I share more about our overall trip itinerary and what we loved most about each place we visited in my Athens Travel Guide, but to give you an overview Santorini was definitely the most breathtaking and picturesque place we visited. You really feel like you’re inside a screensaver the whole time– and there are both quaint corners and sprawling views everywhere you turn.
We were there for two nights and two full days when you added them up, and we thought that was a great amount of time to hit the major sights in Oia and see the majority of that town from land. However, we did wish we had stayed another full day so we could do a boat cruise and see the island from the water! We heard that those cruises last 4-6 hours and are SO worth it for seeing the whole island and the surrounding ones as well.
So getting from Athens to Santorini was actually the only snafu in our travels throughout Greece (and in hindsight with all of the planes/ferries/cabs we took that’s pretty good!). We left for the airport at 8:30 am (as per the recommendation of our hotel), for a 10:30 flight to Santorini, and unfortunately every single road in the city of Athens was blocked due to a marathon that was going on (that we of course had no idea about). So we didn’t end up getting to the airport until 10:00 (when it was only supposed to take a half hour), and we ended up missing our boarding call by a matter of minutes. We had to rebook for a flight later on that day— and got into Santorini later than we would have liked. But as I mentioned, in the scheme of things it wasn’t a big deal at all!
I’ve also heard of there being a number of transportation strikes in Greece at other points in time as well, so I may suggest going in with a plan for your transportation (having your hotel schedule a cab to pick you up, planning to leave for the airport or ferry even earlier than you think you should. etc).
Where We Stayed
Atrina Canava 1894— Ok wow, what a hotel! It’s a family-run boutique hotel that was first founded in 1894 and at one time was a home (can you even imagine living here??). It’s built into the side of the cliff in Oia, and has one of the best views we saw of the coastline and Aegean Sea. There are a number of studio, suite, and villa options for you to say in, based on the number of people you’re traveling with, but we ended up staying in the ‘Atrina Villa with Jacuzzi’ (tip: book it with an American Express Platinum card for a potential free upgrade!) and absolutely loved it. It’s easily one of the top three places I’ve ever stayed in!
We were able to spread out in the two bedrooms and utilized the jacuzzi (which was always hot!) every night. The service was exceptional as well— the power went out randomly one night (we were in a cave from the 1800s anyways) and was fixed almost immediately. They also delivered breakfast to our deck each morning, and the woman who worked in their office on site, Helisa (sp?!), was unbelievably helpful in giving us advice on where to go and helping us secure reservations. The hotel was also located right on the main road in Oia, so we didn’t have to walk more than 10-15 minutes to any of our dining reservations!
We tried to scope out a few other hotels to get a sense of them as well just for fun, but honestly felt that this one had it all (the views, the classic Cycladic architecture, the pool, the service!). A few others that looked exceptional though were Canaves Oia (located close to where we were), Perivolas (further down the street away from the town and a bit more quiet/private), and Art Maisons (located at the opposite end of Oia closer to the windmills on the side of Oia where the sunset is best!). But truly, I don’t think you can go wrong with anywhere in Oia. We were told it was the town to stay in on Santorini, but are definitely interested in visiting Fira next time as well (because there will most certainly be a next time 😉).
What We Did
Photoshoot with Flytographer— On our first morning there I woke up early and met Ioannis, a photographer from Flytographer (a company that has photographers in 380+ cities and matches you to them!) at 8 am for an hour photoshoot. It was awesome. Ioannis was amazing and the photoshoot was such a cool way to get to hangout with a local and shoot at the best photo spots on the island. He was very low key, kind, and gave the best instructions as to where I should stand to get the optimal photos, while still making me feel comfortable the whole time. And even better— the final images are just breathtaking (many of them included in this post and here)! At the very least, book a session with him to get all of your vacation photos out of the way and see Oia at its best (in the early morning!) with someone who knows the area better than anyone else. It was also the optimal time to get photos since not nearly as many people were out and about in the town of Oia that early and the cruise ships hadn’t dropped anyone off yet. Some of the top photo spots in Oia were the 3 blue domes, Anastasis Church, the windmills, the Katro Oia Houses, and of course the sky during/right after sunset! They were kind enough to offer me a discount code to share with you all too– use the code AMYL50 for $50 off a photoshoot with any Flytographer photographer!
