Updated on September 13th, 2021
I have now taken a Greek Island Hopping holiday 6 times & I am always keen to return again. If you are looking to do the same, then this is the place to be! Here, in a first timer’s guide to Greek Island Hopping, I give you everything you need to know. Includes details on Santorini, Mykonos, Paros, Naxos, Ios, Milos as well as Athens & Kos & much more besides!”
Cyclade Islands, Greece – including Paros, Naxos, Ios, Mykonos, Santorini (& Athens & Kos)
I had my first experience of island hopping in Greece when I was a student just about to enter my 20’s (a very long time ago!). My friend had family in Greece & so could offer a wealth of knowledge about the area. I usually have a motto to “Never Go Back” if I’ve returned to a place I really enjoyed, as it rarely lives up to the expectation. Greek island hopping is that rare holiday which, in my opinion, has bucked the trend & never failed to deliver an amazing trip.
I have been back to the same group of islands in different combinations 6 times now. That first time was with 2 girlfriends for a hard-partying couple of weeks. Then, I returned twice with my husband, once with my sister & most recently (Aug 2018) with a friend. I have also contemplated the trip numerous times on my own for a solo travel experience. I think it would be a great destination but if you choose to travel alone my advice would be to do it if you want to take some time out on your own (rather than hoping to meet others), maybe next time I’ll give it a go & report back!
Why Island Hopping?
- The holiday feels longer! For me, if you go away for a fortnight, the 1st week seems to last forever & the 2ndweek flies by. You get to know the place & the days just build momentum & apparent speed. If you move location after 3-4 days, each time feels like the first week & therefore a 2-week holiday can feel like you’re away for a month!
- Every island is different – no matter which ones you choose, each will have a unique feel, experience & reason why you love it. Your choice will depend on what you are looking for. My advice is, decide on your priorities & do your research. I have to say that every time I’ve been planning a trip, I have looked to different island groups (Dodecanese (Rhodes, Kos), Argo-Saronics (Aegina, Poros)) & each time I come back to the Cyclades.
- There is something for everyone, if you have different needs to anyone you’re travelling with, you have a chance to get everything you’re looking for, maybe on the same island, maybe not!
- It’s easier & quicker than flying between destinations. The ferries in Greece are well organised & (mostly!) run on time, give or take (more on this later). There is not the stress or time that is involved in air travel (transfer to the airport, wait at the airport, fly, wait for bags, the transfer from the airport). The Cyclades themselves are also quite close together, meaning often just 2 hours or less & you’re on a different island.
A First Timer’s Guide to Greek Island Hopping
Greece is in the Eurozone which makes things simple. Most restaurants & hotels accept credit cards, but it’s not always guaranteed so you will also need cash. For example, our recent boat tour of Milos only accepted cash payment (€90 per person).
If you are choosing to holiday in August, make sure you book early. This is when a lot of Greek people leave the city & have their vacations on the islands, so ferries can get booked up. As a result, if you plan to start/finish in Athens some of the local businesses close down as they go on holiday. The city is mainly full of tourists & all the sites are busy, but some of the local bakeries, restaurants etc may be closed. Finally, August is also very hot.
The season in Greece is from March-November but peak within May-September, especially July & August, when its manic. If you choose to travel during the key summer months be prepared for heat, crowds at all the key sights (especially at sunset), needing to book restaurants & definitely make sure you have the ferries & accommodation organised in plenty of time. For August 2018 we were sorting these elements out in March/April.”
If you plan to travel out of season, then be aware that there will be fewer people but again all may not be open. Also, the ferries will not be as frequent, so your choice of islands & travel days will be more limited.
Having visited each island in the Cyclades at least once during my years of island hopping. I hope this will help you in selecting your best fit:
It’s absolutely spectacular! Santorini is the quintessential photo you have seen of Greece where the whitewashed villages seem to fall over the cliff down to the waters edge. It’s the blue domed church overlooking the sea. If you have never visited before, then it’s hard to keep Santorini off the agenda. No matter how aggravated you get by the crowds, the view at sunset will melt that away.”
- Santorini is a volcano so if hot springs & volcanic sights are of interest to you then you have to add this island to your itinerary.
