Everything you need to know to plan a Greek island holiday

written by Joanne Owen

updated 31.01.2024

Whether you’re looking for an immersive Greek island holiday in a single idyllic destination, or fancy hopping between a few Greek island vacation spots, read on to discover everything you need to know to plan a holiday to the Greek islands. From researching which are the best Greek islands to visit, to how to get the best deals on inter-island ferries, this will make planning your Greek island holiday a breeze.

Decide which Greek Island to visit

With hundreds of inhabited islands speckling the sparkling Ionian and Aegean seas, deciding which Greek islands to visit for your vacation is no easy feat.

Given that this is the first thing you need to know to plan a holiday to the Greek islands, here’s an overview of a few options to help you hone in on where to head.

Crete comes recommended as a richly rewarding all-rounder. Offering all the beautiful beaches you might want from a Greek island holiday, and exceptional archaeological sites (most notably Knossos), Greece’s largest island is also an excellent adventure destination.

As a result, everyone from hikers, bikers, horse-riders and history buffs will find plenty to do in Crete. The wine’s not half bad, either. In short, there are plenty of reasons this is one of the most popular Greek islands to visit.

Don’t want to use a package operator? In good news for those planning a Greek holiday, it’s easy to travel from Piraeus to Hydra by ferry throughout the year.

The North Entrance of the Palace with charging bull fresco in Knossos at Crete, Greece © Shutterstock

The North Entrance of the Palace, Crete, Greece © Shutterstock

Known as the “Lady of the Saronic Gulf”, historic Hydra is hands-down handsome, and a Hellenic hotspot for those who appreciate unspoiled, old world charm. We’re talking traditional architecture and a joyous lack of motorised vehicles.

Also a delight for hikers, Hydra is the perfect place to slow down and savour life’s simpler pleasures.

No guide to Greek island holidays would be complete without mentioning Corfu. Located between Italy’s heel and the west coast of mainland Greece, Corfu oozes lush, green, mountainous majesty.

Hydra island © Shutterstock

Hydra island © Shutterstock

With a long history of welcoming tourists to its spectacular shores, Corfu is also steeped in ancient legend. If that wasn’t enough, its elegant Old Town capital has UNESCO status.

Still unsure about which Greek island to visit? For an upscale, ultra-peaceful experience, you could consider picturesque Paxi.

Though petite, Paxi packs mighty punch when it comes to laidback luxury. It also offers a bounty of back-to-nature beauty, from enchanting sea caves, to therapeutic thermal springs.

Happily for those of you who are hoping to enjoy an island-hopping trip (more on that later), it’s easy to travel by ferry from Corfu to Paxi.

Pre-book transport — essential to planning a Greek island holiday

Hands-down our number one tip when it comes to planning a Greek island holiday — research and book your transport well ahead of travelling. That applies to flights and ferries — put simply, however you’re visiting the Greek islands, you should book ahead.

Happily, the Greek islands are served by an extensive network of ferry routes that add extra-scenic beauty to your journey. Alongside being practical, and sometimes necessary, boarding a boat is also one of the best ways to see the Greek islands.

That said, travelling by ferry can come with its own stresses. With so many operators covering so many routes, to so many islands, the planning process can end up feeling like a mind-boggling pain in the you-know-what.

So, for clarity and peace of mind — and to secure the best prices — we’ll let you in on a secret that’s guaranteed to transform how you plan holidays to the Greek islands. Simply use Ferryhopper, our trusted travel partner, for all your ferry needs.

The ferry with passengers turns to the port in Greece © Shutterstock

A ferry turns to the port in Greece © Shutterstock

For an invaluable overview that’ll make planning your trip a plain sailing experience, arm yourself with essential facts about Greek ferries.

Next, browse Greek islands ferry schedules to explore routes and prices across multiple operators. With the option to mix and match operators, you can pick times and prices that best suit your needs.

As an invaluable bonus, the Ferryhopper mobile app gives you access to e-tickets, and the facility to live track your ferry, with customer service support available before, during and after your trip.

For more peace of mind, you can arrange port and airport transfers with Ferryhopper’s trusted partner. All of which leaves you free to enjoy the best Greek islands holiday experience.

Get more from Greece — plan an island-hopping trip

Given the sheer number of ferry routes and operators running between the Greek islands, planning a multi-destination, island-hopping trip can seem pretty daunting.

But with Ferryhopper on hand to take the hassle out of planning and booking, you can arrange an island-hopping trip with ease, and confidence that you’re seeing the best route options, and securing the best prices.

