15 Best Greek Island Hopping Itineraries

15 Best Greek Island Hopping Itineraries

Author’s Note: I travel between the Greek island groups by flight and ferry every year and have done so for many years now. In 2023 I island-hopped between Athens, Aegina, Tinos, Mykonos, Delos, Crete, and Naxos. I’ve just booked this year’s epic Greek island-hopping trip to 11 islands in 3 island groups (plus Crete!)

I travel around the Greek islands every year and in this article, I share with you my 15 best Greek island hopping itineraries for every kind of traveler and every kind of holiday, ranging from suggestions for first-timers to season-long itineraries for long-term experienced travelers.

Things to know about Greek island hopping itineraries

The Best Time to Visit

Greek islands are places where people live and thrive all year round. Greek islands do not shut for winter, but the majority of tourist enterprises (many bars, restaurants, taverns, experiences, excursions, and tours) do stop around November, only to re-open in May.

So, the best time for a Greek island hopping adventure is late spring, summer, and early autumn.

Late May until the end of October

Greek ferries come in all shapes and sizes.
Greek ferries come in all shapes and sizes.

Remember, getting there is half the fun!

How Many Islands in One Go?

Depends on how many days you have available. Here are some simple but effective suggestions:

🏝️ Up to 7 days: 2 islands

🏝️ Up to 10 days: no more than 3 islands

🏝️ Two weeks: 3-4 islands

🏝️ Month-long trip: 6 islands

Remember that getting to your island takes time and not all islands are connected with all the others (especially in different island groups), so leave enough time for traveling between the islands.

Getting Around

Ferry is the king. There are many ferry companies servicing national and local island ferry routes that make a wide network of lines that you will be using.

Don’t be alarmed by long hours on Greek ferries, being on board is part of the experience, especially on the smaller vessels.

TIP: if you suffer from seasickness, choose islands serviced by big vessels, not high-speed ferries.

Airplanes from Athens or Thessaloniki offer an easy transfer to your local island group hub, where you can then take a ferry to continue your trip.

For example, you can fly to Rhodes in under an hour or take a 12-hour ferry ride, both from Athens.

A cruise ship at Mykonos Port, Mykonos Island, Greece
A cruise ship at Mykonos Port, Mykonos Island, Greece

Avoid large cruise ships, they steal all the fun hidden in the trips where you mingle with the locals and other tourists, understanding what it really means to live an island life.

For example, seeing an air conditioning unit sent from Athens to a tiny island, secretly placed in a corner of a ferry hull, until a bunch of friends take it out in a matter of seconds during a ferry’s brief docking on the island!

TIP: I get all my ferry information and bookings via Ferryhopper.com  

The Cost of Greek-Island Hopping

Greek island hopping is not more expensive than a regular holiday in Greece.

Cafe on beach at Naxos Island with Portara of the Temple of Apollo in the background, Naxos Island, Greece
Cafe at Naxos Island with Portara of the Temple of Apollo in the background, Naxos Island, Greece

Excluding the inbound flights to Greece you have to take, a ballpark figure of 80-100€ per day could cover all your budget hotels, travel, and food expenses around the islands.

But this is a very small budget and it is very easy to spend multiples of this.

Of course, some islands are more expensive than others, hotels can be luxurious, and the food is Michelin-star, so the amounts spent can go as much as you like, but the basics are still quite reasonably priced. 

How to Choose Your Itinerary

The most important thing to consider when choosing your itinerary is the number of days you have available.

Photo of the fishermen's houses at Klima village, Milos, Greece
Fishermans’ houses at Klima Village, Milos Island, Greece

The islands are separated into island groups and traveling between them means ferry connections and you need to calculate that into your schedule.

After that, consider what you want from the islands – a party scene, ancient history, and archaeology stuff, meeting authentic insular Greece, or utter beachside relaxation.

Combinations of all the above are feasible and actually, many people do that – start with a bigger and fancier island only to end a holiday somewhere low-key.

