If you have more than a couple of weeks to travel, this epic 18-day trip around Greece is a fantastic choice. The itinerary takes you to ancient monuments, idyllic islands, clifftop monuments, family-run wineries and so much more! Start in Athens before hitting the road for a self-guided car trip around the mainland's historic ruins, including Olympia, where the original Olympic Games were held. Then it's time to island-hop to Milos, Santorini, and Crete, enjoying active excursions and relaxing beach time along the way. You'll dine in local taverns, boat around the coast at sunset, and stroll through quaint villages, culminating the trip with an unforgettable hike through Samaria Gorge on the island of Crete.


  • Sample gourmet delicacies on a food tour of Athens
  • Explore the mainland's top sights on a 5-day road trip
  • Hike to waterfalls near the original site of the Olympic Games
  • Sail across Cape Sounio at sunset
  • Sip wine at a local winery on the island of Santorini
  • Hike and visit caves on the island of Crete

Brief Itinerary

Day Highlights Overnight
Day 1 Arrive in Athens & Sightsee Athens
Day 2 Visit the Acropolis & Go on a Food Tour Athens
Day 3 Catch the Sunset Over Cape Sounio Athens
Day 4 Visit Mycenae & Nafplio Olympia
Day 5 Tour Olympia & Hike to Waterfalls Galaxidi
Day 6 Learn About Ancient Traditions in Delphi & Amfissa Meteora
Day 7 See the Monasteries of the Meteora  Kranea
Day 8 Explore the Pindos Mountains Athens
Day 9 Catch the Ferry to Milos Milos
Day 10 Boat Around Milos Milos
Day 11 Relax on the Beach in Milos Milos
Day 12 Take the Ferry to Santorini Santorini
Day 13 Taste Wines in a Local Winery Santorini
Day 14 Enjoy a Catamaran Cruise  Santorini
Day 15 Travel to Heraklion Heraklion
Day 16 Visit the Cave of Zeus & Attend a Wine Tasting Heraklion
Day 17 Explore Samaria Gorge with a Local Guide Heraklion
Day 18 Depart Heraklion - End of Trip  

Detailed Itinerary

Day 1: Arrive in Athens & Sightsee

Monastiraki Square and Sunset over Plaka
Monastiraki Square in Athens
Welcome to Greece! Your private driver will be waiting at the airport to transfer you to your hotel in Athens. In the afternoon, get out for some sightseeing. Those interested in history and mythology might choose to visit the National Archaeological Museum, the Museum of the Ancient Agora, or the Archaeological Museum of Kerameikos. View fine art at Benaki Museum, the Museum of Modern Art, or the National Gallery. You could also go off the beaten path at the Museum of Cycladic Art, where you can buy truly unique souvenirs, or the Museum of Ancient Greek Technology. You'll overnight in the city. 

Day 2: Visit the Acropolis & Go on a Food Tour

The Parthenon at the Athenian Acropolis
Today you'll visit the Acropolis, taking in views of the world-famous Parthenon. This temple, dedicated to the goddess Athena, has enchanted visitors since its construction was completed in 438 BCE. Afterward, the tour continues at the Athens Central Food Market (Varvakios Agora), where you'll sample regional delicacies made by Greek cheese-makers, pastry chefs, and food vendors of all kinds. The evening is free to relax or explore the city.

Day 3: Catch the Sunset Over Cape Sounio

Sounio Sunset tour
A sunset tour of Cape Sounio
Today you'll see an unforgettable sunset when you visit Cape Sounio from Athens on a private tour. After relaxing and exploring on your own in the morning, you'll be picked up in the afternoon and transferred to the cape. First, you'll visit the fifth-century Temple of Poseidon, perched on the headland. Learn all about its history, including how it was dedicated to the god of the sea, Poseidon, and served as a beacon for mariners. Later, you'll have dinner and drinks while admiring an amazing sunset over the water. Head back to Athens after dark. 

Day 4: Visit Mycenae & Nafplio

The Lion Gate in Mycenae
For the next several days, you'll explore mainland Greece in a rental car. Today you'll start in the fabled Homeric city of Mycenae, a UNESCO World Heritage Site — and once the capital of one of the oldest civilizations in the world. Start your adventure into antiquity by walking under the famed Lion Gate into ruins that are part history, part myth. Follow in the steps of King Agamemnon as your guide explains the stories behind the imposing ruins of the citadel. You'll then head towards the historic seaside city of Nafplio, where a delicious lunch awaits you in one of the best restaurants in town. This romantic town, the old capital of modern Greece, is characterized by Venetian fortifications and a beautiful waterfront. After lunch, you'll visit local craftspeople, including a potter and a weaver at work in their workshops, to discover how they carry the traditions of the past into the present. You’ll also see a number of other local crafts and goods and a confectionery where traditional almond pastries are still made the way they were generations ago.
From Nafplio, the trip will take you through the beautiful Peloponnesian countryside towards ancient Olympia. Along the way, you’ll stop at a honey farm to learn about world-renowned Greek honey from a working beekeeper. Spend the night in Olympia before heading out to tour the city on day four. 

