With breathtaking views, world-class cuisine, and fabulous sunsets, the stunning island of Santorini was the perfect location to celebrate two decades of love, laughter, and unforgettable travel memories. The white-washed walls and blue domes of the iconic Greek villages provided a romantic backdrop for our week of adventure and relaxation.
For the first three nights, we stayed in Imerovigli at a resort named Absolute Bliss. You know it is going to be a great week when your terrace offers a view like this.
After enjoying the scenery for a bit with our welcome glass of wine, we headed out on our first hike to explore Skaros Rock. Imerovigli is the highest village on the island, and Skaros rock is the promontory that juts out into the caldera below.
In the 18th century, Skaros castle protected a little village that had been built up the side of Skaros rock. Today, you can still see the remains of the castle and some of the old cave dwellings.
The panoramic view of the caldera was outstanding and offered a unique perspective compared to elsewhere on the island. On the front side of Skaros rock, we hiked down to a picturesque Orthodox Greek church.
On the back side, the view of Imerovigli towering above the rest of the island is mesmerizing.
The sunshine, blue skies, and sparkling blue waters of the caldera provide for gorgeous scenery during the daytime, but the evenings in Imerovigli were absolutely magical. Our first evening, we watched the sunset from our suite’s terrace while enjoying a bottle of local Greek white wine.
We were absolutely blown away by the sunset. Every few minutes the colors changed.
Even the sky opposite the setting sun turned a lovely pink, and the white-washed walls of Imerovigli sparkled.
Our second day brought another hike, the epic Fira to Oia hike. Given we were staying in Imerovigli, we hiked to Oia first before taking a bus to Fira to finish the final leg back to Imerovigli. This picture is taken just outside of Imerovigli with Oia in the distance on the northern tip of the island.
There were a lot of cute Greek orthodox churches along the path, including Prophet Elias.
As we rounded the curve toward Oia, we got a whole new perspective looking back on Imerovigli and Skaros Rock.
We still had a long, undulating path to go to get all the way to Oia, but the views around every corner were breathtaking making every step worth it.
Another cute church was located on top of a large hill overlooking Oia and the island of Thirasia.
From here, the rest of the way was a nice, easy downhill into Oia.
Strolling down into Oia was a cool way to enter into the city with a great view of the coastline below it.
We rewarded ourselves after the long hike with fancy cocktails at Thalami Restaurant and refueled for the final leg of our hike with the classic Greek meal, gyros.
Fira is a busy port town, so after the bus dropped us off, we quickly navigated through the crowds, making only a couple of stops. First, for the best gelato in Europe (per the Gelato Festival), we popped into Vero Latte. Their award-winning Risagalo, rice pudding, flavor was outstanding! Second, we soaked in the views at the famous Three Bells of Fira before finishing the final short leg of the hike back to Imerovigli.
That evening after the hike, we rewarded ourselves with the best meal we had in Imerovigli. We indulged in the multi-course tasting dinner at Athenian House, a World’s Top 50 Discovery restaurant.
Perched on the cliffs above Skaros Rock, this elegant restaurant combines modern Greek cuisine with spectacular views over the caldera and the iconic whitewashed architecture. We were fortunate to get yet another brilliant sunset to compliment the creative culinary journey.
The staff was super friendly and incredible at photography, taking the time to make sure every couple got special photos to remember the evening.
Every course was beautifully plated and absolutely delicious.
They are most famous for their lamb moussaka, and it did not disappoint. Moussaka is a traditional layered Greek dish of eggplant, a tomato-based meat sauce, and creamy bechamel. At Athenian House, the dish is elevated with minced lamb meat and served alongside a lamb lollipop.
For dessert, their specialty was a fancy twist on the traditional baklava. Their baklava has layers of crispy phyllo pastry, peanut butter, chocolate, salted caramel and pistachio.
From the first bite to the last, every detail was thoughtfully crafted, making it a truly special dining experience.
No trip to Santorini is truly complete without venturing onto the sparkling blue Aegean Sea, where you can marvel at the iconic white villages and blue-domed churches nestled on the dramatic red cliffs from a mesmerizing new perspective.
After a couple days of hiking, lying down on the deck of a catamaran while it cruised around the island was a lovely way to spend an afternoon.
The massive cruise ships below Fira really highlight just how towering the cliffs of Santorini are.