The 15 Best Greek Island-Hopping Itineraries

Map of the Greek Islands

First time in Greece: Athens, Santorini, Naxos or Crete

Do you want it all at once, a Greek island experience in a nutshell?

Venetian Harbor of Rethymno, Crete, Greece

Start from Athens and fly to Santorini to admire the unique Cycladic architecture, landscape, sunset, and everything else this unique Mediterranean island offers, only to proceed to somewhere more quiet, but still big enough to live the authentic island vibe.

That place can be:

🏝️ Naxos, one of the largest Cyclades islands with spectacular sandy beaches, vibrant hilly villages, and lots of opportunities for exploring.

🏝️ Crete – the largest Greek island, a world into itself, a place with unrivaled archaeology, beaches, food, and lifestyle. Great off-season option, too.

2. Glittery Islands: Mykonos, Santorini, and Paros

Greek islands are the world’s prime luxurious party dancefloors for the super-rich and famous.

Grace Hotel, Santorini, Greece
The stunning Grace Hotel, Santorini, Greece

Meeting the likes of Jeff Bezos, Beyoncé, Elon Musk, Leo di Caprio, Kim Kardashian, and Magic Johnson is business as usual around Santorini, Mykonos, and Paros during the summer.

TIP: These islands are quite pricy and booked quite early.

3. A bit of both worlds: Santorini or Mykonos, then Paros and Naxos

Greek summertime hotspots are great for the start of the holiday, but do you crave something more relaxing for the vacation’s ending?

Naoussa Marina, Paros Island, Greece

Consider starting off with Mykonos and Paros to get the taste of the Aegean Sea highlife, only to proceed to real-life Naxos for the variety of beaches, normally-priced watersports, ancient sites, and quaint seaside taverns.

4. True Cyclades: Sifnos, Serifos and Milos

Cyclades are all about arid landscapes, traditional villages, sugar-cube whitewashed houses, and spectacular sunsets.

Mandrakia Village, Milos Island, Greece
Mandrakia Village, Milos Island, Greece

Add to this sandy beaches, the azure sea, and a lively central village (called Chora) during the evening for hearty Greek island food, drinks, and summer festivals that bring locals and tourists together like nothing else.

All of this, plus a lot of summerhouses for the Athenian middle class means these islands maintain the classic Cyclades charm while being easily accessible and close to Athens.

5. History Tripping: Mykonos (Delos), Milos and Crete

Greece is, after all, one of the world’s prime destinations for ancient cultures and archaeological sites.

The sacred island of Delos, Greece
The sacred island of Delos, Greece

You will hardly beat the importance of Delos, just off Mykonos, one of the holiest island spaces during Greek antiquity and home to the famous lion statue, the layered heritage of Milos lasting to this day, and the vast archaeological treasures of Crete.     

6. The Party Islands: Mykonos, Paros, and Ios

Vivid nightlife around the Greek islands is nothing new; it’s been going strong since at least the 1950s.

Mykonos Chora, Mykonos Island, Greece
Mykonos Chora, Mykonos Island, Greece

Today’s places to be for lavish parties, day and nighttime, in the nightclubs or beach bars are definitely Mikonos, followed by Ios and Paros. Luckily, they are all close by.

7. Off the beaten path Cyclades: Sikinos, Folegandros and Kimolos

Dreaming of sleepy, quaint islands where the hustle and bustle of the rest of the world has not arrived yet?

Folegandros Island, Greece

Looking forward to some really quiet time, except occasional evening drink, but don’t want to compromise on the food quality, warmth of the locals, and spectacular seaside?

No matter how long you have, divide your holiday time between these 3 islands and enjoy a sneak peek into what the Cyclades used to be decades ago. 

8. Best of the Dodecanese: Rhodes, Symi and Patmos

The Dodecanese island group is diverse and can feel detached from the cosmopolitan allure of the Cyclades, despite the gravitas of the Rhodes as a cultural, touristy, and transportation hub.

