The Ultimate 2-Week Greece Road Trip Itinerary

Alonnisos island, Greece

Experience Greece in all its glory by driving around the country in 2 weeks with this road trip itinerary. 7 stops, endless fun.

While many people think of Greece as the ultimate island destination, with Mykonos and Santorini headlining honeymoon itineraries, it’s also a fantastic road trip destination. The mainland of Greece, from Athens to Thessaloniki via Meteora, Delphi, or the Peloponnese, offers up an amazing array of unique stops.

Below is the ultimate 2-week Greece road trip itinerary, beginning with the mainland and ending on the islands. Begin your ultimate Greece road trip in Thessaloniki. You can fly into here from most cities across Europe or connect in Athens. 

1. Thessaloniki

Thessaloniki, in the north, is Greece’s second-largest city and the capital of the Greek region of Macedonia. It was founded as a Roman city in the 1st century BCE by Cassander of Macedon. Under the Byzantines, the city flourished and was the second largest and wealthiest city in the empire.

Today, Thessaloniki is considered Greece’s cultural capital, with yearly art and film festivals. It also features numerous Roman and Byzantine ruins, plenty of street art, and has been named as one of the best mid-size European cities.

What to see and do in Thessaloniki

  • Ano Poli: Ano Poli, or upper town, is part of the original city layout. In 1917, a large fire destroyed much of Thessaloniki, and the city was rebuilt according to a Byzantine city plan. Ano Poli was not destroyed, however, and remains the most traditional Greek and Ottoman part of the city. 
  • Paleochristian and Byzantine monuments: Thessaloniki has many paleochristian and Byzantine monuments, because of its importance as a Byzantine administrative center. The most well known is Hagios Demitrios, or the Church of Saint Demetrius, which was damaged by the fire in 1917 and later by World War II bombing. Hagios Demetrios is the largest basilica in Greece and has since been rebuilt.
  • Street Art: Thessaloniki is a vibrant second city and is popular with street artists and street photographers. In 2017, it hosted its first street art festival, drawing many artists and musicians; since then the city has been considered the cultural capital of Greece and is one of Europe’s best mid-sized cities.

Insider’s tip: To make the most of this road trip itinerary, rent your car after exploring the city and before moving on to the next destination on this itinerary.

2. Halkidiki

From Thessaloniki, drive around Halkidiki, which comprises three peninsulas on the northeastern coast. It is the birthplace of Aristotle. 

The three peninsulas of Halkidiki are known as Kassandra, Sithonia, and Agion Oros

  • Kassandra is the furthest south peninsula, closest to Thessaloniki, where you will find the largest towns and most developed infrastructure. 
  • Sithonia is less developed and perfect for outdoor lovers. 
  • And Agion Oros, the northernmost peninsula, is home to Mount Athos, a monastic state which only men are allowed to enter.

Halkidiki is also known for its beaches, thermal spas, mountain villages, and the monastery of Mount Athos.

Top 3 things to do in Halkidiki

  • Halkidiki Beaches: You must visit the beaches of Halkidiki!  Some are made up of rocky coves, while others are much more developed and have shops or bars along the beach. Some of the most popular beaches include Kavourotripes, Alykes on Ammouliani Island, Karydi in Vourvourou, and Possidi.
  • Mount Athos: While you can’t visit Mount Athos by land unless you are an Orthodox Christian male with a special permit, anyone can see the monastery from the sea. Boat cruises depart daily from Ouranoupoli or Ormos Panagias and half-day tours take 3-4 hours. 
  • Visit the Thermal Spa: Halkidiki is known for its healing waters, in particular, the spa at Agia Paraskevi, on a cliff overlooking the sea. It has been said that this thermal spa can heal arthritis, skin inflammations, and other chronic disorders. They also offer hammams, hydromassage treatments, saunas, and swimming pools.

3. Meteora

From Halkidiki, drive south to Meteora. Meteora is located in the Plains of Thessaly and is home to six Eastern Orthodox monasteries, all built on top of natural sandstone pillars. 

