The Perfect Greek Island-Hopping Itinerary

Updated on July 30th, 2020

Oia is a must visit in Santorini, especially for the sunsets but don’t expect to be alone. It feels like everybody in the whole of Greece are amassing for the descent of the sun. It may happen every day but in Oia the sun gets applauded as it disappears over the horizon!”


Athens, Paros, Naxos, Milos & Santorini, Cyclade Islands, Greece


SueWhereWhyWhat & friend on the walk from Fira to Oia, Santorini, GreeceA Greek Island-hopping trip is one of my favourite 2 week holidays, so much so I recently visited for my 6th time. For more details on why I love it & what you need to know if you’re planning your first excursion, see A First Timer’s Guide To Greek Island Hopping which will give you all the information on why I chose these islands, how to get around, where to stay etc. My most recent visit was with my friend, Manda, who had not been before, so I was keen to try & give her the best experience & help her fall in love with Greece as well. It also highlighted to me why you should not get complacent when you have visited somewhere before. Manda did fall in love with Greece but a lot of the activities listed here were down to her research & for that, the trip was more enriched. I took advantage & our gift is that you can now too! Thanks Manda!

What do you need to know?

The Acropolis, Athens, Greece. On this trip we spent 18 nights in Greece, 2 in Athens & 4 on each of the islands. I recognise that this may be a challenge for some, so to cut the itinerary shorter I would recommend taking 3 nights per island which gives you enough time to explore & get the essence of each place before moving on.”

In addition, I always plan my trips to get to the next location early & make the most of each day in a new place. It’s not always possible, bearing in mind the timing of the ferries, check-in times etc but I’m never keen on hanging around if my head is “moving on”.


The Acropolis, Athens, GreeceWe started in Athens for a 36-hour whistle-stop tour. The main objective was to see the Acropolis & we were not disappointed. If you choose to start your Greek Odyssey here I have a few Top Tips:

  1. Go early! The gates open at 8am & the earlier you go the fewer queues you’ll face, the fewer people to battle for photos & the cooler & more pleasant your visit will be. It gets hot here & there isn’t a lot of shade so definitely avoid the midday sun if you can.
  2. You need to start at the ticket desk which is a short walk from the entrance turnstile. Don’t get caught up in an unnecessary queue in the wrong spot.
  3. There are guides offering tours as you queue, but I often prefer to do my own thing, have flexibility & move at my own pace. Not taking a tour first thing meant we again bypassed a lot of people in the first section & got the photos we wanted with fewer people standing around.
  4. Wear shoes with a good grip. Much of the flooring is marble which can be really slippery if it’s wet. Granted, it rarely rains in Athens, but they do wash the ground which can make it treacherous if you don’t have the right footwear!
  5. If you’re not taking a tour, then move quickly when you first enter the turnstile. The guides have a lot to say at the entrance & you can quickly progress through this section to get to the Parthenon well before the masses arrive.
  6. Get your “Main Event” photos early. You can stay as long as you like but the later you leave it, the more people you will have in them!
SueWhereWhyWhat and friend at The Acropolis, Athens, GreeceWhere we ate, slept & drank

In Athens, we stayed within a 10-minute walk of the Acropolis, a 30-minute (€10) train ride & an uphill walk from the airport. The train is recommended although they didn’t run as regularly as we expected (30-minute wait). My advice is, if you are in a hurry, it’s rush hour or there are a few of you, taking a taxi could be a better option.

Our Airbnb choice was perfect, close to plenty of bars & restaurants & with an unbelievable view of the Acropolis from the roof terrace!”

We were near the Plaka district of the city & ate at:
  • Skoubri – delicious mezze to start the trip, especially recommend the octopus!
  • Fourteen – great lunch choice with tasty paninis.
  • Yard Cafe – good location & nice food to occupy you while you watch the world go by!

