With two full weeks in Greece you can see many of its unmissable sights, and experience many of its greatest attractions. An ancient country littered with historic ruins, with a stunning view around every corner, on this tour you'll combine sightseeing with relaxing and sailing around on a charter yacht. Start in the buzzing capital, Athens, then move on to the cliff-side monasteries at Meteora and the famous site of Delphi. After a dose of culture and history, head to Mykonos to board your charter yacht for a multi-day sailing tour of the Cyclades islands. Enjoy the famous Aegean winds, sparkling beaches, and a slower pace of life.


  • Explore ancient ruins all over the country, from Athens to Delphi
  • Hike around the cliff-side monasteries of Meteora
  • Unwind while sailing around the Cyclades on a yacht
  • Spend time on tiny Aegean islands and beaches

Brief Itinerary

Day Highlights Overnight
Day 1 Arrive in Athens Athens
Day 2 Ancient Greek Mythology Tour & Acropolis Museum Athens
Day 3 Delphi Archaeological Site & Museum Meteora
Day 4 Explore the Monasteries of Meteora Meteora
Day 5 Meteora - Return to Athens Athens
Day 6 Meet Your Charter Yacht in Mykonos Mykonos
Day 7 Naxos Naxos
Day 8 Heraklia (Irakleia) Irakleia
Day 9 Schinoussa Island (Small Cyclades) Schinoussa
Day 10 Antiparos Paros
Day 11 Paros Paros
Day 12 Mykonos Mykonos
Day 13 Depart Mykonos - Ferry or Flight to Athens Athens
Day 14 Trip End  

Detailed Itinerary

Day 1: Arrive in Athens

Monastiraki Square and the Acropolis
Monastiraki Square and the Acropolis

Welcome to Greece! You'll begin your trip in Athens, home to the iconic Acropolis and so much more. The mythology of this spectacular city precedes it, with towering temples to Classical deities, the ruins of ancient marketplaces rubbing shoulders with lively nightlife, crowded flea markets, and contemporary cuisine. After checking in to your hotel, take a rest or make the most of your time in the city at some of these spots:

  • Check out the views of the unmissable Parthenon. (Pro tip: the Parthenon is the temple, the Acropolis is the hill.) This temple to Athena has enchanted visitors since its construction was completed in 438 B.C.E. 
  • Stop at the sprawling National Museum for a crash course in ancient iconography. Don't miss the room housing the Antikythera mechanism, essentially an ancient astronomical computer.
  • Visit a smaller archaeological site at the Tower of the Winds, then stroll down neighboring pedestrian Aiolou Street to stop at shops and cafes. 
  • Find your perfect souvenir or sun hat in the busy stalls of the Monastiraki Flea Market.
  • Hit the ground running with a night out in the up-and-coming Pangrati neighborhood, or amid the nightlife and mezze of the Psyrri district.

Day 2: Ancient Greek Mythology Tour & Acropolis Museum

The Acropolis
The Acropolis

Today, delve into Athens' centuries of history. Experience the ancient stories surrounding you on a guided mythology tour. Meet your archaeologist guide at Syntagma Square, then head to landmarks around the city, including the Acropolis and the Herodion Theatre. Hear stories about Zeus, Athena, Poseidon, Dionysus, and more, all adding resonance to the archaeological ruins you'll visit on this four-hour tour.

Later, take another guided tour at the Acropolis Museum. Named one of the 10-best museums in the world by National Geographic, this modern museum houses a multitude of artifacts removed from the hill of the Acropolis for safekeeping. You'll learn all about ancient religious practices and daily life. From the museum cafe there are great views of the former hilltop home of the museum's collection.

Day 3: Delphi Archaeological Site & Museum


Today, travel overland from Athens to Delphi, on the slopes of Mount Parnassus. High above the Gulf of Corinth lies one of the most famous historic sites in Greece. It was known throughout the ancient Greek world and beyond as the sanctuary of Apollo and the shrine of his oracle. Today a UNESCO World Heritage Site, Delphi ranks with the Acropolis in Athens, Olympia, and the island of Delos as one of the most important classical sites in Greece. The incredible remains, magnificent mountain setting, and the site's importance in Greek mythology make Delphi a must-visit place in Greece.

The Sacred Way is the main route through the Sanctuary of Apollo, leading from the gateway uphill to the Temple of Apollo. Originally, the way was lined with votive monuments and treasuries erected by various Greek cities, reflecting the diversity of the political pattern of ancient Greece. The monuments themselves have disappeared, but many of their bases have survived.

Lying between the ancient site and the modern town of Delphi, the Archaeological Museum displays a fascinating collection of finds from the site, including friezes, statues, votive offerings, and stele. Exhibits are displayed in chronological order and arranged in 14 rooms.

Later in the day, drive to Meteora (approx. 3 hours) where you'll spend the night.

