Planning Back to the Greek Islands

When we got married in Santorini, Greece 4 years ago, I told my husband that we have to come back again for our 10 year anniversary……. Over the past 4 years, we have been to many different places and nowhere (so far) can replace Santorini as my #1 favorite place on Earth! Well that said, I tried to tell myself okay let’s shorten the 10 years to 5 years! I guess I couldn’t even wait for another year so I convinced my husband that we will go back this year hahahaha!!!

Our wedding photo in Santorini 4 years ago!

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Our wedding in Santorini, Greece

I was actually checking the web for flight prices to decide where I want to go next back in September and typed in Athens, Greece for the sake of tracking its prices and then it showed up as $723! That price was unbelievably low and my heart started to pump! I immediately showed my husband and surprisingly he said let’s book it! That was how we are going back to Greece this year! Right after I booked the ticket, I started to plan for our trip in May…..8 months in advanced LOL! Crazy right? But I found out I was not early at all, there are people who booked one year in advanced! Also, there are a lot of benefits when booking well in advanced and that’s the reason I am posting this to share with you all!

Which Islands?

There are so many beautiful Greek Islands to choose from but I only have enough vacation days for 2 weeks and we have to stay in Santorini for at least 6 days (that’s how much we love Santorini) so we really have a little over a week of time on other islands. We decided the rest of the time to split in two other islands, one is Mykonos, that was an easy choice since it’s probably the 2nd most known Greek Islands. The third one we had a little difficulty so took me some research to decide. I ended up with Rhodes because it has a different feel than Mykonos and Santorini and easily do a day trip to the nearby island – Symi. Final routing is Rhodes -> Mykonos -> Santorini -> Athens; we are saving the best: Santorini for last 🙂

Island Hopping Transportation

For other people, taking the ferry is the most convenient and economical option however for me it’s a different story because I easily get seasick! I rather pay extra to fly rather than getting sick during my precious vacation. Fortunately I found out that booking early can result in significant saving on airfare, sometimes the same as taking the ferry!  I checked Aegean Airlines and Olympic Air every single day! Since I was way too early, sometimes not all the available flights showed up yet but as soon as it shows up, it’s usually the cheapest! For example, I booked the Santorini to Athens flight, the “Go Light” saver fare for 24 euros (included taxes and fees) plus baggage fee of 15 euros! The same exact flight priced at 117 euros two months prior to departure date! We get used to the 3 months prior rule on airfare that this is strictly not the case for Aegean Airlines. One caution about booking well in advanced is Aegean Airlines tend to change their flight schedule so make sure you double check again weeks before departure. I found out one of my flight was moved ahead 2 hours earlier which conflicted with my other flight so I contacted Aegean Airlines and they re-booked us for free! Their customer service is pretty good, I always get a reply within 3 business days.


This is probably the topic I spent the most time on and probably have the most headache with! It’s not too bad for Rhodes and Mykonos but for Santorini…..too many choices! First, which area to stay? We decided not to stay in Fira because it’ll be probably too busy and noisy. We stayed at Firostefani last time and enjoyed it but wanted to try out something new. Finally, we decided to split our 6 days in two villages: 3 in Oia and 3 in Imerovigli to experience a different atmosphere. Oia is a must as it’s the most beautiful village in Santorini, in my opinion. Imerovigli because it is the only place in Santorini to have the view of both the caldera and the sunset! Alright narrowed down to two villages at least that’s a good start!

Oia: I wanted to stay in close to where all the shops are and the post card location of the white washed and blue dome churches. We both don’t prefer the classic wooden furniture and more toward modern furnishing. We would love to have our private balcony. I have looked at all the available hotels in, I like this website because it gives photos of the each room category. My top choices are: Marizan Caves & Villas (for sunset view), Armeni Village, Chroma Suites, Onar Villas, and Oia Collection (modern furnishing and spacious). Those are within my budget of less than 300 euros per night (yes, Oia is very expensive)! I saw photos of the Grande Suite of Oia Collection and absolutely love it and I booked the non-refundable rate to make it less than 300 euros per night. I’ll let you know how it is!

Imerovigli: Another expensive location, we wanted a room with outdoor jacuzzi and right in front of Skaro’s Rock to get the unobstructed view of the caldera and sunset. I was surprised that hotels in Imerovigli cost more than in Oia on average! My top choices were Artemis Villas, Above Blue Suites, Aliko Luxury Suite, Astra Suites, and Vallais Villa. Artemis is not listed in nor other 3rd party internet site, it can be only booked directly with the hotel. I contacted Artemis on Oct and they only have the Honeymoon Suite left!!! Oh boy, people actually booked one year in advanced! I reserved it and hoping for another room to be available since I don’t really like the yellowish style of the Honeymoon Suite. So far, I have no luck 🙁  Vallais Villa was fully booked as well! However, I was lucky one day a studio room was available and I reserved it immediately; I have not seen another available room since then. If you are confirmed to go to Santorini, please don’t wait to reserve for hotel rooms, top rated affordable boutique hotels sold out fast!



  1. Rhodes – exploring the Old Town of Rhodes
  2. Rhodes – day trip to Symi
  3. Rhodes – exploring Lindos and Acropolis of Lindos
  4. Rhodes – Mykonos – exploring Mykonos town
  5. Mykonos – Half day trip to Delos, exploring Mykonos town
  6. Mykonos – Take bus to visit some beaches
  7. Mykonos – Santorini – exploring Oia
  8. Santorini – enjoy our day in Oia, sunset dinner at Castro Restaurant
  9. Santorini – half day volcano tour
  10. Santorini – exploring Imerovigli
  11. Santorini – picking up our rental car and drive to Akrotiri Historical Site
  12. Santorini – with rental car drive around the island Perisa & Kamari
  13. Santorini – Athens – visit Benaki Museum – free on Thursday, explore Plaka
  14. Athens – visit Acropolis, Ancient Agora, Temple of Zeus
  15. Athens – Boston

Count down begins!!! 

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