Best Greek Islands Vacation in 8 Days

A 8 day trip to Greece 
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This is your custom tailored vacation through the Greek Islands that will bring you to the precipice of grandeur. Look out over the never-ending wonder of Greece, where famous philosophers and humanity thrived, and get ready for an unforgettable vacation designed specifically to highlight the famous Greek islands and Athens. 

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Most tours are customized for private travel.

General Information

Detailed Itinerary

Places Visited 

Athens, Mykonos, Delos, Santorini

Departure Dates 

Dates are flexible and customizable for private departures.

Detailed Itinerary 

Day 1: Island Beginnings

Welcome to Athens, the gateway to the islands and the cradle of Western Civilization. At the airport you will be met by a private transfer that will take you into the center of the ancient city, where you can breathe in the history that has inspired people, countries, and the world alike. Acropolis hill rises over the city at its core, literally and figuratively, once that actual center of history. Wander along the foothill of the Acropolis and enjoy a taste of the islands to come with a visit to the neighborhood of Anafiotika, a stunning area of whitewashed homes that climb up the slope of the hill. The neighborhood was built in the 19th century by villagers brought from the Cyclades to give them a reminder of home. The narrow paths are nothing less than charming, as bougainvillea give a burst of color to the immaculate walls. The sweet aroma of flaky filo filled with rich cheese drifts from a tiny restaurant along the stairway, welcoming you inside and into Greece.

What’s Included: transfer, accommodation

Day 2: Historic Possibilities

The wonder of the Athens is at your beckon call this morning on a guided tour of the ancient and modern history of the city that encompasses all of Greece. An overview of Athenian past has you exploring the grand collection in the New Acropolis Museum. The third floor is dedicated to the Parthenon with a panoramic view of the temple on top of the hill. On the first floor you will walk past archaeological treasures guarded by a rail but open for everyone to see just how shallow anyone can dig within the borders of Athens to find remains of the old city. The magnificent display of statues within the foyer not only allows you a sense of the importance of art amongst the Greeks but also shows the attention to detail even with chiseling a person’s beard out of stone, for which each strand of hair looks accounted.

Atop Acropolis Hill is the imposing entryway known as the Propylaea. The thick and massive pillars continue to give the proud and important air to the citadel. The scent of earth and history surrounds you, from the marble of the columns to the marble paved floor, the air swirls with passionate antiquity. Within the confines of the Acropolis you can see the stunning Parthenon, a temple dedicated to the goddess Athena. The celebrated structure has been revered for millennia, for its perfect construction to its richly carved metopes and pediments, displaying the myths of Athens and gods alike. It is not hard to understand why this particular temple is considered the symbol for the Golden Age of Athens, which stands before you like a treasure.

What’s Included: breakfast, accommodation, tour

Day 3: Island Promises

The desire for an island getaway can never be satisfied until you experience the incredible shores of the Greek Isles. Today you will make your way by hydrofoil to the marveled island of Mykonos. You almost have to prepare yourself for the unparalleled beaches, pristine waters, and charming streets yet to come. The pillars of ancient Athens fade from view. The turquoise waters of the Mediterranean reach into the horizon. Disembark at the port of Mykonos where you can see five immaculate windmills on a wing of the island. The wheels spin slowly in the cool breeze of the late afternoon. The waves brush against the shores. You can see the colorful walls of Little Venice, a short group of connected buildings that linger above the waves. The sweet scent of the sea lifts into the breeze. There is no mistaking it, the sands are close and you have arrived.

What’s Included: breakfast, accommodation, transfer

Day 4: Island of the Gods

Enjoy your breakfast by the pool where you can hear the gentle rush of the waves along the sand. The day will bring you along the incredible shores of Delos, the birthplace of the gods Apollo and Artemis. The city was once a prosperous trading port, an ancient civilization with decorated houses and running water. The ruins of the city spread over the valley and along the hillside. There is a grace within the marble ruins of the city that continues to wrap around the remaining columns. At the foothill of Cynthis the propylaea of the Temple of Isis stands over the valley. Between the pillars you can see the remaining bust of Isis situated proudly over the once prosperous city.

The marble lions that guard the Sacred Lake, where Apollo was born, are poised and proud; you can imagine them coming to life at any moment to protect the sacred grounds. The immaculate color of marble washes over the ancient ruins guiding you through history, while at the House of Dionysus there is a vibrant mural that decorates the floor, bordered by a textile of rolling waves. The mural depicts Dionysus, God of Wine, successfully riding atop a tiger. The elegance of the mural, along with the grace and grandeur of the remains of the city are remarkable.

What’s Included: breakfast, accommodation, tour

Day 5: Clear Waters and Stellar Cliffs

The morning arrives with the light shining off of the calm sea. Enjoy your breakfast with the cool breeze of the early day, the aroma of fresh coffee swirling through the air. After breakfast you will have a semi-private transfer to the port where you will hydrofoil through the tremendous turquoise water of the sea. The crystal beaches of Mykonos have dissipated beyond the horizon; however, the cliffs of Santorini now begin to come into view. The boat glides into the caldera giving prime view of the crescent island before you. The whitewashed homes crawl along the cliff side, clustered in distinct villages. Arrive at your fantastic accommodation with a view that overlooks the caldera below. The rocky surface of the protruding tip of the volcano sits at the water’s center. There is an outstanding blue that rises from the sea, blending into the sky, where the sun begins to set.

What’s Included: breakfast, accommodation, transfer

Day 6: Crescent Allure

The day is yours to spend it as you wish along the spectacular cliffs of Santorini. Spend the day lounging by the infinity pool where the endless waters offer a gentle trickle to the perfect panorama. You could even visit the spectacular lost city of Akrotiri, believed to be the basis for the lost city of Atlantis. The city was covered in ash from a volcanic eruption over three thousand years ago. Now the preserved remains of the city sit untouched, slowly being excavated to help Greece and the world understand a large part of our past.

Walk down the ancient main street surrounded by buildings that were once shops, homes, and warehouses. Jars stand outside with traces of oil and wine inside. The rich scent of volcanic earth drapes over the city. You can almost imagine the bustle of the main street during the height of Akrotiri’s existence. The area known as Complex Delta encompasses four houses. One room is decorated with the spring fresco. The texture of the mountains gives a special sensitivity to the rocky landscape covered in blossoming lilies. Colors burst from the wall, graceful and elegant against the textured ashen exterior of the buildings. The magic of the island isn’t just within its views but also within its superb past.

What’s Included: breakfast, accommodation

Day 7 – Return of Antiquity

Soak in the gentle panorama of your view at breakfast once more. The rich perfume of Greek coffee is lifted by the breeze. A semi-private transfer will take you from your hotel to the port. Board the hydrofoil and sail across the Mediterranean back to sensational city of Athens. The afternoon is yours to enjoy the city once more, bringing you to the footsteps of the Acropolis. Let the sun drive across the sky as you enjoy your time along the Plaka, the oldest continuously inhabited street in Athens. The charm of the cobblestones and the narrow pathways brings you to an entirely different city than that which you left. The sweet aroma of revani, cake soaked in simple syrup, rushes along side you, settling you back into Athens.

What’s Included: breakfast, accommodation

Day 8: Island Dreams

Today you will journey from the Athens city center to the airport for your flight home. Your time along the ancient sights and the islands was nothing less than stellar, showing you the sensational wonders of the ancient and the modern, from cosmopolitan beaches to pillared perseverance, splendid panoramas to lavish art. Although you may be on your way home, whenever you miss the islands all you have to do is close your eyes and remember your extraordinary holiday; Greece will be here waiting when you’re ready to return.

What’s Included: breakfast, 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.