Temple of Poseidon before you start on your way to Kea, followed by the villages of Kythnos. Visit the capital of the Cyclades on Syros and the home of the Cyclops on Serifos, then search for the Venus de Milo's cousin on Milos before you end your trip on the double beach of Kolona.


  • See the oldest settlements in the Cyclades on Kythnos
  • Visit the Cyclades' capital on Syros
  • Swim in the clear waters of Milos
  • Relax on the double beach at Kolona

Brief Itinerary

Day Highlights Overnight
Day 1 Arrive in Athens Athens
Day 2 Sail to Cape Sounion and the Temple of Poseidon Sounion
Day 3 Sail to Kea Kea
Day 4 Sail to Kythnos Kythnos
Day 5 Sail to Syros Syros
Day 6 Sail to Serifos Serifos
Day 7 Sail to Milos Milos
Day 8 Sail to Kolona Beach Kythnos
Day 9 Return to Athens, Depart  

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 both the iconic Acropolis and so much more. The mythology of this spectacular city precedes it, with towering temples to Classical deities and the ruins of ancient marketplaces rubbing shoulders with lively nightlife, crowded flea markets, and contemporary cuisine. Make the most of your time in the city at some of these spots:

  • Check out the views of the can't-miss 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 BC. It's probably the first thing that comes to your mind when you think of ancient Greece and is visible from many of the city's high points.
  • Stop at the sprawling National Museum for a crash course in ancient iconography. Be sure to seek out 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. 

Spend your evening exploring the up-and-coming Pangrati neighborhood or amid the nightlife and mezze of the Psyrri district.

Day 2: Sail to Cape Sounion and the Temple of Poseidon

Quite the dramatic setting for the temple!
Quite the dramatic setting for the temple

Board your boat this morning and make yourself at home. Once you've settled in, you'll head down to the Athenian Riviera, full of both history and stunning island views.

Your adventure will take you along the coast to visit the Temple of Poseidon, providing you with historical background on the way. The cliffs overlook the Saronic Gulf, with one of the best sunset views Greece has to offer and seven islands to spot in the distance.  Keep an eye on the Doric columns, where Lord Byron once carved his name.

Day 3: Sail to Kea

Ioulis at sunset
Ioulis at sunset

Set sail today for the island of Kea, also known as Tzia and the closest Cycladic island to Athens, potentially stopping at the protected harbor and town of Vourkari or swimming at a more remote beach along the way.  You'll approach from the west to the port of Korissia and main town of Ioulis.

Visit the archaeological museum and nearby carved stone Lion of Kea or walk along the island's many marked hiking trails through the hills or royal oak forest. You can also visit Karthea Bay, a point only accessible by boat or hike and home to ancient temples to Apollo and Athena.

Day 4: Sail to Kythnos

Sunset at Kythnos
Sunset at Kythnos

The western Cycladic island of Kythnos is home to one of the oldest settlements in the Cyclades, dating all the way back to roughly 10,000 BCE. You'll spend today visiting its five main villages of Merichas, Chora (also known as Messaria), Dryopida, Loutra, and Kanala.

It's now home to Greece's first wind park and an increasingly sustainability-focused infrastructure. Take a dip in Loutra's thermal springs, walk through Messaria's labyrinthine streets, or visit some of the country's largest caves at the Katafiki Cave in Dryopida.

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Day 5: Sail to Syros

Homes on the coast
Homes on the coast of Syros

Head to Syros today, home to the capital of the Cyclades. You'll be greeted by the domes of the Greek Orthodox and Catholic churches atop the hills of Ano Syros and Ermoupoli, churches that join together for yearly Easter celebrations.

Follow the cobblestone streets through the squares and past architectural features like the Ermoupoli City Hall designed by Ernst Ziller, also responsible for many of the mansions and national buildings in Athens. Visit the Vaporia neighborhood, home to the mansions of 1800s sea captains, or the medieval hilltop settlement of Ano Syros for expansive sea views. The yearly music festival attracts visitors from around the country to the Apollon theater, built in 1864 as a replica of La Scala in Milan.

Day 6: Sail to Serifos

Shorefront tavernas
Shorefront tavernas

In Greek mythology, Serifos was the island where the infant Perseus and his mother washed up from the sea and later returned after killing Medusa. It was used as a place of exile during the imperial Roman era, but now is sought out by those who are considerably more enthusiastic about making the trip there.

Visit the undeveloped beaches, hike up to what's left of the hilltop Venetian fortress, or explore the sites of former mines and caves once thought to be home to the Cyclops. Top off your day at one of the tavernas on the shore of the main town.

Day 7: Sail to Milos

It's called the Island of Colors for a reason
It's called the Island of Colors for a reason

Milos is rumored to be the next Greek luxury destination, boasting more than 70 crystal clear beaches and stunning sunsets. It's also home to a dormant volcano at Kalamos, one of the island's oldest volcanic centers. The volcanic steam and gases emitted into the atmosphere reach temperatures of 100 degrees Celsius.

The Venus de Milo statue was discovered on Milos, so scope out its historic catacombs and amphitheater or extensive network of dirt roads and see what you can find for yourself.

Day 8: Sail to Kolona Beach

Beach between the bays
Beach between the bays

Circle back to the other side of Kythnos to the double-bay beaches of Kolona, considered some of the prettiest in the Aegean. The narrow strip of sand connects the main island to the Agios Loukas islet, surrounded on all sides by clear water.

Take a loop hike up to the hilltop to take in the view from above or simply spend the day on the sand. There are few umbrellas or organized facilities on the beach, which can be crowded during the high season, so be sure to travel prepared.

Day 9: Return to Athens, Depart

Monastiraki Square at sunset
Monastiraki Square at sunset

Time to say farewell to Greece. You'll head back to Athens after breakfast to catch your flight, either home or onward to your next adventure.


Map of Sailing Holiday in the Aegean - 9 Days
Map of Sailing Holiday in the Aegean - 9 Days