- You can get a direct flight to the UK & back, so it is a great start/endpoint of your trip. Or get a flight back to Athens for your onward journey.
- When I was there most recently I stayed centrally in brightly decorated Sweet Pop. It was perfect, close to but hidden away from the crowds with its own pool in a warren of small streets.
- One of the best things to do in the Cyclades Islands is the hike from Fira to Oia. You can check out my in-depth guide for all the details.
- As I’ve eluded to before, it’s crowded & that can make it unpleasant, especially at the peak time of year. If you have a choice, my advice is to go outside peak times (even visit between November–March if you can) for fewer people, if that’s how you would prefer your experience.
- If you’re in Greece for the beaches then be warned, this is not the best island. Santorini is essentially an extinct volcano & is so beautiful as a result of it being a caldera. The downside of this is that you only get black sandy beaches (or the Red Beach). In the heat of the days, the coarse sand can seriously burn your feet & the rocks by the water make it a challenge to enter the sea while retaining your dignity (not to mention the fish that seem to have developed a taste for nibbling tourists!).
- Its’ popularity means that Santorini is expensive, among the most of all the islands. Advice is that if you want a view with your food then be prepared to pay for it. For a more reasonable alternative, enjoy your drinks with a view & then head away to eat, it will cost you less & your meal will often be of higher quality.
- Due to the spectacular scenery, Santorini is a cruise ship destination so when the ships are in (at least 1 at all times), expect a lot of people in the small labyrinthine streets. You will not be alone!
- If you’re planning to do all of your internal travel by ferry, then either put Santorini at the start or end of your itinerary (the ferry from Athens can take 10 hours).
For everything you need to plan your visit, check out my Ultimate 2 Day Santorini Itinerary.
Mykonos is famous as the glamour island with a reputation for great nightlife. The main town has the archetypal whitewashed maze of streets filled with cafes, bars & boutiques.”
- You can fly directly into Mykonos from the UK so again it is useful to have at the start/end of your trip.
- Mykonos is booming for tourists & celebrities with money to burn which means there are plenty of funky hotels, bars & restaurants to choose from.
- Mykonos, like Santorini, is a cruise ship destination which means when the ships are in, the tiny streets can feel overcrowded & slightly claustrophobic. I have only visited once a few years ago & we stayed overlooking the port. Every morning we woke up to a different cruise liner from the one we saw when we went to bed at night.
- Mykonos is also one of the most expensive islands in the Cyclades so if you are choosing Greece as a less pricey option, you may want to avoid this island. I heard (hearsay, granted) that for 2 sunbeds & a parasol for the day on one particular beach they were charging €100, most of the time we paid €10!
For your perfect location then you can use the search box below – Chora is the heart of the village. Semeli Hotel comes highly recommended.
- Again, Paros is beautiful, but in order to see this for yourself then head away from the port town of Parikia to Naoussa which has a small harbour area & beach bars to rival some of the more famous islands, but here it’s a lot more low key.
- The beaches in Paros are lovely, with soft sand & most are well organised with sunbeds & parasols. However, they can be too well organised & in my opinion overcrowded & expensive.
If you’re looking for a classier island experience, then Paros is for you. It has the harbour, the bars by the sea, the sandy beaches & the small streets full of shops with good quality gifts, jewellery, clothing & restaurants”
- Nice small bars & restaurants right on the waterfront.
- For all of the reasons above, Paros is again one of the more expensive islands in the Cyclades so if you’re on a bit of a budget then bear this in mind. Cocktails are €10+ and on one beach (Santa Maria) we paid €25 for 2 beds on the beach for the day & could barely move them as they were so tightly packed. There are plenty of other beach options though.
- If you like a wild party atmosphere, then I would direct you to one of the other islands, as Paros tends to be more of “a few drinks & dinner with a gorgeous view” kind of place.
- The best restaurants in the best locations can tend to be booked up so make sure you either book the evening before or stick to the less prestigious locations. I often like to be more spontaneous, hence it’s in the avoid section!
For all the details you need to plan your visit, head to What to do in Paros for 2 days.
