Looking for thoughts/advice on planning trip to Greece in 2025

3-4 couples (> 50 in age) are planning a trip to Greece in 2025. First question is whether it’s better to go in Spring or Fall.

The ideas for where we visit range from Athens, Delphi, the Peloponnese Peninsula, Santorini, Crete, and Rhodes. That’s a lot of ground to cover so we’re trying to figure out how to best work this out logistically over a two week period. Since we fly into and out of Athens, we can spend a few days there to see the major sites. But then how to work out seeing some of the other mainland sites like Delphi. Is there some place to stay outside of Athens that would work for that? Use tour/guide to maximize use of time?

There are a lot of islands to visit, so we’ve narrowed it down to Santorini and maybe Crete (or Santorini and Rhodes even though Rhodes is further). The thought is to spend at least 5 days on Santorini, possibly renting a villa/house to fit in all the couples at once.

Thanks for any input or words of experience.

If you are looking to go into the water on any of the islands, my suggestion is September.

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Many of the islands shut down in mid October so last weeks of September are best.

Thanks for the input so far. Based on some off the board input, we may stay longer on Crete and less so on Santorini. Still a question about Rhodes.

I loved Crete!!!

Been to all three

  1. Crete is a very large island and many people spend their entire vacation there. Typically not Americans, more Euro types.
  2. Santorini is shocking. Amazing. Love it, going back. 5 days is a lot…
  3. Rhodes is a nice, the medieval walled city is fun, but not sure about what else you’d do that can’t be done elsewhere.

I want to be as delicate and sensitive as possible when describing Athens. It’s a shit hole.

Must see the plaka, walk the algor to the acropolis, and parthenon. Then get out.


I’ve commented in the body of Brig’s post, below.

Thanks again everyone for the great input. Another specific question:

Is it worth spending a few days on the Peloponnese Peninsula?

We want to see Delphi but don’t know whether it’s worth spending more time on the mainland before we hop over to Crete or one of the other islands. Thanks.

For Athens, those 3 things and the Changing of the Guards are the 4 must sees. Can do them all in a day.

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In 2022 we spent 5 nights in Santorini, 3 nights in Naxos and 2 nights in Athens. I think I would have removed 1 night in Santorini and tacked it onto Athens. We are also more city people and “type A” and in Santorini it’s not easy to get between the towns so you are kind of “stuck”. If you like to open a book and read all day you’ll like Santorini - but it’s like 35-70 EUR each way to get a taxi to go anywhere, so it adds up really quick. There was an outdoor movie theater showing like Jurassic Park3 or something cheesy and it was 70 EUR in cab fair for me and my wife so we said no. There is a cute town within walking distance called Finikia - I highly suggest you find it and go if you stay in Oia it’s a ~10 minute walk and great non touristy restaurants abound.

Naxos is great if you like hiking and outdoors stuff, great easily accessible beaches and some really great food. Most food for the Islands are grown on Naxos its the biggest “green island”. I know you didn’t mention it, but its between Santorini and Athens via the high speed ferry.

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Yup. And you can drop by the Olympic stadium, too, for a look. All in a day.

I found the national archeological museum very compelling if you are into ancient art.
Did you say how long you are going for? In the Peleponese, I’ve enjoyed the ruins at Olympia and the city of Nafplion (to see the theater at Epidarus) but you are adding a lot of travel time. If going for three weeks or more and are passionate about ancient architecture, yes. But I wouldn’t take time away from Crete to do it.

The Meteoras is a world wonder for me but more suitable for a 10 day driving trip of the mainland.

I thought you gave up on Santorini due to crowding.

We did the same 3 this past September, and loved them all. I liked the idea of staying on a popular/known/“fancy” island and a less known, more down to earth (and much less expensive) island.

We did. I understand that they addressed the road issue in and around Oia, which required cars to go all the way down the backside of the caldera and up again to bypass the one-way mess at the southern end of Oia (it was almost faster to walk across all of Oia down to Ammoudi than taxi!)

Crete. The collective wisdom of our group is that we’re going to spend a few nights in Chania old town - to be able to explore the western part of the island.

Then we move some resort/hotel east of Heraklion as a base for exploring the eastern part. Is there such a thing as an adult’s only and quiet/restful resort in the Heraklion region? We don’t need anything big and fancy; just a serene place to relax in between trips to the Knossos Palace or other local treasures in the region. It looks like with such a goal, we’d skip Malia and Sisi and maybe go as far east as Eloundas? Any thoughts or suggestions appreciated.

I’ve been to Greece and Crete a dozen times, Santorini twice. I have not been to Rhodes.

Santorini is breathtaking, but tiny.

In Athens, there is a place I go to every time. It is an unimpressive acre on top of a hill across from the Acropolis. It is called the Areopagus. Apparently it is the place where the word ‘demokratia’ was first spoken. Walk up the worn, slippery steps, and give thanks.

Crete is beyond belief. Please do not plan your entire trip. Leave a day or days to just get lost.

I completely agree with Chania as a base. 30 miles and an hour away is Milia, an agrotourism retreat where food and setting compete for beauty at the highest level.

non-commercial post: 20+ years ago a Greek-American friend of mine, Ted Manousakis, went back to his roots and started a winery in Vatolakos. I represented them briefly. The wines are excellent. This is halfway between Chania and Milia.

Dan Kravitz

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I’ve stayed in Elounda a bunch of times and Chania once. They are at opposite ends of the Island. I like both.

We loved Crete and wished we would have stayed longer. Depending on your interests, there are a number of amazing places on the island. We truly enjoyed a stop to St George Selinari Monastery on the National Road. It won’t take long, but it’s one of the most peaceful places I’ve ever been on the planet. Although most of Knossos is a rec-creation, it is one of the must see stops on the tourist route. And if you are into military history, the sites at Souda Bay and Maleme are worth a visit - we were lucky to catch a US aircraft carrier at Souda Bay for a memorial service.

Like most places, the experiences are just watching people, browsing the markets, enjoying the seaside, eating amazing food, and drinking good wine. There are a number of small seaside villages that are worth a stop. We stayed at a hotel in Elounda with a great thalassotherapy circuit - the Blue Palace. Dinner options on property and in the next town as well as private pools in addition to the seaside and larger hotel pools, including the thalassotherapy pool. They even have an incline to take you down to the seaside.

Don’t skip on Crete - it’s fantastic.

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It’s been several years, but I was struck at how cheap Crete was (outside the hotels) compared to Santorini, Mykonos, etc.