Day 5: Tour Olympia & Hike to Waterfalls

The Millenia Tour: Ancient Olympia & Galaxidi Day 2
Walking around the ancient ruins of Olympia
This morning is devoted to Ancient Olympia, the most important athletic, religious, and political center of the ancient Greek world. Here your guide will let you into the secrets of the temples, the training area, and the original stadium where the ancient Olympic Games were held for centuries. The Archaeological Museum onsite displays world-class masterpieces and treasures, like a breathtaking statue of Hermes and the infant Dionysus sculpted by Praxiteles.

Then it’s time for an outdoor adventure and a memorable lunch. After an easy guided walk through a stunning gorge, you'll arrive at a pair of waterfalls. Your lunch will be served picnic-style, right by the river. You’ll have the chance to swim too! After leaving the waterfalls, continue to Delphi, where you will spend the night.
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Day 6: Learn About Ancient Traditions in Delphi & Amfissa

A view over the valley of Amfissa

Today you'll head to the regional capital of Amfissa, where Greece's last handmade bell-maker will show you how livestock bells have been forged by hand in his family for generations. Afterward, stroll through the cobbled streets of the old leather-tanning district. Here, in one of Europe's last remaining tannery workshops, you’ll see what a tanner’s working life was, almost unchanged from a century ago up to today. Enjoy lunch under the shade of the large tree in the town square, where you will taste local delicacies prepared in the village.

After lunch, it’s off to Delphi, where you’ll marvel at the ruins of the Temple of Apollo and the Athenian Treasury. You’ll have plenty of time to soak up the magical scenery before visiting the Delphi Museum, home to some fine examples of ancient Greek art, including the world-famous bronze statue of the Charioteer of Delphi. Head north across the mainland towards the Meteora. A few miles before reaching your destination, you will have dinner in a traditional family-run restaurant in the foothills of Mt. Koziakas. You will spend the night in a charming family-run guest house in the pretty village of Kastraki, right under the towering rocks of the Meteora.

Day 7: See the Monasteries of the Meteora 

The Meteora at sunset

Today's highlight is a visit to the Meteora, a stunning natural phenomenon featuring enormous sandstone columns formed millions of years ago. These remote rock skyscrapers became dwellings for Christian Orthodox monks; by the 14th century, large monastic communities were flourishing on the summits of many of these rocks. Today, six monasteries are still functioning, and you will visit two. 
After lunch, you'll visit a local icon painter. In his tiny workshop, you’ll have the chance to learn about the tradition and make your own miniature painting. Then it's a stop at the small but original Book Museum, where you'll get to try your hand in Greek penmanship and hear out about Greek classrooms of the past. Then continue to Kranea, where you'll spend the night.

Day 8: Explore the Pindos Mountains

Scenery in the Pindos Mountains, Greece
Today, the last day of the road trip, takes you to the Pindos Mountains, the most scenic mountain range of central Greece. You will explore the little-known Forest of the White River, a group of small mountain villages hidden in the depths of a massive forest. Visit a beautiful (but rarely visited by tourists) monastery with thirteen domes, then see the spot where three rivers meet. You can go for a swim in these turquoise waters before continuing your drive through the gorge. Your last stop will be at an impressive stone bridge. Have a late lunch before heading back to Athens on the National Highway. 

Day 9: Catch the Ferry to Milos

Whitewashed buildings on Milos
Enjoy the ferry ride to Milos. The island has more than 70 beautiful beaches and is also home to a dormant volcano. Milos is associated with one of the most famous works of art in the world — the Venus de Milo statue now on display at the Louvre Museum in Paris — because the sculpture was discovered here. There's still plenty of history to explore here, including the historic catacombs and amphitheater.

Day 10: Boat Around Milos

Colorful rock formations on Milos
Today you'll go on a boat tour around Milos, making stops along the way to swim and explore. You'll also visit Sykia Cave. Later in the day, you'll have plenty of activity options to choose from. Hike to the cliff-diving spots in Sarakiniko, visit the prehistoric village of Fylakopi, or walk around the idyllic fishing villages of Mantrakia, Klima, and Filopotamos.