- Naxos has some of the best beaches of all the Greek Islands I’ve visited. If you’re looking for fine powdery sand, then this is the place for you. Agios Georgios is basically right by the main (port) town of Chora so you can avoid needing transport altogether if this is what you are looking for.
Naxos is also the largest & most fertile of all the islands & if you choose to hire some transport I would thoroughly recommend a trip into the more central area, especially at dusk when the light makes the landscape appear even more beautiful.”
- Don’t miss a short walk from the port in Chora to Portara, Apollo’s Temple where you can get excellent sunset views (albeit with lots of other tourists!)
- Naxos tends to be one of the least expensive islands in this list.
- This is becoming a much more popular island & I noticed on my recent trip that the crowds have grown considerably.
- Naxos has the feel of a place which is more a package destination than for the independent traveller.
On my last trip, I stayed at Iliovasilema which was a great location with a lovely pool.
Check out my post on 21 Best Things to do in Naxos for all the details.
- This is the young ‘party’ capital of the Cyclades, so if that’s what you’re looking for then include Ios in your itinerary, but even if you’re not, don’t dismiss it entirely. I have visited with both on my agenda. Be aware that if you prefer an early night you could be coming home when everyone else is heading out for the night, which can make everywhere seem very quiet!
- Ios has some beautiful sandy beaches which make exploring the island worth the effort.
- If you’re not in the mood for late-night party goers in their 20’s, then Ios is probably best avoided, especially between June–August.
- Milos is stunning & one of the smaller and quieter islands in the Cyclades, with far fewer tourists than many of its more famous neighbours.
A boat tour is highly recommended to see the best coastal features of the island & the beaches that are inaccessible by any other means. It also allows you the opportunity to swim in small bays with crystal clear water.”
- The bus links (especially from Adamas) are very good, meaning there is no need for a car to explore the island.
- The beaches can be beautiful (e.g. Sarakiniko – a stunning white rock beach) but I would say don’t go to Milos expecting endless fine sandy beaches.
The perfect hotel on my last stay was the family-run Hotel Eleni. Make sure you book breakfast as it is a real treat! For all the details you need to plan your visit, head to What to do in Milos, Greece – 21 Incredible Reasons to Visit
- I realise this isn’t an island, but it is a good option as a start/endpoint of your trip! There are a lot more flight options available internationally. When I met my sister in July 2016, she flew from Sydney, Australia & I came in from London. We landed & got straight on an open-topped bus tour to make the most of our one day in the city!
- The port in Athens, Piraeus is so busy that you can get to any island in the whole of Greece from here & will have the largest choice of times & seats to best meet your needs. But a word of warning, it is very large. It’s important that you know which quay your ferry is departing from. Also, arrive early so you can relax as you negotiate the chaos!
- The Acropolis is truly stunning and there are other ancient sites as well as the museum to keep you busy. I’ll be covering this in more detail in the coming weeks so please keep your eyes peeled.
- I would recommend 1 or 2 nights in Athens. This allows you to see the key sights without eating into your island time.
- Athens can be packed full of tourists, especially at peak times (August). However, as all the Athenians tend to leave, not all the local bars, restaurants etc are open.
- It’s not an island so you may want to focus all your time away from the city if that’s the purpose of your visit.
For your stay, I recommend the Plaka area of the city for a central spot with plenty of bar & restaurant options.
- As an alternative adventure – I did once get an overnight ferry to Kos & flew out of there!
- This is more the realms of traditional package holidays which is kind of why I always go island hopping… to avoid this!
The first time I visited I was a spontaneous student with very little planning. We waited until we got to each port to find accommodation. This is still an option today as there are people trying to fill their rooms. However, it is not always the best way to get the ideal location.
The first place we arrived as students, a man picked us up at the port & promised we would be staying in town. As he told us to get off the bus, a guy shouted that we were a long way away. Just as the doors shut we jumped back on. We did still manage to pick up a room from a lady at the bus stop in the town. However it’s probably not best idea to leave it this late!”
Nowadays I’m a little less “fly by the seat of my pants” & prefer to have a good browse of all options & carefully choose the location before arriving.
