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Greece itinerary help

Going to Greece in winter Break. Dec 20- Jan 4. We will spend 2 days in NYC and fly out from NYC to Athens. We want to Santorini as well. Any other city /town? Looking for culture, food, explore small town/village, food. Some historical places.
Please suggest.

Posted by
1446 posts

You should keep Athens for at least three days at the end of you trip before you fly home. If it were me that late in the year i would choose to fly to Chania Crete and find accommodation in the old town. There will be few tourists around but the locals will still give you an authentic Greek experience.

You will have to research Greek ferry schedules to see if there are any still running from Crete to Santorini. It is probably your best bet to fly back to Athens and connect to a flight to Santorini if there are no ferries.

Posted by
78 posts

Any help would be appreciated. Dec 20-Jan 4. Flying to crete, then want to go santorini and finish out in Athens. Can go to other places if you suggest. Big questions - how many days in each place?

Posted by
15794 posts

AFAIK, there are no flights between the islands. To go from Crete (Heraklion) to Santorini by air, you'd fly through Athens. Or take the high speed ferry from Heraklion to Santorini. I loved Chania, note that it's a schlep from the airport or the Heraklion city center by public transportation. It's about 2 hours by car, anywhere from 2.5 to 4 hours by bus, which is how I did it. Chania has a charming small town feel (and lots of history), much more than its big sister, Heraklion, which does have a very good archaeology museum and the ruins of ancient Knossos. Santorini is scenic but quite touristy.

Posted by
78 posts

Thank you. Love to spend time in chania. How many days should I reserve for crete? How many days for Santorini?
My current flight takes us to crete and then ferry is a week after. Is spending a week worth out of our : weeks trip to Greece?

Posted by
1446 posts

A week in Chania will go by pretty quickly. There is lots to see and do in that area of West Crete. You might want to look for seat sales and fly to Athens and transfer to Santorini. Chances are you can be in Santorini much sooner than using the ferry. Two or three nights in Santorini should be enough time to visit. Then finish with 3 nights in Athens.
Here are some images of Chania and west Crete .
Chania 2024 https://www.flickr.com/photos/stanbr54/albums/72177720318408008/
Western Crete https://www.flickr.com/photos/stanbr54/albums/72157632115757899

Posted by
78 posts

Thank you. I will stick to it. I hope it’s not too dull in December. I looked at the flight to Santorini via Athens but seems expensive(1700 for 4) + 5 hrs flight time commitment. But will keep looking.

Is napfilo worth making a day trip from Athens? Or just stick to Athens only?

Posted by
6 posts

Hey Bushrat,

Santorini in winter (December to early January) offers a much quieter, more peaceful experience compared to the bustling summer months. Here's what you can expect and some tips to make the most of your time there:

What to Expect in Santorini During Winter
Weather: While it won’t be warm enough for swimming, the weather is usually mild with temperatures ranging between 10°C (50°F) and 16°C (60°F). There can be occasional rain and wind, but the sunny days can be gorgeous, especially in Oia, which has a unique microclimate protected from northern winds.

Crowds: Santorini is famous for its sunsets and views, but in winter, the island is calm and free from the typical tourist rush. You'll have iconic spots almost to yourself for taking photos or just soaking in the beauty.

Closed Establishments: Many restaurants, shops, and wineries will be closed, as winter is off-season. However, some services still operate:

Wineries: Most will be closed, but you can check out Koutsoyannopoulos Wine Museum (https://kwm.gr/) which might be open.
Transportation: Uber isn’t operational until April, but taxis can be booked in advance through services like Vip Santorini (https://Www.viptransferssantorini.com) .
Activities: While water activities are limited, you can:

Walk along the caldera for breathtaking views.
Visit historical sites like Ancient Thera or Akrotiri.
Explore picturesque villages like Oia (great winter spot), Fira, and Pyrgos.
Enjoy quiet sunsets, especially in Oia, which faces the sun all day in winter.
Getting Around
Renting a car is a great way to explore the island on your own schedule. The roads will be quiet, making driving stress-free. However, plan your routes as some attractions and towns may have limited services.
Alternatively, book transfers online to ensure reliable transportation.

How Long to Stay
Santorini is small, so 2-4 days is enough to explore the key highlights in winter. While many suggest Fira for its accessibility to restaurants and amenities, I strongly recommend staying in Oia. Oia has a unique microclimate that’s protected from the north wind and enjoys sunlight throughout the day, making it a much more comfortable and enjoyable base during winter. Plus, its iconic charm and quiet atmosphere in the off-season provide a truly memorable experience.

Enjoy your winter adventure! Let me know if you'd like recommendations for Athens or other towns to add to your itinerary.

Posted by
15794 posts

I was happy to wander in Chania for 5 "lazy-ish" days in October, when the weather was warm and mostly sunny. I loved both my Athens visits of about 4 days each.