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3 weeks in Greece – how to enjoy 3 island groups and Athens on your first visit

itinerary for greece
One of the most common questions I am asked is about a suitable itinerary for a trip to Greece, especially the Greek Islands. Not surprisingly these are usually asked by first-timers and I remember the plethora of information I waded through for my first trip – confusing, exhausting and very frustrating ! Many people seem to like to go for around 3 weeks give or take a day or two so, in addition to the content I’ve already posted on some of our favourite Greek Islands I’ve put together this high level itinerary for 3 weeks in Greece. I hope it helps !

There are 6 different ‘groups’ of islands in Greece and the important thing to know is that is it NOT possible to fly or ferry between most of them. To move from the Cyclades islands for example you will need to get back to Athens and either drive or Fly to the Ionians or the Sporades islands. Most people want to see the picture postcard white sugar cube architecture of the Cyclades, especially for their first trip, so this itinerary focuses largely there as well as including Crete and the Saronic islands near Athens. If you have more time or if you would like to see a very different group then I would suggest replacing Crete with the Ioanian islands and spending some time on Corfu and/or Lefkada, Kefalonia or Zakynthos ( there is an international airport on Corfu and domestic ones on the others).

So, my (flexible) suggestions for 3 weeks in Greece ;

Day 1 & 2

Fly into Crete – preferably Chania 

Chania is a lovely town in the northwest corner of Crete and is serviced by an International airport with connections from Athens and most major European cities particularly from June – September. There is quite a lot to see and do so your two days will be very busy but it is a good introduction to Greece being not too small nor too big.

Try and spend one day doing a day trip to one ( or several ) of the famous beaches nearby – Balos, Falasarna, Ellafonisi and Stavros are all amazing. Avoid the long stretch from Platanias thorough Garanis which is wall to wall Brits and half-naked europeans who don’t leave their hotels.

3 weeks in Greece

Chania Venetian harbour

3 weeks in Greece

Falasarna beach

We stayed in a cheap and cheerful family run hotel in Chania with stunning views of the harbour and port town. It gets very lively at night but everything is at your doorstep ; PORTO ANTICO

Day 3 & 4


Drive or catch the bus to Rethymnon ( about 2 hours) which is a lovely seaside town with a beautiful venetian port and amazing medieval architecture. There are some lovely garden restaurants and lots of small quiet alleys in the Old Town where I recommend you stay.

We only did a day trip to Rethymnon to stop and visit friends but wished we had stayed longer. Casa Vitae Hotel is in a fantastic location and is very good value too !

Day 5


Heraklion is the largest city and the capital of Crete. Its airport is the 2nd busiest in Greece ( an option here is to fly into Heraklion and out of Chania if the flights suit better).  This is where the Minoan civilization flourished so there are many Minoan Palaces and archeological sites to visit. You can easily access  traditional villages, Medieval castles, Byzantine monasteries and nice beaches close by as well.

OLIVE GREEN is a new modern hotel in a great location in the Old Town and again is amazing value for money. 

3 weeks in Greece

Day 6 , 7 & 8 

Ferry to Santorini

It is possible in the summer months to fly from Crete to Santorini on certain days but I do love the Ferries. Huge, comfortable and a relaxing way to both exit and enter the wonderful towns on the islands they are run with an amazing chaotic efficiency that will leave you both bewildered and impressed. 

Santorini is a must do for any trip to Greece and one of those places on the planet that not only meets your expectations but probably exceeds it. In saying that it is very important to choose your accommodation carefully. The whole point of Santorini is to enjoy the jaw dropping views over the Caldera and having a place where you can do that at your own pace and leisure makes a world of difference. It can get a bit crazy when the cruise ships come in each day so again a lovely room, preferable with a pool and terrace makes for a great escape for the afternoon siesta and when you reemerge for dinner most of the tourists will have floated away !

We really enjoyed staying in Oia which is considered the most picturesque village, although several friends have also enjoyed Imerovigli which is about a 20 minute walk along the nice flat footpath that runs along the Caldera seam. There is a surprising amount of things to do on Santorni – beaches, wineries, caves, hot springs and sunsets. Try and do a sunset cruise on a small boat – you will avoid the crowds at the best vantage points and it’s absolutely magical sailing around the Caldera !

We loved everything about staying at ARMENI VILLAGE – fantastic location, great service, stunning views and lovely cave rooms that were well priced compared to many.

3 weeks in Greece

DAY 9, 10 & 11 

Ferry to Milos

We spent 5 days on Milos in 2017 and loved every minute if it. Read all about it HERE !

