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How to Plan Your First Vacation to The Greek Islands in 10 Steps

How to Plan Your First Vacation to The Greek Islands in 10 Steps

Did you know Greece has 2,654 islands?

It's no wonder folks get confused with which Greek islands to choose from during vacation planning.  But, there's good news! Fun fact: only 164 of the islands are inhabited and the rest are rocks.  So this tid-bit can help narrow down the planning for your dream trip!

Let's briefly review Greece's island geography

There are hundreds and hundreds of blogs and articles published about the Greek islands.  There are the most romantic, the most beautiful, the best for activities and water sports, and so on. Even more lists to confuse you. To have a more objective decision making process and assessing what your biggest needs are, let's start with (and briefly review) Greece's geography and topography. 

Greece's islands are located in bodies of water on either side of and below the mainland.  There are 7 groups of island chains including Crete, although the North Aegean Islands don't form a chain and belong to both Greece and Turkey.  Most of the island chains are in the Aegean sea with only one chain in the Ionian, the western side.

You have the Cyclades located in the Aegean Sea islands (in between Greece and Turkey), which are made of volcanic rock and have little to no vegetation.  An important fact to consider if you are an avid beach lover.  These beaches will tend to be rockier.  And world famous Santorini, for example, is not known for its beaches.  You might consider these as some of the most well-known islands; such as Santorini, Mykonos, Ios, Naxos, Milos and so on. 

The Cyclades in red

The Cyclades in red

Also in the southeastern Aegean Sea are the Dodecanese islands.  These are much closer to Turkey and Crete and may be your best options if you are choosing to tie them into a trip to Turkey. Some of the most beautiful are Rhodes, Kos, Karpathos, Kalymnos, Patmos, Leros and Symni. 

The Dodecanese in red

The Dodecanese in red

Then there are the Saronic (7 main islands) and the Sporades islands (comprised of 15 islands west of the North Aegean islands), which are smaller chains of islands in the Aegean Sea. And some closest to Greece mainland. Hydra being one of the most popular. 

Islands in the Ionian Sea (think towards the Italy side) will have more vegetation and cooler waters and climates.  There are 7 larger more well known islands you may have heard of; Kerkyra (Corfu town), Paxi (tiny gem), Lefkada (connected to the mainland by a causeway) , Kefallonia (the largest), Ithaki (mythical home of Odysseus), Zakynthos (famous for Shipwreck beach), and Kythira (low key to tourists except for July/August and considered part of Attica).  But there are several smaller ones as well.  Each island will have a distinct landscape and its own rich cultural history.  They all offer something for everyone if you chose to stay only in that chain of islands. 

The seven largest Ionian sea Greek islands 

The seven largest Ionian sea Greek islands 

Island hopping within the same chain of islands can be ideal, but it is often popular to visit islands from chains that are in close proximity, depending on what you are looking for, the amount of time you have, and whether you want more low-key travels or the busyness of tourist season. 

Now that you have the lay of the land, let's review 10 questions to help you narrow down what you are really after. 

10 steps to help determine your perfect trip to the Greek islands

Read through each of the 10 questions and jot down what you are looking for out of your trip. After assessing your answers, scroll down to the bottom for island recommendations and a sample itinerary. This won't take long and will be worth the preparation!

1.  Why the Greek islands?

What is calling your attention?

2. Do you already have any islands on your bucket list?  

Ask yourself why you are choosing those. If yes jot down the names and your thoughts. If not, all good! Keep reading.  

3. Who are you planning to travel with?

Solo, friends, family, lover?

4. What is your travel style?

Want a more local experience? Off the beaten path? Touristic? Quiet? Hidden Beaches? Iconic sights? More culture? Super Instagram worthy? Far away from tourists? Don't mind tourists?  Looking for the best parties? Need infrastructure?

5.  What is your budget?

Economy, moderate or luxury?

6. When do you want to go to the Greek islands?

Spring break? Summer holiday? Fall time?  The hotter the better?  Lower temps, please?

7. How long do you want to stay in the Greek islands?

Do you want to stay in one place? Travel to a few islands? Hit up mainland Greece?

8. What activities are you into?

Visit museums? Stay outdoors? Water sports? Food tours? Wine tasting?  Just relax?

9. Do you want to visit any other countries during your trip?

Or just stay in Greece?

10.  How do you want to get there?

Ferry? Flights? Sailing?  

7 Sample Greek Island Itineraries

1.  For the solo traveler looking for peace, quiet and culture

Navagio Beach

A. Island hopping Zakynthos, Kefallonia, and Ithaki

B. Island hopping Astapalyia and Symi

C. A week in Crete



2.  For the party traveler looking to meet people

A. Opt for a group tour with a company like Intrepid (median age 35) or Contiki (18-35). Their trips will have iconic, but social itineraries. 

B. Athens, Mykonos, Ios and Paros, Athens

C. Island hopping Corfu and Zakynthos

D. Athens, Mykonos, Paros, Santorini, Athens 

santorini sunset

3. For a classic and iconic island hopping experience

A. Athens, Mykonos, Santorini, Ios, Athens

B. Corfu, Athens, Mykonos, Santorini, Athens

C. Athens, Mykonos, Santorini, Crete, Rhodes

4. For the lovers and the romantic getaway

A. 3 days in Corfu and 3 days in Kythira

B. Island hopping Spetses, Hydra, Santorini

C. Party in Rhodes, then hop to Milos and then Crete

5.  Spending time in Turkey

A. Visit Rhodes, Kos, and Symi 

B. Nysiros, Tilos and Leros

C. A week in Rhodes 


6.  For some adventure and downtime combined

A. Kalymnos, Kos, and Nisyros

B. A week in Crete

C. Mykonos, Santorini, Zakynthos

7.  Greek island hopping on a budget

A. Athens, Zakynthos, Athens

B.  A week in Symi

C. Paros and Ios


Greek Island Hopping Resources

  • Flights from Athens to Zakynthos can be flown on Olympic Air
  • The currency is the Euro
  • Cash is generally preferred on the islands. Try to get euros from your bank before traveling. Although there will be plenty of ATMs.  You may have difficulty using your credit card or debit card. 
  • Don't drink the water! Bottle water only. Tap water is OK in Athens.
  • Small tips are expected at restaurants.  You can round up your bill or offer a euro or two depending on the restaurant and cost of your meal. 
  • If you are from the USA, have no fear! Driving is on the right side of the road, although there will be more manual shift cars available than automatic. Make sure to reserve in advance. 
  • Greece has an abundance of fresh veggies in their cuisine making it an easier travel destination for vegetarians and vegans. 
  • Popular ferry operators can be found using Let's Ferry and Greek Ferries and Ferries in Greece  If you know your exact route you can also buy direct from the operator such as Blue Star Ferries
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Dreaming of a trip to the Greek islands? Put Zakynthos at the top of your list.

Dreaming of a trip to the Greek islands? Put Zakynthos at the top of your list.