Two-Week Greece Tour: Wine, History & Legends

A 14 day trip to Greece 
5 out of 5 stars
4 reviews

Beauty becomes grandeur and legend becomes history during your personalized luxury tour of Greece offering an odyssey of adventure. Stunning ruins, bleached mountains, whitewashed homes, and turquoise waters accentuate the iconic charms of the mainland as the Peloponnese and Cycladic islands connect the deep well of antiquity with contemporary comforts. Uncover the path of the Minotaur and listen for whispers of the Oracle at Delphi, and then search for wisdom at the Parthenon dedicated to Athena and watch the sun fade beyond a majestic caldera. Indulge in marbled lanes, dramatic fortresses, and the lush countryside for an epic exploration only Greece could accomplish.

Customize This Trip For Me
Most tours are customized for private travel.

General Information

Detailed Itinerary

Places Visited 

Athens, Cape Sounion, Delphi, Spetses, Epidaurus, Agionori, Nemea, Mycenae, Santorini, Chania, Heraklion, Palace of Knossos, Acropolis

Departure Dates 

Dates are flexible and customizable for private departures.

Detailed Itinerary 

Day 1: Athens – Arrive in Greece’s Bustling Capital City with the Day at Leisure

The city of Athens is vibrant and alluring with a blend of Greek history amid the contemporary lifestyle of the lively cafes, sophisticated bars, and restaurants that brim with live musical performances. Your private transfer will greet you at Athens International Airport upon your flight’s arrival and escort you into the heart of the welcoming city. The remainder of the day is yours to get acquainted with the distinctive ambiance along the foothills of the Acropolis. Byzantine churches offer dazzling mosaics within the neighborhoods with village-like ambiance as restaurant terraces fill with the aroma of blossoming bougainvillea.

Enjoy your time of settling in with plenty of time to have a leisurely dinner and take advantage of all that your hotel has to offer.

What’s Included: airport transfer, accommodation

Day 2: Athens – Discover the Ancient Life of Athens with a Full Day Tour

The sunlight washes over the neoclassical houses decorating the streets of the Monastiraki neighborhood. Narrow paths and alleyways weave between vendors and elegant homes, with antique bookshops and an open-air market emitting the aroma of refreshing oranges. Your day will officially begin after breakfast as you meet your guide for an engaging tour of the mesmerizing history layered within the heart of Athens including the birth of Western Civilization through philosophy, art, and architecture. Walking along the slopes of the Acropolis, you will have a fabulous view of the Parthenon above as you marvel at its symmetrical appearance.

Before reaching the top of the hill, your guide will stop at many of the fascinating ancient sites winding along the slopes, including the Odeon of Herodes Atticus. The second-century theater was built as an auditorium nestled into the natural hollow of the mountain. The theater remains in use during the annual Athens & Epidaurus Festival in summer utilizing the fantastic acoustics and well-designed space for Greek operas, musical performances, and dance recitals steeped in within nearly 2,000 years of majesty.

Continue to ascend the marble walkway to pass through the grand gateway known as the Propylaea to reach the world-renowned Parthenon. The elegant ancient structure was erected between the fifth and fourth centuries BC as the ultimate sacred shrine dedicated to Athena the patron goddess of the city. Your guide will be alongside as you explore the 136 fluted Doric columns that stand nearly 35 feet tall with a bulkier base narrowing at the top to produce the illusion of a symmetrical, balanced structure from every angle.

What’s Included: accommodation, tour, breakfast

Day 3: Athens – Explore Fascinating Museums and Visit Cape Sounion

In the morning, the dining room of your hotel will fill with the delightful aromas of freshly brewed Greek coffee and semi-sweet orange juice. You will once again meet your guide with an eager eye ready to discover more of the fascinating layers in and around Athens. The National Archeology Museum offers a different perspective on Greek history as one of the greatest antiquity museums in the world. The sleek design, fantastic displays, and distinct purpose of connecting the museum artifacts to their original destination.

After exploring the vast collections of the museum, you will venture to the coastline at Cape Sounion. The bustle of Athens fades to the tranquility and grandeur of the Temple of Poseidon towering above the Aegean Sea. While the magnificent statue remains safe in the National Archeological Museum, the massive columns and sensational view over the glistening water is unforgettable. At sunset, the burning orange in the sky reflects against the marble standing nearly 200 feet above sea level, and you can end your day in this tranquil setting before returning to town for dinner and a quiet night.