Day 4: Explore the Monasteries of Meteora

Cliff-top monastery in Meteora

Discover some of the six cliff-side monasteries in Meteora that remain open to the public: Varlaam, Great Meteoron, Aghios Stefanos, Rousanou (renowned for a marvellous depiction of the Second Coming), Holy Trinity (featuring an old church dating back to 1475), and Aghios Nikolaos Anapausas (adorned with very significant post-Byzantine murals). Some are still inhabited and used by monks and nuns today. The area is a UNESCO World Heritage Site and is one of the largest pilgrimage sites in Greece.

Tread the same paths that monks used for hundreds of years to reach these holy places, climbing almost 1000 feet (300 m.) in the air above the canyons of the Pindos Range. Before the paths were constructed, the monastery residents used nets and rope ladders to hoist goods (and sometimes their fellow clergy) to the clifftops. You'll experience both living history and panoramic views as you explore.

Day 5: Meteora - Return to Athens

Up on the clifftop

Spend a bit more time this morning hiking around the incredible cliff-side monasteries, before returning overland to Athens.

Plan your trip to Greece
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Day 6: Meet Your Charter Yacht in Mykonos

Windmills of Mykonos

Transfer to Mykonos by ferry or airplane, and from the port or airport travel by taxi to the marina. Your charter yacht will be docked there, and your crew waiting to welcome you on board.

Welcome to Mykonos, an idyllic getaway for cosmopolitan fun lovers. A magnet to the world’s most glamorous personalities since the 1970s, Mykonos today also attracts nature lovers, foodies, and athletes. In Mykonos you will discover remarkable beaches, adrenaline-inducing water sports, a refined local cuisine, and an unprecedented bar scene, all among picturesque architecture, breathtaking views, iconic windmills, and maze-like streets.

Day 7: Naxos


Today, sail to Naxos, where you can enjoy a free day to explore as you wish. In the active main town you can shop and admire the Venetian architecture and castle area. There are also opportunities for both laid-back relaxation, and water or land activities.

Day 8: Heraklia (Irakleia)


Head to Heraklia today, a diamond-shaped island south of Naxos, and close to Ios island. With just over 150 inhabitants, the permanent tranquility and beauty of Heraklia is evident all around. When you arrive at the charming port of Agios Georgios, you may feel like you've traveled back in time.

Day 9: Schinoussa Island (Small Cyclades)


Today sail to Schinoussa (the Island of the Sun), one of the most beautiful small islands of the Aegean. It belongs to the Small Cyclades complex, and is close to Naxos, Irakleia, Koufonisia, and Keros. It's home to many endemic plants, and is an important migratory station for many birds.

There are two villages on the small island, Chora and Messaria, with about 256 inhabitants. Schinoussa owes its name to the mastic tree shrub that grows all over the island. The port, Mersini, is considered one of the best shelters for small boats in the Aegean. Its inhabitants are involved in agriculture, farming, fishing, and tourism.

Day 10: Antiparos


Today, arrive in Antiparos, a small island that has stood its ground as an alternative offshoot to neighboring, tourism-oriented Paros, with its fancy nightlife.

Significant archeological findings have been made on Despotiko, an uninhabited island west of Antiparos, as well as at two other neighboring virgin islands, Tsimintiri and Stroggylo. The oldest Cycladic settlement was discovered on Saliagos, an islet off Antiparos. There's a lot to explore while traveling around these islands on your yacht.

Day 11: Paros

Classic Greek island architecture
Classic Greek island architecture

Explore the small island of Paros, which is frequently overlooked in favor of its more famous Cycladic neighbors. You'll quickly learn that Paros has a special charm of its own, and it's quite traditional in nature. Highlights include the 4th-century Panagia Ekatontapiliani Church, and beautiful beaches with sheltered swimming areas made from rock formations.

Day 12: Mykonos

Beach in Mykonos
Beach in Mykonos

Feel the famous Aegean winds while relaxing on one of Mykonos' stunning beaches for the day.

Later, take a sunset sailing tour to the nearby island of Delos, where you'll enrich your knowledge of ancient Greek history. The Cyclades islands (kyklos means circle) got their name from the fact that they encircle the sacred island of Delos. The island is a UNESCO World Heritage Site and one of the most important archaeological sites in Greece, plus it's said to be the birthplace of Apollo and Artemis.

Day 13: Depart Mykonos - Ferry or Flight to Athens

Ancient ruins in Athens
Ancient ruins in Athens

You'll "check out" from your yacht at 9 am and make your way back to Athens, either by ferry or flight.

After arriving back in the capital, spend the rest of the day relaxing or exploring, depending on your time of arrival. 

Day 14: Trip End

Farewell Greece

All too soon it’s time to pack your bags and be transported to the airport or to the port for your journey back home or to your next destination.


Map of Essential Greece: Athens & Greek Cyclades Sailing Adventure - 14 Days
Map of Essential Greece: Athens & Greek Cyclades Sailing Adventure - 14 Days