The earliest monasteries were built around the 14th century, though there is evidence for human settlement as far back as 50,000 years ago and evidence of monks living there from the 9th century. The original access to the 24 monasteries was only by ropes or ladders that could be removed, for security.

Today, it is easier to visit the monasteries, as there are now staircases built into the rock. There are only 6 monasteries remaining.

What you cannot miss in Meteora

  • Monastery of the Holy Trinity: Built in 1475, this is one of the six remaining monasteries. It is inhabited by just four monks and is located atop the cliffs. 
  • Old Hermitages: Many monasteries were destroyed by the Ottomans or fell into ruin. However, what many people don’t know is that prior to the monasteries there were small hermitages that housed the early monks. Some of the more well known include the Doupiani and Badovas hermitages. You can visit these with a tour guide.
  • The Pindos Mountains: Explore the Pindos Mountain range, home to not just the monasteries but also small villages and flowing streams. 

4. Delphi

After leaving Meteora, drive to Delphi, home to the ancient Oracle and today an incredibly impressive set of ruins. Once considered the center of the world, and marked with a stone called the omphalos (navel), Delphi is notable for its importance to Ancient Greek city-states and there are many monuments built by the various governments. For this reason, it is a UNESCO World Heritage Site.

What is Delphi famous for

  • Temple of Apollo: The Temple dedicated to Apollo at Delphi was located at the heart of the sanctuary. The ruins we can see today are actually the ruins of the third temple built in the 4th century BCE. This temple was damaged by the Romans and later destroyed by Christian zealots in an effort to stamp out paganism.
  • Treasury of Athens: The Treasury of Athens was built at Delphi to commemorate their win at the Battle of Marathon in 490 BCE. It is located directly below the Temple of Apollo on the Sacred Way, meaning that all who went to the temple passed it. Its location signified the importance of the city-state of Athens. A treasury would have held votives and offerings from the city-state to the god, and there were other treasuries at Delphi and other sites around Greece.
  • Archaeological Museum of Delphi: The Archaeological Museum of Delphi is one of the most visited museums in Greece. It is located outside the sanctuary. Some of the most important artifacts in the museum include the frieze of the Siphnian Treasury, the Charioteer of Delphi, and the Metopes of the Treasury of the Athenians.

5. Athens

Delphi is only a few hours north of Athens, which is your next stop. The capital of Greece is one of the greatest capital cities in history. Early settlement dates back to 1400 BCE, while evidence of humans dates back to between the 11th and 7th century BCE. 

Today it is a sprawling city that blends the ancient and modern and is a must-see on your ultimate Greece road trip. 

Insider’s tip: Return your rental car here before exploring, you can explore the city using its public transport network and on foot.

Athens highlights

  • Acropolis and Acropolis Museum: the Athens Acropolis is one of the most prominent symbols of Antiquity. It sits on a rocky outcrop above the city and is home to a number of building ruins. The most important structure atop the Acropolis is the Parthenon, but there are nearly 20 other buildings. The entrance to the Acropolis is through the Propylaea, a monumental gateway that marks the end of the Sacred Way. Other buildings or structures here include the Theatre of Dionysus, the Erectheum, and the Temple of Athena Nike.
  • Ancient Agora: the Ancient Agora is the best-known example of a classical agora. It is located northwest of the Acropolis. If the Acropolis was the spiritual heart of the city, the agora was considered the commercial heart of the city. It was here that the merchants met, some people lived, and where assemblies would have taken place.
  • Temple of Zeus: The Temple of Zeus is a temple in the center of modern Athens. It was begun in the 6th century BCE but was not completed until the 2nd century AD. The temple almost immediately fell into disuse but while it was active it was the largest temple in the Roman Empire. Today just 16 columns remain yet it is one of the most important ruins in the city.
  • Explore Plaka: walking through Plaka is surely an experience you can’t miss. This is the oldest neighborhood in Athens. The streets are narrow and the labyrinth is home to tourist shops, cafes, tavernas, galleries, and more.
  • Benaki Museum: The Benaki Museum, located within a historic mansion in Athens, houses Greek works of art from prehistoric to modern time. While its focus spans Greek culture over its history, the Benaki also has an extensive Asian art collection and houses a restoration and conservation workshop.

