Whenever I visit a place for the first time I try to see as much as I can in order to determine where I would want to spend more time.  The challenge of visiting the Greek isles is the sheer number of inhabited islands (over 200) sprinkled across the Aegean, Ionian, and Mediteranean Sea.  The following are some practical considerations when planning a trip to Greece.

About Greece 

The islands are divided into six main island groups (archipelago), including the independent island of Crete.  It is typically easier to travel within an island group than it is to hop from island group to group as the flights don’t typically cross the groups but rather always lead back into Athens before going back out to an island group. 

The following are the island groups and a few of their cities:  

  • Cyclades: Mykonos and Santorini
  • Crete: Chania and Rethymnon
  • Saronic Gulf: Hydra, Poros 
  • Ionian: Corfu, Paxos 
  • Sporades: Skiathos (Mama Mia was shot on this island)
  • Northeast Aegean: Chios

For reference, check out the 13-day Itinerary to Athens, Greek Islands, and Istanbul

When To Go 

The busiest time to visit the Greek Isles is between July and September with August typically being the very busiest.  If possible, book your trip in late May/June or late September/October so as to avoid the crowds, extreme temperatures, and overpriced accommodations and food.  

What to Experience  

  • Ancient History: Consider focusing your trip on Athens, Corinth, the Peloponnese, Rhodes, and Crete.
  • Cuisine & Wine: Consider focusing your trip on Santorini (wine), Crete, Sifnos, Naxos, Peloponnese.
  • Beaches: Consider focusing your trip on Crete, Santorini, Skiathos, Ios, Rhodes.

How to Get Around  

  • Cruise Ship: If you want to climb aboard and unpack and allow the ship to get you from place to place a cruise is optimal.  Many cruises depart from Athens and stop at Santorini, Mykonos, and Rhodes. Personally, I’m not a cruise ship person due to the nature of traveling with a crowd but this style of travel does make it easy to see a lot in a short amount of time.  
  • Inter-island Ferry Service: Due to last minute schedule changes and multiple operators, making inter-island ferry transportation very challenging.  Prior to departing the US, identify 2-3 Greek travel agencies near your first hotel in Greece to assist with making ferry service plans.  Check out Hellenic Seaways or Hellas Speed Cat for schedules and pricing.  
  • Charter, Private Yacht:  While researching private charters I learned that the weather can be highly unpredictable and the stories of being caught at sea in a large storm were frequent.  The thought of being caught on a small yacht in a storm was what prevented me from booking this option. 
  • Flying: 25 islands have their own airport.  If you will be using air travel for your trip, consider planning your itinerary around the airports that you can access.  We found the flights on Olympic Airlines and Aegean Airlines to be highly convenient if only a little more expensive than utilizing the ferry.  Flights were especially helpful for the islands at the furthest distances or when we were facing an overnight voyage on a ferry boat.  Be sure to book your flights at least 4-months in advance as the planes are small and seats can sell out.  

What to Keep In Mind

  •  Visiting Santorini and Mykonos: While beautiful they are extremely touristy.  If you prefer to go off the beaten path you may want to arrive into Santorini in the afternoon, spend the night (after the cruise ship guests have left), and enjoy the island early the next morning before the day tourists return.  
  • Cruise Ship Schedules: Due to the thousands of people arriving on an island all at one time, it’s smart to check the cruise ship schedule in advance of your trip to ensure you don’t get swamped by the day tourists.  Or, plan your day to visit the off the beaten path sights while the cruise ship guests are making their way through the highlighted attractions.  
  • Stay Near the Airport/Port: The mistake that we made in Crete was renting a villa that was 1-hour away from the airport and port.  While we had a driver we spent a lot of time in the car traveling back and forth.  This was not an efficient use of our travel time however, it was also why we ended up in Plaka and visiting Spinalonga Island.  
  • Orthodox Easter: Each location celebrates Easter in its own way whether it be fireworks, parades, and festivities.  The dates for Easter vary but the later it occurs in May the better the weather will be.   

Mary Beth I have a passion for creating and experiencing unforgettable moments and sharing those with others. I hope that this story has helped you experience one of those moments.

Leave a Reply

Your email address will not be published. Required fields are marked *