Island Hopping in Greece: How to Get the Most for Your Money

Island hopping in Greece is one of those dream vacations that everyone fantasizes about doing at some point in their lives.

Well, at least I did.

For YEARS.

Then finally, I got my chance to go to Greece in late May/Early June of 2019. Despite never having been before, I had a feeling that I’d love it so planned to stick around for a while: three and a half weeks, most of which I planned on spending in the islands.

However, as dreamy as those azure waters and white villages are, let me be the first to tell you something really, really important: Islands Hopping in Greece is pretty expensive.

Seriously.

I had slight panic attacks when I first started looking at buying ferry tickets. Enough so that I had to readjust my Greek island hopping plans several times to keep myself more in budget.

That being said, I also discovered a fun, easy, adventurous, and affordable way to see plenty of Greek islands without blowing out my bank account. So now, a few years and several visits to Greece later, I like to think I figured it out how to crack Greece without breaking the bank account. 

Interested? Good- you should be.

Here’s what you need to know about Island hopping in Greece based on my personal experience.

Island Hopping in Greece: Ferries

When it comes to islands hopping in Greece, the most obvious option is to use the ferries. At first glance, the ferries seem like the easiest and most affordable option to get around.

This isn’t necessarily always true. 

To start with, the ferries are not as cheap as you would hope. Prices will vary depending on the routes and the ships and will get significantly more expensive the longer you wait. I’ve paid over $100 CAD per ticket on some of the trips I have taken when I didn’t book far enough in advance. Keep in mind that these costs (for many ferries) are also for the economy class and likely don’t include anything else- not even a reserved seat. 

The ferries, even the fast ones, can sometimes take a few hours. Especially if they are not direct. No, it’s not the end of the world but that still ends up being half a day when you also consider that you need to get to the Port an hour early at least. Sometimes even earlier if you book your ticket online and need it printed (which has to be done at the respective ferry office and comes with a small printing fee of 1-2 euro).

So, if you are planning on using the Greek ferry system for island hopping I suggest planning your route in advance and booking early. I use FerryHoppper for my tickets. These days, most tickets can be delivered to your mobile device so try to chose options for that. Otherwise you need to go to the port early and find someone to print them. Finally, I will say I think that the ferries are really only your best option if you plan on spending a few days on the islands and only visiting a couple. If you have a quick trip and want to see lots, there is a much better option- more on that to come. 

Island Hopping in Greece: Flights

Another way to experience islands hopping in Greece is by flying between the islands. As can be expected, flying around the Greek islands tends to be pricier than the ferry. However, flying does have the added advantage of being much faster and perhaps even easier.

Flight prices will vary depending on time you fly, the airline, where you are flying, the season, and how far in advance you book your flight. These days flights are getting more and more expensive, so I definitely recommend planning ahead and booking early. Keep in mind many of these flights don’t include luggage either, and that can add a significant cost to your ticket. 

Flights are typically more expensive but they are a lot faster. This isn’t a big deal if you are hopping between islands that are only a 2-3 hour ferry ride apart. But say, Santorini to Athens for Example is a 9 hour ferry ride. In this case, it’s easier and better use of your time to fly. 

A couple of things to note; there are not always direct routes to the islands. Sometimes you will need to backtrack through Athens, so keep that in mind and factor that in to your decision. Also, not all islands have airports which is more limiting when it comes to island hopping in Greece. 

Island Hopping in Greece: Sailing

The first time I visited Greece, back in 2019, I was invited on a press trip to do a sailing tour. I spent a few weeks exploring the islands on my own by ferry before I joined a 10-day sailing tour through the Cyclades. We started and ended in Santorini and visited 7 islands along the way. We got to spend at least half a day on each island which, at first, I worried wouldn’t be enough time but it actually ended up being perfect. Being able to experience so many different islands allowed me to experience more and see the differences between them.

Tiny Iraklia and Schinoussa were absolutely adorable. I never would have through to go to either on my own and I loved how non-touristic they were. As such, prices were much more reasonable as well which I definitely appreciated. Both islands were tiny with not much going on, so they made the perfect place to spend half a day enjoying the pristine local beach before grabbing a meal and drinks at a local taverna.

Syros was another island that surprised me. The capital of the Cyclades, it had a completely different feel than the other islands. We went into Ermoupoli which had a real city feel, more like something you would find in Italy or the South of France, compared to the small white villages that I had grown accustomed to exploring on the other islands. It was definitely worth exploring.

Of course, we also visited some of the main islands as well: Naxos, Paros, Ios, and the famous party island: Mykonos. Originally, I planned to visit Mykonos on my own for a few days as well, but cancelled those plans once I saw the ferry prices. For me, that half a day was the perfect amount of time to spend. I didn’t go to any of the beach clubs, but we explored town, saw a stunning sunset, and even half a day nearly emptied my wallet: 17 euro cocktails, anyone?

