A Custom Greek Island Cruise Vacation in 12 Days

A 12 day trip to Greece 
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From the pillars of the Golden Age of Athens to the crystal waters of Mykonos, from the ancient ruins of Ephesus to the rising cliffs of Santorini, this custom tailored tour will take you beyond the dreams of antiquity and into the harmonious wonders of the Mediterranean. You will cruise through Greece where castles sit along the waterfront and myths have inspired Western Civilization for millennia. Let the sirens’ song summon you and the diversity of the islands captivate you. This is your time, your harmony, your Greece. 

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Most tours are customized for private travel.

General Information

The ruins of Knossos Palace in Heraklion, Crete, Greece
Detailed Itinerary

Places Visited 

Athens, Mykonos, Kusadasi (Ephesus), Patmos, Rhodes, Crete, Santorini

Departure Dates 

Dates are flexible and customizable for private departures.

Detailed Itinerary 

Day 1: A Luxurious Welcome

Arrive in Athens airport and be met by a private transfer. The arid hills that surround the city offer a romantic hideaway feel as you journey into the ancient city center. You can’t miss the Acropolis rising over the city with its ornate pillars shimmering in the sunlight. Along the foothill of the Acropolis you will find the Plaka, one of the oldest streets in the city. Passionate restaurateurs beckon to you, the freshness of thyme and dill drifts through their open doors. Ancient mansions line the street, giving an echo to people’s footsteps bouncing off of the walls. The beauty of the ancient world is apparent and inherent with your appearance in Greece.

What’s Included: transfer, accommodation

Day 2: The Chronicles of History

The divine perfume of Grecian coffee brings you out into the Athenian world, its dark richness mixing with  sweet sugarcane. Today you will venture into the city and witness its remarkable history on a guided tour. Within the open lobby of the Syntagma Square metro, beneath the palace of King Otto I, you can see the layers of ancient Athens climbing up the wall. Listen to your guide as they point out the rolling past of the city, from streets that led to the port, to ancient burial grounds, to Byzantine churches, all discovered within the last 15 years, giving the residents and visitors alike a deeper connection to, and sensation of, Athenian history.

To many the past has always been romantic, especially those labeled as such by history. The classics have always been held in high regard, which you can now experience for yourself as you step onto the marbled plateau of Acropolis Hill. The Golden Age of Athens continues to glisten with revel; you understand the grandeur of the Parthenon as it stands within yards of your touch. Its pillars are ornate; while the temple looks as though it was constructed perfectly from every which way you look. Myths are carved along the metopes that wrap around the structure and give homage to past battles, from Troy to the Titans, all while celebrating Greek victory and celebrating Athena. The essence of the goddess of wisdom thrives within the beauty of the Parthenon and it is easy to see why.

What’s Included: breakfast, accommodation, tour

Day 3: Enthusiastic Cruising

Antiquity stays in Athens as you venture out into the Mediterranean, cruising the graceful waters and arriving along the coastline of Mykonos. The island is famous for its beaches and cosmopolitan life all wrapped up in the classic whitewashed walls of Mykonos Town. Five windmills line the shore just outside of town, making them look almost like watch towers, guarding the village from the worries of the sea. The waves brush up against the edges of Little Venice, where the homes and stores rise colorfully above the rush of water, once giving easy sea access to merchants. Let yourself unwind in Mykonos and enjoy the island however you desire.

What’s Included: breakfast, accommodation, transfer

Day 4: The Seclusion of Beaches

The day is yours to luxuriate in Mykonos however you wish. With so many gorgeous beaches to explore it would be a shame to not at least relax on one of their pristine shores. The cool waters and hot sands that surround the island are ideal no matter which beach you choose. However, if you prefer more secluded shores you can make your way over to Agia Anna beach at Kalafatis. The quiet waterfront is not crowded giving you a serene and almost private view of the water’s three shades of blue. Dip your toes into the cool sea as the rolling hills give the beach a bay-like quality, protecting the shore and the people from the crowds and the rush of the outside world.

