I could go to two places every single year—Italy and Greece. I love these two countries and want to explore them more or return to cities that I love. This summer, I have trips to both of them. First, I’m back to Greece on points and miles.

I have a friend who has had a trip to Greece as a dream destination since I got her into points and miles a few years ago, and this was the year for making her dream come true. She worried I wouldn’t want to return to Greece since I’d been there twice. I quickly told her that I was all-in because there are always more islands to discover!

 

Flights to Greece

My flights to Greece started with a paid positioning flight to JFK from Denver on JetBlue. Usually, I fly United to keep my elite status with them, but they don’t have a flight to JFK, so I paid about $300 to fly JetBlue. Before my flight, I visited the Capital One Lounge in Denver. I met a reader while there. (That is always so fun, and she had just returned from Hawaii using points and miles for a family of nine – go, Alicia)! My flight was delayed for about an hour, and I worried it would be canceled – this was a great reminder of why I prefer to stay the night before my award flight begins – much less stress!

My overnight stay was at the Hyatt Regency JFK at Resorts World, where I had previously stayed. I used a free night certificate and enjoyed a free stay. Globalist status meant that I could use the Club Lounge for breakfast and get late checkout the next day.

 

 

International Flight to Greece

This is where it got interesting. I had initially booked one of Jess’s favorite flights—Houston to Manchester in Singapore Airlines business class—and then onto Santorini with Austrian Airlines. A week before the trip, my Austrian Airlines flight was canceled! We would miss a day in Santorini if we kept the Singapore flight because there were no flights that day to Santorini.

I started looking on search engines for another flight and found a booking on United for a Brussels Airlines flight from JFK to Brussels, Athens, and then on to Santorini for 88K United miles. So I booked that and canceled the Singapore Airlines flight, and the miles were quickly redeposited in my account. Oh, the beauty of points and miles!

 

Brussels Airlines Flight to Santorini, Greece

While this was on what I felt was an older airplane, the service was great, and the seats were quite comfortable. You can read my complete review of this flight here.

 

 

Lodging in Santorini

Originally, I used Hyatt points to book Canaves Oia Suites, but it was 135K points for 3 nights, and I didn’t want to spend that much as I have a lot of other trips coming up. I’ve previously stayed in Airbnb and decided to check out that option. For $732, we could stay 3 nights, and the place had two bedrooms, had great options, and was a fifteen-minute walk to Oia from the cute village of Finikià.

Our Casa Itaca Luxury Winery Cave apartment was perfect. Daniele was the perfect host and arranged transportation to and from the airport for us. The driver charged us $45 for the ride from JTR airport to our Airbnb. Daniele met us at the Finikià main parking lot and carried our bags for us. It was a 5-minute walk to the house. Unfortunately, my friend broke her ankle last winter and is still recovering. I think she overestimated her ability to walk on cobblestone and steep streets, so it was a slow walk for her.

 

 

Daniele was so accommodating, though, and provided water and treats on the Airbnb. The air conditioner had gone out the day before (what luck), but we slept comfortably with fans.

 

 

Thoughts on Our Airbnb and Location

I have only stayed at Airbnbs in Santorini, and this was my favorite one. The two bedrooms were great and spacious, and the decor is adorable! Daniele could not have been a better host. A mini-market is a short walk from the house, and several restaurants are nearby.

 

Activities in Santorini

Because our air conditioning didn’t work, we waited to walk to Oia until the evening when it cooled down. We went at about 5:00 to explore the magnificence of Oia and have dinner at Skiza Cafe, one of my favorite spots to eat. 

 

 

 

 

We booked a catamaran cruise with Sunset Oia on our second full day. They picked us up at the village parking lot at 8:55. There were only 14 people on the cruise, and it was relaxing and fun. The pasta, chicken, shrimp, Greek salad, and pita were delicious. They were followed by yogurt and cherries, and it was a dessert I could have had repeatedly.

 

 

 

 

Honestly, there is not a ton to do in Oia, but I love it regardless. It is quintessential Greece to me, and I never tire of wandering the streets and shops.

 

Visiting Crete with Points

The island of Crete was an island that I had never been to. We paid cash to fly Aegean Airlines there. It only took a flight back to Athens (30 minutes) and a flight to Crete to arrive at the Chania airport. We took a taxi to our hotel – Domes Zeen Chania, a Luxury Collection Resort, by Marriott. This hotel was 82K Marriott Bonvoy points/night. I used three 85k Bonvoy free annual night certificates to book this hotel. I earned these from the Marriott Bonvoy Brilliant® American Express® Card, the Ritz Carlton Card (only available as a product change now), and from spending $15,000 on my Marriott Bonvoy Brilliant card during a challenge they had earlier this year.  

You can read my review of the Domes Zeen Chania here. It was a really great stay, and we loved the town of Chania.

 

Activities in Chania

We were supposed to take a walking tour of Chania.  However, the hotel goofed on our taxi arrival and we missed it. We went to the Old Town instead, and it did not disappoint. It’s called the Venetian Harbor for a reason – I felt transported to Italy. There were cute alleyways to explore, wonderful restaurants, a lighthouse, and a Mosque—it was wonderful.

 

 

 

I also took the opportunity to participate in one of my favorite activities—a massage at the Jungle Spa. This was in an outdoor area, and it was blissful. At one point, I was dreaming.

Because my friend had mobility issues with her ankles, we didn’t do other tours, but these are some that looked interesting on Viator:

• Elafonisi Beach Tour
• Samaria Gorge Hiking
• Rethymno Quad Safari
• Palace of Knossos

 

Adding on Another Destination

We booked transportation from Chania to Heraklion Airport for a flight to Vienna, Austria. I really wanted to stay at the Park Hyatt in Vienna and convinced my friend, Deanna to do this. We flew on Austrian Airlines to Vienna for about $250 cash. You can read my review of the Park Hyatt Vienna and our short time in Vienna, Austria (including our flight home) here.

 

Bottom Line

Going back to Greece on points and miles was a dream. This was my third trip to Santorini, and I kept saying that I should quit going there when I travel to Greece, but I keep returning with people who haven’t been to Greece before. Can you even go to Greece without experiencing Oia? Not according to me! Maybe someday I’ll be able to bypass it, as there are other islands I want to check out (Naxos and Milos will probably be next)! What is your favorite Greek Island, and why?

 

Related Posts

• How to Go on a Greece Girl’s Trip and Not Go Broke-including a Luxury Flight
• Greece on Points and Miles
• Friday Family Vacation to Greece
• Domes Zeen Chania Resort Review
• Brussels Airline Review