The Best Places I’ve Stayed in Greece

As I sit staring out at the three week old gray mush that was once snow outside my window, I find myself looking up flights to anywhere warm. When that feels unrealistic, I scroll through old photos instead.

Scrolling through my camera roll, I am reminded that I have been lucky enough to work for some luxurious hotel companies and travel to objectively beautiful places for work. But when I think about those trips, what I mostly remember is waking up early after a late dinner that was labeled fun. I remember setting alarms. I remember wishing I could stay under the covers and order room service instead of heading to the next group activity. I do not think I am alone in that feeling. It is the blessing and curse of work travel.

If someone showed up at my door right now and told me I could go back to one place I have already been, it would not be any of those places. Not because they were not beautiful, with impeccable service. That is just not what I crave when I am traveling for myself.

I am always looking for something in between. The amenities of a hotel with great food. Not having to do the dishes every night. But also your own kitchen. Real space. Outdoor space, which we do not have living in New York. Somewhere that feels like it exists beyond you being there.

The place I would go back to without a second of hesitation is Crete, Greece.

It is the place I measure most other trips against.

Below are some of my favorite places I stayed and meals I loved, along with a few stray recommendations from my time in Greece.

An organic farm about 20 minutes from the Chania airport that was built over 400 years ago. It has been a working farm for most of that time. It gives Call Me By Your Name villa energy, if it were set in Greece.

For most of its history it was a single villa. It has since been divided into three separate spaces, each with generous living areas, enormous backyards, and private pools. You genuinely feel like you have your own house.

Danai Kindeli, the owner, has had this place in her family for over 100 years and eventually turned it into a small hotel. She is a true local and will not steer you wrong. Some of the best food recommendations from the entire trip, including Athens, came from her.

The kitchens are stocked with fruits, vegetables, and eggs from the farm, along with homemade breads and local butters and cheeses. You could easily not leave the property the entire time. They also offer additional dishes and wine you can purchase. Eggplant pasta, snack plates, endless cheese. At one point my husband asked for cheese and they brought out a wheel roughly the size of his head.

It is ideal if you want something low key and are not interested in 24 hour room service or over attentive staff. It is relaxed. After days exploring Crete, it felt like the right place to come back to. We spent more than one day not leaving at all, just reading by the pool and eating strawberries, meat, cheese, and drinking wine.

In low season, April through May, which I would recommend before the heat sets in, rates are around 350 euros per night, which is not cheap. But I have stayed in plenty of 200 square foot hotel rooms for more. Here, you actually feel like you are living somewhere, with a private backyard closer to the size of a football field, which I cannot say about anywhere else I have ever stayed.

When my husband and I went to Crete, we wanted at least one night near the water. After a little Googling, I found a tiny place called Loutro.

You can only get there by a fairly intense hike or by ferry from Sfakia. There are no cars. The entire “town” is one row of small hotels, restaurants, and beach chairs lined up along the sea.

It is very simple. And very special.

The hotel can only be booked by email. You pay for everything in cash. The person at the front desk had strong Soup Nazi from Seinfeld energy. No small talk. But somehow it still works.

The rooms are extremely simple, almost spare, but kind of perfect in their simplicity, with a small deck overlooking the water. You walk straight outside and into the highly concentrated salt water of the piercingly clear Libyan Sea and float almost instantly. Nothing else really matters.

The rocky beach is covered in the most beautiful stones, marbled in rust and deep onyx tones. I will not comment on how many rocks I brought home with me, other than to say I stayed under the airline weight limit.

One night is enough. When we stayed a few years ago, it was under 100 euros per night.

There really is not much else like it.

Although I was jet lagged for most of our one night stay in Athens, I remember wishing we could have stayed longer.

Monsieur Didot is a small, B&B in the quiet residential quarter of Kolonaki. It is named after Firmin Didot, the legendary type designer, so it was obviously up my alley.

The space is beautiful without trying too hard. The breakfast was lovely. And it is walkable to the Acropolis and basically anywhere else you would want to go while you are there.

It felt like the right kind of place to land after a long flight. Quiet, well designed, and easy.

Some of the most memorable meals I had in Greece. Although honestly, a few of my favorites were the ones cooked at the farm.

Salis (Chania) Incredible seafood and wine in the old town.

Evogonia - Simple, very good food just outside the crowds of Chania. Nothing flashy. Just solid.

Matzena Kuzina del Sol - Oaxaca style Mexican food with not a single tourist in sight. Slightly outside the city center of Chania and completely unexpected in the best way.

Stratis (Loutro) - Definitely the best restaurant in the area. Set back from the main road, overlooking the ocean, with great souvlaki.

Biolea (Astrikas) - An olive oil producer where you can tour the facility and then have one of the best lunches of the trip overlooking the cliffs of Crete.

Outdoor movie theaters are a staple in Greece and can be found all over. We went to one in Athens it overlooked the Acropolis. It was magical.

Flying to Crete was extremely easy. I have heard enough horror stories about long, intense ferry rides that if you are prone to seasickness, I would skip it.

I have also been to Santorini and Mykonos and, personally, I would pass. They are beautiful but very touristy, commercial, and expensive. I think other islands offer more.

The one exception is a sunset boat with Panos and Alex in Santorini. Panos is actually from the island, which immediately sets him apart. He was the only person we met there who was. His 90 year old neighbor prepares the meal ahead of time. It is simple and delicious.

Notably, Panos is very into EDM, which on paper, club music on a tranquil boat, would normally be a hard no for me. But the whole experience is strange and wonderful. Long stretches in the water, interesting local history. The most dramatic sunset you will ever see. It was truly unforgettable.

Thank you so much for reading. It genuinely helps when you subscribe, like, or share this letter. And if there are topics you would like me to cover, I would love to hear your thoughts here.

I will be back next time with an interview I am very excited to share.

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November 4, 2025

I’m writing this from my bed in Queens, my preferred office even before toe surgery turned me into a temporary Jeff Jeffries from Rear Window. These days I sit by the window, watching the world pass and growing mildly suspicious of the woman who lugs a large purple duffel bag out every morning. She’s probably just going to the gym. Probably.