I’ve been to 27 Greek islands. There are 3 I’d return to in a heartbeat — and 2 I’d leave off my itinerary next time.

Symi is easily one of my favorite Greek Islands because it feels more lowkey than some of the more famous spots like Mykonos or Santorini.

For stunning views overlooking the bay, I recommend hiking up the Kali Strata’s hundreds of stairs. I also suggest joining a full-day boat trip with Poseidon cruises or hopping on a water taxi to visit one of the nearby beaches.

In my opinion, Milos has some of the most stunning beaches in Greece.

One of the most well-known spots is Sarakiniko Beach, which is famous for its lunar landscape — a series of smooth, white, volcanic rock formations that resemble the surface of the moon.

I recommend renting a car to explore Milos by land, but don’t skip a boat trip around the island as well — some of the best swim spots are only accessible from the water.

Several tiny fishing villages also add a unique factor to this island. In some of them, traditional boathouses have been renovated into cozy, waterfront villas and hotels. I recommend booking one for a truly immersive experience.

Skiathos is a charming island filled with great local shops and some of the best Greek food I’ve had during my travels. It also has a lively nightlife scene, with plenty of bars and clubs that stay open late.

During the day, you can hop on a boat or a bus to explore the many beaches in the area. In the evening, I recommend taking advantage of lengthy happy hours at the many cocktail bars offering sunset views.

If you love “Mamma Mia,” Open Air Cinema hosts special screenings of the movie — after all, parts of it were filmed on the island. I recommend grabbing tickets early because they sell out quickly.

Mykonos is known for its upscale beach clubs, lively bars, and cute old town. It delivers on all of these fronts, but in my opinion, it does so at a cost.

It’s known as one of the pricier Greek islands to visit, and although I enjoyed my time there, it’s not somewhere I feel the need to go back to.

Instead, I recommend taking a multi-day Greek Island sailing trip that stops in Mykonos. That way, you can see it and experience some of the hype, but you don’t have to stay for more than one night.

Going into my trip, I knew that Kos was more touristy than other islands I’ve visited. However, although it’s beautiful, I ultimately found it to be underwhelming.

Instead of unique gifts, I found that most of the old town was filled with typical tourist shops. The beaches were OK, but also seemed less picturesque compared to those I’ve visited on other islands.

Since Kos has an international airport, I think it’s best suited as a starting point for reaching other destinations.

This story was originally published on September 19, 2024, and most recently updated on February 23, 2026.