6. Mykonos island

From Piraeus, the port of Athens, take a ferry to Mykonos. This takes around 2-5 hours depending on the ferry but can take up to 24 hours if you take a slow boat.

Mykonos is quite possibly the most famous of the Aegean islands and a paradise for everyone from celebrities to backpackers. Hora is a vibrant town where you can spend both time and money in the many designer boutiques or hip restaurants.

The island of Mykonos is well known for its sunsets and parties, but it has a quieter side too. You can rent a car or scooter to get around Mykonos, and this can be done on arrival. 

Best things to do in Mykonos

  • Alefkantra aka Little Venice: this 18th-century district in Hora transports you back to Italy, with its Italianate mansions and delightful balconies overlooking the sea. Mykonos’ famous windmills are just above you. Alefkantra is where the sea captains of the 18th and 19th centuries lived and the neighborhood remains a charming, quiet, residential area.
  • Ano Mera: Mykonos’ second city is located in the center of the island and is much quieter than its sister Hora. Go for the beautiful 16th century Panayia Tourliani monastery, known for its wood-carved iconostasis.
  • Ftelia: history buffs must visit this Neolithic settlement just north of Ano Mera. It also has a 14th century BCE Mycenaean tomb.
  • Beaches of Mykonos: Mykonos has many wonderful beaches. If you have a car or scooter you can explore at your leisure. Some of the beaches are organized with umbrellas, chairs, etc while others are unorganized and you should take what you need with you.

Editor’s tip: Once you are done with the Aegean sea, why not keep exploring the Mediterranean with an Adriatic sailing adventure? There are over a thousand Croatian islands waiting for you!

7. Santorini

Take the ferry to Santorini, one of Greece’s most well-known and popular islands. This will take around two hours. The glimmering whitewashed buildings of Fira (Thera), Oia, and Imerovigli look out over the sea and provide incredible – and very romantic – sunset views. 

Spend a few days here to explore the island’s east coast, visit the many wineries, and enjoy the rich history and landscape. To get around the island, rent a car in Fira.

Before heading back, if you have extra time, consider taking an Ios day trip – easily accessible by ferry from Santorini year-round-  to explore its scenic beauty

What to do and where to go in Santorini

  • Hike the trail between Fira and Oia: The hiking trail between Fira and Oia is a popular one, especially around sunset (end in Oia for the best views) but it also helps you work off all that great Greek food – one of the best cuisines in the world – and wine! The trail winds along the caldera rim and has epic views of the sea.
  • Take a volcano cruise: Santorini is known for its volcanic activity – after all, the eruption of Thera is the eruption that ended the Minoan civilization on Crete. The best way to experience the volcanic activity in Santorini is to take a cruise out to the smaller volcanoes in the caldera for a hike up the volcano and a swim in the hot springs.
  • Visit Akrotiri: Akrotiri is a Bronze Age Minoan settlement, with evidence of habitation into the 5th millennium BCE. It was destroyed in the 16th century BCE eruption that wiped out the Minoans. Akrotiri was first excavated in 1867 although modern excavations in the late 1960s revealed the extent of the site. Akrotiri is considered the source of the Atlantis myth.

Greece is a great road trip destination, even on the islands. 

  • If you can include the amazing mainland sites like Delphi, Meteora, and Athens, you really get a great sense of the history and culture of Greece. 
  • The islands add yet another dimension – they have extensive history and influences but also showcase the beautiful modern way of life. 

Using this ultimate Greek road trip itinerary, you will experience the best of both worlds. Enjoy!

Chrysoula is a travel blogger born and raised in Athens with a professional background in Tourism and Marketing. Through the pages of Athens and Beyond, she wants to help visitors make the most of their trip to Athens and show them how to navigate the city like an insider.