There are some destinations that are amazing to visit once, and others that keep calling you back. For me, Greece falls firmly into the second category. Even after multiple visits, I find myself searching for award flights and planning another trip almost every year.

Part of the magic is how different each Greek island feels. One trip can be spent wandering the whitewashed streets of Santorini, while the next can be spent relaxing on the beaches of Crete or exploring the charm of smaller islands.  Every island offers a different experience, which makes it easy to return without feeling like you’re repeating the same vacation. Previous trips to Greece included visiting the following islands:

• Santorini: Every trip so far, I’ve traveled with new people, and how can they not see Oia?? Every time I go there,  I am still awed by the many beautiful photo moments.
• Mykonos
• Paros
• Crete
• Athens, of course

This year, two of my daughters and two of my granddaughters headed there once again. We checked out two new islands, though: Ios and Milos. Here’s how it went.

 

Flights

We actually started our trip in London for a few days, and I went to the Harry Styles concert with some of my family. I flew from Denver to LHR on AA using AAdvantage miles.  It was 112.5K miles plus $5.60 for a business-class flight. I switched my original flight for one that cost more in miles but had timing that was much better for me.

 

Santorini

We stayed at this Airbnb in Santorini. It fit five people comfortably, it had incredible views, and the host was totally responsive. It was also well decorated and had a plunge pool and two seating areas. My only complaint was all the stairs, but, hey! That is Santorini (and Oia in particular)!

In Oia, we did all the typical Oia things:

• Wandering through the streets and stores
• This Catamaran tour
• Eating good food. We love Skiza Cafe, but found Oia Gefsis this time and fell in love! It’s more spendy, but we loved it so much that we had two dinners there!
• Watching the sunset!

If you stay with a smaller group, there are hotels you can stay at, but we wanted to stay together, so we chose an Airbnb.

 

 

 

 

 

  

Ios

I chose the island of Ios simply so we could use Hyatt points for a stay at a Mr. and Mrs. Smith hotel:  The Liostasi Hotel. You can read my review of that hotel next week. We stayed in a suite for 48K points per night and thoroughly enjoyed it.

Most of our time was spent lying by the pool, reading, and looking out at the Aegean Sea, but we did go to Diaseli Estate for one of my favorite cooking experiences ever! Helen showed us around her family’s cheese factory and helped us make incredible spanakopita, falafel, and tzatziki. It also included a cheese tasting and wine for wine tasters. They packaged up leftovers that we could eat for the next two meals. It was a core experience for us on our family trip to Greece.

 

 

 

 

Milos

We used Ferryhopper to book a ferry from Ios to Milos. It was a nearly four-hour ride that stopped at three islands.  I actually enjoyed the pleasant, air-conditioned ferry.

I chose Milos as our third stop because a family member had liked it and told us about it, and I wanted to try a new island. We stayed at this Airbnb for three nights. Renting a car is the best way to explore Milos since many of the island’s best spots are spread out. We rented a car at the port and drove about 20 minutes to the Airbnb, which was about a 20-minute drive to Pollonia, a cute fishing village.

We walked around Pollonia in the evening and ate at Yalos, which was delicious, and followed up our meal gelato. Perfect evening. Other activities:

• Went to the port (Adamantas) and shopped, and rented loungers near the beach
• Went to the cute village of Klima
• Climbed to the top of the castle in Plaka for sunset views; ate in Plaka
• Went to the Catacombs (a waste of a fee)
• Went to the stunning Sarakiniko Beach
• Rented lounges at Firiplaka Beach (go early to the beach to beat the crowds!)

There are also hotels in Milos you can choose from across various brands or through a portal.

 

 

 

 

 

Flights Back to London

We flew Aegean Airlines to Athens and then British Airways back to London. I then met my husband there, and the eight of us headed to Norway. To be continued….

 

Bottom Line

 I am often asked what my favorite place to travel to is. After visiting these three islands and enjoying the great food in Greece, I have to say Greece is up there. It is a place I return to again and again. Now, which island should I go to next?

 

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