Historical Greece and Beautiful Santorini Vacation

A 11 day trip to Greece 
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Find beauty within history and elegance on this vacation that will take you through the wonders of Greece’s antiquity and onto the stunning cliffs of Meteora. Stroll through pillared walkways and stand beside the steps of the Parthenon. Walk among champions in the ruins of Olympia and listen to the predictions of the Oracle at Delphi. Whether within the ancient city of Akrotiri or settling within the picture perfect villages of Santorini, open your eyes and let the beauty of history and modernity course through you. 

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General Information

Rocky view of Meteora in Greece at sunset
Cliff view of the Meteora pillars and monasteries
Detailed Itinerary

Places Visited 

Athens, Olympia, Delphi, Meteora, Santorini

Departure Dates 

Dates are flexible and customizable for private departures.

Detailed Itinerary 

Day 1: Histrionics of History

Your journey begins as the plane soars over the Atlantic en route to the fabulous past and beautiful present of Greece. The legends of ages have been whispered through books, poems, movies, and music that beckons to you. As your flight continues into Europe you can easily imagine the splendor of history being inspired by the Golden Age of Athens, and predictions of the oracle at Delphi, and the pride of the Olympics. The adventure through Grecian wonder has only just begun.

What’s Included: breakfast, dinner

Day 2: Athenian Wisdom

Welcome to the wonderful city of Athens where the dedication to the goddess Athena continues to drape over the city’s reputation, in its name and in its architecture. The Acropolis watches over the ancient city with the pillars of the Parthenon shimmering in the morning light. The marble temples that continue to look out over the city have decorated the skyline for millennia, coveted by Athenians and occupiers alike. Rising up the foothill of the Acropolis is the charming Cyclades neighborhood of Anafiotika.

The whitewashed walls rise up the slopes of the Acropolis giving an island feel to the mainland, built by settlers from the islands that helped build King Otto I’s palace. Bougainvillea drape over the ceilings and walls giving the white glimmer of the neighborhood shade and color. The cobblestone pathways are narrow and elegant, meandering beneath ancient history. The luscious aroma of baked saganaki cheese and creamy olive oil lingers in the streets. There are plenty of ways to get acquainted with Athens, this is just one of the best.

What’s Included: transfer, accommodation

Day 3: The Beginnings of History

Let the morning shine over Athens bringing with it the delicious scent of fresh coffee, dark roast mixed with a touch of sugar. Venture out of your hotel and the real tour of Athenian history begins, from the ancient to the contemporary. King Otto I’s palace gives a pink sheen to the Syntagma Square, Constitution Square. Once the building stood for European aristocracy, now the white marble palace holds the Greek Parliament. Centuries guard the palace with stern looks, gazing far into the distance as if ready for the impending raid that will never come. On the hour there comes a chant in the distance, a collection of soldiers marching through the square. It is the changing of the guard, a series of choreographed steps and salutes to the Unknown Soldier that takes the old guard out and brings the new guard in.

The jewel of Athens has been winking at you since you arrived in the city. Follow your guide to the top of the Acropolis where the stone steps give way to a mountain paved with marble. The Propylaea is the entrance gate that has proudly stood in watch over the temples, allowing and denying entrance for thousands of years. Its columns are impressive and intimidating, thick and tall. Step through the entrance and find yourself at footsteps of the Parthenon, one of the most famous ancient temples in the world. This isn’t just a picture in a postcard; you can see the intricate detail of the pillars, each one shape by the architect to be a specific puzzle piece, allowing the temple to look perfect from every angle. You can see the detailed carvings that decorate the metopes, telling bits of battle myth and history, from the Titans to the Amazonians, all the while celebrating Athena and her city, Athens.

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

Day 4: Earlier than History

Go deeper into history as you watch the marble columns of the Parthenon fade into the horizon. The hills roll into the distance with the distinct spread of olive trees lining the earth. The lush scent of the trees and the earth spreads across the countryside. Walk through the giant monoliths of Mycenae, once believed to be built by giants because of the gargantuan size of the stones. Within the ruins of the rising walls is the tale that Homer once described in the Iliad, that of Agamemnon. His tomb sits within a beehive mound, where a gold plated mask of his was once found. The sun is warm in the sky and the stones are cool to the touch. Lions Gate rises over an entryway where two lions are engraved standing against, and supporting, a pillar. The gate, over 10 feet tall, guides you into the ruins of Mycenae and the majesty of the past that once thrived and fell within its walls.

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

Day 5: The Beginning Games

When the morning sun reaches over the edge of the earth you will venture out into the remains of Olympia, where the games that continue to bring the world together every four years were begun. Along the east colonnade of the Palaestra are pillars that line the walkway. Once a roof would have hovered over the path in an opulent gleam. Marble columns continue to decorate the historic site including the impressive remains of the ancient Temple of Zeus. The grandeur of the ruins is a glimpse into the depth of culture and prosperity of the city; the height of what remains of the temple is magnificent. Within the museum are 42 figures that decorated the two pediments of Zeus’s temple. You can also witness the figures of Zeus and Centaurs that once lined the entryways of the temple. 

