Island Hopping in Greece – 11 Useful Planning & Organizing Tips

Island Hopping in Greece – 11 Useful Planning & Organizing Tips Go to the Cyclades.




Greece’s many islands are divided into different groups. The most famous is the Cyclades and for good reason. Cycladic islands boast the famous Greek island architecture: white-washed cubic houses with blue doors and shutters, separated from each other by tiny streets lined with fuchsia bougainvillea flowers. These islands are also known for their breathtaking views of the Aegean sea and romantic sunsets. Last but not least, Cycladic islands are conveniently located close to each other. Since the 60s, Greek island hopping has actually meant travelling through the Cyclades.


Make sure you’ve planned enough days for island hopping. If you can only take a week off, it’s best to visit just one island, at most two. For holidays of about 10 days, you can comfortably visit 2 islands. For proper island hopping, however, you should set aside 2-3 weeks. If you’re going on holidays, it should feel like holidays!

Why you’ll need at least 2 weeks for island hopping (3 islands or more): 

If you fly in and out of Athens, you’ll probably spend the first and last days of your trip there and may possibly need to book hotels there, too. Practically, this means two fewer days for the islands.

Even though the islands seem close to each other, the ferry reality is quite different. While it can be charming to take the ferry from one Cycladic island to another, the travelling time can be anything from 2 to 8 hours since not all islands have a direct ferry connection to each other. In addition to the travel time, you should also factor in the time you’ll spend waiting for the ferry to arrive. Unlike airplanes, ferry delays are quite common.

Depending on your itinerary, you might arrive at a crazy hour (like 2:00 a.m. or 6 a.m.). Ferries, as opposed to airplanes, usually don’t have a single destination. They visit one island after the other and if the time of arrival can be convenient for the first island, it can be very inconvenient for the second or third island on the itinerary. This means that on the first day of your holidays you might need to wait some time until you can check in to your hotel (if you arrive at 6 a.m for example) even though you might be very tired.

Even if the ferry itinerary has ideal arrival times, every time you change islands, you should consider the time you’ll spend in going back and forth from the hotel/hostel and checking in and out.



Plan the right itinerary for you. Decide what you enjoy most while on holiday and choose islands that offer those activities. In almost all Cycladic islands you’ll find a bit of everything, but often the character of each island is very unique: one island is full of beaches with emerald water, another has an awesome nightlife, while yet another has great hiking paths. So ask yourself how you’d most like to spend your time. What sort of crowd do you want to meet? Are you on a budget or is the money flowing freely? Once you prioritize your needs and wants, choose one island that will be your main destination. Then, add a couple of islands that are easy to visit from your main/core island. An easy way to do that is to check your core island’s ferry schedule and choose islands that are before or after it on the route.


When creating your itinerary, try to avoid islands that would require taking more than one ferry. There are so many beautiful islands to choose from that I think this kind of hustle is unnecessary. If, nevertheless, you want to do that, make sure you plan plenty of time between the arrival of the first ferry and the departure of the second. Depending on the type of ferry, the route, the weather etc. a ferry can arrive 2 hours late. If you have a tight schedule, you might have some moments of agony until you know for sure that you’ll catch the second ferry.


Some islands in the Cyclades — like Mykonos and Santorini — are world famous and extremely popular. These are beautiful islands, but during high season can be extremely crowded. Consider visiting less famous islands, that not only are very beautiful but also offer more space, better service and more reasonable prices. If you simply must visit Mykonos and/or Santorini for Instagram-worthy photos and bragging rights, then try avoid visiting them during the high tourist season: 15th of July — 15th of August and, if possible, visit them during May, June or September which are not as busy.


Are you on a tight budget? Choose a budget island! There are some Cycladic islands that are popular amongst younger crowds where you can camp for free. Free camping is prohibited in Greece, but in one way or another it happens on many islands. Donousa island is a very good example. There’s a beach café/bar/restaurant called Kedros next to an amazing beach that shares the same name. The bar’s owner allows people to camp for free on the piece of land that’s next to his bar. Another example is the Aegiali camp site on Amorgos island which costs as little as €4 in low season and €5.5 in high season. Generally speaking, the less famous an island is, the better prices it’ll have. Also, keep in mind that traditional ferries are usually much cheaper (in some cases half the price) than high speed boats.


Pack light. If you plan to move from one island to another, you won’t want to carry a lot of weight. Also, if you plan to visit one of the popular islands in the Cyclades, you’ll be amazed at the beautiful summer sandals and dresses you’ll find at the local boutiques. So, if you’re missing a summer hat, sandals, a beach towel and summer clothes generally, buy them on Paros, Naxos, Santorini, Koufonisia or any other island you plan on visiting. Not only will they be of good quality and unique design but they will become wearable souvenirs of your trip. Some sandals at boutiques may be more pricey (€40-60 or more) than the ones you’ll find in chain stores, but they are totally worth it!


Check if you can fly from your home country directly to one of the Cycladic islands. During summer, there are charter flights to Santorini, Mykonos and some other islands from several European countries. These popular islands have frequent and direct ferry connections with most of the other Cycladic islands. Flying directly to a Cycladic island can save you a day or two as you won’t need to travel through Athens (Piraeus port) or spend the night there before your departure.


If you decide to visit some of the lesser known Cycladic islands, find a room to rent from the official island page. The rooms to let are something between a hotel and a hostel. The majority of them are very clean, with their own bathroom and maybe a sea view balcony. Some of them are not listed on the big travel websites but are listed in the official island page.

The price can be as low as €40-50 per double room during the high season and less during the off-season. It does require more work from your side as you probably need to call or send an email, agree on the price and dates and sometimes send a deposit. This type of booking is a great deal and in some cases you may even find a room when it seems there are none available. If you’re a solo traveller and want to book a double room for yourself outside of high season, you can ask for a better price. Often they can give you a double room that usually costs €50 for €30-35. If you are a group of three, they might be able to add a portable bed in a double room and if the double room costs €50 they will charge something like €60 per night (€20 per person) or €65. Also, sometimes room-to-let owners will pick guests up from the port. This has happened to me several times, which is an amazing service considering the price of the room and that it’s not a five-star hotel. This won’t happen at the most popular islands during the high season, unless you’re indeed staying at a five-star hotel, and paying more than €150 per night. 


Before choosing an island, decide whether you want to rent a car. There are islands that cannot be fully explored unless you have a car and others where you won’t need one. Tinos, for example, is scattered with beautiful villages and beaches, but they can only be reached by car. If you go to very small islands like Donousa, Iraklia or Koufonisia you won’t need a car as you can go almost everywhere on foot or use the local bus service for excursions that are a bit further away.


The following tip, even though it won’t help plan your trip, it will help you to start fully prepared for it! Download one of the following apps: Findship (free) or Marine Traffic (€5.49). These apps track all the ships (vessels, ferries) in real time. You’ll see where your ferry is located and how far it is from the port. In some Cycladic islands, bus routes are planned according to when the ferry arrives. In both Santorini and Anafi, for example, the bus to the port leaves an hour before the ferry comes in. The bus drivers check these apps for ferry delays, so that, they won’t arrive two hours ahead of time. If your ferry is delayed is best to wait in a café enjoying a coffee or a cold beer than standing on the dock.


Good luck with your planning and rest assured that no matter how bad your planning skills are, it’s almost impossible not to have a blast while being in Cyclades!