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Home » Destinations » Europe » Greece

My Ultimate Two-Week Itinerary for Island-Hopping in Greece

Modified: Apr 21, 2025 · Published: Feb 5, 2025 by Dave Lee |

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 leaped (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.

Selfie while driving around Ios during my island-hopping adventure in Greece.
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. I hope you'll be inspired to plan your trip to Greece by the end.

For those seeking organized Greece tour packages, this itinerary offers a comprehensive guide to experiencing the best of the Greek islands.

Table of Contents

  • Greek Islands
    • Rhodes
    • Santorini
    • Ios
    • Paros
    • Mykonos

Greek Islands

Rhodes

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 a 50-minute drive) of the old town is the Acropolis of Lindos, a significant site in ancient Greece and home to the Temple of Athena.

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.
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 lives up to its reputation as a romantic honeymoon destination.

Santorini was formed by a massive volcanic eruption about 3,600 years ago. The eruption caused the island's center to collapse, creating a caldera. It also shaped Santorini's dramatic cliffs and submerged crater.

It was one of the planet's most significant and destructive eruptions, earning it a Decade Volcanoes designation. Although dormant today, the volcano that shaped Santorini remains technically active.

The island's dramatic landscape includes volcanic beaches, hot springs, and whitewashed villages with blue-domed churches built along the caldera rim. Luxury hotels of all sizes provide infinity pools with sweeping sea views.

The day after I settled into a guest house in Fira, the capital of Santorini, I joined a sunset cruise to Nea Kameni, one of the small volcanic islands in the caldera. It's an otherworldly place to walk. Before the tour ended, we also had the opportunity to watch the sunset from the water.

Additional highlights from Santorini:

  • The Fira to Oia walk takes you through villages along the caldera's rim.
  • Sunset from the town of Oia at the northwestern edge of Santorini.
  • Red Beach (requires a short hike)
  • White Beach (accessible by boat)
  • Black Beach
  • Ancient Thera (the ruins of a mountaintop city)

I spent three days in Santorini before continuing to the Greek island of Ios. The high-speed ferry ride took about 45 minutes.

Ios

Mylopotas Beach on Ios.
Mylopotas Beach

Ios is known for attracting young travelers who want to party at its beach clubs and bars. However, I was pleased to discover that even during the height of the summer travel season, you can still experience its quieter side.

I checked into the Hotel Mediterraneo Ios, a 3-star hotel with room balconies that offer sweeping views of Chora, the island's main town.

I rented a small car and drove around Ios. Beyond the scenic drive, highlights included visiting the Tomb of Homer, the stunning and secluded Paralia Agia Theodoti beach, and the more developed Mylopotas beach.

A highlight of my third and final night on Ios was a walk through Chora to the hilltop Church of Panagia Gremniotissa to watch the sunset. The following day, I boarded another high-speed ferry for the one-hour ride to Paros, north of Ios.

Paros

Walking around Paros at night.
Parikia, capital of Paros

As I continued island-hopping in Greece, my costs rose, and I spent fewer nights on each island. Paros boasts postcard-perfect villages, such as Naoussa and Parikia, characterized by whitewashed houses and cobblestone streets. I found it particularly charming to walk around at night when the sun wasn't so fierce.

For convenience, I spent my two nights on Paros in Parikia, where I could easily find lodging within walking distance of the ferry. On my one full day on the island, I took a water taxi across the small bay to Kolympethres Beach. The water was crystal clear, making the trip well worth it.

Here are some more of the top beaches on Paros:

  • Kolymbithres Beach is known for its unique granite rock formations.
  • Golden Beach is a sandy beach popular with windsurfers.
  • Faragas is a small, secluded beach on the south coast of Paros.

My final ferry ride of the two-week trip took me from Paros to Mykonos, lasting approximately 50 minutes.

Mykonos

Mykonos is a must when island-hopping in Greece.
Windmills on Mykonos

Mykonos may have been the island I'd heard mentioned most often in my lead-up to island-hopping in Greece. It's world-famous for its party scene, frequently referred to as the "Ibiza of Greece," and attracts a jet-set crowd. For some reason, I also thought it was a backpacker-friendly destination, but I was in for a rude awakening.

I do not recommend arriving in Mykonos in July without booking your accommodation in advance. The cheapest hotel I could find was $100 per night, which is significantly more expensive than the rates I have paid elsewhere.

As a result, I only spent two nights on Mykonos before catching a flight to Athens to conclude my first trip to Greece. Still, I made the most of my time by taking numerous walks through the attractive main town, including the "Little Venice" area and the nearby windmills of Mykonos.

After two weeks of island-hopping in Greece, I left with countless memories, from Rhodes' historic charm to Santorini's breathtaking caldera and Ios's hidden quiet side. Each island offered a distinct experience, proving that Greece is more than just a destination—it's an adventure worth taking.

Related Stories

  • Windmills on Mykonos in Greece.
    Best Things To Do in Old Town Mykonos: A First-Timer's Guide
  • Parikia, Paros.
    Discover Paros in the Cyclades: Beaches, Trails, and Villages
  • Chora, Ios.
    How To Explore Ios in One Day: Beaches, Scenic Drives, and Sunset
  • Santorini boat tour.
    Santorini Sunset Cruise: Sailing Into Golden Hour
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About Dave Lee

Dave is the Founder and Editor in Chief of Go Backpacking and Feastio. He's been to 68 countries and lived in Colombia and Peru. Read the full story of how he became a travel blogger.

Dave at Ahu Ko Te Riku on Rapa Nui (Easter Island), Chile.

Hi, I'm Dave

Editor in Chief

I've been writing about adventure travel on Go Backpacking since 2007. I've visited 68 countries.

Read more about Dave.

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