Shopping through Oia— Throughout our stay in Oia we shopped all around the main street and the winding alleyways that had the prettiest little jewelry, clothing, and art shops. It was a lot of the same after a while (tons of embroidered dresses, evil eye accessories, colorful jewels, and Greece-inspired pottery and art), but it was fun to look through nonetheless. We found out late on that the best shopping was in Paros and Mykonos! But we all got a piece of pottery from a store called Amanjena— it was so unique and contained the prettiest colors we saw in pottery during the trip.
Walk down to Ammoudi Bay— We took the steep walk down to Ammoudi Bay in Oia and would highly recommend exploring that area! There are a bunch of old fashioned tavernas on the base of the cliff, fisherman boats bobbing in the waves, and seafood everywhere you look. We decided to eat at Dimitris Ammoudi Taverna and had the best time watching the boats come in and looking up at the sprawling cliffside.
Lay by the pool— We got the chance to lay by the hotel’s pool at Atrina Canava 1894 twice during our stay and it was honestly one of the most serene and scenic spots I’ve ever spent time in. It contains overgrown bougainvillea, old stone walls, and a refreshing pool that overlooks the vast sea below. They have a little pool bar there too, where you can order a club sandwich or a fun cocktail! It was intimate, quiet, and just what we needed to wind down in between exploring.
Watch the famous Oia sunset— This is one of the top reasons to visit Oia! The sunsets are over-the-top gorgeous and they seem to melt right into the horizon— everyone crowds to the west side of Oia near the Oia Castle (including all of the yachts and sailboats on the water!) and it’s most definitely a bucket list sunset spot. Keep scrolling for our recommendation for the best sunset-viewing bar.
Hike from Oia to Fira— We did half of this hike (lol) on our last day in Santorini and it’s a great way to get another perspective of the island and cliffside. I think the whole hike takes about 2 and half hours, and takes you along the coast to another village town on the island— Fira. We actually ended up driving through Fira on our way to the ferry when we were departing Santorini and heading to Paros, so we got to see a bit of it that way, but I’ve heard that walking to it from Santorini is a must– we just ran out of time.
Next time we visit we definitely want to do a boat excursion (I heard from a friend that the Sunset Oia one was incredible!) and visit one of Santorini’s wineries since the way they grow grapes is so rare (a recommendation I got a number of times for this was Santo Wines).
Where We Ate
Atrina Canava 1894 Pool Bar— On our first afternoon in Santorini, right after we checked in, we sat the pool for a little bit and ordered club sandwiches to split and a few cocktails! It was super convenient, in the most serene setting, and delish! Their signature cocktails were especially tasty.
Fino— We had dinner on our first evening here and it’s a cozy little spot in the town of Oia, that served Mediterranean food and local wines. You can’t go wrong with the house white wine anywhere in Greece, but it was especially good here! We also really loved the ricotta gnocchi in goat cheese (with truffles!) and the lobster spring rolls. Expect a chic atmosphere with lots of honeymooners… and stray cats.
Dimitris Ammoudi Tavern— This was the old fashioned taverna that we dined at at the bottom of the cliffside on Ammoudi Bay! They had exceptional hummus and cheese dip— and of course fresh fish galore. It is super laid back— I wore a bathing suit and jean shorts and was totally fine. We heard that you can also walk down the dirt path right past it and around the corner to cliffs you can jump off?! Next time for SURE.
Sun Spirit— This is the bar that the receptionist at Atrina Canava 1894 told us to go to for the sunset and it did not disappoint. She made a reservation for us and timed it so we wouldn’t miss the sunset, and it was the best spot on in Oia (from what we could tell!) to catch the view. There’s a 20 euro drink minimum per person, but you can easily meet that with two glasses of local wine! Skip the cheese board though— it wasn’t the best and the views and wine were better!
Pitogyros— After we had drinks during the sunset at Sun Spirit, we decided to skip out on our dinner reservations and pick up gyros and fries instead to bring back to the villa and eat in the hot tub (like who did we think we were??). Anyway, BEST DECISION EVER. This spot came highly recommended to me, and was one of my favorite meals of the trip. I believe I got the #33 (the chicken gyro!) and the parmesan cheese fries and both were too good to be true and hit the spot. This is the ideal grab-and-go spot that you have to make sure you hit!
Note that a few other places that were on our list but we didn’t make it to for dinner or drinks were Naos, Catch Rooftop Bar, Katakies Hotel Champagne Bar (scroll down on their page for a tidbit about Brad Pitt!), and Armeni (we definitely want to do Armeni next time, as you can get there by boat which would be a really cool experience).