A guide to planning the ultimate Greek islands itinerary

A sunny haze of lemon groves, turquoise waters, meandering street cats and sleepy, whitewashed villages; it’s no surprise that the Greek islands have drawn people for centuries. A scattering of jewels across the Aegean and Ionian Seas, you’re spoilt for choice when it comes to a vacation; each island has its own rhythm and its own story to tell. With such sensory delights in store, the question isn’t whether you’d visit the Greek islands, but which Greek island should you visit first? In this guide, we’ll help you plan a Greek islands itinerary that suits your pace and priorities – whether you’re after a short beach getaway or a grand, island-hopping adventure.

Planning your perfect Greek islands itinerary

If you dream of sipping a cold glass of wine to the sound of calm waters lapping the shore, here are …

A brief overview of the Greek islands

The Greek islands are popular for a reason; there’s simply something for everyone in this beloved archipelago. Of these 6,000 islands, over 200 are inhabited, spread like jewels across the Aegean and Ionian Seas.

The islands are divided into several main groups: the Cyclades (includes Santorini and Mykonos), the Dodecanese (Rhodes and Kos), the Ionian Islands (Corfu and Kefalonia) – then there are the North Aegean Islands, the Sporades, and the Saronic Islands near Athens.

Each group has its own distinct character, landscapes and cultural influences, so whether you’re looking for beaches, myths and history, local life, culinary experiences, boutique luxury or nightlife, there’s bound to be a combo of islands that will tick your boxes.

Choosing the right islands for you

Before booking your trip, think over how you’d like to spend your time on a Greek island. If your priority is to really get under the skin of the place and you want to take each day slowly, you might be better off visiting one island, or perhaps two, that really suit you. If your priority is experiencing the diversity of the islands, however, you could hop between three or more. This also depends on your length of trip (we’ll go into that later).

Chatting to one of our local travel experts in Greece takes a lot of the decision-making off your hands, as their in-depth knowledge of the islands means they can make suggestions, plan your itinerary, and book your accommodation, activities and transfers for you.

Seasonal Greek islands itinerary planning: when is the best time to visit?

The best time to visit the Greek islands is during late spring (May to early June) and early fall (September to mid-October). During these periods, the weather is pleasantly warm, the sea is perfect for swimming, and the islands are far less crowded than in the crush of peak summer (late June-August).

The flowers are blooming in the spring, while the harvests of fall make for delicious food experiences and still warm weather. Winter months (November-February) are blissfully empty! However, many tourist facilities are closed, temperatures are cool, and beaches can be windswept.

Island hopping in Greece: best ways to explore

The most affordable, most convenient way to travel between the Greek islands is by the ferry network, which is wide-reaching and reliable. Choose islands in close proximity with each other; while island-hopping is fun, it’s not so fun traveling the long distances between disparate islands (there’s 370 miles between Crete and Corfu!).

If you’re keen to squeeze your top choices into one trip, however, you could fly between some of the bigger islands. You can use online booking sites to secure your spot on a ferry, or our local travel experts based in Greece can sort all transfers for you.

Planning a short trip to the Greek islands

If you only have a few days to spare, focusing on one or two islands is the best way to enjoy the Greek islands without feeling rushed.

• The popular combo is Santorini and Mykonos in the Cyclades, known for their stunning beaches, sweeping ocean views and iconic photo opportunities – though it gets extremely crowded in these two Greek gems and prices are high.
• As a lesser-visited alternative, try pairing Paros’ stylish accommodation and chic harbor towns with Naxos’ laid-back villages and scenic hiking; or you could combine Corfu’s diverse, ‘bit of everything’ quality with the smaller, village feel of Paxos.
• Alternatively, the Saronic Islands near Athens like Hydra or Aegina are charming and peaceful, and can be reached easily from the mainland.
• Or, choose a larger island to base yourself with lots to do, such as Crete. With limited time, you can make the most of the beaches, the pretty local towns, and the delightful cuisine.

How to spend 10 days or more in the Greek islands

You’ve got a good stretch of time to spend island-hopping – lucky you! With 10 days in Greece, you can get beyond the usual tourist trail and explore some of the more laid-back, characterful islands. Be sure to pick islands with good ferry links, and get ready for an enchanting trip.

• The Cyclades are very popular – but to skip the obvious Santorini, Mykonos route, try a loop of three such as Syros, Tinos, Naxos; or Sifnos, Milos, Folegandros. These islands offer an alluring mix of historical sites, sun-splashed beach days, al fresco dining and local rhythms, all with a slower, more authentic feel than the well-known destinations.
• Another rewarding region is the Dodecanese, where islands like Leros, Nisyros and Tilos are full of hospitable locals, volcanic landscapes, and even medieval castles.
• The North Aegean is also fantastic for a more rugged, forested experience; combine Ikaria and Chios if you like your travels a little wilder and off-grid.