We also got a long list of recommendations which we just didn’t have time to make the most of, or were closed during our visit, namely Kalamaki Bar, Wine O’Clock, Takis Bakery, Anglais Athens & Couleur Locale

What next time?

The Acropolis Museum is highly recommended by everyone & was the only thing we actually regretted not doing for our whole trip. If in Athens & you have enough time, please visit. I have it on good authority that you won’t be disappointed!


WShocking pink flowers light up a backstreet view in Paros, Greecee came into Parikia on a large passenger ferry from Athens which was an experience in itself. As a foot passenger, you wait on the car deck as they slowly lower the gate & you get your first glimpse of the island with its iconic windmill at the port… and then you walk off into the chaos & frantic race to get away as quickly as possible!

We had chosen to stay in Naoussa which was a 15-minute (€20 for 2) taxi ride away but well worth it for a beautiful port, marina & labyrinth of tiny streets to explore & get lost in at night. (NB – We got a bus back to the port when we left which was easy, on time & cost €1.80 per person).”

A beach bar by the shore of the Greek Island of Paros, GreeceWhen we arrived in Paros, one of our priorities was to spend some time relaxing on the beach & there were plenty of options to choose from. For the first afternoon, we went to the local beach which was a 10-minute walk away. Although convenient & with a nice breeze, there are much cleaner & nicer beaches on the island which make the effort to go further afield worth it!

Monastiri Beach

The shore of Monastiri Beach on the Greek Island of Paros, GreeceWe were up early (ish!) to get the boat to Monastiri at 10.30am. The 10-minute boat ride cost €6.50 each return but it is reliable & a great way to travel for a day at the beach. Monastiri is very picturesque, with hikes around the area & an archetypal blue-domed church right, beach bar & water sports area.  The water is crystal clear & has a very gentle slope to get in, meaning that you can walk quite far before you get to waist height (if you even make it this far!). It is also sheltered from the wind which makes it a popular choice among tourists & locals.

The walk to the church is a must as it is hugely photogenic to view from the rocks or climb on to the roof.

It was a public holiday the first time we visited (we loved the beach so much we went twice!) which meant that although we were only on the 2nd boat of the day, we were lucky to bag the last couple of sunbeds (& they’d run out of shades). 2 beds & a shade was €12. Our 2nd visit was much more relaxed & way less busy. If you want to give the sunbeds a miss, I would recommend going to the church where there is a tiny beach & rocks that you can lay on for the day, it’s quiet & the water is crystal clear.

Santa Maria Beach

Catch of the day (Squid) dries in the sunshine & SueWhereWhyWhat with friend by a church, Paros, GreeceThe next day we took a recommendation & got the bus to Santa Maria (€1.80 one way from the bus terminal). We had been told to head for ‘Small’ Santa Maria but as we got off the bus & didn’t see any signs we ended up at ‘Big’ Santa Maria instead. I have to say we weren’t overly impressed, the beach was packed with beds, so much so that you could barely manoeuvre & we were charged the most of any beach at €25 (2 beds & shade).


In Naoussa, the shopping was some of the best we saw in terms of quality & variety. Be prepared that the island is not cheap, but they do have an excellent choice and you can spend hours getting lost among the narrow streets & spend a small fortune!

Where we ate, slept & drank

We again booked Efi’s Rooms via Airbnb & we loved it. We were greeted with coffee, homemade biscuits & plenty of recommendations and information. The house is perfectly located right in the centre of Naoussa but the jewel in the crown is the amazing view (again!) from the roof terrace where we spent the start & end of each evening to make the most of the sunset & watch the world go by below us.

