Classic Greece Vacation 2019

Beautiful windmill villa in Oia, Santorini, Greece
A 12 day trip to Greece 
4.97 out of 5 stars
153 reviews

Updated for 2019, discover the awe of classic Greece on this 12-day vacation through the holiest sites of antiquity and the need-to-see islands of today. Stretched across the mainland of Greece and speckled along the Mediterranean are the majesty of history and the charm of the contemporary. From the oracle at Delphi to the caldera of Santorini, visit the quintessential sensations that make Greece exceptional. Sit along Greece’s beaches, see the mountains, and be ready to enjoy the classic delights.   

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General Information

Ocean view from the white houses of Santorini, Greece
View of the famous rock formation, Meteora in Greece with an Eastern Orthodox monastery built atop
An infinity pool view blending into the Aegean Sea in the background | Grace Hotel, Auberge Resorts in Santorini, Greece
Groups of tourists exploring the Acropolis of Athens with the Partheon and the Erechtheum temples in view
Aerial shot of Saint Paul's Bay in Rhodes, Greece
Caryatid pillars on the Erechtheion Temple in Acropolis, Greece at sunset
Panoramic view of Oia, Santorini, Greece at midday
Coastline view of Little Venice with waves splashing in the foreground and colorful buildings in the background | Mykonos, Greece
Upward view of one of the monasteries on Meteora in Greece
View of monasteries on top of Meteora rock pillars with the village of Kalambaka in the background
Rocky view of Meteora in Greece at sunset
View of the ancient Library of Celsus in Ephesus, Turkey
Close up of the intricate architecture in the city of Ephesus, Turkey
Tourists walking through the streets of Ephesus, Turkey appreciating the ruins and the architecture
Upward view of the intricate architecture of the Library of Celcus in Ephesus, Turkey
The mountain top of the Acropolis of Athens
The white, battered walls of the Paraportiani Orthodox Church in Mykonos, Greece
The old city square of Rhodes, Greece
View of Santorini, Greece and a couple of windmill villas at dawn
The facade of the Celsus Library in Ephesus, Turkey
Cliff view of the Meteora pillars and monasteries
Detailed Itinerary

Places Visited 

Athens, Mycenae, Olympia, Delphi, Kalambaka, Piraeus, Mykonos, Kusadasi, Patmos, Rhodes, Heraklion, Santorini 

Departure Dates 

Dates are flexible and customizable for private departures.

Detailed Itinerary 

Day 1: Classical On the Mind

Depart home with the wonder of classical Greece on your mind. From antiquity, with the pearled statues carved from marble and with the famous quotes of philosophers, to the classic architecture of the Cyclades, the archetypal dreams of Greece are at your fingertips. They beckon to you like an irresistible song of the sirens telling you to come closer and stay awhile. With statuesque history in mind and the gentle sweep of the coming beaches lingering in your ears, it is hard to keep the excitement from boiling over as you make your way ever closer.

What’s Included: breakfast, dinner

Day 2: A Classic Welcome

Arrive in Athens and let your eyes wander through the rolling hills outside of the city. The famous olive trees spread over the arid mountains giving the outskirts of the city a luscious scent of soothing oils. Once in the city center you can see the variety of the life beneath Acropolis Hill; the pearl columns and porticos stand over the bustling streets of both modern and classic Athens. Settle into your comfortable accommodation and traverse the beauty of the city, where the cobblestone streets of the ancient city are filled with shops, markets, restaurants, and people. Stand around the wonders of classic Greece and revel in the delight that you’ve arrived.

What’s Included: transfer, accommodation

Day 3: Touring Antiquity

Today you will venture out into Athens and travel back through time to visit the famous sites of the city that have inspired Western Civilization for millennia. Within the wonders of history are the dreams of many, where people wish to see what had once stood proudly over the city, or how the statues had been positioned. Visit the New Acropolis Museum where you can journey through the richness of Athenian art.  The stunning structure of the museum gives a prominent home to the ages of the city while at the same time giving a splendid view of the Parthenon along the third-floor, where the windows offer a panorama of the famed temple. View the Caryatids, detailed statues of woman dressed in togas with their hands modestly at their sides that were once the support for the Erechtheion on the Acropolis. There are five statues but six basins; the empty basin is a reminder of the Caryatid displayed at the British Museum in London.

Out into the open air museum of Athens brings you to the base of the Acropolis. The stone steps start to smooth and glint as they shift to pure marble. The gentle light of the afternoon reflects off of the magnificent columns of the Propylaea, the entrance gate to the Acropolis. Standing beneath the edges of Western Civilization elevates your heart rate. The classic image of days gone by stands on the opposite side of the gate. Step through the Propylaea and stand at the top of Acropolis Hill. The modern city of Athens sprawls around the hill, from the water’s edge to the reaching mountains. On the left are the replicas of the Caryatids supporting the Erechtheion, a temple dedicated to both Athena and Poseidon. On your right is the impeccable Parthenon, where the architect shrewdly constructed the dedication to the Goddess of Wisdom in a way that would look perfect from every angle it was viewed. The porticos continue to adorn the entrances of the temple while their carvings are on prominent display. The earth is rich and the breeze is welcome as you circle the wondrous classic of Western Civilization.