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

Day 6: Whisperings of Antiquity

The morning stretches over the ruins and gives a beautiful frame to Delphi sitting on the slopes of Mount Parnasssus. The mountaintops roll through the sky casting shadows over the remains of the once great city. Look out over the mountain range and you can see where people from all over western civilization, from kings to politicians, would venture up the foothills to visit the oracle. The cool air is filled with the scent of granite and time. Stones rise up the mountainside. This was considered to be the place that human beings were closest to the gods. The Sacred Way is a footpath paved with stones during the Roman period with a width of over 10 feet. The Temple of Pronoia Athena is one of the most iconic images of Delphi, for its rotunda and the shifting color of the marble. Fragments of columns encircle the round platform and connect to the standing pillars that remain before the backdrop of triumphant peaks. Within the midst of them you can close you eyes and almost hear the prophecy of the oracle lingering along the hills.

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

Day 7: History High in the Sky

Within the skies, over looking the city of Kalamaka, are the monasteries of Meteora. Built into the limestone precipices that tower over the city are stunning churches that have blessed and watched the valley for centuries. Stairs ride along the cliff to the top, each precipice home to a different monastery. From the top you can make out the sensational structures that are camouflaged by the rocks from below. The mountains ramble along the skyline in the distance. The city sits silently along the dale. The largest monastery is the Holy Monastery of Great Meteoron. Beneath the main floor where, along the depths of the cellar, are not only ancient casks of wine but also a collection of tombs from monks past. The odd shape of the windows creates a magnifying effect reflecting light onto specific frescos and icons throughout the year. When the sun shines the stories are told with such vibrancy that spirit comes to light and life.

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

Day 8: Crescent Splendor

The pristine sheen of the Mediterranean sparkles beneath you as you fly from Athens to Santorini. Once on the famed island you have a semi-private transfer to your hotel where the leisure of Santorini will wash over you like waves on the shore. Look out over the caldera where the majesty of the island begins. The calm water lulls against the rocks below. Sailboats glide through the sea. The whitewashed walls that are known to grace the fronts of postcards and paintings glisten in the afternoon light. This isn’t just a historic island, this is the island of fantasy, where blue roofs color the skyline and trails meander between villages. Relax, revel, and enjoy your time on Santorini.

What’s Included: accommodation, breakfast, transfer

Day 9: Luxurious Leisure

Watch the morning sun angle the light on the whitewalls of the island homes, giving a pink hue to the early day. The day is yours to spend it as you please with the entirety of the island at your whim. For a fabulous treat you could journey through the caldera on a catamaran. A semi-private transfer picks you up from your hotel and takes you the marina. The scent of the sweet sea and fresh grilled seafood blends together for a sumptuous moment. Once aboard the catamaran the wind blows through your hair. The cool air is a delicate grace. Step onto the shores of the volcanic tip, where at its peak you can see the wisps of smoke that escape from the cracks. Dip your toes into the hot springs where the clear color of the water shifts to a royal blue, taking away the ground below but adding a sensational radiance. Along the northwest cliff of the island you can see the sparkle of Oia, an immaculate village made of whitewashed homes and marble streets. When the sun drifts behind the horizon a golden orange absorbs the entire sky and drapes over the town.

What’s Included: accommodation, breakfast

Day 10: Antiquity Returned

History is speckled all over Greece, from the mainland to the islands; with another day at leisure you could lounge along the oxidized cliff side of the Red Beach, or you could visit some of the ancient glory of Santorini set within the city of Akrotiri. There is theory that Akrotiri is the location of Plato’s mention for the Lost City of Atlantis, covered by ash from a volcanic eruption over thousands of years ago. Today the city is preserved in its ashen state, giving presentation to how people once lived. Along the main road you can see warehouses and home where jars hold trace remnants of oil and fish after all this time. The air is filled with the scent of hardened ash and ancient earth. The West House is a small but well-organized building. The ground floor is for workshops and the kitchen. The upper level has a room embellished with stunning frescos and a frieze of a flotilla in miniature that wrapped around the four walls depicting an immense voyage, telling a story about the journey. The sensation of Santorini is not just within its panorama but within its rich history as well.

What’s Included: accommodation, breakfast

Day 11: Remembering History and Island Beauty

Today you will watch the crescent shape of the island fade into the waters of the Mediterranean as you make your journey home. The colors of Santorini continue to shine in your thoughts while the Greece’s past will always be at the forefront of your memories. You have witnessed the legendary beauty of antiquity set deep within the rising stones of the country’s past and on the cliffs of Santorini’s caldera. The history and magnificence will never leave you and is always ready for another visit.

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.