Boats at Naoussa, the small harbour in Paros, GreeceNB: If you have a choice of restaurant & are visiting during peak season, make sure you book for the best table options

  • Les Amis – this came highly recommended & we agreed it was one of the best meals we had on our whole trip. We booked the night before & the roof terrace was already full, so we were on the street. We loved this location but if you can, get onto the terrace.
  • Café Karino – Great location just at the marina & serve all day breakfast which was very welcome having arrived early!
  • Sommaripa Consulate – Fantastic spot for sitting on the balcony while watching the sunset & bustle of the marina below.
  • Mare Nostrum – ideally book & get a table at the back (square marina). We didn’t & were at the less atmospheric but bigger section. Pasta was good but very filling!
  • Ragoussis – a bakery which was the perfect stop to pick up delicious breakfast, lunch & snacks on the way for a day at the beach!
  • Tsachpinis – on the square marina & very popular, meaning we had to book or get a table at 11pm. We opted for grilled Calamari & the ubiquitous Greek Salad.
  • Vavayias – nice bar on the water & a great stop for pre & post dinner cocktails.
  • Meat Bar – the cheapest meal of our visit to Paros, tasty traditional kebab & a view over the balcony to one of the busiest cross-sections in the town.
What next time?

Lageri Beach is a nudist beach but comes highly recommended as having a lovely atmosphere. Apparently, you don’t have to fully strip to take your place on the sand!

If you have transport or would like to go further afield:

Lefkes is a village in the centre of Paros which is picturesque & worth a visit for exploring its traditional streets.

Golden Beach is supposed to be lovely but is a much longer bus journey to get to.


Crowds gather at Portara, Apollo’s Temple, the ruined arch at sunset on the shores of NaxosWe arrived in Naxos & stayed in a hotel within an easy 10-minute walk from the port which made life a whole lot easier on arrival (if a little hot & sweaty to get there!). Google Maps is a huge help in terms of locations, directions & working out what is walkable. In comparison to Paros, Naxos is less expensive & also has some of the best beaches in the Cyclades (in my opinion).

Sunset at Portara (Apollo’s Temple)

This is a must-do in Naxos & so close to the port that you can see it as you come in on the ferry.

Dusk is a great time to visit so you can see the sun go down behind the temple. If you do go at this time though, expect to have your elbows at the ready to protect your space as everyone jostles for position to get ‘that shot’ during sunset. It is breathtaking & well worth the effort.”

Agios Georgios (St Georges) Beach

A lone ship in a pink sunset, Naxos, GreeceThe beach is within an easy walking distance from the port & the town. Sunbeds for the day can be €8 for two but we chose to spend a little more & treat ourselves for €10 at Naxaki. The beds had more space & the service was fantastic. We loved it here so much we barely moved for 3 days & it was great to catch up on a bit of reading!

Portara, Apollos Temple, the ruined arch at first daylight on the shores of Naxos, GreeceWhen I was with my sister we plumped for the area at the end – Flisvos which was the same price with a lovely beach bar & restaurant to get some shade, as well as water sports facilities.

Hire a car/ATV/moped & go exploring

In previous years I have hired an ATV & used it to explore the island. Naxos is the biggest & most fertile island in the Cyclades so it is well worth hiring your own transport & heading to the centre, particularly at dusk where the light makes it look even more beautiful.

Old Town (Old Market Shops)

As with all the islands, one of the most fun evening activities is to get lost in the maze of streets in the old town, in particular going deep into the Old Market Shops. There are some amazing jewellery stores & my favourite, locally made pottery shop – Morfes Workshop.

A beautiful orange sunset and rays across a darkening calm, blue grey sea, Naxos, Sunset, GreeceWhere we ate, slept & drank

We were staying in the Iliovasilema Hotel which was a great location in the main town of Chora, between the port & Agios Georgios Beach, with a pool.

  • Ginger – good homecooked food (especially the bread) with excellent, friendly service.
  • Restaurant 520 – this has a fantastic balcony with views out to sea & is a great spot for sunset cocktails & dinner. The menu is limited but with real care, attention & their own little ‘twists’.
  • The Ocean Club – there is way more nightlife going on here than the couple of cocktails we had, but it’s a great spot to sit by the water & watch the world go by or party into the early hours.
  • Ippokampos – Nice restaurant right on the beach at Agios Georgios. The food was good but for some reason, we ordered a number of dishes, all with a base in cheese which meant it was very filling. Take my advice & go easy on the cheese!
  • Naxaki – on our final night we decided to stay late at the beach, have dinner & watch the sunset from here. The food was delicious & the view amazing!
What next time?

