Spent a week in Greece for our 21st anniversary, 80% of our time in Santorini, 20% in Athens. One word to describe Santorini, UNREAL! We arrived in Santorini late on a Monday night and I was bummed about missing the sunset, but very quickly got over it because it was just so stunning at night! After checking into our hotel, we took a walk through the town and up to the Oia Castle, super close to where we stayed.
We stayed at the Oia Mare Villas https://oiamarevillas.business.site/ I read many reviews on Expedia and TripAdvisor as I am particular about cleanliness and location. It was the perfect pick I must say! I highly recommend! This isn’t a “you will hardly be in your room” it doesn’t matter where you stay kind of trip. One of the nice things about Santorini is relaxing at your hotel, enjoying the views from your room. We spent mornings and nights out on the balcony just staring out! Loving where you stay plays a huge factor in the overall experience, in my opinion anyway. I saw rooms ranging from $100-$600+, we were right in the middle at $348/night in euros ($400 in dollars) and so worth it! Oia Mare is clean, beautiful, a great location with a very friendly, helpful staff. Quick to reply over email as we prepared for our trip, they set up our transfer from the airport to the hotel with their porter that carried our luggage through the town to our room. Cars/buses drop you off at the main road near the Post Office since the streets are narrow and no cars allowed inside. The location is a short walk from the main road, down the caldera so feels private, but also not too far from all the shops and restaurants. Super easy check in, welcomed with a glass of wine. Anxious to wake up early the next morning to catch the sunrise up at the Oia Castle. Absolutely beautiful!
First reaction to this maze of a place is we’ll never be able to find our own way to and from our hotel, but actually the town is quite small and after a few times, it is surprisingly pretty easy to figure out. It is lots of steps, so no problem getting your daily workout in. We had a nice breakfast by the pool two of the four mornings we were there which was included with our stay. And being able to watch the sunset from our balcony was killer!
Ammoudi Bay! A must do when in Santorini! One of the reasons I chose to stay on this side of the Caldera was the walkway down to Ammoudi Bay, 300 steps down! A relaxing 3 hr. dinner right by the water. Do not rush your dinner! Jay tried to order dessert before he was even done with his meal and the gal looked surprised and told us to enjoy our meal. We got this reaction a few times. So when it Greece, take your time, savor and enjoy the long meals and slower pace of life! Do order the fish! It was really good which was the case everywhere; fresh, tasty and they debone it for you. It really was a dream to watch the sunset from here. All the restaurants along the bay seem similar. We chose Dimitris which was Jay’s favorite meal of the trip. The owner was lovely! She taught me how to eat the lobster legs. I regret not trying the Octopus, but for sure next time! https://www.dimitris-ammoudi-restaurant.com/
We weren’t planning on taking the donkeys up back to our hotel, but after a few steps going uphill, we caved and did it. It was a pretty ride up seeing all the city lights and ended up being one of the funniest moments. Jay’s donkey was a little all over the place 🙂
Tours – we did two tours through Viator, both were great! The first was the Santorini Sunset Luxury Catamaran with BBQ, drinks and transfer. It was a nice boat with a small group of roughly 16, so lots of space to get your own comfy spot to relax. It was lovely to lay in the warm sun for hours. The water was cold but felt good. The boat stopped at Red Beach, White Beach and a small volcanic island and ended at Ammoudi bay. Sunset was beautiful on one side with a view of Oia on the other, and seeing the Ammoudi lights at night was amazing.
The next day we did an ATV Quad Santorini Experience Tour which I loved. It was a great way to see other parts of the island and love when the tour guides share some history! We drove by the black sand beach which I definitely want to spend a day there next time. Then went to Emporio which is the town most of the population lives. We visited an old castle, walked through the super narrow streets of old villages which were built that way for protection from the wind and pirates! It was really cool to go up to see the view of all three islands that were once one before the volcano erupted. We ended with a drive through the most authentic village Megalochori where we stopped for a coffee and got to chat with other couple on the tour which was really nice!
We started off anniversary day with a fun photo shoot with Flying Dress Photo! Super easy one hour shoot with Dimitris. He literally took us on the edges of Santorini!
Then two of our favorites, Starbucks and affogato. We spent most of the afternoon by the pool/deck area of our hotel. The perfect spot to relax and take a nap!