For my latest trip, we had a combination of apartments through Airbnb (Athens, Paros) & hotels through Booking.com (Naxos, Milos, Santorini). With the exception of Paros & Santorini, our accommodation was in walking distance of the port which made life really simple (& a lot cheaper!). Check my Island Hopping in the Cyclades post to read more.
Getting There & Back
This is where it’s important to choose your islands. Some have flights to & from UK airports which means you can start in one place & fly home from another. I have often started in Athens & come back from either Mykonos or Santorini (or once, Kos). This means that all your travel is one way. Although many of the islands have airports they don’t all fly internationally.
Then plan your route in a circular motion to minimise ferry time between your desired stops. This can take some time when planning.
There are flights available internally between the islands (I took one with my sister from Santorini to Athens) but I can assure you that by the time you have gone through the process of check-in & security, a ferry is a way more pleasant experience!
As mentioned numerous times, the best way to get around the islands is by ferry. It’s now easy to book online & make sure you do it in plenty of time as the number of seats may be limited. I recommend Ferryscanner.
When booking & travelling please bear a few things in mind:
Type of Ferry
- Not all ferries are the same. You may be in a combination of larger car ferries & smaller foot passenger “Speedjets”. The larger ferries to me are more magical but may take longer (loading & unloading the cars for example). You may be able to go outside for some or all of the journey too. Also, there is something exciting when, as a foot passenger you wait on the car deck to exit, see the huge gate go down in front of you & get your first glimpse of a new island as you walk off before the cars. When you book, you won’t always know which type of boat you will be on. I quite like the element of surprise!
The Speedjets are more practical & quicker to load & unload as all passengers are on foot, as such they are often faster between destinations. The only view is through the (unclear) window & there is no option to get fresh air (a little challenge on a rough crossing, see below!). Also, there is never enough space for storing luggage, so it tends to be (very!) chaotic at times.
- Travelling with someone does not always mean you will get seats next to each other (even if they are booked together). There is usually a big kerfuffle at the start of the journey as everyone realises this & tries their luck. Wait for things to settle & then work out how important it is for you. Nowadays, more than before it does seem organised that you have a booked seat & are expected to sit in it unless it’s not busy. A great trick my sister used once when we got on to find someone occupying our window seat (who refused to move) was to claim to be ill & grab the sick bag. Miraculously we soon got our allocated seat when it was vacated!
- Seasickness. Bear in mind that some of the crossings can get quite rough, especially on the smaller boats. If you do suffer from seasickness please take tablets or whatever works for you. I was once on a very rough crossing (Naxos to Milos) & it seemed that everyone apart from us was suffering. If you are lucky enough not to get sick yourself, the smell makes it a challenge to stay that way!
- If you book the tickets online, you will often be required to pick them up from a local travel agent. This can be done at any time but if you’re like me, usually just before you travel. Make sure you leave plenty of time for this as you will need to go to a specific agent which isn’t always obvious & sometimes pay €1 (per ticket) for printing.
- When you book make sure to leave your mobile phone number. That way the ferry company contacts you if there is a delay. This saves you having to wait longer than needed at the port.
At the port
- All the ports have “holding areas” which can offer shade & seating if you’re early. Be warned it can get chaotic when there is more than one ferry. In Paros, once they forgot to unlock the gate for the pedestrians patiently queuing to board.
We were panicking & felt trapped as we watched our boat leave without any of us. Fortunately, we were only going 40 minutes to the next island (Naxos) & were able to board the next ferry, 30 minutes later. Others were not so lucky & a lady heading to Amorgos was told to “go & see a travel agent”! She was understandably livid. So, my advice would be stay near the back and when you see the boat, head to it & make sure you’re not stuck or trapped by sheer number of passengers & bags.
Car Hire / Moped / ATV etc
Hiring a car for the whole trip could be an option with the car ferries, but it’s not one I have ever done or explored. Bear in mind the extra cost if you plan to start & end in a different location. Also, the most authentic places to stay are often those with small lanes, best explored on foot. This means parking options could be limited. If you choose to stay further away & more off the beaten track then this would be a feasible alternative, especially for the larger islands away from the port areas.