We felt guilty for not going further afield to find some more of the beautiful beaches which I have visited on previous trips. Plaka Beach is less busy but with restaurants & a pleasant excursion if you have your own transport. The buses also go there from the terminal at the port.


SueWhereWhyWhat reclines on the stunning white rocks of Milos & swims set in inviting azure seas, GreeceWe arrived in Milos at night but luckily again were staying in the port town of Adamas which meant a flat, easy walk to our hotel & a very warm welcome! Eleni who owned the hotel provided us with a bus timetable which proved an invaluable tool for our time on the island, as well as some restaurant recommendations which we used throughout.

Sarakiniko Beach

We had been told that this is a ‘must do’ when visiting Milos & I couldn’t agree more. We got the bus from the main square (€1.80 each way as usual) & on arrival, it felt like we were walking on the moon (Sarakiniko is nicknamed “Luna Beach”).

The beach is made of volcanic white rock which has been eroded by the wind & waves. It literally looks like you are walking on marble.”

Take a couple of hours to explore (we arrived just after 11 & left at 1pm), swim, relax & marvel at the beautiful rock formations (you can make camp for the day but there is limited beach & no shade). Make sure you have your camera as this spot is stunning!


We got the bus again to this inland town which is very picturesque & well worth a visit. Our first stop was to climb to the top of the Kastro which is a church on top of the one very dominant hill. My advice is to get there early & go straight up. This is partly because you can avoid the intense heat, there are fewer people (we were alone), but mostly as it stops you from looking at it for a long time & talking yourself out of the climb (it looks way worse than it actually is!). The views from the top are well worth the effort as you take in the whole island, stunning villages & the sea surrounding Milos from this vantage point.


The beautiful colourful houses that sit directly on the shores of Klima, GreeceFrom Plaka, we decided it was only a 30-minute walk to get to the picturesque fishing village of Klima. In the midday sun, we started our trek, realising ½ way that it was all downhill & we would need to make it back up in the heat before we could get the bus back home.

The walk was worth it (a drive would be even better!), despite arriving very hot & with a huge sense of foreboding about the return journey.”

Klima is a collection of gorgeous fishermen’s cottages, all painted brightly, with the sea lapping against them. It’s very picturesque & with a welcome restaurant in the centre for some shade & a chance to cool off.

When we finally decided to brave the walk back up the hill, I came up with the genius plan of trying to hitch a lift & after a few unkeen drivers passed us, we struck lucky with a couple who gave us a lift all the way back to Adamas. On our return, we celebrated with an ice cream while reflecting on how fortunate we were. Klima is stunning but if you opt for a boat tour, you will see the village from there (although not at such close quarters). My advice is to think carefully before you brave the walk, knowing you may have to climb back up in the heat. Be prepared.

Round Island Boat Tour

The imposing and impressive coastline of Milos, GreeceThis was the 2nd time I’d visited Milos & my second boat tour. I can report that not all are created equal! When you’re looking to book a tour, I have a few Top Tips:

