Thanks to its thousands of islands, Greece is one of the best places in the world for island hopping holidays. Its Mediterranean location and good weather year-round means it’s always a good time to visit. And the best way to get a feel for life on the Greek islands is on a Greek Island hopping tour.
Each island has its own unique charm to enjoy, and the ferry system makes it easy to get between them. That means you can combine a bit of everything into one island hopping trip and get more for your money. This Greek Island hopping itinerary for 14 days covers five of the best Greek Islands, but you can adapt it to suit your trip. Whether you have two full weeks or less, simply pick out the bits you like the most and save the others for a later date.
Suggested routes for Greek Island hopping
Where you choose to start and end your island hopping tour will depend on flight routes, the time you have and your own bucket list. For that reason, I’ve kept this island hopping itinerary as flexible as possible.
What you see below is just a suggested island hopping route, based on the Greek ferry routes. It will allow you to maximise your travel time while minimising the time you spend on board a ferry.
Of course, feel free to skip any islands that don’t your fancy. I would still recommend sticking to this rough order, though, because it’ll be easiest to plan with the ferries. If you start on a different island, just cycle through to the end and finish up with the first part of the itinerary.
Getting around the Greek Islands
The best – and pretty much the only – way to get around the Greek Islands is on the ferries. There are several ferry companies that operate a wide range of routes, so it’s always easy to get to your next destination.
Like a lot of things, the ferries lack a certain amount of order and can be a total disaster if you’re not prepared. I wrote a massive guide with 20 important things you need to know about taking the Greek island ferries, so I recommend giving that a read before finalising your plans. It’ll help you with everything from knowing how much time to leave between islands to avoiding any unnecessary issues.
Greek Island hopping itinerary – 14 days
As I mentioned, this is just a suggested itinerary based on my own Greek Island travels. If you prefer a slower pace, then you may only want to visit 2-3 islands. But if you like to see as much as possible and maximise your time, this Greek Island itinerary will help you see a great selection in just 14 days.
The suggested hotels are the ones that I can recommend based on personal experience, but they’re also within walking distance of the port. That means you don’t waste any travelling around the islands – unless you want to, of course!
Days 1-2: Crete
Crete, the largest Greek island, has two airports: one in Heraklion and one in Chania. Most visitors head straight to Chania, regardless of which airport they fly into, but Heraklion is a fantastic city to stay in too. I should know – I lived there for two months!
Crete is much bigger than you would expect, and it takes around two hours to drive between the two airport cities. Both have their own pros, so I would suggest exploring the one you land in.
It won’t affect the rest of this itinerary because the ferries depart from both places, but they depart on alternate days in winter. Make sure you plan ahead if you’re visiting between October and May or re-jiggle your days to fit the ferry schedule. In the summer, the ferries depart from both cities daily.
What to see in Crete: It’ll depend where you’re staying, but Crete has no shortage of beautiful beaches and great food. It’s one of the cheapest Greek Islands and also has some incredible local dishes. Make sure you try dakos, a type of bruschetta, and the local cheeses. Both of best followed by some traditional Cretan rice pudding.
Where to stay in Crete: You’ll want to stay in either Heraklion or Chania, which is lucky because they’re both near airports! If you’re staying in Heraklion, you’ll be able to get a gorgeous little Airbnb for a very reasonable price. In Chania, we stayed in the Lucia hotel and the location (and views) couldn’t have been better!
Days 3-5: Santorini
Now you’ve had a couple of days to settle in and experience Greek hospitality at its best, it’s time to set sail. This is a Greek Island hopping itinerary, after all!
Our next stop is the one you’re probably most excited about: Santorini. Santorini is the first stop on the Seajets route from Crete, and the journey takes around 2-2.5 hours. If you want a slightly more comfortable ride and you’re staying in Heraklion, I recommend taking Minoan Lines’ Santorini Palace. It leaves at roughly the same time but it’s a lot nicer inside, and will only set you back a few more Euros.
I’m going to be straight-up honest here and admit it wasn’t love at first sight for me and Santorini. I was just as awed as everyone else when I first glimpsed its unique, rugged cliffs from the ferry, but I was kind of disappointed when I finally disembarked.
What to do in Santorini: The thing about Santorini is there isn’t much there. Unless you’re super wealthy, in which case it’s basically a dream come true. The best way to spend your time here is, ideally, lounging around an infinity pool. As the evening draws closer, wander the streets, enjoy some incredible seafood with a view and watch one of the best sunsets you’ll ever see.
Where to stay in Santorini: If you can, splash out a little to stay in Oia or Fira. It will be worth it. Santorini is expensive wherever you stay, so you may as well stay somewhere that’s (kind of) worth the over-inflated price.
Days 6-9: Naxos
Next, we’re moving on to my favourite island by far: Naxos! Lots of visitors completely skip Naxos, but I think it would be a real shame if you did too. Not only was it my favourite island, but there are far few tourists on Naxos. That means you can enjoy a completely different side of the Greek Islands, and it’s one everybody should experience.
What to do in Naxos: Naxos is a pretty small island and there’s not much beyond agriculture outside of Naxos Town. The town is a lot bigger than it first appears, and it’s full of winding alleys, cute boutiques and photogenic scenes. Spend your days exploring – don’t miss the old market! – and then enjoy an incredible harbour dinner after.
If you do venture out of the main hub, a short bus ride will take you to one of the many beautiful Naxos beaches. Or if you’re looking for a little more adventure, hire a quad and drive out into the impressive, yet desolate, mountains. You never know what you might find!
Where to stay in Naxos: Naxos has no shortage of hotels, but the seafront ones are easily the best. As well as fantastic views, you’ll be right on top of the action. We stayed at the Coronis Hotel.
Days 10-12: Mykonos
When we first started putting together our own Greek Island hopping itinerary, I knew Mykonos had to be on there. It was the island I was most excited to visit, and it didn’t disappoint. Mykonos was everything I wanted it to be: beautiful beaches, boutique hotels and photogenic windmills.
Yes, the food and hotels are expensive. But if you’re only there for a couple of nights, it’s not hard to justify.
What to do in Mykonos: Nothing! Make Mykonos your relaxation island. After all that island hopping, reward yourself with some downtime by the pool and follow it with a stroll on the beach if you get restless. If you have a driving license, it’s well worth hiring a quad or a car to explore this tiny little Greek island. The mountains are small enough to climb for sunset and there are lots of isolated corners to discover.
Where to stay in Mykonos: You’ll have no lack of choice when it comes to luxury hotels. We stayed in a small boutique hotel called the Ftelia Bay and it was fantastic, but I don’t think you can go wrong on Mykonos.
Days: 13-14: Back to Crete
Depending on how long you have and when your flight is, head back to Crete for a day or two. Now is the time to see anything you didn’t get to see at the start or just enjoy some time at one of the island’s many resorts. You’ll also have a new appreciate for the Cretan food prices after visiting the more popular Greek Islands!
Got more than 2 weeks in the Greek Islands?
If you have more than 14 days for your island hopping trip, you won’t want to miss Syros.
Syros is a little bit tricky to get to on this route, but it’s well worth the effort. You’ll need to take a short ferry from Mykonos to get there and the ferries usually leave in the early afternoon. That means you’ll need to factor an extra travel day, but you could easily swap out two of the islands above or fly in and out of Mykonos to make it easier.
Syros is a really amazing island and was one of my favourites. There’s a lot to explore, so you could easily fill 3-4 days or more.
Whether you decide to add to your itinerary, you won’t regret a Greek Island hopping trip. It’s one of the most beautiful parts of Europe and a trip that can be as lazy or as fast-paced as you like.
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