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Island-Hopping in Greece: The Ultimate Two-Week Itinerary

Selfie while driving around Ios during my island-hopping adventure in Greece.

For a few weeks one summer, between visits to Bodrum and Bucharest, I lived my best life island-hopping in Greece. After several months of backpacking through Turkey, Georgia, and Armenia, I made the leap (or at least boarded a ferry) from Bodrum to the island of Rhodes. From there, I visited some of the most famous Greek Islands, including Santorini, Mykonos, Ios, and Paros.

Driving around Ios

In this overview of my Aegean adventure, you’ll learn a little about each island’s reputation and how I experienced it. By the end, I hope you’ll be inspired to plan your own trip to Greece.

Greek Islands

Rhodes

Palace of the Grand Master - Rhodes, Greece.Palace of the Grand Master - Rhodes, Greece.
Palace of the Grand Master

My island-hopping in Greece began with four nights on Rhodes, which is easily accessible from Turkey by ferry. Rhodes is best known for its Medieval city, a UNESCO World Heritage Site at the island’s northern tip. The old town is pedestrian-friendly and walkable. It’s a fun place to put your phone away and imagine what it would’ve been like to live there centuries ago.

Highlights of the Medieval city include:

  • Palace of the Grand Master
  • Street of the Knights of Rhodes
  • Archaeological Museum of Rhodes
  • The many large entry/exit gates built into the walls around the city

Just north of the old town is the Mandraki Marina, where the Colossus of Rhodes, one of the Seven Wonders of the Ancient World, once stood. The 108-foot-high bronze statue of the Greek sun god Helios was built at the marina’s entrance in 280 BC. Less than 60 years later, it collapsed during an earthquake and was never rebuilt.

About 30 miles south (and 50 minutes driving) of the old town is the Acropolis of Lindos, a significant site from ancient Greece and home to the Athena Temple. I only saw these structures from afar while on a self-driving island tour. Another highlight of that drive was renting an umbrella and chair on Tsambika Beach, about midway between Lindos and the old town.

Rhodes is the fifth-largest Greek island, covering 541 square miles. During my stay, I felt like I barely scratched the surface of all there was to see. However, it still served as a worthy introduction to what I could expect from island-hopping in Greece.

Santorini

Santorini is a popular option when island-hopping in Greece.Santorini is a popular option when island-hopping in Greece.
The town of Oia on Santorini

I flew into Santorini Airport via a 50-minute direct flight from Rhodes. This island is truly one-of-a-kind and worth its reputation as a romantic honeymoon destination.

Santorini was formed by a massive volcanic eruption about 3,600…

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