What’s Included: breakfast, accommodation

Day 5: Let Yourself Go Together

Let yourself get lost along the winding streets of Mykonos Town, also known as Chora. The charm of the town is set within the whitewashed walls that stretch along the cobblestone paths. Restaurants set tables next to the calm sea. You can look out into the horizon and watch ships come and go out of view. The colorful stripes of fishing boats add an extra vibrancy to the water. Stroll along the paths of town, where the candied perfume of baklava drifts through the streets. The relaxed pace of the city mixes with the glamor of the cosmopolitan as the structures house a wealth of affluent shops such as Coach and Bulgari. Continue wandering and find local artesian shops that fill the streets with light and ambiance. There is never a shortage of romance on Mykonos, especially when traversing the lovely paths of town. 

What’s Included: breakfast, accommodation

Day 6: Harmony along the Mediterranean

Today you will once again board your cruise ship, departing Mykonos, and setting sail along the turquoise waters of the deeper Mediterranean. Look out over the sea, the mist brushes against your cheeks. The wind grazes your hair. Surrounding the ship is open water in all directions making the sea a darker yet crisper blue. When the sun starts to set over the horizon it seems to sweep across the entire sky giving a passionate glow to the dusk.

What’s Included: breakfast, dinner, accommodation, transfer

Day 7: Never Ruins

The new dawn brings you to the port of Kusadasi set within Turkish waters. The stunning blue of the water gives a cobalt radiance to the morning. The port is known for the nearby city of Ephesus, one of the best-preserved Greek and Roman cities within Asia Minor. The city was once the trade center of the ancient world bringing together the west and the east. Walk along Curete, one of the three main streets of Ephesus which will take you from the Hercules Gate to the Celsus Library. Once fountains, monuments, statues, and shops lined both sides of the street, but have been replaced by the pillars and remnants of the city’s decadent past. The Library of Celsus continues to be a masterpiece of classic architecture. The façade is two stories tall with pockets filled with statues on the both the first and second story. The Greek-Roman senator Celsus’s tomb is beneath the library along with a sepulchral monument to him. The city’s ruins are a work of art unto themselves, not only for what they represent, but also for how long they have survived.

Your exploration continues as you venture back into Greek borders and onto the shores of Patmos. The history of the island is palpable with a monastery towering over the island, built on top of a citadel where a honeycomb of  caves continues to stand, said to be the location where St. John the Divine wrote the Book of Revelations. If you desire you can journey up to the monastery and see the exceptional construction of the building, along with the persistent caverns that weave through the mountain. From the outside the religious center looks like a fortress; from the inside the church looks like a tranquil garden with pebbled squares and romantic arches. You can hear angelic voices chanting liturgy as you wander through the entryway and around the gardens, a unique collection of sights and sounds that welcome you to the Patmos. Frescos decorate the main chapel dating back to the 17th century. The fragrant air of myrrh and frankincense drifts along the garden. Look out over the island of Patmos. The sea blends into the sky on the horizon as the sun sets in the distance bringing the day full circle.

What’s Included: breakfast, accommodation, transfer

Day 8: Take the Romantic Rhodes

The morning brings you to the coast of Rhodes where the colossus once stood over the port welcoming travelers and scaring pirates. Today the island is rich with history reaching back in time and up into modernity. The island, and its history, is yours to explore giving you the opportunity to see the Acropolis of Lindos or spend the day strolling through the charming streets of the old city. A castle is situated along the coast of Rhodes, giving an imposing brick structure great positioning for protecting the island. Now the castle looks like something out of a fairytale, where strolling down the more than 200 streets gives you plenty to explore and lots of private hideaways to find. The Street of the Knights is one of the best-preserved medieval relics in the world. The avenue stretches 1,968 feet long, paved with cobblestones and once leading from the Acropolis of Lindos to the port. The castle continues to line much of the street, bringing you from the Greece beachside to within inches of mainland medieval Europe. Relax in the main square. The trickle of the fountain gives a sweet echo to the bustling life around you.  

