When Kyle and I decided on Greece for our annual two week end to wedding season trip, I knew Santorini had to be on the list. I’ve followed some of the hotels there on Instagram for years and constantly pin the most beautiful sunset views. Follow along to hear about our meticulously planned and researched trip to one of the most romantic islands in the world!
We woke up early in Athens to make our 8am flight, board the plane and 45 minutes later we land in Santorini. The airport is on the east side of the island and we had a transfer from our hotel waiting for us. Note! There are not a lot of cabs on the island, either plan to use the bus (we didn’t but it actually looked really nice), rent a car or utilize a transfer! We stayed in Oia which is on the most northwestern point of the island, it is famous for the sunsets, restaurants and gorgeous luxury hotels. I had created a 27 hotel spreadsheet to try to decide where to stay in Santorini, so my anxiety was a bit high to see if we did in fact make the right choice. Oia is kind of funny because all those photos you see on Pinterest and Instagram are from where it is walking accessibility only, so our transfer pulled up to the side of a hill in a not so aesthetically pleasing area for our concierge to come get us. Markos, our amazing concierge, meets us to help with our bags and we walk up toward the walking street of Oia. It is a 180 flip, the street is marble and you see high end designer sunglass stores, jewelry stores and hotels I’ve seen plastered all over Pinterest. This walk literally takes maybe 2 minutes to go from where the heck are we to Pinterest perfect. We get taken to our hotel, Solstice Luxury Suites, and oh my goodness did we make the right choice. The three suite hotel is located just beside Armeni Boutique Hotel which is home to Lycabettus Restaurant, one of the most famous fine dining restaurants in Oia, mostly from its location of its patio being perched on a tiny cliff that sticks out among the white washed cave hotels. We had this famous view from our patio which was pretty epic. We quickly made bets with each other on how many proposals we would witness there over the next three nights!
Markos was able to check us in to our room right away and we freshened up before walking down to Ammoudi Bay (some say its 300 stairs are equivalent to 1000 actual stair steps, we didn’t count) where we sat at Ammoudi Fish Tavern for lunch. We started with some wine for me and a Mythos for Kyle along with their famous sundried octupus. We ordered the catch of the day for our entree, our server even walked us back to the case where they had all their fish displayed. We settled on white seabream, a fish we really enjoyed in Portugal. Our first travel mistake occurs when we do not ask the weight of the fish. It was 1.25 kilos priced at 65euro per kilo. WHOOPS. It was delicious but we definitely will be keeping weight in the front of our minds for future seafood orders. We head back up the steps to relax in our caldera view hot tub for the afternoon (get a suite with a hot tub or pool, actually just stay at Solstice because everything was perfect).
We had planned to eat at Fino Cocktail Restaurant which is located a bit off the walking path for a romantic dinner on the cutest terrace. We grabbed a bottle of the recommended Santorini white and started with the lobster spring roll (fresh, almost like a salad roll minus the noodles) and split the truffle gnocchi and grilled octopus. Fino is definitely more of a fine dining twist on classic greek food and was the perfect start to our time in Santorini. Didn’t take many great photos here, we were distracted by the amazing food!
The bed at Solstice was soooo comfortable so we had a bit of a sleep in with breakfast delivered to our room. Breakfast orders are done the night before and you can pick up to 3 styles of eggs, 4 sides (greek yogurt, fresh fruit, meat, cheese etc), 2 desserts (we got pancakes with walnuts and honey literally every day because they were so delicious) and your selection of juices, smoothies and coffees. We knew breakfasts would be big here and allowed us to spend less on lunch as the breakfast would have easily cost 30euro/person at any Oia restaurant.
After our very filling breakfast we wandered to the east side of Oia to being the walk to Imervilgili. I had done some reading on the hiking path from Fira to Oia and did not check which half was “the actual hike”, it’s between Imervilgili and Oia, we attempted and turned back around 45 minutes in when my shoes were literally beginning to fall apart. Great views, but did not sign up for cardio. We head back to the hotel to drink wine in the hot tub (this is a vacation after all). On the way we grabbed some gelato and found a dream ceremony location!
