The Best Greek Island-Hopping Itineraries

Kleftiko, Milos
Kleftiko, Milos | © Harout Arabian/Flickr
Ethel Dilouambaka

Greece is an ideal destination for island hopping. With its wide collection of islands, each with their own character and specific appeal, Greece offers a variety of options for you to discover its distant islands. While sailing aficionados will be freer to choose their destinations as they go, we have prepared a series of itineraries for those adventurers who prefer to rely on ferry companies. Here are the best island-hopping itineraries around Greek islands.

The Sporades Islands

Located on the eastern coast of mainland Greece and more specifically, northeast of the island of Evia (or Euboea), the Sporades island group features dense vegetation, rocky landscapes and stunning blue waters. Less accessible than the Cyclades, these are the perfect alternative destinations if you want to avoid the packed ferries to more popular horizons. Our itinerary takes you along the magnificent islands of Skyros, Alonissos, Skopelos and Skiathos. If you opt for a tour with a sailing company, chances are you will be able to stay in one or two islands according to your preferences.

View of Alonissos

The Ionian Islands

The verdant Ionian islands, located on the western part of Greece, in the Ionian Sea, are famous for their turquoise waters, breathtaking beaches and picturesque villages. These were not so easily connected in the past, but since May 2018, a new ferry line connecting has revolutionized island hopping in the Ionian Sea. All summer long, the company Joy Cruises offers three departures per week from Corfu (Kerkyra) and allow visitors to stop Paxos, Lefkada, Ithaki, Kefalonia and Zakynthos. A great news for those longing to explore these magical islands.

View of Vathy & Ionian Sea, Ithaca, Greece

The Cycladic Islands

The epitome of the Greek islands, the Cycladic islands are world-famous for their whitewashed houses, blue doors and windows and their pristine beaches. The most popular include majestic Santorini and cosmopolitan Mykonos, but it boasts a few gems such as Syros, Tinos, Sifnos, Amorgos, Paros, Milos, and the lesser-known islands of Koufonissia, Iraklia, Schoinoussa and Keros. You can definitely enjoy a week-long trip around the closest islands or take full advantage of a sailing charter company and take it easy on the yacht deck for an afternoon.

Monastery of Hozoviotissa, Amorgos

The Dodecanese islands

A bit further to the east of Greece and close to the Turkish mainland lie the Dodecanese islands, which includes Rhodes, Patmos, Kos, Astypalea, Kalymnos; and the lesser-known, though still enchanting, Symi and Kastellorizo. The archipelago includes a few uninhabited islets as well which offer the same charm as the more popular destinations, if not a more authentic appeal. Ideal for scuba divers, hikers and those loving water and wind sports, the Dodecanese islands are filled with historic centers and a traditional culture which will seduce the more discerning travelers.

Port of Kastellorizo

The Argo-Saronic Islands

Perfect for those pressed by time, the Argo-Saronic islands are the islands closer to Athens and the Attic peninsula. Conveniently connected to the Greek capital, they still offer relaxation, tranquility and a touch of exoticism. Whether you opt to visit the most famous islands of Aegina and Hydra or want to explore the pine-covered islands of Poros and Spetses, you are sure to find plenty of beaches and secret coves to explore.

Hydra island

The Northeastern Aegean Islands

Situated off the coast of Turkey, the far-flung islands of the northeastern Aegean Sea (which include Chios, Samos, Lemnos, Lesvos and Ikaria) have been shielded from mass tourism, and therefore, remained virtually unchanged throughout the decades. The archipelago can be explored by ferry although connections are few and not always convenient. You would be better off booking a sailing boat as the area counts a few dozen people-free islets where you can escape reality. Lemnos will seduce you with its fascinating volcanic formations dotting the island and you will fall in love with Chios and its mastic-producing villages. Lesvos is the place to be for divers and Ikaria will enchant those seeking an authentic way of life. Larger than the Cycladic islands, the Northeastern Aegean islands can be visited over several days, as they offer a wide choice of activities and options.

Finally, if you opt for traditional ferry routes, we highly recommend you take advantage of the website Ferryhopper, which allow you to find the best ferry connections according to where you want to go.

culture trip left arrow
 culture trip brand logo

Volcanic Iceland Epic Trip

meet our Local Insider


women sitting on iceberg


2 years.


It's the personal contact, the personal experiences. I love meeting people from all over the world... I really like getting to know everyone and feeling like I'm traveling with a group of friends.


I have so many places on my list, but I would really lobe to go to Africa. I consider myself an “adventure girl” and Africa feels like the ULTIMATE adventure!

culture trip logo letter c
group posing for picture on iceberg
group posing for picture on iceberg

Every CULTURE TRIP Small-group adventure is led by a Local Insider just like Hanna.

map of volcanic iceland trip destination points
culture trip brand logo
culture trip right arrow
landscape with balloons floating in the air


Connect with like-minded people on our premium trips curated by local insiders and with care for the world

Since you are here, we would like to share our vision for the future of travel - and the direction Culture Trip is moving in.

Culture Trip launched in 2011 with a simple yet passionate mission: to inspire people to go beyond their boundaries and experience what makes a place, its people and its culture special and meaningful — and this is still in our DNA today. We are proud that, for more than a decade, millions like you have trusted our award-winning recommendations by people who deeply understand what makes certain places and communities so special.

Increasingly we believe the world needs more meaningful, real-life connections between curious travellers keen to explore the world in a more responsible way. That is why we have intensively curated a collection of premium small-group trips as an invitation to meet and connect with new, like-minded people for once-in-a-lifetime experiences in three categories: Culture Trips, Rail Trips and Private Trips. Our Trips are suitable for both solo travelers, couples and friends who want to explore the world together.

Culture Trips are deeply immersive 5 to 16 days itineraries, that combine authentic local experiences, exciting activities and 4-5* accommodation to look forward to at the end of each day. Our Rail Trips are our most planet-friendly itineraries that invite you to take the scenic route, relax whilst getting under the skin of a destination. Our Private Trips are fully tailored itineraries, curated by our Travel Experts specifically for you, your friends or your family.

We know that many of you worry about the environmental impact of travel and are looking for ways of expanding horizons in ways that do minimal harm - and may even bring benefits. We are committed to go as far as possible in curating our trips with care for the planet. That is why all of our trips are flightless in destination, fully carbon offset - and we have ambitious plans to be net zero in the very near future.