What’s Included: breakfast, accommodation, transfer

Day 9: A Touch of Venice and a Spot On the Cliff

The castle along the port of Heraklion, Crete has stood guard over the city since the Venetians occupied the island. The rustic brick continues to look proud and powerful against the harbor behind it. Remnants of the Venetians are apparent throughout the city, from the winding streets that reach over the old port where ships were once built and fixed, to the fortified walls that continue to surround parts of Heraklion. Dive into the wonderful myths of the island with a visit to the Knossos Minoan Palace, where the infamous Minotaur was housed within the king’s labyrinth.

The ruins’ love story was one of epic proportions, when Ariadne gave Theseus the yarn to help him find his way through the maze. Although you’d be hard pressed to find a tangle beneath the ruins of the palace, the essence of the story and the majesty of the site live on. Large stone steps climb into a grand open portico that was once surrounded on all sides by staterooms and dining areas. The queen’s room has stately griffins poised on the walls. A fresco of dolphins drapes across the North Propylaea. There is even an image of people performing what was called a bull ballet, dancing on and around the bovine in hopeful elegance. As the day winds down you will make your way back to the port, board your cruise ship, and arrive along the cliffs of Santorini.

What’s Included: breakfast, accommodation, transfer

Day 10: Unfathomable Color

Today Santorini can open up to you like the caldera, with vast amounts of splendor to see no matter where you look. For a sensational day that will take you to all the majesty of the island you can experience the passion of the locals on a romantic sunset cruise. Don’t let the name fool you, the cruise begins at mid-day in order to show you the unparalleled magnificence that is Santorini. Enjoy a semi-private transfer to the harbor where you will board a spectacular yacht. Weigh anchor and set out into the caldera where the water blends into three shades of turquoise. Pass the lighthouse that stands high over the sea on a wing of the island. Sail past the celebrated Red Beach, the oxidized earth of the cliff rises into the plateau. Traverse the grandeur of the White Beach where the limestone gives the shore its name but the sand is as black as night. The last volcanic eruption brought lava to the surface of the sea; as it cooled it created jagged, black rocks that reach out from beneath the waves. When the sun begins to set you can see the golden orange wrap around the sky, bringing in the evening dark like a shade. The vibrancy of dusk is illuminating and for a moment it feels like of the world is in perfect harmony.

What’s Included: breakfast, accommodation

Day 11: Finding Atlantis

On your final day in Santorini you can hike along a cliff side trail or sit in a café overlooking the caldera; you could visit the black sand of the Red Beach or taste the finest wines of the island. There is always something amazing to take part in, including a visit to what archaeologists believe to likely be the fabled city of Atlantis. The ancient city of Akrotiri is considered Greece’s Pompeii. The ruins have been covered by ash from a volcanic eruption keeping the city’s remains in tact and unspoiled for thousands of years. The romance of history is bright within the preserved colors and vibrancy of Akrotiri. The main street is lined with stores and warehouses where traces of oil and fish have been found in large ceramics. The building of Xeste 3 is a large edifice at least two-stories tall that held fourteen rooms on each floor. Some of rooms are decorated with marvelous wall paintings, including A Seated Goddess, whose hooped golden earrings and multi colored duck necklace add a shimmer to the wall and to history itself. Beneath the wonder of the ruins is the far deeper majesty of human ingenuity and the perseverance of a strong foundation.

What’s Included: breakfast, accommodation

Day 12: Harmonious Asides

Today you will venture to the airport to begin your journey home. Your time across Greece took you from the mainland to the islands, where passion was strong, antiquity was near, and the waters were stunning. Although your holiday may be coming to an end, the memories of the sights and sounds, flavors and aromas of Greece will always be close at hand, bringing you to the precipice of your holiday whenever you’d like.

What’s Included: breakfast, accommodation, transfer


Starting Price 

This trip is customizable for your private travel.

What's Included 

  • Accommodations
  • In-country transportation
  • Some or all guided tours and activities (dependent on season)
  • Expert trip planning
  • 24x7 support during your trip
The starting price is based on travel during the low season for a minimum of two travelers staying in shared 3-star accommodations. Please inquire for a custom trip quote based on your travel preferences and travel dates.