If you are considering a charter to the Greek Islands your most difficult task may be deciding your itinerary! Each island has a unique splendor and charm. Tiny whitewashed villages seem brighter than sunlight itself, vendors roam on donkeys through winding roads that date back a thousand years.

This 14 day itinerary will give you a great taste of the marvels that are Greece.

Greek Islands Luxury Yacht Charter Itinerary

Greece has regional designations for groups of islands that can be a logistical starting point to construct an itinerary.

• The Ionian Islands: Corfu, Zakynthos, Ithaca, Lefkada, run down the west coast of the mainland
• The Argo-Saronic Islands: Aegina, Salamina, Poros, Agistri, Hydra, Spetses, are situated around Athens and the Argolis Peninsula.
• The Sporades: Evia, Skyros, Skiathos, Skapeols, along the eastern side of the mainland
• The North-East Aegean Islands: Samos, Thassos, Lesvos, Samothraki, Chios, Limnas, situated off the coast of mainland Turkey
• The Dodecanese: Rhodes, Kos, Patmos, Kalymnos, Symi, Karpathos, south of the NE Aegean Islands off the Turkish coast
• Cyclades: Naxos, Mykonos, Delos, Paros, Santorini, Kynthos, Kea, Milos, main islands southeast of Athens

Of these islands the Cyclades, liberally populated with archetypal Greek towns congested with appealing restaurants, shops, and signature beaches, have attracted the highest volume of tourists for decades. Paros is the new Mykonos for the Greeks, very lively and chic, but not as touristy as Mykonos. Naxos has amazing white sand beaches and Antiparos is a very exclusive and expensive hidden gem where Tom Hanks and his wife of Greek origin, Rita Wilson, own a home.

The Argo-Saronic Islands, Hydra, Poros and Spetses, lack the tourist crowds and retain an authenticity that is culturally charming and visually beautiful. The islands’ close proximity to Athens is a time saver and ports are well protected from the Meltemi winds.

The ideal time to cruise around these islands is during May, June, July, September and October. The end of July and August are very windy and seas can grow uncomfortably rough.

Greece – Cyclades and Saronic Islands – 14 Day Itinerary

1st day: Athens - Kea Island

Kea is an island of the Cyclades archipelago, in the Aegean Sea, 60 km southeast of Athens. After decades of depopulation the island has been popularized by Athenian yachtsmen who appreciate its remote charm yet proximity to the city.

Ayia Irini is a Bronze Age settlement dating to the late Minoan period. The classical era lyric poets Simonides and Bacclides come from this island. The Byzantine Empire brought prosperity to the island until control by the Venetians during the Middle Ages. The Turks also occupied the little island. This checkered past contributes to an intriguing archeological and architectural legacy.

On your visit be sure to include time for leisurely seaside dining at the picturesque fishing hamlet of Vourkari, popular for its local charm and excellent restaurants.

2nd day: Kea Island to Kithnos Island

The Island of Apollo Kithnos or Thermia is a quiet, unspoiled island favored by Greek tourists. Anchor in crystal clear water that gently laps white sand beaches. The traditional villages of Chora and Driopida are very picturesque and offer panoramic views. Loutra resort has warm, curative, sulfur spa waters that tradition says come from Vesuvius and have been a healing source since ancient times.

3rd day: Kithnos Island to Siros Island

Rocky Siros, or Sira, is the commercial, administrative and cultural capital island of the Cyclades. This is a very popular destination that offers something for everyone. There are excellent restaurants, tavernas with live music, shops, even a casino. Beautiful beaches are ideal for watersports.

History buffs can visit archaeology sites dating from 2800 to 2300 BC. In the 19th century Siros was a wealthy and powerful port. Impressive neoclassical buildings and large mansions from this era remain intact throughout the island.

4th day: Siros Island to Mykonos Island

Mykonos is a whitewashed paradise of magnificent natural beauty. Mykonos has been a famous tourist Mecca for decades, with a history stretching back over 2,000 years. It has long been a playground for the rich and famous boasting beautiful beaches, delightful shops and restaurants and a vibrant nightlife. Here locals and backpackers mingle amongst the jet setters, artists and celebrities from all over the world. The renowned architecture of whitewashed houses, diminutive storefronts and Byzantine churches, emerge along narrow, winding passageways as if sculpted from the cliffs. The cosmopolitan flavor of Mykonos is a delightful contrast to the simplicity of other islands.