  • ½ island vs full island – I have done both & can categorically say that Milos is so beautiful with amazing geology that it is well worth taking the full island tour if you can.
  • ½ day vs full day – some tours go around half the island & stop for a sit-down lunch, so take all day. This means that you will often go out slow & see the sites but return quickly. The better option is that if you have a full day, see the whole island.
  • Ask & book as soon as you arrive on the island. That way you get the best choice & the sellers will recommend the best day for the wind (which can impact where you start, which direction you head, half or full island). Whatever they say about the best day, take their advice if possible. Weekends will also get booked up quickly.
  • Look at the extras – many offer underwater photos, unlimited bar etc & ask about the number of people on the boat as some to me look too crowded.
  • Tourist boats can be 2 tier & very overcrowded. If you opt for a yacht there are likely to be fewer people & if you do, go newer rather than older.
  • Ask a few people before you decide. The attitude of the sellers will often give you a steer as to how the tour is likely to be & cheaper does not always mean better. The boats get back to the harbour after 7pm & this is when they do their selling, so you can more easily see what you’ll be travelling in.
  • This time we opted to go with Eleni Sailboats & would highly recommend the company. It was owned by the same family business as our hotel & clearly nurtured in the same way to make the experience special. The tour was €90 per person (cash only), payable on the day.
  • I was so blown away by the day & the beauty of Milos that I am dedicating a whole article to it, so please watch this space!
Where we ate, slept & drank

The stunning coasts around Milos, with views of Kleftiko & Polyagios, GreeceWe stayed in Hotel Eleni, very close to the port in Adamas & I could not recommend it highly enough. The hotel is run by Eleni herself who is the most adorable, enthusiastic & helpful person you could wish for on reception! Apart from a lovely clean room, great outside terrace, the breakfasts were amazing (a huge array of options for only €7.50 per person) & her husband & son also run the boat touring company which I would recommend.

  • Flisvos – this place came recommended from our hotel, specialising in fish with a great view over the boats in the harbour.
  • Marianas – the eggplant saganaki & mussels in ouzo were delicious!
  • Yankos – Apparently a great spot for breakfast but we went for dinner & it was very nice – especially if you like a huge pile of meat!
  • Mostra Café – nice place for a drink overlooking the harbour but bear in mind that Adamas is not the part of Milos to head for the best sunset views (that’s Plaka!).
  • Vipera Lebetina – Again with a balcony overlooking the harbour.
  • Palaios – a bakery in the centre of Plaka with a delicious selection of cakes & pastries. Well-earned after the climb up to Kastro!
  • Astakas – Perfectly positioned for a refreshing stop after the long, hot walk to Klima
What next time?

From Plaka, we walked via the windmills of Trypiti which look great & on closer inspection are all converted into houses. Some are available to stay in which struck me as an opportunity for a unique experience on my next visit – try Aera Milos for details.


A stunning sunset over Santorini's whitewashed buildings & piles of stones on the walk from Fira, overlooking the bayThe ferry into Santorini is an experience which doesn’t really do justice to the beauty of the island. My top tip is to get the public bus from the port to wherever you are staying (or at least the main bus station, €2.30 per person to Fira). It is a barren landscape on the journey from the port, up the side of the caldera via scary switchbacks as you slowly ascend.

We arrived at the bus station in Fira & walked to our hotel from there. When you’re at the bus station make sure you photograph the timetables as these will prove invaluable for your stay. Taxis are less reliable, with fewer available across the island but if you need one my advice is to call (+30 698 8279111 worked for us). The bus station can be a bit confusing & the drivers a little unhelpful, so arrive early to make sure you minimise any issues.


Oia is a must-visit in Santorini, especially for the sunsets but don’t expect to be alone! It feels like everybody in the whole of Greece are amassing for the descent of the sun once you arrive in Oia. For the best spots & ‘front row’ make sure you arrive early enough (when we were there sunset was around 8pm & people seemed to be ‘in situ’ from 6.30pm, I advise to arrive by 7pm, bearing in mind there will also be a lot of people doing exactly the same as you, on the bus).  If you’re hoping to get a sunset view with your drinks or dinner, then definitely book or get there in good time. It may happen every day but in Oia the sun gets applauded as it disappears over the horizon!

Fira to Oia Walk

SueWhereWhyWhat on the walk from Fira to Oia, Santorini, GreeceThis is a 10km walk along the edge of the caldera & I couldn’t recommend it highly enough (& don’t listen if you’re put off by anyone!). It took us 3 hours, mainly because we stopped a lot to take photos as the views are spectacular. My advice is to start early – we left at 7.20am to avoid the main heat & the sun in our eyes all the way. We were very grateful we did this as we arrived into Oia at 11am with crowds building & the day starting to be searingly hot.