Then Cavo Tagoo! This place was on my bucket list the whole year and was incredible! https://www.cavotagoo.com/santorini/
Welcomed with Champagne! Then a cart of the fresh catch of the day came by which after prepared was so soft and buttery, the best! Jay still votes Dimitris for best fish, I vote Cavo Tagoo, so must revisit both! Amberjack which is my new favorite fish was also amazing! Shrimp and Langoustines also very good, but yet again the fish was the star of the day! The most delicious amazing dinner! A dark chocolate dessert and more champagne! Definitely still on the bucket list for another return!
Just mesmerizing! I would have liked to stay here all night, but we had a flight to Athens to catch.
Restaurants – other restaurants worth mentioning. There are so many along the streets, but I think we picked some winners! Thalami for breakfast has an amazing view and a simple yet very yummy breakfast. We had the bread basket, Greek yogurt with fruit & honey, and a dessert pastry. We also got the salmon toast but I’d pass on that one next time.
Terpsi – another ahhhmazing view for breakfast! Morning mimosa and since we heard it was Fall already had some pancakes with pears, walnuts and cinnamon.
218 cafe – was just so relaxing, the view with some Rose, could have stayed there all day! The food was fine, it was more about the view here and the drinks. They had a good affogato and a cookie. Worth a stop for a drink and dessert. We love the orange pie here in Santorini!
Niko’s – finally a Gyro! so cheap and super yummy! Fries are in the Gyro!
Kastro – where we had our first meal, had a good burrata salad, fish, seafood stew and where we got our first taste of Orange Pie!
Meteor Cafe – good for a night cap because they are open late and have good martinis. Vegas drink prices though!
Highlights – if we had one more day in Santorini, we would watch the sunrise, walk the beautiful streets, spend hours at Ammoudi Bay and party at Cavo Tagoo! If we had two we’d spend a day at Perissa beach and check out the other towns like Fira.
- Oia – definitely recommend staying here! We got a small feel for the other towns which are similar but feel a bit more spread out. I like the convenience of being right in the middle of a smaller town. I’m sure the other towns are just as nice, and can’t really go wrong with anywhere in Santorini, but if we came back we would still stay in Oia for the beauty and convenience. The streets are just so lovely to walk along!
- Ammoudi Bay – the water right at your feed, watching the sunset, a dream!
- Cavo Tagoo – the view, service, music and food were all excellent. The best meal of the trip! Would love to go back and get a day bed and hang out there for a full day!
Getting Around
- Transfers to and from the airport and hotel coordinated through the hotel. The hotel also arranged our taxi from Oia to Imerovigli
- Most tours do a pick up from the Main Road by the Post Office
- We did take the bus from Imerovigli to Oia and it wasn’t bad, a short 15-20 min ride for like $2 euros each. Pretty easy to ask around on how to use the bus or have your hotel help you get a taxi
- Did hear it was easy to rent a car and drive here, just make sure you get your international driver’s license online
Links to tours
Catamaran Tour
ATV Tour – make sure to get an international drivers license online
Booking – I am a fan of using Delta Vacations, our sixth time to use them and have always been pleased. I am not an expert world traveler so I like the security in knowing that there will be someone available 24/7 to help with anything if needed (I have gone outside of Delta when traveling with friends who travel). I book the roundtrip flights at the start and end and at least 3 nights hotel with Delta since that is the requirement to book a package and then I book any hotels or flights in between myself. Delta didn’t have hotels in Santorini, so I booked Oia Mare Villas through Expedia and our roundtrip flights from Athens to Santorini through Ryanair.
Itinerary – there were a few changes to the original itinerary mainly on places to eat. I was happy to change things as we wanted. Enjoy just walking around and picking what calls you!
Monday 9/20 Arrive in Santorini at 5:40pm
- Check in/Settle at Hotel/Grab dinner around hotel
- we stopped at the first restaurant we saw, Kastro
- walked around town, stopped for a nightcap at Meteor Cafe
Tuesday 9/21
- Breakfast at hotel
- Watched the Sunrise at Oia Castle – short walk from hotel
- Walk around shops and Explore-Go to Poniros Jewelry Shop and make a right to see the view of the blue dome church, the entrance is by the other jewelry shop Alexandros – left first day there open to leisurely check things out
- Dinner at Dimitris at Ammoudi Bay – 5pm reservation
Wednesday 9/22
- Breakfast around hotel – we walked in at Thalami Restaurant
- Santorini Sunset Luxury Sailing Catamaran Cruise with BBQ, drinks, transfer; Pick up outside Atlantis Oia Drive Centre (opposite the Post Office of Oia) at 12:50pm
- Niko’s for dinner – walk up Gyro spot!