The site’s comparison function really comes into its own when booking multi-island trips, as does the live tracking app. No more worrying about whether you’re paying over the odds, and no more worrying about whether your ferry is running on time.

Not sure where to start? For a quintessential multi-island jaunt, we recommend taking in the magic of Mykonos, Santorini and Crete. One of the most popular island-hopping trips for very good reason, visiting this trio of top islands rewards travellers with an undeniably diverse experience.

Mykonos with famous windmill © Shutterstock

Mykonos with its famous windmill © Shutterstock

Mykonos, for example, is exhilaratingly cosmopolitan when it comes to nightlife, restaurants and a range of resorts and villas that cater to everyone from young families to 24-hour party people.

At the same time, Mykonos boasts captivating natural beauty and some of the region’s finest beaches.

Meanwhile, Santorini is justifiably famed for its legendary awe-inspiring sunsets, iconic blue dome churches and spectacular volcanic landscapes. Add to that out-of-this world seafood, stunning beaches and quaint villages, and Santorini offers an unforgettable island experience.

Another island-hopping itinerary that’ll please everyone from couples to families kicks off on Kos. From here, you can easily take a ferry to Kalymnos, Astypalea or Nisyros.

The beautiful birthplace of Hippocrates, Kos itself is rich in ancient attractions, beaches and activities for all ages. Take your pick from cycling, sailing and windsurfing, or enjoying Aquatica Water Park. Kos is also the liveliest island of the Dodecanese.

Lastly, to enjoy the best of both worlds on an island-hopping trip — cosmopolitan buzz and back-to-nature tranquility — we recommend a route that combines popular Rhodes with lesser-visited Symi, Tilos or Halki.

After exploring the Old Medieval Town of Rhodes, a UNESCO World Heritage Site, and enjoying the island’s many, many beautiful beaches and bars, board a ferry to nearby Symi.

With an abundance of restored neoclassical buildings and mansions, Symi is a place to unwind in style.

Alternatively, take a ferry from Rhodes to Tilos. Energy self-sufficient, this tiny island is Greece's first official “green island” and exudes a wild beauty that gets under your skin.

More green goodness awaits on bijou Halki, also easily reached by ferry from Rhodes. Heading towards becoming one of Greece’s first emission-free islands, Halki is esteemed for its enchanting scenery, secluded beaches and lovely laidback vibe.

Decide when to visit

When planning holidays to the Greek islands, you’ll want to consider when’s the best time to visit.

In general, all the Greek islands are at their most idyllic just outside the super-peak period that runs from early July to the end of August.

These months draw huge numbers of visitors that raise prices and can cause crowding on otherwise idyllic secluded coves.

All that considered, planning a Greek island holiday between late May and early June, or in September, is a good idea. During these months, you’ll enjoy warm weather with fewer crowds and fairer prices.

Kerkyra, capital of Corfu island, Greece © Shutterstock

Kerkyra, capital of Corfu island, Greece © Shutterstock

Just be aware that some ferry routes are reduced outside the summer months. So, when planning a Greek island holiday, checking schedules before making firm plans should sit high on your planning list.

Related, it’s also worth bearing in mind that timetables for some of the shorter, less popular routes might not be available months and months in advance. So, we recommend checking Ferryhopper's fare engine on a regular basis. This enables you to view all available routes for major companies the moment they go live.

We also recommend checking summer ferry timetable schedules in late February/early March. And the reason? If, for example, you were hoping to book a ferry from Athens to Santorini in December, with the intention of travelling in August, it might not be available so far in advance. Best to check Ferryhopper from early spring.

Planning your trip to one of the many Greek Islands? Check out the snapshot The Rough Guide to the Greek Islands or The Rough Guide to Greece. If you prefer skip the hassle of planning and booking, use the expertise of our local travel experts to make sure your trip will be just like you dream it to be.

We may earn commission when you click on links in this article, but this doesn’t influence our editorial standards. We only recommend services that we genuinely believe will enhance your travel experiences.

This article was brought to you in partnership with Ferryhopper.

Joanne Owen

written by Joanne Owen

updated 31.01.2024

Joanne is a Pembrokeshire-born writer with a passion for the nature, cultures and histories of the Caribbean region, especially Dominica. Also passionate about inspiring a love of adventure in young people, she’s the author of several books for children and young adults, hosts international writing workshops, and has written articles on the Caribbean and inspirational community initiatives for Rough Guides. Follow her @JoanneOwen on Twitter and @joanneowenwrites on Instagram.

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