This Greek Island hopping itinerary will show you all the best islands in Greece.

Thanks to its thousands of islands, Greece is one of the best places in the world for island hopping holidays.

A Greek Island hopping holiday almost guarantees great weather thanks to Greece’s Mediterranean location. And then there’s the islands themselves…

The Greek Islands are a truly magical place to explore. And the best way to get a feel for life on the Greek islands is on a Greek Island hopping tour.

As you’ll quickly discover while island hopping in Greece, each island here has its own unique charm to enjoy.

Exploring the islands and finding what makes each one unique makes for a fun and exciting trip.

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How to spend 2 weeks island hopping the Greek Islands

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Why island hopping the Greek Islands is great

Unlike some destinations, Island hopping is super easy here.

The Greek Island ferries provide regular, comfortable transport between many of the islands, making 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.

With each island offering something completely different from the next, it’s easy to feel like you’ve had multiple trips in one.

The Greek Island hopping itinerary for 14 days below 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.

Of course, if you have time to visit even more islands in Greece, you can also add those on too!


I’ve put together a downloadable packing list for Greece so you can make sure you don’t miss anything.

It’s interactive, too, so you can print it off or check it off on your laptop as you pack. 

Click here to download yours for free.

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 the ferries.

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.

Seajets Caldera Vista ferry in the Greek Islands

Getting around the Greek Islands

The best – and pretty much the only – way to get around the Greek Islands is on the local ferries.

There are several ferry companies that operate a wide range of routes around the Greek Islands, 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 this 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.

Most of the ferries in the Greek Islands follow a round route, starting and ending in the same place with several stops in-between.

Therefore, it’s best to stick to just one or two ferry routes when planning your Greek Island hopping trip.

As the 14 day Greek Islands itinerary below proves, that still leaves you with plenty of options!

A dreamy Greek Island hopping itinerary for 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.

They’re also mostly 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. You can start your Greek Island hopping from either of these popular towns.

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 stayed there for two months when I was living in Greece!

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.

Your choice won’t affect the rest of this itinerary because the ferries depart from both places. However it, will affect which day you can depart if you’re visiting Greece in winter because they only leave on alternate days.

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.

Click here to check the ferry schedule and availability.

What to see in Crete:

It’ll depend where you’re staying, but Crete has no shortage of beautiful beaches and the tastiest Greek 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 are best followed by some traditional Cretan rice pudding.

If you want to experience the traditional side of the Greek Islands, Crete is the best place to do it. If you stay in Heraklion, this value-for-money tour will show the famous Zeus Cave as well as a local oil factory, finishing with a traditional Cretan lunch.

And if you choose to base in Chania, you can get to know Crete through this wine and food walking tour.

RELATED READ: What to pack for a trip to Greece

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 rental apartment for a very reasonable price. Our studio was only around 200 Euros per month, but you can get enjoy a luxury stay for less than elsewhere, too.

In Chania, we stayed in the Lucia hotel and the location (and views) couldn’t have been better!

Santorini sunset Greek island hopping

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, unfortunately, that didn’t last long. I was kind of disappointed when I finally disembarked. It’s definitely most impressive from the water!

That said, Santorini is still worth visiting on your Greek island hopping trip and I would still love to go back. It has a great mix of cute streets, busy nightlife areas and secluded beaches.

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. Alternatively, get back on the water and soak up those impressive cliff views under the sunny Greek sky.

This semi-private catamaran cruise includes a buffet BBQ with drinks, as well as plenty of stops for swimming and snorkelling.

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. 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.

The Secret Legend Suites are one of the best options as the budget end of the spectrum (if you can call it that!). If you want to go all out, the Elite Luxury Suites offer the full once-in-a-lifetime Santorini experience you can’t get elsewhere.

If you’d rather stay away from the action (and save some money), there are several hotels worth checking into. I loved staying at Kalisti Hotel & Suites in Fira. It was close enough to everything, but peacefully located in a quiet spot.

Greek Island Ferries in Naxos Greece

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 fewer tourists on Naxos than the other Greek Islands.

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 Old Town. The town is a lot bigger than it first appears, though, 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!

For a more eco-friendly (and higher calorie-burning) option, you can also rent an e-bike to get around.

If you have more time to spend on Naxos, it’s well worth taking a trip to some of the smaller Cyclades Islands from here, too.

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 and it was perfect. Right on the waterfront, we could people watch and soak up the atmosphere from our balcony.

Mykonos beach on greek island hopping itinerary

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. If you’re on a super strict budget, consider spending just one full day in Mykonos – but don’t skip it altogether.

Mykonos was the last Greek island we visited, and I would recommend making it yours too. It’s the grown up island – classy, mature and self-assured – and it’s a great place to round up a Greek Island hopping trip.

It was also the perfect place to celebrate my birthday:

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.

Alternatively, hire a local to show you around (and share the stories you would never otherwise hear).

You can see all the best spots on Mykonos in less than a day, but the memories you take away are sure to last a lifetime.

Where to stay in Mykonos:

You’ll have no lack of choice when it comes to luxury hotels on Mykonos.

We stayed in a small boutique hotel called the Ftelia Bay and it was fantastic, but I don’t think you can really go wrong here – everything is pretty dreamy.

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 appreciation for the Cretan food prices after visiting the more popular Greek Islands!

If you’ve found any new favourite, you might want to consider taking a cooking class here before you go.

Syros island hopping in Greece

Got more than 2 weeks in the Greek Islands?

If you have more than 14 days for your island hopping trip, there’s one more island 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.

The ferries usually leave once a day, in the early afternoon.

That means you’ll need to factor in an extra travel day, so you’ll need an extra three days to make it worth it.

Alternatively, 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.

Best of all, you can enjoy a nice hotel in a prime location for a very affordable price in Syros.

We stayed at the Nisaki hotel and it was absolutely perfect. Situated at the end of the breakwater and just minutes from the town centre, we couldn’t believe it was one of the most affordable hotels we’ve stayed at in Grece!


Even though Greece is fairly safe, you shouldn’t travel without insurance. Make sure your policy covers you for healthcare and cancellations, as well as any activities you plan to do.

I use and recommend World Nomads because they cover things that most insurers won’t.

Check the price here or find out more about why I use them

Is island hopping Greece expensive?

The thing about the Greek Islands is they’re all different! The cost of an island hopping trip in Greece is going to vary a lot depending on where you go.

Generally speaking, the more popular islands like Santorini or Mykonos can be compared to somewhere like Ibiza.

The lesser known islands are much more affordable, with prices closer to somewhere like Malta.

If you’re looking to keep costs as low as possible, I recommend checking out my guide to island hopping Greece on a budget.

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.

Pin the image below to save this itinerary for later: 

2 weeks in the greek islands itinerary

Alajode UK travel blog and vlog by a female digital nomad
Jodie Marie Dewberry

Jodie has been travelling the world full time since 2017, sharing the most unique places in the world along with tips for living as a digital nomad. She is a passionate wildlife photographer and has worked with a number of prominent travel brands, including airlines, tourism boards, hotels and tour operators.

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