What’s Included: accommodation, tour, breakfast

Day 4: Athens – Experience the Allure of Delphi and the Ancient Oracle

After an early breakfast, your guide will lead you north to the incredible city of Delphi, home to the famous Oracle of Apollo. The sacred city now lies in ruins along the plateau of the Mount Parnassus soaring upwards of 8,061 feet above the Gulf of Corinth. Upon arriving in the ancient city, you follow the Sacred Way, the original road leading from the entrance gate to the Temple of Apollo spanning approximately 656 feet. Votives and treasuries once lined the street and are reflected in the remaining bases and pillars that connect the present to the past.

Little remains of the Temple of Apollo, but the formerly powerful and majestic religious site retains its essence of grandeur. A collection of Doric columns from the fourth century BC rise above sixth-century BC foundations bringing together the ground-plan of an Archaic temple and the style of the late-Classical period. The gigantic theater spreads across a slope of the mountain with foundations laid in the fourth century BC. The 35 rows of rounded stone benches can accommodate 5,000 spectators. Whether standing on stage or sitting in the stands, the theater provides the best views over Delphi and the Pindus Range, which will be yours to take in.

What’s Included: accommodation, tour, breakfast

Day 5: Athens – Relish a Day-Trip to the Serene Island of Spetses

Step aboard the early ferry bound for the island of Spetses. The gorgeous azure waters of the Aegean Sea splash around the windows of the hydrofoil for a relaxing ride to the island port. The long naval tradition of Spetses resulted in an essential role during the War of Independence in 1821 while the homes, shoreline, and landscape retain an individual character. Elegant sailboats glide over the sea having debarked from the old harbor as the sunlight glints against the orange-tiled rooftops covering the buildings that ascend the hilly slopes away from the water.

The briny scent of the sea breeze fades beneath the rich aroma of freshly brewed coffee emanating from the charming cafes along the waterfront. As you stroll around the narrow alleyways hiding boutique shops and quiet restaurants filing with the fragrant citrus of lemon and grilled seafood, you can discover a gorgeous white and black pebble mosaics that feature mermaids, octopi, anchors, and billowing sails. Explore the neighborhood past the port-side beach of Aghios Nikolaos where the sophisticated mansions called kapetanospita overlook the esplanade.

From the edge of Zogeriá beach, you can indulge in the relaxing aroma of pine trees, the refreshing sound of the azure sea lapping against the shoreline, and a breathtaking view sweeping across the water to the coast of Nafplio. The day is yours to determine the course, and your guide will ensure that you have the right level of relaxation and activity.

What’s Included: accommodation, tour, breakfast

Day 6: Nafplio – Travel Ancient Corinth and Uncover the Secrets at Agionori

You will leave behind the splendors and the charms of Athens after breakfast bound for the beauty of Greece’s first capital city, Nafplio, which is located along the shores of the Peloponnesian Peninsula. You will stop in the city of Corinth along the narrow isthmus connecting the Peloponnese to the mainland to discover the compact but extensive ruins of the ancient city. The majority of the remaining site date back to the Roman occupation of Greece occurring during the second century BC beginning with the Battle of Corinth.

The former streets of the city attracted Romans and Greek alike eager to follow the path of legendary Jason of the Argonauts, who stole the infamous Golden Fleece and later drew Christian pilgrims interested in following the gospel of St. Paul who taught in the city. The Temple of Apollo shines as a beacon of antiquity predating the arrival of the Romans. Before excavations on the ancient city began, the columns of the temple acted as the only visible sign of previous settlement existing beneath the sprawl of the contemporary city. The remarkable Doric columns ran six by 15 reaching 174 feet and 70 feet wide. Each column stands over 23 feet tall and were crafted from individual pieces of limestone surrounded by white marble stucco.

Before reaching Nafplio, you can stop once more in search of the hidden castle of Agionori, located approximately 2,296 feet above sea level. Sheep climb along the rocky mountainous terrain with cyclopean boulders suddenly rising into the form of a castle. The structure was erected between the thirteenth and fifteenth centuries AD using the large rocks as a foundation set on the summit for a 360-degree view of the surrounding landscape. Villagers have taken the stones from the castle ruins over the centuries and used them to bolster agricultural terraces on which they grow produce. With yet another day to take it all in, you can organize your afternoon and evening based on your mood and preferences.

