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.
Are you planning a trip to Greece ?
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 its easy to find a quiet spot, a cove, beach, laneway or entire village that retains complete authenticity year-round.
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
DAY 1-5 Athens itinerary
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.
Athens is pretty compact and very walk-able so most people like to choose a place 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 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.
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 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 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 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
DAY 8-10 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 8 arrive and explore Oia
- Day 9 Explore the island including wineries
- Day 10 Day trip to Tharasia
Further reading : 3 days in Santorini – a complete itinerary
DAY 11-14 Milos itinerary
We spent 5 days on Milos and loved every minute if 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.
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!