Most first time visitors to Greece quickly realise why most people return again and again. With so much to see and do and so much diversity across the mainland and the different groups of islands its impossible to see much in a short time. But if you only have 2 weeks in Greece for your first visit it is possible to cover a lot of ground and ensure you be planning your next visit before you’ve even left!

There are 6 island groups – the Cyclades, the Dodacannese, the Saronic islands, the Sporades Islands, the Northern Aegean islands, the Ionian Islands, and Crete, so island hopping in the Greek Islands might be popular but it does require some research, as most of these groups do not connect with each other by ferry or flights.

Here’s our suggested itinerary that will allow you to visit two island groups and Athens. I’ve chosen Greek islands that are popular with 1st timers but also give you a fair bit of diversity. You may also want to read The Best Greek Islands for families or The Best Greek Islands for Couples as well. 


Whether you’ve been before or it’s your first time it can be hard to process all the information out there. Be sure to check out our complete Planning Guide as well as our FREE 13-page downloadable itinerary.

If you are feeling really overwhelmed you might like a Trip Consultation perhaps!?

And come join our private Facebook Group where you can ask questions and get advice from real travellers!

When to visit Greece

The best times to visit Greece are April-June and September-October. The weather will be a bit milder and it will be less crowded.

High season is late June to early September, and prices will reflect that as will the crowds, the number of cruise ships and accommodation availability. In saying that Summer is not exactly terrible especially in some of the lesser-known spots. The water is warmer, there are blue skies every day and a fabulous holiday atmosphere as Greece is at its absolute prime.

They say this is when the Gods smile the most and even in the most popular tourist towns and islands it’s easy to find a quiet spot, a cove, beach, laneway or entire village that retains complete authenticity year-round.

Orthodox Easter is an especially wonderful time to visit Greece as it becomes very festive with parades, parties, and on many islands bonfires, fireworks and other activities and traditions.

There are other festivals throughout the year that can vary from place to place and can be quite incredible.

Best beach and swimming weather: June to September
Best sightseeing weather: March to June and September/October 

caldera view

2 Weeks in Greece – Logistics and order

Many people have Athens as their first destination when visiting Greece. We recommend flying straight through to your furthest island and leaving Athens until the end, for several reasons:

1. You need to be back on the Mainland at least one night before your international flight home to give yourself a buffer in case of ferry or flight cancellations. You could do a few days in Athens at the beginning and one at the end, but the airport is a long way from the ancient centre so you will save time and money if you do it all in one block at the end.

  1. Yes, you’ve possibly just done a long international flight. So what’s one more hour? In fact, Santorini is only a 40-minute flight. Get all your airport stress over and done with and out of the way.
  2. It’s so much nicer to wake up, jetlagged, on a Greek island, than in a big, crazy city.
  3. The shopping in Athens is fantastic. Don’t drag all your shopping around with you. Do it all at the end. This way you can also realistically pack just a carryon for a week or two ( or 5 in my case) and check a box, duffel or cheap suitcase home, packed with goodies.
  4. You cannot fly between most Greek Islands. By flying to your furthest ones you are then likely to have fairly short ferry trips between islands.

Day 1-5 Santorini itinerary

Santorini is a bucket list destination for most people and for good reason. Despite the cruise ships and the crowds it remains one of those places that not only meets your expectations but probably exceeds it.

If you choose where to stay carefully you can enjoy your own jaw dropping views over the Caldera and have a place where you can escape from the day trippers. It can get a bit crazy when the cruise ships come in each day so a room with a pool and terrace makes for a great escape for an afternoon siesta and sundowner’s. 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 Santorini with  beaches, wineries, hot springs, great shopping and some of the worlds most iconic and photographed sunsets. Try and do a sunset cruise where you can avoid the crowds and still get absolutely mesmerising views.

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.

  • Day 1  Arrive and explore Oia. Book a restaurant like Strogili for dinner at sunset.
  • Day 2  Do a highlights tour including wine tasting and sunset. If you’re up for it then take in The Greek Wedding Show too!
  • Day 3  Visit Akrotiri, Greece’s Pompeii, and red beach. Follow it up with the 9D Atlantis Experience and, if time permits, a few wineries as well.

Further reading : 3 days in Santorini – a complete itinerary

DAY 5-8 Paros itinerary

For many people Paros is the perfect Greek island. Not too small nor to big, with something for everyone. It’s also strategically located as it’s often 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.

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 nightclubs 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 residents, Tom Hanks and Rita Wilson.

  • Day 5  Arrive and get to know Naoussa
  • Day 6  Day trip around Paros – Parikia, Aliki, Drios, Piso Livadi, Lefkas, Santa Maria and Paros Park.
  • Day 7  Day trip to Anti-Paros 
greek fishing village
medieval village greece

DAY 8-11 Milos itinerary

We spent 5 days on Milos and loved every minute of it.

We’ve sent many friends since and will definitely be returning. It’s a special place – whilst part of the Cyclades it is quite unique in many ways and luckily unable to get very busy YET with little development and still under the radar of most cruise ships and big tour groups.

3 days will allow you to get a good feel for Milos 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 ) 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 there are a few other great accommodation options as well.


  • Day 8 arrive and explore Pollonia
  • Day 9 explore the island on a guided tour and learn about the culture and geology
  • Day 10 half-day cruise to Kleftiko and hang out at southern beaches
  • Day 11 transfer to Athens 
milos beach
greek fishermans huts

DAY 11-14 Athens itinerary 

ruins in greece

Athens, of course, is the capital of Greece and home to some of the most iconic and important historical sites and monuments in the world. It is a big, pale, sprawling metropolis which offers a lot for visitors and is worth a 3-day visit as a minimum, but more if you can manage it.

You have a lot of options to get to Athens which cover by air, sea, rail, driving and even on foot!

Apart from the many things you can do in Athens itself it is also feasible to do a day trip to Meteora & Delphi and/or Olympia although Meteora is a long day. You can also 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 the acclaimed musician Leonard Cohen and many famous playwrights, the original ‘bohemians’ for over 20 years. There is a well priced 1 day cruise that takes in Aegina, Poros, Hydra and Spetses as well.

Athens itself has great shopping ( don’t miss the huge department store, Attica), incredible food and a lively night-time 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. The Acropolis museum is world-class and needs to be enjoyed either before or after visiting The Acropolis itself, but there are many other excellent Museums too – the highest number per capita in Europe!

Athens is pretty compact and very walk-able so most people like to choose a place to stay either in 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 stroll between each other so you can’t go wrong.

One of our favourite places to stay is Zillers Hotel. 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. They only have 6 rooms though so book early!

I also love the new Ergon House which is part of the world-famous delicatessen and restaurant and is the first ‘foodie’ hotel in Athens.


monataraki athens

With this itinerary you will spend 2 weeks in Greece visiting 5 islands, and possibly more depending on what day trips you choose from Athens, as well as spending time in and around the fascinating ancient capital.

You will take in stunning vistas, fascinating historical sites, and information, hang out at beautiful beaches, visit medieval villages and world-class wineries. You will see authentic fishing villages, sail on the clearest azure water you’ve ever seen and indulge in some of the best food and nightlife on the planet.

Not bad for just 14 days in Greece. I guarantee you will love every minute!

Don’t forget Travel Insurance!

It’s important to make sure you are covered for medical expenses    ( some countries may include this in health insurance) but also for lost baggage, flight and ferry delays and cancellations, theft, and emergencies, including something that happens back home while you are away.

This can save you tens of thousands of dollars, or even more.

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