If you are planning to do the walk, then I would also check the weather. We went on a cloudier day which was perfect. It’s a moderate walk with some hills but make sure you also wear sturdy shoes as there are some parts where you walk on ash & gravel. Flip Flops would be challenging but that said I did it in my Birkenstocks & was fine, if a little dusty!”

We also used the guide by Santorini Dave which was excellent to tell us where to go if we had a few doubts.


Santorini skyline, GreeceWell worth a visit to one of the Top 10 outdoor cinemas in the world for €8. We were lucky to be there when they were showing “Mamma Mia: Here We Go Again” which was magical (but unexpectedly emotional!). The films start at 9.30pm but the doors open at 8.30pm to allow you time to settle, buy your cocktails & snacks etc. If it’s a new or popular film then I would advise arriving early (capacity is 185), but we read a lot of scare stories on Trip Advisor, turned up (after dinner) at 7.40pm & were one of the first in the queue. The seats are a combination of deck chairs (front row), directors chairs (mainly) & bar stools (cheap seats for latecomers!). There is also an interval in the middle for comfort.

Kamari Beach

This is a black volcanic course sand beach (all beaches here are black sand except Red Beach), a short bus ride from Fira. As a result, the sand gets very hot so lie directly on it at your peril & don’t leave your bed without your flip flops! It also gets rocky towards the water which makes it a challenge to take a dip while still retaining your dignity, especially as there are also nibbling fish! It’s €10 for 2 beds & shade & you can buy water shoes for €8, which I would recommend if you’re planning a few visits.

Santo Wine

SueWhereWhyWhat wine tasting at sunset, Santorini, GreeceFor our final night, we booked a sunset slot (7.30pm) for a Wine Flight Tasting Session at Santo Wines for €45 (once we had added a cheese & seafood platter for dinner). You can get the bus for Perissia & ask the driver to stop. The view, as everywhere in Santorini was spectacular & another angle again on the caldera & the sunset. A perfect way to end a perfect Greek Island Hopping experience!

Where we ate, slept & drank

We stayed at Sweet Pop Hotel which was an oasis just steps from the madness of the main square. It has very funky décor, small but functional rooms & a pool to relax by during the day. The staff were all very friendly & helpful with recommendations.

  • Bacchus, Kamari – good, friendly restaurant between the bus stop & the cinema.
  • LotzaOia – gorgeous view over the caldera & we got in just after sunset without a booking. If you want the front seats around the balcony, then I would advise booking.
  • Melenio Bakery & Café, Oia – perfect stop at the end of our 3-hour walk from Fira – the Orange Pie was delicious!
  • Vitrin, Oia – Great views & a very welcome beer after our big walk & cake!
  • CharacterFira – Amazing views of the caldera, very good Italian food & recommend going downstairs for a bit more atmosphere.
  • Galini Café, Firostefani – Beautiful café with delicious breakfast either as a stop on the Fira to Oia walk or as a short walk in its own right from Fira. It is worth the effort for the food & the views!
What next time?

The Port during the day and a beautiful sunset above the white buildings of Paros, GreeceYou can take boat tours around the caldera that take you to volcanic springs & the White Beach which I have never done, among other attractions. You can also take an excursion to the Red Beach which is again rocky but interesting to see. I have been on previous trips, but this time felt we were busy enough!

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  1. Love this! I just did a little version of Greek Isle hopping in September and loved it too! Can’t wait to get back and hit some of the islands you mentioned. Great info! It makes me happy on this dreary winter day 🙂

  2. Great itinerary for do it yourself Greek Island hopping! We’ve only visited Athens and Santorini on your list. Friends of ours are planning island hopping next summer and will definitely share with them.

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