The alternative is to hire transport individually on each island if you need it for a day or two. This is a great choice if you want to explore but you can also choose your method. Most islands offer car, moped, ATV etc & varying these can also add an element of fun into the trip.
Your choice of transport to hire may also depend on which island you’re on. For example, when we visited Ios, we were recommended to go for a car. There are lots of hills which would mean struggling too much on any other form of transport. It will also depend on the comfort factor. For example, Naxos is the largest island. If you are keen to explore extensively then again car would be the best option.
Bear in mind that many of the islands have hills, which make them stunning to visit (Santorini being a classic), but more challenging if, like my husband & I, you always opt for the cheapest, least powerful engine size on your moped/ATV. Numerous times I was told I was too heavy on the back & had to “get off & walk up the hill”…Charming! 😉
Often a good option when you first arrive at an island for quick & easy transport to your accommodation but the costliest choice as a result. In Paros, we were staying in Naoussa which is about 15 minutes’ drive from the port town, Parikia. We were charged €20 for 2, (€10 per person) & he also unsuccessfully tried to recruit more people for the trip. We ended up getting the bus back for €1.80 each – bargain!
Also, taxis will not always be available & you may need to walk & wait. I wanted to make things easy when my sister & I arrived in Santorini by getting a taxi. There is nowhere to stay within easy reach of the port & the slope is very steep with lots of switchbacks to get to the top of the hill, it is a volcano after all! In the end, we were able to walk to our hotel from the bus station making it a much quicker & cheaper option all round.
Leaving Santorini we thought it would be more convenient to get a taxi to the airport from Fira. The buses only went every 90 minutes. We were advised to walk to the taxi rank & wait in the queue. We got there to find several people who had been waiting over 10 minutes & not even seen a taxi. A couple in the queue had started phoning to book a car & I was able to get a number from them. When the cab arrived, we were told that you need to book as taxis are limited on the islands. This was not what we were heard at our hotel, or on any of the signs at the stop. We ended up paying €20 for a 10-minute drive. If you need a number to try +30 690 7012871 (Santorini).
If you choose not to get your own transport the buses are a great option & on most islands serve the key tourist areas, to & from the beaches. On my visit in August 2018, there seemed to be a flat €1.80 per person for each one-way journey. This was either paid beforehand (if there’s a kiosk) or on the bus itself. This fare was consistent except for a few trips on Santorini when we were charged €2.30 each.
If you can, get yourself a timetable (or photograph the ones on display at the terminals) & ask at your accommodation where the nearest stop is. Usually, it will be one terminal for the town. If you don’t go to the terminal it can sometimes be hard to identify where the stop actually is.
Don’t expect a super regular service, especially on the less busy islands & routes, (1 per hour for example). They do thankfully run pretty much to time though.”
When we arrived in Santorini there were lots of shops at the port offering “Transfer to All Hotels”. It may be worth it if you have a lot of luggage or are staying somewhere more remote. But if you keep walking you will see the stop for all the buses €2.30 one way to Fira & ideally you can walk from the bus terminal.
This may also be a more direct route on some islands to the beaches. However, expect to pay more than the bus. For example, in Paros, we got the boat to & from our favourite beach, Monastiri for €6.50 each return. It was €1.80 for each bus journey.
If you are staying in the port town either ask your accommodation for directions or check on Google Maps. Often you will be able to walk, which again saves time & money.
One of the most quintessential Greek experiences is exploring the maze of small streets & old towns by foot. This will be completely different depending on if you visit during the day or night. In the daytime, many shops may be closed as these areas really come to life at night. The labyrinthine streets can be magical but also very busy. Bear this in mind when choosing your accommodation & transport options.
There are so many islands in Greece to explore. For more on my recent trip taking in Athens, Paros, Naxos, Milos & Santorini with a full list of recommendations for accommodation, activities, restaurants etc in my post A Perfect Greek Island Hopping Itinerary. Or to find out why Milos should be part of your itinerary check out my dedicated post.
Don’t fancy Greece? – I also did a similar kind of trip a few years ago with my sister in Croatia, flying into Split & out of Dubrovnik, via stops in Brac & Hvar. Also, highly recommended & please let me know if you’re keen to know more!
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