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

Day 7: Nafplio – Visit the Ruins of Epidaurus and Enjoy the Wines of Nemea

The charm of Nafplio reflects the Venetian, Ottoman, and contemporary Greek charms captured in the architecture, seaside views, and collection of three separate fortresses. The distinct island fortress of Bourtzi was erected as a pirate deterrent in the fifteenth century approximately 1,968 feet from the port. Your immersion into the epic antiquity of the Peloponnese continues with your arrival at Epidaurus. The small city remains famous as the site of the grand Ancient Theater with celebrated acoustics. The pure sound allows spectators in the back of the 55 rows to hear the performers without the need of amplification. The theater remains in use each summer during the Athens & Epidaurus Festival.

Enjoy the authentic charms of Nemea, a wine-growing region that boasts a history of production dating back 3,500 years. The vines resemble the strands of the Nemean Lion, a mythical beast impervious to human weapons and eventually defeated by Hercules during his twelve labors. Sporadic olive groves provide shade to the sun-drenched scenery changing the dynamic characteristics of the wines by the way the grapes soak up the nutrients in the soil. You can visit a winery known for producing historical wines that appeal to a modern palate. You will taste a sample of a wine made from the typical Greek grape Agiorgitiko. The aromas of plum, cherries, and black pepper drift upwards from the glass paring well with archetypal Greek cuisine like moussaka and dolmades.

What’s Included: accommodation, tour, breakfast

Day 8: Santorini – Traverse Remarkable Mycenae before Flying to Santorini

Depart the glamorous setting of Nafplio early to reach the nearby site of Ancient Mycenae. The fascinating archeological setting acts as the point where enchanting mythology and tangible history converge. The walls are made of Cyclopean rocks known for their size reaching over 42 feet tall and 23 feet thick. The fortifications surrounded the citadel with the entrance marked by the dramatic Lion Gate.

The solid construction consisted of gigantic stone blocks crowned by a central relief of two elegant lionesses flanking a single column. The main path winds along the ascending slopes to reach the Great Court where Agamemnon’s Palace once stood. You will then continue back to Athens to reach the airport for your brief, scenic flight to Santorini. The evening air brings a fresh, cool breeze over the village of Oia as it hovers over the famous island caldera reaching upwards of 328 feet above sea level.

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

Day 9: Santorini - Delight in a Day at Leisure on the Famous Santorini Caldera

In the morning, you will soak in the elegance and the drama of Santorini from your private view in the northern village of Oia. The panoramic view easily lives up to your expectations with the sunlight glistening against the azure water of the caldera and spreading over the iconic whitewashed walls and blue window-trimming of the homes scattered across the island. The day is yours to indulge in the beauty of Santorini at your preferred pace taking to the southern corner of the island in search of the ruins of ancient Akrotiri or relaxing on the pebbled shoreline of Red Beach.

For a fantastic introduction to the island, you will set off on a sunset cruise that will bring you out into the remarkable caldera. As the captain hoists the sails, the breeze will brush against your cheeks to carry the refreshing scent of the briny water and tiny salt crystals sticking to your skin. The sweeping panorama of the island from inside the heart of the volcanic crater showcases the diversity of the landscape as shaped by eruptions over the millennia. From the dark pebbles that shape the coastline at Black Beach to the bleached cliffs that slip into the crystal-clear water at White Beach, the scenic beauty will astonish you.

You can step off of the boat and into the natural thermal springs from the volcanic island of Nea Kameni at the center of the caldera. The height of the island reaches 416 feet above sea level with smoldering fumaroles acting as a constant reminder of the active geothermal activity below. The warm, dark water possesses minerals with therapeutic benefits for your skin for smoother and softer results as you bask in the waters reaching up to 95 degrees Fahrenheit. After a truly relaxing time, you will return to the boat and to your hotel to enjoy the evening as you would like.

What’s Included: accommodation, tour, breakfast

Day 10: Santorini – Embrace the Flavors of Santorini on a Wine Tour

In the morning, your breakfast will be delivered to your suite allowing you to indulge in the comforts of your room while enjoying the view over the sparkling caldera. The shops along Oia open for the day along the marbled streets with the aromas of baklava and Greek coffee emanating from the mouthwatering bakeries. Your guide will greet you where the main road and the pedestrian pathway of the village meet, and then whisk you into the history of wine production on the island. Your guide will point to a series of wineries along the slopes of the island leading to your first destination.