Our final night in Imerovigli was a chill one. A complete 180 from the fancy dinner the previous evening, we procured some fruit, crackers, cheese, and wine from the local market to enjoy a private dinner on our terrace as the sun set…in our swimsuits, of course, so we could also relax with some wine in the jacuzzi.
Leaving the honeymoon suite at Absolute Bliss was hard, but we luckily still had three more nights at a resort in Oia to continue to soak in all the Santorini magic. We had very few activities planned for these days aside from wandering the beautiful village and enjoying the resort amenities. The one exception was our transfer day between resorts. We hired a guide to take us around the island for the day until it was time for check-in. Some of the highlights of our day trip to the southern parts of the island included the red sand beach, the highest point on the island at Prophet Elias Monastery, the villages of Pyrgos and Megalochori, and the ruins of Akrotiri.
Oia can get crowded during the day with cruise ship day trippers, so we wanted to stay in Oia for our last few nights to make sure to enjoy the calm mornings and evenings. We had heard some horror stories that Oia was too crowded and filled with over-eager influencers ruining everything, but we were pleasantly surprised how quiet the city could be if you avoided the hot spots.
Since this was our 20th anniversary, we hired a professional photographer, the talented Gerald Hazizi, so that we could have some memorable photos from this iconic village and not a bunch of terrible selfies or poorly taken photos by other tourists. Our first morning in town, Gerald essentially gave us a tour around town of all the most beautiful places. It’s like stepping into a postcard. The iconic blue domes, the windmills, the stone castle walls…
After our early morning photoshoot, we came back to our resort, the Andronis Luxury Suites, to enjoy a late breakfast on our terrace.
We were impressed by the quality and variety of food delivered to our terrace each morning. The stuffed croissants with fried egg and chorizo on top were the best, and we just could not get enough of the views.
The creative, delicious food for breakfast should not have come as a surprise though, as one of the best restaurants on the island, Lycabettus, is part of the resort. We booked the special Sommelier’s Table almost a year in advance to get the most extraordinary spot for our special 20th anniversary dinner.
National Geographic has named the Lycabettus Balcony as one of the most beautiful in the world, and we got to sit in the giant pink chairs on the edge of the cliff overlooking the sparkling blue waters of the caldera while we indulged in a multi-course tasting menu.
Each course was beautifully presented and paired perfectly with a special international wine.
The “pasta” course, squid tagliatelle, was the surprise of the night. Instead of pieces of squid being served with pasta, the tagliatelle itself was actually made out of squid! We normally are not huge fans of squid given its texture, but we were blown away that they were able to prepare it in the shape and texture of al dente pasta. Incredible!
Similar to Athenian House, the sommelier and waitstaff were incredibly friendly, knowledgeable, and excelled at taking pictures.
Our experience at Lycabettus was certainly a memorable one. The combination of impeccable service, romantic ambiance, jaw-dropping scenery, and imaginative cuisine made it the perfect place to celebrate our big milestone together.
Our last full day in Santorini was all about relaxing. We spent the morning lounging around on the sundeck and cooling off in the infinity pool at our resort. We had the beautiful views over the caldera all to ourselves and enjoyed the peace and quiet for a while.
In the afternoon, we headed to our resort’s sister property, Andronis Arcadia, where we were allowed to enjoy their amenities too. This property was on the other side of Oia, facing the open Aegean Sea.
Here, we found more of a party atmosphere. Dance music was playing. There were multiple pools including one with a swim-up bar. And a lot more people. For lunch, we enjoyed the bao and sushi at their Asian restaurant by the pool, and then we spent the afternoon getting cocktails from the swim-up bar and napping on bean bag chairs.
For our last sunset in Santorini, we skipped the crowded spot by the windmills and wandered to the quieter side of town. With the sunset nearly all to ourselves, we couldn’t see it sink into the sea, but the sight of the iconic white buildings glowing against the fiery red and orange sky was just as beautiful.
If you’re thinking of visiting Santorini, especially Oia, don’t let talk of crowds and influencers deter you. While you may face crowds during peak times, the beauty of the entire city is worth it. Timing is key. For example, our sunrise walk on the final morning allowed us to explore the iconic spots without the crowds, even snagging a selfie with the iconic three blue domes.
We had so many quiet moments to ourselves. Sunrise in Oia can’t be beat.
We couldn’t have had a better ending to our unbelievable week in Santorini.
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