Cruise like a celebrity through the glittering waters of the Cyclades on this nine-day itinerary.  The Cyclades are some of the most quintessential Greek islands, and you'll see seven of them from the decks of your yacht, along with plenty of time to explore onshore. From lesser-known spots like beach-lined Milos and petite Antiparos to favorites like bustling Naxos and cosmopolitan Mykonos, you'll scope out this island chain in style.

Highlights

  • Swim in the clear waters of Milos
  • Taste the island agriculture of Naxos
  • Rub elbows with the Mykonos jetset
  • Tour the Cyclades' capital on Syros
  • See the oldest settlements in the Cyclades on Kythnos

Brief Itinerary

Day Highlights Overnight
Day 1 Arrive in Athens Athens
Day 2 Sail to Spetses Spetses
Day 3 Sail to Milos Milos
Day 4 Sail to Antiparos Antiparos
Day 5 Sail to Naxos Naxos
Day 6 Sail to Mykonos Mykonos
Day 7 Sail to Syros Syros
Day 8 Sail to Kythnos Kythnos
Day 9 Return to Athens, Depart  

Detailed Itinerary

Day 1: Arrive in Athens

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 Spetses

A more relaxed way to get around

Head south to the island of Spetses. Though it may look like just a small fragment that has broken off from the Peloponnese on a map, this island has been occupied since the Mesolithic Age and was the first of the Greek islands to raise the flag of the revolution against the Ottomans in 1821. It now draws a more boutique crowd to its quiet streets, where private cars are banned from many parts of the town.

The annual Armata festival celebrates one of the major Spetsiot naval victories of the war for independence and attracts swarms of visitors. But you can explore this history at any time of year at Bouboulina's Museum, devoted to Laskarina Bouboulina, a heroine of the Greek revolution. You may have already been greeted by her statue in Dapia Square

Head to Zogeria Bay to find a favorite secluded beach, accessible by boat or a roughly 4-mile bike ride from the main town. If you'd prefer a livelier scene, while away your day at Kaiki Beach Club, complete with sun loungers, water sports and games, and an onsite restaurant.

End your day in style with dinner at On the Verandah on the terrace of the Grand Poseidonion hotel. This chalet-inspired boutique hotel has been housing Greek glitterati since 1914. The creative Greek contemporary fare is good enough to compete with the impressive ocean view.

Return to your berth to spend the night onboard.

Day 3: Sail to Milos

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.

Return to your berth to spend the night onboard.

Day 4: Sail to Antiparos

Antiparos port

The scenery on petite Antiparos has drawn celebrities including Tom Hanks to buy villas on its picturesque shores. In the heart of the old town sits the Venetian Castle, which was originally built to protect the town from pirates in the 1400s and now wraps around many of the town's central buildings.

Kambos village in the island's center is home to just a dozen inhabitants. Its whitewashed churches set the scene for the traditional atmosphere, as do the nearby Glyfa and Livadia beaches. Roughly ten minutes away you'll find the ancient Cave of Antiparos up Agios Ioannis Hill, known for its stalactites and stalagmites.

Return to your berth to spend the night onboard.

Day 5: Sail to Naxos

Hiking the Portara in Naxos

Time to head over to bustling Naxos. With an active main town where you can shop and admire the Venetian architecture, a historic Kastro (castle) area, and expansive beaches, the island offers opportunities for both laidback relaxation, as well as water or land activities. Try out some of these options:

  • Hike up to the summit of Mount Zas, the mythological childhood home of Zeus, the ruler of the gods, and the highest point in the Cyclades.
  • Head inland to the town of Chalki, home to the island's oldest market and a petite, shady square perfect for whiling away the afternoon. Stop at the kitron distillery to sample the local liqueur and learn about its distillation process over the years.
  • Visit the Temple of Demeter at Sangri on your way. Multiple deities of fertility were worshipped here, particularly the goddess Demeter. The temple was constructed in 530 BC, during the tyranny of Lygdamis, and represents a precursor of classical Athenian architecture. 
  • Stroll to the Portara, the entrance to the Temple of Apollo. Construction on the temple began in the sixth century BCE but was never finished, but the still-standing entranceway has become one of the hallmarks of the island. You can find it on the islet of Palatia, just over a causeway from the heart of Naxos Town (Chora).

For dinner, wander up the hill through the streets of the Kastro neighborhood to pick out your favorite of the area's tavernas, where you can sample the island's fresh produce in its best forms.

Return to your berth to spend the night onboard.

Day 6: Sail to Mykonos

Bright balconies of Little Venice

Move on to Mykonos, one of the most famous islands in the Cyclades. Known for its glitzy restaurants and nightlife, art scene, and jet set crowds (it was recently home to a Gucci pop-up boutique), Mykonos is one of the most quintessential Greek isles.

If you need to get your toes in the sand immediately, head to remote Agios Sostis beach to find your own isolated paradise. Or for a more active experience, Ftelia Beach is known for its excellent windsurfing.

Follow it up with a stroll through Little Venice, an 18th-century neighborhood where colorful former captains' mansions and seaside restaurants seem to sprout straight from the sea. It's also right next to the island's famous hillside windmills for great photo ops.

Return to your berth to spend the night onboard.

Day 7: Sail to Syros

Homes on the coast

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.

Return to your berth to spend the night onboard.

Day 8: Sail to Kythnos

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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.

Return to your berth to spend the night onboard.

Day 9: Return to Athens, Depart

Wave to the city

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

Map of Luxury Cyclades Yacht Cruise - 9 Days
Map of Luxury Cyclades Yacht Cruise - 9 Days