Spend a couple of days exploring its majestic multilayered heritage, proceeding to picture-perfect Symi and spiritual Patmos.

(I must admit, I’d spend a few days exploring Kos Town on Kos Island as well).

Panormitis, Symi Island, Greece
Panormitis, Symi Island, Greece

9. The Up-and-Coming Dodecanese islands: Rhodes, Karpathos and Kasos.

Again, after Rhodes proceed to hilly Karpathos, a place with the cutest island hilly village out there, the Olympos.

Palace of the Grand Master, Rhodes, Greece
Rhodes old town with Palace of the Grand Master, Rhodes island, Greece

After that, do not miss Kasos, one of the remotest islands in Greece and a gateway to Crete.

10. Low-Key Dodecanese: Rhodes, Halki and Tilos

Perfectly tailored for those not keen on ferries, this itinerary will take you to the quietest islands of the Dodecanese.

Halki and Tilos feature great beaches, small family hotels, traditional taverns, and calmness that rejuvenates. 

11. North Aegean Pearls: Samothraki, Lesbos, Ikaria

Completely different in nature and customs from the rest of the insular Greece, and with thriving local population, these islands are real Greece.

Chora, Samothraki Island, Greece
Chora, Samothraki Island, Greece

Samothraki with its wild beauty cliffs and waterfalls, Lesbos with its high-brow culture, the homeland of Ouzo and pristine nature, and Ikaria, one of the world’s blue zones will make you think hard about moving permanently to these west Aegean havens. 

(I would try and fit in a day visiting Pythagoreia on Samos island as well).

12. Magical Saronic Gulf Islands: Aegina, Hydra and Spetses

The Hamptons of Greece – Hydra, Spetses, and Aegina not only played crucial roles in Greek history but represented a playground for Greece’s old money as well as for the international creative elite, royalty, and yachting crowds.

Aegina Harbor, Aegina Island, Greece
Aegina Harbor, Aegina Island, Greece

Seriously, it takes all of one minute to fall in love with Aegina or Hydra.

You can do all of them on an Athens day trip, too.

13. Ionian Islands: Corfu, Paxoi, and Ithaka

Elegant, lush, and picturesque, with Venetian, British, and Russian heritage and close to mainland Greece, these Ionian Sea islands are surrounded by cooler and more poignant-colored waters than any of the other islands.

Paleokastritsa Bay, Corfu, Greece
Paleokastritsa Bay, Corfu, Greece

Corfu town is like a small Bologna set in Greece, while Ithaka, besides its natural charms, is the home of the mythical king Odyssey.

And for Paxos (Paxoi), well, watch “Maestro” on Netflix and try not to fall in love instantly.  

14. Long-Term Island-Hopping: The Small Cyclades

The small Cyclades is an archipelago surrounded by bigger Cycladic islands. Comprising 5 inhabited islands – Schinoussa, Koufonissi, Iraklia, Donoussa, and Amorgos.

The beautiful waters of Koufonisia Island, Greece

These places are the best destinations for avoiding the crowds. If low-key is your thing, you could easily spend a month discovering them.

TIP: Don’t avoid the local Skopelitis Express ferry, the heart and soul of the Small Cyclades.

TIP 2: If on Amorgos, make visiting Hozoviotissa monastery your No. 1 priority.

15. Long-term Island-Hopping: Cyclades-Dodecanese (Milos, Santorini, Astypalaia, Rhodes, Nisyros, Kastellorizo)

When traveling for a month, options are endless.

Megistri Harbor, Kastellorizo Island, Greece

This is my favorite, where you start quite close to Athens, from Milos (the island even has its own airport), only to proceed further down the Cyclades route towards the gate of the Dodecanese – Astypalaia island.

From there, via Rhodes and Nisyros (an island-active volcano that you can actually visit), go to the easternmost point of Greece, to the magnificent and tiny eastern Mediterranean island of Kastellorizo.