5th day: Mykonos Island - Delos Island

Delos is one of the most important mythological, historical and archaeological sites in Greece. The island has been inhabited since the 3rd millennium BC and was a holy sanctuary long before Greek mythology made it the birthplace of Apollo and Artemis. The Delos oracle was just one, albeit powerful, manifestation of the sacred on the island, which today features extensive ongoing excavations. Access to numerous landmarks, ancient art and architecture make this island a compelling destination.

6th day: Delos Island to Paros Island

Arriving by sea to Parikia, the capital and harbor of Paros, yachtsmen are welcomed by an impressive traditional windmill. Paros, with a history stretching back some 6,000 years, has many significant monuments from various periods of the past. The island is characterized by dazzling white houses, churches and stairways enlivened by colorful doors and windows, and surrounded with bougainvillea and wisteria. The church of Panagia Ekatontapiliani and the Archeological Museum are well worth visiting. Naousa, just north of Parikia, is a picturesque fishing port that has excellent seafood restaurants, entertainment and nightlife. Many beaches and coves are suitable for a variety of watersports, especially wind and kite surfing. Christi Akti beach is the site of the Windsurfing World Championship.

7th day: Paros Island to Santorini Island

The island of Santorini, also known as Thira, is extraordinarily beautiful and provides visitors an unforgettable experience. Years ago the only means of ascent was by foot or donkey, but today a cable car transports people from the old port to the village, balanced precariously 260 meters above sea level on the edge of a cliff. The volcanic island has magical scenery unlike anywhere else in the world. There are numerous small islets, many traditional villages, castles, monasteries, museums, vineyards, farmlands and spectacular beaches, including the black sand beach of Perssa. Santorini is one of the most magnificent and unforgettable destinations in the Aegean.

8th day: Santorini Island to Sifnos Island

Sifnos is a charming island, known since ancient times for the production of art, pottery, and gold and silver mining. The unique cuisine of Sifnos is also world famous and it is worth venturing into a local taverna to sample the fare. The medieval village of Kastro is a delightful place to visit.

9th day: Sifnos Island to Serifos Island

Serifos is a lovely island dotted with traditional villages and coastal resorts. The harbor is lined with outdoor restaurants and tavernas and is an ideal spot to enjoy a carafe of local wine while absorbing the view. The white houses and churches of Chora, the capital of Serifos, are perched high on a hill overlooking the harbor. At the entrance to the village is a grouping of windmills, some of which have been turned into most unusual houses. On a clear day the panoramic view from here includes the islands of Sifnos, Naxos, Paros and Antiparos.

10th day: Serifos Island to Hydra Island

Hydra is one of the most impressive islands of the Saronic Gulf and has long attracted photographers and painters who love its quaint, little, crescent shaped harbor. Clustered here are an intriguing assortment of restaurants, shops, markets, and galleries that cater to tourists and locals alike.

11th day: Hydra Island to Poros Island

Sail through the narrow channel of the Peloponnese to reach the lush green island of Poros, where old pine forests still stand in the south and center of the island and the landscape is fertile and mountainous. The town of Poros features neo-classical architecture, enticing tavernas and a variety of shops. Scattered throughout the island are archeological sites and historical points of interest.

12th day: Poros Island to Aegina Island

Aegina, located just 27 kilometers from Athens, was a rival and a great sea power in ancient times. Aegina has a long and very colorful history with roots in Greek mythology, as a center of trade, of strategic importance, of war, slavery and even as a pirate headquarters. It also has the distinction of being the first place in Greece where the Greek flag was raised at the end of the War of Independence. The traditional fishing village of Perdika welcomes yachtsmen to the island. The town is a busy place, especially popular on weekends with Athenians.

13th day: Aegina Island to Marina Alimos (Athens)

For the final time we raise our sails bound for mainland Greece. Arriving in Athens at any time of day there is always much to see and do. The old district of Plaka, nestled at the foot of the Acropolis, is extremely touristy but can also be amusing. For those who prefer something more upscale, downtown Athens has superb gourmet restaurants, elegant designer shops, numerous theaters and other entertainment venues. In this very cosmopolitan center Athenians, as they have done for time immemorial, stroll arm in arm along the busy streets, or relax at one of the many coffee shops and observe the world passing by.

14th day: Marina Alimos to Airport (ca. 35 min.)

Today you have to say goodbye to your captain and crew, reflect upon your memorable sunny holiday, and begin planning your next trip to Greece.

See our Greece Luxury Yacht Charter Guide for further information on Chartering in Greece.