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How to Plan a Greek Islands Vacation for the First Time

When you’re planning a holiday to the Greek Islands, it’s more than choosing a few beautiful beaches and booking your flight.

There are dozens of islands to choose from, ferry routers to consider, as well as the more obvious things, like your accommodation options. I’m going to give you some tips on things to consider when booking a Greek Islands vacation for the very first time. 

How to Plan a Greek Islands Vacation for the First Time

Choosing The Right Greek Islands For Your Travel Style

You need to think about what it is that you enjoy the most. If you want dramatic sunsets, cliffside towns and the iconic blue domed churches, choose Santorini. Stay near Fira or Oia, for the classic views and sunset spots. 

If you want lively beaches and nightlife scene, go for a Mykonos holiday. You’ll find beach clubs, restaurants and late-night parties all close to the town. Mykonos towns puts you near ferries and day trips to the quieter beaches, should you want them. 

For a mix of history, varied landscape and some more family-friendly options, consider Crete. Explore Chania for the charming Venetian streets and amazing food. You can drive or join a tour to Balos Lagoon, for turquoise waters and more remote beaches.

If you only have a few days, pick just one island and relax. If you have a week, or more, you can always island-hop, as the ferries connect the major islands.

Best Time Of Year To Visit The Greek Islands

Choose the late spring (April to June) or the early autumn (September to October) for warm weather, fewer crowds and lower prices. You’ll get warm sea temperatures for ocean swimming, and clearer skies for beautiful island views. 

The summer months (July to August) brings hotter days and more lively nightlife, especially on the more popular Greek Islands. Ferries will busier, hotel rooms will have higher rates and there will be crowded beaches. Try and book your ferries and accommodation early, to save the most money. 

Winter (November to March) is the quietest and cheapest, but many island businesses close and the ferries reduce their schedule. You can still taste authentic Greek food without the crowds, and enjoy slower travel. 

Deciding Between Popular Islands And Hidden Gems

You can choose between the more famous islands or quieter spots, depending on what you want to see and how you like to travel. The more popular islands have easy ferries, lots of hotels and lively nightlife. Whilst the hidden gems have calmer beaches, local life and fewer tourists.

If you’re wanting the iconic sights with easy connections, pick the well-known islands, and pair them with Athens. You can spend a day in central Athens, visiting the Acropolis, the Parthenon and the Acropolis Museum.

For slower days, go for the smaller islands, as you’ll get quieter beaches, local tavernas and beautiful landscapes. The ferries will be less frequent, but you’ll get a slower vibe to your trip. 

How To Navigate Ferries And Island Hopping

Ferries are the best way to move between Greek Islands. The routes do change by season, so always check the schedules for your planned travel month, and book popular routes early if you travel during the summer.

Choose islands within the same group, to keep your ferry times short. For example, stick to Cyclades or Dodecanese clusters when your holiday is less than 10 days long. Give yourself around 2 to 4 nights per island you visit, so you don’t feel rushes. 

Conventional ferries are slower, cheaper and usually let you move around on board, whereas the faster ferries will save you time, will cost you more, and they can be rough in the wind. 

Always make sure you pack light, and keep your day essentials in a bag for a short transfer, arriving at the port at least 30 to 60 minutes before departures, and have your printed or mobile tickets and ID ready.