3 days however will allow you to get a good feel for it and you should be able to see most of the best sites. We stayed in the beach ‘resort’ village ( I use the term resort loosely as it is still pretty quiet and largely undeveloped) of Pollonia and would again. It has a lovely village atmosphere, a decent number of beachfront tavernas and shops and a laid back friendly vibe. We stayed at Unique Milos Suites but a great hotel option is also Delmar Hotel which is just around the corner.

5 days on Milos

Do a full day or half day boat trip to Kleftiko

5 days on Milos

Sarakinko’s extraordinary moonscape

5 days on Milos

the quaint village of Klima with its colourful fisherman’s huts

Day 12, 13 ,14 & 15

Ferry to Paros

I’ve written a lot about Paros and it remains our favourite island. Busier than Milos but quieter than Crete it ticks a lot of boxes being not too small and not too large and offering something for everyone. It’s also strategically located as the first Ferry port from Athens to the popular Cyclades islands and therefore a great place to access the mainland coming from the other direction. Its neighbour, Naxos is also a wonderful island and its likely your ferry will stop there so consider a night or two there as well if you have time ( Nastasia Village have gorgeous renovated rooms under $100!).

We like to stay in Naoussa on Paros which many say is like a small version of Mykonos with a lively mix of tavernas, bars and nighclubs as well as lovely whitewashed alleys full of great cafes and boutiques and gelati stores. We don’t stay right in town though as it can get noisy in the wee hours of the morning but both Paliomylos Hotel ( where 30 of us stayed in 2016!) and Papadakis Hotel are a short walk to town and have great views on the neighbouring hill, with fabulous, friendly service.

Again there is a lot to do on Paros so ideally you need to spend at least 3 days there. Make sure you do a sailing trip to the neighbouring ‘Small Cyclades’ islands and, if time permits, hire a car and catch the car ferry over to Antiparos. It’s only a 12 minute trip and if you’re lucky you might bump into its most famous resident, Tom Hanks !

3 weeks in Greece

Sailing the Small Cyclades islands

3 weeks in Greece

Naoussa harbour

3 weeks in Greece

The Church of a Hundred Doors in the Port town of Parakia

Day  16, 17, 18 & 19

Ferry to Athens

Athens is only a 3 hour trip from Paros on a high-speed ferry. There is a LOT to do and see in Athens but you can also use it as a base to see a number of incredible sites on the mainland as well as explore the nearby Saronic islands.

There are daily day trips to Meteora & Delphi  and/or Olympia. Meteora is a long way so you may want to spend a night there. You can catch the ferries out to the Saronic islands which are really lovely. We especially like Hydra which has no cars or scooters and was home to Leonard Cohen for many years. Alternately there is a 1 day cruise that takes in Aegina, Poros, Hydra and Spetses and is apparently quite good.

Athens itself has great shopping ( don’t miss the huge department store, Attica), incredible food and a lively nighttime scene with thousands of tavernas and cafes to choose from. There are a lot of new hotels and restaurants many with incredible rooftop views especially of the Acropolis. Dont miss the Acropolis museum which is very impressive.

Athens is pretty compact and very walkable but most people like to stay either in the Plaka or around Monastiraki  or Syntagma Square’s. We also like Psiri which reminds people a lot of Melbourne. All of these however are an easy 15 minute between each other so you cant go wrong.

  In 2017 we stayed at the new ZILLERS HOTEL and could not fault it. Beautiful rooms right on Mitropoleos street which is one of the main dining streets of Athens and runs parallel with the main pedestrian shopping street of Ermou. It has a fabulous rooftop bar and restaurant and is really very inexpensive for what you get. It only has 6 rooms though so book early !

3 weeks in Greece

the famous Monastraki Square with the Acropolis behind

3 weeks in Greece

one of many great swimming spots on Hydra

3 weeks in Greece

the main port of Hydra

3 weeks in Greece

A for Athens rooftop bar and hotel

3 weeks in Greece

Parliament as seen from the rooftop bar of the famous Grand Bretagne Hotel

3 weeks in Greece

Ermou shopping street

3 weeks in greece

Temple of Poseidon at Sounion near Athens

Day 20 – Home ( or continue elsewhere)

You may also like to read ;

 So you’ve been to Mykonos and Santorini – what next !

Why we chose Paros for a special celebration

How to have holidays more often !



  1. kathymarris

    This is a perfect itinerary for first-timers to the Greek Islands. I think most people, including myself think it’s so easy to get to the different islands, but as you have pointed out they are all in different groups and not so easy to get to. This would be my dream holiday and I sincerely hope I’ll get here someday! I have pinned this to Pinterest for future reference.

    • Anonymous

      We did an island hop starting with a few days in Athens then we hopped to Andros from Rafina, then onto Tinos, Syros and finally Paros. We then went back to Athens for a few more days but staying in a different district. We then traveled by bus to Zakynthos where we stayed for 7 weeks.

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