Island pleasure-seeking: the best things to do on the Greek islands

Beaches are a given on the Greek islands – and yes, they’re as dreamy as you’d imagine. The diversity of the beaches across Greece is what’s truly spectacular – from milky-blue waves to sea-green saline lakes surrounded by trees; with shores of soft sand or a bed of white pebbles. It’s not all about sun-tanning and swimming, however! Here are some activities beyond the beach towel…

Explore the great outdoors

For sea lovers who are keen to get active, there’s always paddleboarding, sea kayaking, snorkeling or even scuba diving, offered on many of the islands (though check in advance if the scuba visibility is up to par). Renting a sailboat is another chic option if you like to luxuriate on the water’s surface instead of the shore.

If you can tear yourself away from the idyllic coast, there’s a hiking wilderness to venture into. Hike pine-fringed mountain trails on Andros, admire dramatic caldera views from the cliffs of Santorini (or try nearby Folegandros for a similar effect), or enjoy atmospheric, volcanic hikes on Nisyros.

For cyclists, many islands are excellent for either road cycling or mountain biking – Naxos, for instance, has lots of flat trails. Climbing and via ferrata are also popular if scrambling the cliffs is your thing – Kalymnos is great for this.

Cultural experiences galore

Almost every island in the Greek archipelago is steeped in history and culture, as this is one of the most ancient nations in the Western world. Think tiny village churches, centuries-old monasteries, Venetian castles and ancient Cycladic ruins.

You could spend time exploring the old marble-carving arts in Syros, and its spontaneous bouzouki performances (a type of folk music), or the local summer parades in Tinos and other islands.

The Palace of Knossos on Crete is an impressive relic of the Minoan people; while Delos is one of Greece’s most important archaeological sites, with well-preserved temples, theaters and mosaics protected by UNESCO.

Seafood, tavernas and culinary treats

Divine culinary dishes are one of the most memorable parts of a trip to Greece, and every island has its own local flavor. Of course, fresh fish is the star of the Aegean, grilled and served with lemon and olive oil. You’ll also find just-caught octopus drying in the sun in Anafi, chickpea stews simmering away on Sifnos, and crumbly feta cheese pies in Ios.

It’s so easy to eat well here – and dining is where local Greek hospitality really shines. Just pull up a chair at a family-run taverna and let the home-made dishes roll out slowly, as a neighborhood cat rubs against your feet.

Frequently asked questions about island hopping in Greece

For now you’re probably eager to chat to our local Greece experts about your fantastic vacation to the Greek islands, but to finish, let’s cover some final questions.

How many days do you need for a Greek islands itinerary?

If you only want to visit one island, don’t spend fewer than 3-4 nights there so you can really relax on your trip. A week is perfect for a short break, but to take it slowly and island-hop, 10 days or more is the dream amount of time.

In what order should I visit the Greek islands?

It totally depends on what your priorities are for your Greek island vacation. Many visit the Cyclades as they’re very popular with iconic scenery (Santorini, Mykonos, etc), and they truly are stunning – but can get busy.

To avoid the crowds, there is a plethora of smaller, lesser-known islands to take a chance on; some so tiny, with villages so local and authentic, you’ll feel like you have them to yourself.

Of course, other beloved islands such as Crete, Corfu or Kefalonia are also great all-rounders that promise a dreamy experience.

What is the best way to island hop around Greece?

Ferries will be your main way to get around, but domestic flights can sometimes help link far-flung islands, if you have a hitlist of favorites. For a shorter trip (a week or less), it’s best to stick to one or two of your choice islands. For a longer trip (10 days or more) a good rhythm is to spend 2-3 nights per island; but it’s really up to you.

What is the best Greek island for first timers?

Again – it depends on your vision! If you are dreaming of the blue-domed churches of Santorini with its sea views to the horizon, your best bet is to visit in the shoulder seasons (April-May, September-October) or try a lesser-visited cousin such as Folegrandos (similar cliff-edge villages and glorious hiking).

Islands such as Crete have something for everyone – nightlife, great food, outdoor activities and spectacular beaches – with the opportunity to get away from the tourist centers if preferred. If you’re visiting Athens, the islands near the mainland such as Hydra are great to tack onto your trip.

However, if you want to feel truly among locals and away from the hubbub of visitors, renting a car and traveling around lesser-visited, but still well-connected islands like Milos, Syros or even Kefalonia can be a great way to really experience local islander life.

Make it happen

To start planning your dream Greek islands itinerary, get in touch with our local travel experts today. They’re based on the ground in Greece, with all the local knowledge required to plan an itinerary in the Greek islands that’s just perfect for you.