Day 11: Relax on the Beach in Milos

Vibrant blue waters off the coast of Milos

Relax on Milos today. There's no shortage of beaches to choose from! The island’s villages are lovely, too, including the stately Plaka (the island’s capital), the harbor village of Adamantas, beautiful Hivadolimni, and Emporios with its small lagoon. Whitewashed Chora is home to quaint churches, such as Panagia Korfiatissa. Adamantas, built like an amphitheatre overlooking the Aegean Sea, is the second largest natural harbor natural in Greece and is famous for its nightlife. You might also opt to visit Apollonia on the northwestern tip of the island.

Day 12: Take the Ferry to Santorini

Sunset in Santorini
Sunset in Santorini

Catch a ferry to Santorini. On arrival, you'll take in the island's central caldera — the site of one of the largest volcanic eruptions in history — rising above you. The island's volcanic history has led to the formation of some of the most unique beaches in the Greek islands, along with the dramatic cliff views on the island's caldera side. Spend your day relaxing at the beach or strolling on one of Santorini’s scenic walking routes. 

Visit Prophet Elias Monastery, the highest spot on the island. Walk around Megalochori, one of the most picturesque villages on the island. You could also go on a walking tour of the village of Emporio. Take a break for lunch before heading to Red Beach, one of the most scenic and interesting beaches on Santorini. In the afternoon, you'll have the chance to sample wines at a local winery nearby. At sunset, catch the views of the Blue Dome Church at Firostefani and the spectacular landscape below. For dinner, sample the island's signature cherry tomatoes and white eggplant, typically served as side dishes with fresh seafood. 

Day 13: Taste Wines in a Local Winery

Boats off the coast of Santorini

Explore the southeastern part of the island today, starting with a visit to the village of Kamari. Stop into Panagia Episkopi, the oldest Byzantine church on the island. Relax on the beach after lunch, then head to Canava Ouzo for a guided tasting of locally produced spirits, including ouzo. Another option is to visit Avantis Winery to taste wines and explore the viticulture tradition of Santorini. You'll also be able to tour the tomato factory in Vlychada. The tomato is one of the most famous and traditional products of Santorini, and you'll learn about its cultivation and the culinary traditions associated with it during a visit to a nearby farm.

Day 14: Enjoy a Catamaran Cruise 

Hiking Along Santorini's Caldera
Watching the sun go down in Santorini
A catamaran cruise is a wonderful way to spend part of your last day on the island. Start the tour on picturesque Ammoudi Bay, then sail to nearby hot springs for a refreshing dip. Continue cruising past a historic lighthouse before stopping at the Red Beach for swimming and snorkeling. Then you'll sail to the White Beach, enjoying a traditional Greek barbecue on the boat. 

Day 15: Travel to Heraklion

Heraklion harbor
Heraklion's harbor
Bid farewell to Santorini and get ready for another fascinating island — Crete! Take the ferry to the port of Heraklion. In the afternoon, you'll visit Heraklion's Archaeological Museum, with one of the largest collections of Minoan artifacts in the world. This is an excellent crash course to prepare you for the site you'll visit tomorrow — the 3500-year-old Palace of Knossos, a sprawling maze of royal chambers, grand staircases, storerooms, and workshops. This evocative Bronze Age site is believed to be Europe's oldest city. Have a relaxing meal in a beachfront restaurant before tomorrow's excursion.

Day 16: Visit the Cave of Zeus & Attend a Wine Tasting

The Palace at Knossos
The day starts with a guided tour of the Palace at Knossos. Next, you will journey to the mountainous East Crete and the Dikti Mountains with your guide. You will visit ancient Cretan villages, engage with locals, and take in views of the region's stunning landscapes. Break for coffee under an ancient tree in the traditional village of Krasi before touring the Cave of Zeus. On the trip back, you will visit a family-owned traditional ceramic workshop and a Byzantine monastery. Finish the day with a meal in an authentic Cretan tavern.

Day 17: Explore Samaria Gorge with a Local Guide

Samaria Gorge with a Local Insider
Samaria Gorge with a Local Insider
Hike through the majestic Samaria Gorge today with a private guide. The gorge is home to around 450 species of plant and animal life; it's also a UNESCO-protected Biosphere Reserve. You will pass through Cretan forests of pine, cypress, and ancient holly trees, natural water springs, and abandoned villages and churches. You will crisscross a river multiple times — sometimes over wooden bridges, sometimes hopping from rock to rock – but it’s not a difficult hike. Just don’t expect to navigate these trails as effortlessly as the gorge’s native residents, the Cretan ‘kri-kri’ mountain goats! Head back to Heraklion for one last Greek-style dinner before the trip ends. 

Day 18: Depart Heraklion - End of Trip

Hiking along the coast of Crete
The trip comes to an end today. You'll head to the airport to catch a flight out. Safe travels!

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