First timers in Greece!

Posted by a bennett (San Diego) on 02/07/26 02:04 PM

Looking for any advice on our itinerary for Greece this September. We have roughly 16 days. We are looking for a somewhat relaxing vacation. We will be celebrating my gfs 40th birthday. We are looking for a somewhat slow paced and relaxing vacation. We are mainly looking for beautiful beaches, amazing food!!! Not looking for a night life, somewhere to have a drink or 2 after dinner would be great but not looking for clubs. We enjoy being active… we would love to do some hiking. We are planning on renting a car if necessary everywhere and definitely want to explore villages and sights but not looking to drive for hours a day or spend time in museums (we aren’t history buffs:)) I should also add we are trying to do places that we can fly to. I get extreme seasickness and I don’t want to risk being taken out for a day or 2 over a bumpy ride.

Roughly considering the following…

Milos 3 days
Crete 5 days
Naxos 4 days
Athens 2 days

Is this the best order to visit the islands? Trying to land as early as possible in Athens to get a flight out to the island that same day. How many hours between landing would one need?

I know with Milo’s we would lay back over in Athens before flying into Crete and then it looks like Crete flys directly into Naxos.

We aren’t really sold on 2 nights in Athens but I know we will have to do 1 night atleast before flying out and to be on the safe side with any delays coming from the islands. Where is the best place to stay if we just do a night, probably near the airport would be best.

We are open to any other island suggestions as well. Thanks for the help! Happy travels.

Posted by stanbr

Nanaimo, BC, Canada

02/08/26 12:21 AM

1664 posts

Your plan can be done however you are looking at a number of hops that will take up at least a total of one full day of your 2 weeks.
Your plan to fly to Milos for 3 days. Fly back to Athens and connect a flight to Crete. Fly from Crete to Athens and connect to a flight to Naxos. Fly Naxos to Athens before your return flight.

You are going to be spending a lot of time waiting around airports.

If it were me I would fly direct to Chania on day of arrival in Athens. You need a minimum of 2 hours to make a connection. In September it is still at the early end of the high season so maybe 3 hours for the connection.

You are going to love Chania particularly if you can find a hotel inside the city walls. The old town and waterfront promanade are beautiful.
My advice would be spend 7 nights in Chania. There are lots of day trips in the area that can be done by excursions or the local KTEL bus goes pretty much anywhere you may want to go for day trips. Consider taking the bus to Kissamos where you can hop a ferry that takes you to Gramvossa where there is a lovely beach, a shipwreck and a pirate fortress. The excursion then takes you to Balos Lagoon which is a huge beach area.

I can recommend Wanderlust tours which can take you to the best locations in West Crete. Max 12 people. Since we stopped driving we have taken 4 of their tours.

Your week will fly by in west Crete.

Fly back to Athens and connect to a flight to Naxos. As far as I can see, there is no direct flight from Chania to Naxos so you have to connect in Athens. You can be in Naxos by noon.
In Naxos I would suggest you look for a hotel at St George beach. Its a lovely sand beach and is really part of Naxos town just a 10 minute stroll around the headland to Naxos waterfront promenade. Naxos has other excellent beaches along the west coast with newer resort hotels built in the last decade.

Greece is a destination best experienced slowly. Thus I am suggesting you drop Milos. Dropping that hop is going to give you about a full day of extra time on Naxos or Chania.

Your plan to spend the last 2 days in Athens is good. You always want to be in Athens the day before your return flight. We were on a delayed aircraft Naxos to Athyens and half the passangers missed their return home flights.

For fun here are some images of Chania and Naxos
Wanderlust tours Chania https://www.flickr.com/photos/stanbr54/albums/72177720318394812
Chania 2024 https://www.flickr.com/photos/stanbr54/albums/72177720318408008/
Trip around Naxos https://www.flickr.com/photos/stanbr54/albums/72157634605629689
Naxos 2025 https://www.flickr.com/photos/stanbr54/albums/72177720329571437/

Posted by JoLui

France Southwest - Occitanie

02/08/26 12:46 AM

3495 posts

We are looking for a somewhat slow-paced and relaxing vacation.

We would love to do some hiking.

We are planning on renting a car if necessary and definitely want to
explore villages.

Considering the time you have available, everything you've said about what you want to do and how you want to spend your vacation in Greece, you should skip one island.

How do you plan to explore villages, go hiking, and relax if you only stay, for example, 3 days on Milos? Within those 3 days, there will be two half-days of flights and transfers. So that will basically leave you with only two full days.

The same goes for Naxos, which is the largest island in the Cyclades.
Not to mention Crete, which requires at least 15 days to explore even part of it.

Are you sure you can't travel by ferry? From Heraklion to Naxos, while there are flights in September, they're only three times a week. Having to fly to Athens to cover the barely 100 miles between Milos and Crete is quite a detour.

All these trips will take up a lot of your time, time that will be anything but slow and relaxing.