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Greece Itinerary Help

My husband and I will be in Greece for almost two weeks in May 2025. This is our first time in Greece. I am having trouble with our itinerary and need some expert help!

Our itinerary is restricted by the fact that we are spending Monday, May 26-Friday, May 30 in Athens as part of a trip scheduled by my husband’s job. We are staying at the Four Seasons Astir Palace Hotel, which is about 30 minutes from Athens on the coast. While we are there, we will be able to sightsee in Athens and hopefully take a day trip to Delphi.

We fly into Athens in the morning on Friday, May 23, and have Friday-Monday on our own. We will fly out on Tuesday, June 3rd, and so have Friday-Monday (since we need to be back in Athens Monday night to fly out Tuesday) also on our own. We would love to fit in an island or two, and a bit of the Peloponnese around our time in Athens.

We are in our 40s and enjoy history, good food, and beautiful scenery. We love a road trip and have no problems driving in foreign countries (we have driven all over France, Italy, England, and Scotland). We are not huge hiking or beach people—though we are open to experiencing both since beaches are a huge part of Greek islands. I want to avoid hugely touristy places, so I am hesitant to go to Santorini or Mykonos—the crowds thoroughly ruined our trip to the Amalfi Coast many years ago and I want to avoid a repeat experience. We would rather see a more traditional island with some historical sights and good views without battling crowds and instagrammers.

We are wondering if flying to Crete upon arrival would be a good plan, then taking the time at the end of our trip to drive some of the Peloponnese? Do we have enough time to make this worthwhile? We are open to any and all suggestions.

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I can see your challenge. You basically have three nights at both beginning and end of your trip to do something else.

I think your idea of seeing a bit of the Peloponnese would work at the end of your trip. You can return to the airport to rent a car and drive to Nafplio and spend three nights. It is a good amount of time there and you can make day trips from there.

Your three nights before are a bit tougher because you will be jet lagged that first day. If you want to go to Crete, I would go to Chania. Stay in old town and spend all your time there. You can see quite a bit in the 2 full days you would have there.

If you don’t have airline tickets yet, it would be best to fly there on one ticket. We did that a couple years ago on United which I know has hub in DC. Otherwise will need to build in some cushion time in Athens which you want to avoid if you can, given your limited time.

It would be even better if you could add a day or two to the beginning of your trip. We spent 11 nights in Crete (4 in Chania) and would love to go back.