What’s Included: accommodation, breakfast, tour

Day 4: Standing on Bronze

Wave goodbye to the pearl-like pillars and the Golden Age of Athens. Today you depart the city on your way to the famed city of Olympia, but first you will stop to experience the splendor of Mycenae. The Acropolis situated over the valley is where you can find the remains of the Bronze Ages site. The ruins recall the once powerful past of the Mycenaean civilization that dominated the Mediterranean around the 12th century BC and are linked to the Iliad and the Odyssey. The Treasury of Atreus, also called the Tomb of Agamemnon, gives you a sense of awe, from the climbing stones to the open door that looks as though it supports the hill above. The mask of Agamemnon was found within the tomb where remains of houses encircle the grass above.  Stand beneath the Lions Gate where you can see the large limestone carving of two lions pressed against a pillar; the stone is wedged as the adornment over the entrance. While at Mycenae you aren’t just walking along the steps of history but within through the celebrated poems of Homer. Discover the glory of eternal fame before making your way to Olympia.

What’s Included: accommodation, dinner, tour

Day 5: Pride and Games

Everyone knows the story of the Olympics, how even warring city-states would put down their swords during the integral games that happened once every four years. There is always much more to history than what people learn in grade school and today is your chance to not just learn about the Olympic games but to revel in their truths and myths while standing within their founding city: Olympia. There is a sense of competitive edge to the air, where past athletes wrestled and ran for themselves and country.

The remains of the ancient city streets are lined with pillars where ceilings once stretched the length of the pathway. The Heraeum is a temple dedicated to Hera, Zeus’ wife. The temple is the oldest known Doric building and once held a table on which garlands were placed, prepared for the victors in the games. The pillars are circular and you can see where the stones were cut and placed together. The temple’s design was feminine and empowering, giving homage and strength to the goddess and those that paid her tribute. Throughout the classic site there is the ever-present feeling of wonder, of pride, and of the cool breeze that flows in from the hills. In the afternoon make your way through the city of Patras where a medieval castle stands side-by-side with a Roman Odeon, before settling in for the night in Delphi.

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

Day 6: Facing the Oracle

The sunrise casts a glow over one of the most important archaeological sites in Greece, one which has attracted travelers from all over the world for thousands of years all wanting a private visit with the eminent Oracle. The town is quaintly situated along the hillside, with stone streets and stairs that climb through the landscape. The red-shingled roofs give a redbrick color to the city’s crown. At the foot of Mount Parnassos, situated between twin rocks, is the sanctuary of Delphi. The Temple of Pronoia Athena is on prominent display. Within the stone circle lie wedges of columns that once surrounded the center, with pillars that continue to rise, framing the mountainous background of the site.

The scent of pine and aged marble fills the temple air. You can see the open space and tiered benches of the stadium situated near the theater that rises up the hillside. On the back of the wind you can almost hear the whisper of the oracle willing you to ask the question to the priestess of the temple. There may no longer be an oracle of Delphi but the magic of the city and the ruins continue to surround the legends. As the day begins to fade you will make your way to Kalabaka for the evening.

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

Day 7: A Matter of Monasteries

The city of Kalabaka sits beneath the looming cliffs of the surrounding mountainside. The city is pleasant and quaint, cast in the present and blessed shadow of Meteora. Meteora means “middle of the sky,” and that is where you will find the monasteries, over 1000 feet above the city, atop varied pinnacles beside the Pindos Mountains. Six different monasteries stand over the valley with views of the snowcapped mountains in the distance, the stone splendors reachable by staircases carved into the mountains themselves.

The stained glass and vibrant walls within the churches celebrate the history of Christian orthodoxy, with paintings that harken to the Sistine Chapel; ceilings and walls painted with gilded splendor that connotes the dedication to, and prestigiousness of, the church. Explore the inside walls and alleys, where you would never know that the surrounding winds rush past the protruding buildings. The stature of each structure and the sensational interiors, along with their ability to build such a display of grace and elegance along a pinnacle of great magnitude, will more than delight you; it will take your breath away. In the afternoon you will return to Athens with the phenomenal visit playing like a slideshow in your memories.  

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

Day 8 – The Chic Delights of Mykonos

Today you climb aboard your cruise liner and touch down on the celebrated shores of Mykonos. The island is known for its sensational stretch of beaches where the glassy color of the water laps calmly at the shores. Whether you prefer to spend the day luxuriating with your feet resting in the hot sand at Super Paradise Beach or would rather stroll through the labyrinthine streets of Mykonos Town, the remainder of the day is yours to enjoy the island. Along the lovely meandering paths of the town you will find the colorful walls of Little Venice. The buildings are pressed together and sit above the rush of waves at the port, once owned by wealthy merchants and presumed pirates. The remaining buildings are classic Cyclades, with pristine white walls that help reflect the sunlight keeping the interiors cool in the depths of the summer sun. The stone walkways are quaint and inviting as they pave the way to precious boutiques, chic shops, and mouth-watering restaurants. The more you walk the more you can follow the aroma of fresh grilled seafood and lemon zest. The easy wash of the waves is somewhere in the distance. The town gives you the freedom and illusion of getting lost, even though it doesn’t seem that big.  Enjoy the serenity of the island as the orange glow of the sun starts to cover the sky.