You will soon notice that instead of the familiar trellises, the vines are woven like baskets in order to keep both the grapes and vines protected from the harsh winds. The volcanic soil fortifies the flavors of the grapes while also instilling the vines with natural minerals, which results in a more intense taste. Santorini specializes in producing white wines, embodied in your first sample made from 100 percent assyrtiko grapes. The straw yellow hue contains aromas of citrus peel and honey giving way to a fresh, crisp feel on your palate perfect with seafood, white meats, and savory fresh cheeses.

What’s Included: accommodation, tour, breakfast

Day 11: Crete – Venture to Crete and Settle into the Comforts of Chania

Over breakfast, you can once again indulge in the spectacular view of Santorini from the comforts of your suite overlooking the caldera. Sailboats and fishing boats venture out onto the water as boutique shops are hidden in the labyrinth of Oia. As the morning continues, the shops open their doors with local clothing, paintings, and photographs. Porters will carry your bags to meet your private transfer at the edge of Oia where you can then continue to the airport and arrive in the enchanting historical harbor town of Chania, on Crete. The evocative Venetian quarter overlooks the marina where colorful fishing boats wade in the water and the dramatic watchtower closing in the port.

The remainder of the day is yours to wander among the colorful coastal townhouses that blend atmospheric Turkish and Venetian architecture. The historical charm of the Venetian harbor provides a tangible history deriving from the pastel-colored architecture and labyrinth of taverns, shops, and homes et beneath the Mosque of Kioutsouk Hasan. The house of prayer punctuates the skyline with multiple domes. The structure was erected in the seventeenth century making it one of the oldest buildings in Chania. The contrasting Church of Agios Nikolaos reflects the grandeur of Venetian devotion with bell tower and minaret with a double balcony while the interior boasts a stunning collection of bronze chandeliers floating between the tiled floor and vaulted coffered ceiling.

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

Day 12: Crete – Enjoy the Walls of Samaria Gorge and Treasures of Chania

Your guide will greet you early in the day to escort you to the stunning walls of the Samaria Gorge. The staggering view of Europe’s longest canyon encompasses the nearly 10-mile long steep walls to reach heights of 776 feet above sea level. The water flows from the northern mountains south to the quiet, rich shores of the Libyan Sea. The limestone walls flicker with white as pathways wedged between the rocky crests lead down to the teal-blue waters. Enjoying a hike in the earlier hours of the day allows you to avoid the head of Greece’s southernmost island.

The lush trees fill the air with a pleasant herbaceous aroma leading to bursts of sage and chamomile amid the blossoming white peony and irises in spring. The geological thumbprints along the walls reveal unique striations of umber, silver, and cream showcasing the evolution of the gorge spanning the millennia. Upon returning to Chania, the remainder of the day is at your leisure to relax along the esplanade or explore more of the city’s maze-like alleyways. For a refreshing afternoon, you can bask in the sunlight and golden sands at Falassarna, where the olive groves brush against the edge of the shoreline and clear turquoise water laps beneath lines of lounge chairs.

What’s Included: accommodation, tour, breakfast

Day 13: Crete – Walk the Paths of the Minotaur and the Archeological Museum

Travel to the capital of Crete and Greece’s fourth-largest city at Heraklion with an introduction to the power and prestige of the Minoan culture at the Palace of Knossos. The fascinating archeological site dates back to the twenty-first century BC with the main palace grounds erected around 1450 BC. Walking around the capital of the Minoan civilization reveals an impressive scale of baths, private apartments, and frescoes exploring the far reach of the culture from historic trade.

Taking a step away from the ancient grounds of Crete leads you into a gallery brimming with artifacts on display in the Archeological Museum of Heraklion. The contents of the collection date back to prehistory on the island reaching more than 7,000 years old and leading up to the Roman Empire. The incredible history and captivating aesthetics of the gallery culminating in works like the statue of Isis-Persephone holding a sistrum and the actual fresco of the Bull-Leaper.

What’s Included: accommodation, tour, breakfast

Day 14: Crete – Return to Athens and Depart for Home

In the morning, the history of the Palace of Phaestos accentuates the fascinating myths of Knossos. Phaestos represents the unrenovated perspective of an ancient Minoan palace with ruins dating back to the seventeenth century BC. A paved courtyard looks out over sunbaked hillsides. Colorful fishing boats wade in the old harbor in view of the old walls and preserved Venetian fortress. Your private transfer will greet you in the lobby of your hotel and escort you to Heraklion International Airport, where you will soon reach Athens and continue home with your international flight.

What’s Included: airport transfer, breakfast


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.