Thursday 9/23
- Breakfast around hotel – we walked in to Terpsi
- ATV Tour pick up at 8:20am for a 10:00am-1:30pm tour
- We originally were going to Taxi/Bus to Thira for the rest of the day to explore with a dinner reservation at To Briki, but decided to cancel and just hang out in Oia since there are so many similar spots and thought easier to stay close. We went to 218 cafe which was super relaxing! I would like to try To Briki next time! https://www.tobriki.com/
Friday 9/24
- Check out, leave bags at hotel, our flight to Athens wasn’t until 11pm so we had the whole day to spend our Anniversary in Santorini
- Anniversary Photos in Imerovigli with flyingdressphoto
- Rest at Oia Mare – we were going to hang out in Imerovigli for the day but decided to go back and spend the afternoon at our hotel back at Oia Mare. They held our luggage and encouraged us to use all the amenities. They had a nice bathroom and shower for us to use after a day out in the sun. They booked our taxi to Cavo Tagoo for dinner but kept our luggage and brought it with them later when they picked us up at Cavo Tagoo on the way to the airport. Super helpful and convenient!
- Dinner at Cavo Tagoo Santorini – 6-8pm reservation
- Fly to Athens 10:55pm
Saturday 9/25
- Day in Plaka – started in Monastiraki Square and walked to Syntagma Square. A day of walking around, eating, shopping. These two blogs were helpful for me
- https://www.earthtrekkers.com/2-days-in-athens-itinerary/
- https://www.introducingathens.com/two-days-in-athens
- Dinner at MS Roof Garden – such a lucky pick! Amazing view of the Acropolis and Monastiraki Square.
Sunday 9/26
- Acropolis Tour at 11:30am-1:00pm
- Grabbed Lunch at one of the closeby restaurants that had a view of the Acropolis, Makriyianni’s for good pizza and pasta
- Original Dinner plans were at Cinque Wine & Deli Bar in the Psyrri Neighborhood, but I scheduled it for the wrong day! Bummer because it looked like a fun spot to wine taste. We ended up picking a spot that wasn’t that great. Can’t pick all the good ones I guess! Pass on Voliotiko Tsipouradiko Psiri if you see it. Looks like a cute garden restaurant but eh not worth it, pick a better one.
Monday 9/27 – Fly home at 12:15pm
I think two days in Athens was just right. A day to walk around and a day to see some history. There are tons of cute streets and alleyways of restaurants to choose from. I really don’t know how you pick. It does feel like a normal downtown city area so has its’ sketch feel here and there depending on time of day and what alleyway you are on. Stay where the people are, which there are tons out so overall seems like a pretty lively day and nightlife. We stayed at the Crowne Plaza which was fine but nothing to be excited about. I recommend staying somewhere nicer and a little closer to the main squares.
After a day of walking around, took a nice long nap then back out for dinner and really stepped into a gem, must have been the flowers that lured us in. View of the Acropolis and food was delicious! Best meal in Athens! https://www.msroofgarden.gr/
Acropolis Day! Did an hour and half tour through Viator, which I think is just the right amount of time, not too long. It really is quite amazing to see places that were here before Jesus’s time. Aftewards, had a refreshing lunch at the row of restaurants outside of the Acropolis; Fresh juices, pizza and pasta at Makriyianni’s.
An amazing week! I hope the details of our week were helpful. Per the gals at our hotel in Santorini, they did say September and May were the best times to visit, still warm but not super hot and crowded like the Summer months. We were also there at unique time where you don’t have the crowds coming off the cruise ships. Either way, if you get out early like by 8am to walk around you will get to walk the streets with less crowds or late at night around 10-11pm. Most shops are open til midnight.
Travel Guidelines during this time September 2021. I always checked the Greece embassy website for the latest updates. https://gr.usembassy.gov/covid-19-information/
- Needed only vaccine card and Passenger Locator Form to enter Greece. The PL form was super easy to fill out online and then you get an email with your QR Code. We did get a Covid Test the morning that we left just in case, but we didn’t end up using it anywhere
- To return to the US, you do need a Negative Covid PCR Test taken within 3 days of travel. The hotel in Athens scheduled one for us at a clinic that was just down the street from the hotel. Our test was at 8:30am and we got email results in the afternoon. Thank goodness the process was pretty easy. They ask for the results at the gate and again at the boarding counter if you checked in online.
- It is a risk to come in the case you test positive, so I did bring my work computer just in case. At least the Greece government covers your hotel stay in the unfortunate case that does happen.
Wishing all those who travel an unforgettable, seamless travel experience! Video of all our favorite Santorini Views below.
Travel Sister Rowena de Guzman 