What’s Included: breakfast, accommodation, transfer

Day 9: Along the Ottoman Empire

Arrive in the morning along the shores of Kusadasi, home to much of Greece’s history that now sits within the borders of Turkish waters. Step ashore and visit the ancient city of Ephesus, once an established port city. The port had a vast role in the country’s past due to its strategic location and the surrounding fertile valley.  Meander along the paved street which will take you to the central ruins. Pillars line the walkway giving you a feel for what the city may have been once. It is easy to imagine the grandeur, including where the Temple of Artemis stood, one of the Ancient Wonders of the World. The current ruins may not be as vast as the ancient temple, but they are no less magical. The quiet sound of shuffled feet on pebbles fills the empty air. You almost gasp as you reach the remains of the Library of Celsus. The pillars are stacked atop one another, separated by metopes, creating an opulent two-story façade. Where Artemis’s temple once stood you will find a single column, almost like a tribute to one of the greatest and most humbling structures that had ever been built. 

After your visit to Ephesus you will journey to the island of Patmos where you have the option of visiting the cave where John the Divine wrote the Book of Revelation. Whether within the impressive monastery or the serenity of Chora, which means Patmos Town, the remainder of your day will be splendid. The white walls of houses in the town stretch from the shoreline to the mountainous plateau, situated beneath the grand monastery. The streets can only be described as quaint, where each corner you turn brings you to another square filled with bright tables and chairs that make you want to take a seat and sip a coffee. The monastery is proud above the town like a medieval castle insuring the protection of all within its sight. From the mountaintop to the seaside, Patmos will give you a chance to bask in the tranquil comfort the island.

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

Day 10: Along the Classic Rhodes

Step onto the shores of Rhodes with the eclectic mix of culture and history making its mark on the old city. Enjoy a day to discover the many luxuries of the island at your own pace, including the Acropolis of Lindos. Overlooking the modern town of Lindos, the Acropolis also has a backdrop of the open sea, where the blue of the water blends into the sky. The gentle breeze comes off of the sea bringing the sweet and salty aroma with it. The theater sits below the Temple of Athena where the circular auditorium was hollowed out of the side of the hill once holding 1,800 people. The old agora gives way to five remaining pillars where a grand staircase rises above the citadel giving you a view of the sensation below.  The Acropolis of Lindos is one classic remnant of the ancient Greek community that thrived along the shores of Rhodes, giving you another moment of connecting serenity with wonderful remains of an inspiring civilization.

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

Day 11: Venetian Port to Pristine Cliffs

Arrive in the capital of Crete, Heraklion, with the beauty of its Venetian past decorating the port. The castle proudly stands on the outer limits of the city guarding  the continuing rich history of the city and island. The morning and the city are yours to discover along with their gems as you see fit. The Knossos Minoan Palace, home to the notorious Minotaur, is a short distance outside the city center, The bohemian cafes of the city rest along Deadalou, where the boisterous conversation of artists and those who want to be around artists mixes with the sweet scent of fresh pastries, candied baklava and luscious Cretan pancakes, a pancake as thin as a crepe, stuffed with rich cheese, and covered in honey. The Venetian Loggia stands out just off of the main square with its prominent demeanor, arched windows and open marbled gallery. Your footsteps echo as you walk through the foyer.

Your afternoon finds you along the cliffs of Santorini where the famed whitewashed buildings bring you face-to-face with the postcard images of places you’ve always wanted to visit someday. Whether you prefer to stroll along the pathways-a-plenty of the capital Fira or explore the villages of the island, there is plenty of time to spend indulging in the grandeur of views and exceptional antiquity that has made the island so popular. You could even visit the ruins of Akrotiri, fabled to be the remains of Atlantis, and known to be Greece’s Pompeii. Frescos depict gods and life within the ancient town, such as a man holding stems of fish after a morning at sea. The structure known as the West House has storerooms, workshops, and a kitchen on the ground floor. The upper floor holds a spacious room used for weaving and two rooms embroidered with magnificent murals. Pots were found in the precise positioning of where they would have been thousands of years ago, complete with trace remains of fish, oil, and wine. The wonder of the city sits within its majesty, its mystery, and how it can transport you back to the way life could have been.

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

Day 12: The Classics Always Delight

Today you will return to Athens with the memories of the past winking at you from afar. Your time in Greece has taken you along the steps of the sacred temples that have mystified humanity for millennia; you have taken to the seas to experience the islands’ waters and the rush of fascination that comes with each shore. You have walked with gods and epic poems, Grecian antiques and Venetian remains. There is no telling what more you could have seen. You do know, however, that classic Greece has been no less than a delight to experience, practically taking your breath away around every corner.

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.