Without a doubt, sailing was the perfect method for Greek island hopping because we got to see so much at an affordable price. Remember, with sailing you sleep on a boat so not only was our transportation taken care of (8 islands in total including Santorini) but that was also our accommodation as well.

I also want to point out that our transportation wasn’t just getting from point A to point B- but involved a bit of an adventure alone the way. Sailing is incredible- I absolutely loved it. We saw sea turtles and pods of dolphins- a few of which even stayed with us one day and played around the boat. We also had swim stops nearly every day (weather-dependent) which included swimming through caves and free diving around a WWII plane wreck. It was incredible and, again, not something I would have been able to do on my own.

Essentially, built within the price of the sailing tour we had: accommodation, transportation, a guide, and daily activities. When you compared pricing and break it down like that, there’s no question that sailing is the best value when it comes to island hopping in Greece and, based on my experience, also the most enjoyable. I loved my first sailing trip to much that I’ve actually run 2 ESBT group trips on the same boat with the same skipper. 

My Favourite Cycladic Islands for Greek Island Hopping (Cyclades)

I love pretty much every island in Greece but I will admit that the smaller ones that I got to experience on the sailing tour stole my heart. They were so much less touristic than the bigger islands, as a result restaurants were cheaper, and overall they just felt a little more special. These are some that stood out to me. 

Amorgos

Amorgos surprised me which how beautiful it was. The hora (old town) was perched up on a hill that we needed to rent a car to get to. We also did a mini road-trip to a nearby monastery built into a cliff, and a photo stop by the water where we saw a Greek Wedding (I secretly wanted to crash it). The landscape was beautiful and the hora was adorable. I also really enjoyed the port area where I had the best moussaka ever that I’m pretty sure I will be craving for the rest of my life. 

Iraklia

Iraklia was somewhere I had never heard of before my Greek Island sailing tour and, even if I did know of it, probably not somewhere I ever would have gone on my own. Yet I LOVED it. It’s tiny. The small town can be walked in 10 minutes and consists of two small grocery stores I think 4 tavernas (we did a ‘taverna crawl’ before dinner to check them out) and a beautiful beach. It was the perfect place to relax for a half a day and there were only a few other sailboats in the harbour which meant very few other tourists.  

Koufonisi

This tiny island is the cutest. There are some nice beaches right by the marina but if you walk further along you will get to even more beautiful ones and a cool tide-pool type formation that you can swim in (looks epic if you have a drone). There’s also a really cute windmill bar for drinks. I also slept on the deck of the sailboat the night we spent here and got to see the most magical sunrise. I loved it here.

Sifnos

Another little island. We went to the smaller port here and it was just an entire shoreline of beaches and beach tavernas. The perfect place for swimming and snacking! Very quiet, very relaxing, very scenic. 

Folegandros

This island is a bit bigger than the others. There are a couple of beaches by the main port- you can climb down a cliff to a gorgeous one (worth it). Then take the bus to Chora. It’s quite a pretty town but the main draw for me was sunset here. Climb up to the church to watch- I promise it’s worth it! There is also a really fun little bar in town called Beezbar. 

Thinking of Joining a Sailing Tour to go Island Hopping in Greece?

This is the tour I took, but Intrepid Travel also offers a few more options for Greece sailing tours.

• Mykonos to Santorini
• Athens to Santorini

Ready to Book Your Trip?

Don’t forget travel insurance!

Please do not travel without travel insurance! I’ve had to use it multiple times throughout my travels and it has saved me thousands of dollars. You can learn more about travel insurance here. If you are looking for a provider I love and recommend SafetyWing. For Canadian readers, take a look at SoNomad.

Book your accommodation

I love and recommend booking.com for accommodation. They have a range of hostels, guesthouses, hotels, and resorts. Plus, the platform has a great loyalty program that means the more you book, the more you can save. 

Book your tours

My go-to tour provider that I love to recommend is GetYourGuide. They have options all over the world and partner with local companies for everything from day trips to food experiences and even airport transfers. 

Get connected

If you want to have data while travelling for online maps or any other needs, an esim is one of the easiest solutions. I have used esims around the world from Brazil to Uzbekistan, Greece to the USA- they are super easy and you don’t risk losing your home sim! There are two brands I have used and recommend so I suggest comparing both. 

Airalo: download the app, pick what country you want an esim for, and after you purchase it follow the installation instructions. You can use promo code HANNAH3326 to save $3USD on your next esim purchase.

Truely: This one is easier in that it’s a one-time download instead of downloading an esim for each country. It also allows you to hotspot and tether- which not all esims do. Check out options here.

Not sure what to pack?

I have destination-specific guides for some countries but you can also check my travel essentials and camera gear if you are looking for some ideas. 

Looking for a travel buddy?

Check out my group trips!