Markos, our hotel concierge had set up a reservation for sunset at Strogili Restaurant so we head there around 6pm and get walked right in to a reserved table. It was roped off and everything for us, right on the edge of the patio for a perfect sunset view. The servers were amazing and the food was just as good. We started with another Santorini white wine and mussels saganaki (feta, tomato sauce, fairy dust, I don’t remember what else but it was seriously magic). We watched the sunset and our server brought some blankets to keep us warm. Most guests left immediately after sunset after just having a drink or two. DO NOT MAKE THIS MISTAKE, the food here was some of the best in Santorini, come for sunset and then stay for dinner. We had the pork pappardelle and rack of lamb. As it got a bit chillier after we finished our entrees we moved downstairs to the protected outdoor terrace to finish our wine. Travel Tip: Utilize your concierge for reservations, we never would have been able to sit where we did without Markos. We head back to the hotel to yes, have yet another hot tub. The views of Oia are stunning at night, the glow from all the other cave pools and the lights from the nearby restaurants, we were so in the action but yet our patio was so private, it really was the perfect balance.
The day started with breakfast on our terrace again, it was such a relaxing way to start our mornings. Kyle always knew he wanted to ATV or take a side by side around the island, we had discussed it pretty much the day we booked the flight there. Markos set us up with a side by side that was brought to the hotel’s parking spot and we set off on a day trip to explore the island. Our plan was to head to the most southern point of Santorini to see the lighthouse and then go to the black sand beach and Santo Wines winery. We did not regret opting for the side by side as we were able to cover the island twice as fast, Santorini is literally all mountain and the ATV’s definitely move slower than the side by side’s or cars. Make sure you have an International Drivers License to rent any sort of motor vehicle. Kyle absolutely loved ripping around on the side by side and it was so easy for me to be able to take photos/video and give him directions to our next destination.
The black sand beach was a pretty basic beach, but all the sand is black from the volcanic rock. We grabbed a drink at a beach bar and swam in the sea before hopping back on to head to the winery. Santo Wines is famous for their white wines and one of their dessert wines that appears to be red but is actually a sundried white! Dennis was our server on the patio where we ordered a 16 wine flight and a cheese board. There was more cheese than either of us imagined, come hungry, its 24euro and for the amount of cheese on it was the same cost as buying at a market off a side street in Oia. The views were breathtaking and I went into work mode when I asked about some of the wedding ceremony locations on the property.
On our way back to Oia we stopped at Imervilgili to wander for a bit. The cliffside is much higher than in Oia so it is definitely worth it for the views! Our runner up hotel was here actually! Check out Sophia Luxury Suites if you are wanting to stay in Imervilgili! We saw SO many couples here doing bridal portraits, I reached out to a local photographer and he said its the best spot because you get the views of Oia without competing with as much tourist traffic. We didn’t get a chance to do professional photos, which I do regret a little bit because his schedule didn’t fit with ours but definitely reach out to @kimon on Instagram!
Markos had made a reservation for us at Oia Gefsis for another sunset where we had some bubbles & red wine and some fresh mussels. To be honest this wasn’t our favourite dining experience. The sunset view was great but the mussels were pretty average so we opted to skip dinner here. If you were to pick one sunset restaurant, go with Strogili for sure! Kyle had found a restaurant with amazing reviews called Melitini that we had planned to visit for lunch but we decided to call to see if they had a table that night! They held us a table inside and we made our way over. It’s a fairly simple tapas style greek menu, with only beer and house wine, but SO delicious. We tried the santorini salad, fava, grilled octopus, lamb sausage and the meatballs. Here simple is best, everything is basic but so full of flavour.
We woke up and enjoyed some coffee while watching the sunrise. I savoured that one a bit longer this morning, we really didn’t want to leave! We headed out for an early walk to get all the pictures we (aka I) wanted before the flood of tourists from the cruise ships made their way to Oia. We noticed the traffic significantly increase on the island by about 10/10:30am. We wandered over to Oia Castle, a very famous spot to watch the sunset if you didn’t want to be in a restaurant! We got my favourite photo overlooking the two blue domes and the pink church bells (hint – it’s a private walkway which is super common in Oia but it currently doesn’t have a lock, follow these GPS coordinates and go left at the gate 36°27’41.0″N 25°22’31.0″E) We walked over to the very far west point for Charisma Suites, yes you can stay in a windmill if you want to live your life like the current Bachelor!
Once we started to notice all the cruise ship guests filling the cobblestone paths, we made our way back to our suite for our last breakfast. When we arrived back we saw that Markos had left us some olives, a gift box of honey products and a bottle of wine for us. They truly were the best to us! After our last stack of walnut and honey pancakes, we packed up and left our bags with Markos at their office. We had a few hours before needing to be at the ferry terminal to catch the boat to Milos so we went for another wander around the island to grab a few more photos and of course some Santorini white wine!
So that is Santorini! It is definitely a must on your bucket list for romance. We wouldn’t spend much longer than a few nights on the island, it’s perfect for dining with amazing views but we really were ready for some beach time! We left Santorini to head to Milos – keep an eye out for a post about the island of 1000 beaches!
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