There are 227 inhabited Greek Islands and we share our adventures to three of them in this article! We Greek Island hopped from Crete to Paros to Milos to Santorini and back to Crete.

If you are interested in learning more about the Greek Islands of Paros, Milos, and Santorini come aboard our virtual ferry and check out this article on what we loved and did at each.

As I mentioned above there are 227 islands in Greece that are inhabited. It can definitely feel overwhelming in trying to figure out which ones and for how long you would be able to visit.

There are super popular and touristy ones (hello Mikonos and Santorini) and ones that none of us have ever heard of who don’t live in them (including people from Athens and Thessaloniki.)

We made the decision that we would ferry hop once we arrived in Greece and that our only flights would be on and off the island of Crete. From there it felt that the best way to get the most of out of our travels would be to visit islands that were at least somewhat closer to Crete. (These are the Cyclades. There are groups of islands West of the mainland and closer to Turkey for instance as well.)

The final decision we made was we wouldn’t go to an island if we couldn’t spend at least three nights.

With that our trip to these Greek Islands went as followed:

Paros (Four Nights) Ferry from Crete.

Milos (Three Nights) Ferry from Paros.

Santorini (Three Nights) Ferry from Milos.

We used Ferryhopper and I would highly recommend this resource (we had one ferry cancelled and had to reschedule a few dates and everything was completely refundable more than a day in advance.)

I also spent 12 days in Crete and you can read more about that adventure HERE!
Below I share our highlights from each island, while I loved each of these islands your options are truly limitless. The only item I would recommend is if you are fortunate enough to be able to go on a ferry hopping adventure in the Greek Islands to make it so!

Paros Greece Adventure Highlights:

1. Paros Cooking Lessons. We walked from our hotel near the port to Flora’s family farm where we spent the morning cooking with her, watching her dog hide a bone from her other dog, and learning what really went in a Greek Zucchini Fritter! It was a wonderful experience and if you like to cook this is for you!

2. Argonauta Hotel. There are TONS of options on where to stay in Paros. We chose the port town of Parikia because we could walk from the ferry and the excellent bus system in Paros made it EASY to get around the island without renting a car.

3. Byzantine Route. This old cobbled stone road starts or ends in the small mountain village of Lefkes (the bus will drop you 10 minutes from the trailhead) and walking this historic trail that dates back to 1,000 AD was a wonderful choice for a hike! We used All Trails to find the trailhead and hiked to the end and came back up. Bring your sunscreen!

4. Moriatis Winery. Detailed and interesting vineyard tour to learn about the family history of this vineyard, the climate of Paros, and the impact it has on crops, especially grapes. Wines are also great and staff was wonderful! There were some little used beaches in the town of Naousa and Paros Park and the bus are nearby as well.

5. Mira Restaurant. All food is good in Greece. But this was one of our favorites in Paros!

Milos Greece Adventure Highlights:

1. Sea Kayak Milos. This was probably the best kayaking day I have ever had! (Slightly inching out almost getting flipped by a whale in Glacier Bay in Alaska.) It was a 20k day that included hard paddling, hidden caves, private beaches, sunshine, and excellent company. If you found yourself with only one day on Milos I would recommend going with Rod! (Rod and his wife Petrinela also run a guesthouse in the village she grew up in that the other kayakers raved about.) He also has people come from all over Europe just to go on these custom trips he creates!

2. Hotel Eleni. If my Grandma’s soul was given another human life on Earth I am pretty sure she is running a traditional Greek hotel on Milos and her name is Eleni. What a sweet sweet woman and family! We could walk to our ferries and to the buses and the beach is across the street. If you are able to go sailing with her son we would recommend it as well! We will never forget Eleni’s love and warm energy.

3. Paleochori Beach. We took the bus to this epic beach that was a beautiful way to spend the day. There were fascinating erosion formations of the rock layers and mining that reminded me of Artist’s Palette in Death Valley National Park. There is a traditional taverna, a more upscale “Mikonos esque” beach club, and a few other mid range restaurants for you and the cats to enjoy a meal after sand and sun!

4. Milos Mining Museum. When I went sea kayaking Jill went to the Adamantas Beach and to the Mining Museum which she said was very interesting, she recommends the audio tour!

Santorini Greece Adventure Highlights:

I must start by saying I was hesitant to come here. It seemed very touristy and packed with cruise ships. It WAS packed with cruise ships but we found an island that still has hidden gems, local experiences, and a way to still feel off the beaten path. I was thoroughly surprised by how much I LOVED Santorini and the reason it gets so much tourism is the fact that it is simply STUNNING. It was one of the most beautiful places I have ever been.

1. The Grand View Hotel. By staying here in the quiet town of Megalochori we were able to avoid the super wild crowds and shopping sprees in Fira and Oia. The Grand View team was wonderful (they loved me practicing my bad Greek with them), it had the best view (the caldera cliffs into the Aegean Sea) of any lodging I have ever had, and the bus stop/wineries/restaurants were all a short walk away.

2. Fira to Oia Hike. A legendary hike that starts smack dab in an outdoor shopping mall, weaves you through volcanic cliffs and ashes, and finishes at the most famous picture in all of the Greek Islands (the village of Oia.) A truly moderate 10k ish hike, I would highly recommend anyone who likes to trek to give it a whirl. Following the All Trails app to stay on trek through the towns is VERY HELPFUL!

3. Sailing and Swimming Tour. We arranged ours directly with Sofia and the team at Grand View and this small group Sailing and Catamaran Tour with Jimmy and his team was amazing! The caldera cliffs, swimming in the hot springs, homemade greek food on a beautiful day, and yes Raki if you want it. I definitely recommend this splurge!

4. Raki. Wow. This was a delightful culinary experience! There are a smattering of wineries and other lovely tavernas that you can enjoy as well when walking through this village.

5. Akrotiri. For the geologists, archaeologists, and those that haven’t been to a place like Pompeii Italy this is an excellent half day experience.

The Island Hopping Route we chose in Greece was lovely, and coming to the conclusion that you will never experience it all can be a calming state as an adventurer.

Each island has its charm and unique energy in Greece but the odds of going to all 227 of them (unless you are a ferry operator) are bleak.

We did four islands over 3.5 weeks and could have probably done two or three islands instead. If we had done five it would have felt way too rushed.

We hope this gives you some fun ideas for your adventures in Greece or a way to learn more about some of the most beautiful and special islands on Earth!

Comment below with your favorite Greece stories or any questions on this article and thanks for reading!

Because Adventure Feeds the Soul,
Mike