Santorini Days 1&2


We were up bright and EARLY on our last morning in Rhodes.  Our cab picked us up at the ungodly hour of 4 AM so we could head to the airport for our 6 AM flight.  This early flight seemed like a great way to maximize our time in Santorini at the time of booking, but I don’t think I would book something that early again.  It made for a very exhausting day and I think I would be ok with having less time, but being able to more enjoy it.

But anyway! (Nothing like starting off a post with a complaint, right?)  There are a lot of places that you could stay in Santorini.  Oia and Fira are two main locations, Fira being the bigger of the two.  Both of these are located on the “caldera” side of Santorini, which is the inner part of the crescent and is characterized by whitewashed houses hanging off of the cliffs.  There are also a lot of places to stay on the eastern side that more gently slope out to beaches, like Kamari.  The whole island is only 11 or so miles, so things are fairly easy to bus, cab, or drive to.  We decided to stay in Oia to get that caldera experience and to take advantage of those famous sunset views.

We got checked-in and settled in our AirBnB around 11 and immediately set off to walk around and get some food.  I CAN’T EVEN describe how amazing and how happy we were with our AirBnB selection.  Our apartment was a “cave house” on the side of the cliff and had a fantastic patio area.  We spent so much time out there relaxing, talking and sharing beers.  This patio was certainly a highlight of the trip.

The view from our doorstep.
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From the gate/walkway.  The stone thing in the left corner is a hot tub.
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From the other corner.  Our neighbors in the smaller apartment to the right were an adorable couple from London on their honeymoon.  We loved hanging out with them!

We decided to walk around and hit some “close-by” spots on our list.  I really prefer to do something “easy” that involves a good amount of walking around on the first day in any location.  I think it balances nicely with the normal stress of a travel day and you don’t have to worry about being somewhere at a set time (like you would if participating in an organized tour), or fighting with crowds (like if you decided to visit a major site with an entrance and/or lines or museum).  We took the famous Oia steps down to Ammoudi Bay.  There are 350 steps down to the bay, and this is a popular spot for donkey rides (we met several donkeys who do not have a concept of personal space on our way down).  The walk was fun, and it was hard not to take photos at every corner we went around.  The views were awesome and just kept getting better and better.

We’re going down, Bob’s yelling “TIMBER”.


Down by the water, there are several tavernas and boat tour operators.  By the time we made it down, places were just starting to open up for lunch and we settled on Dimitri’s.  We had our pick of seats, but weren’t quite brave enough to pick a table RIGHT on the water.  If someone bumped your table, you could just topple right into the treacherous rocks below (dramatic).  Also, our seats provided some much needed shade!


We decided to get a spread of items to share since we all wanted to try different things and consulted the waitress for her recommendations.  We ended up with mussels in garlic sauce, Greek salad (natch), tomato fritters (apparently a Santorini specialty), and fava (yellow split pea dip served with pita).  The fava was reaaaally good and reminded us of hummus.  I also really loved the tomato fritters, which is surprising because I’m usually pretty squicked out by the texture of warm (but still raw) tomatoes.

After our walk we soldiered on to find some form of water.  I had read about a little path off of Ammoudi Bay where you can find a “beach”, so we asked our waitress about it.  She let us know it was really more of a cliff that has stairs into the water than a beach, but we decided to give it a go.

You know how when you travel with a group of people, and you come up with an idea and it doesn’t go exactly as it expected and you feel completely responsible and like everyone in the group is mad at you?  Yeah…that was sort of the experience at this cliff/beach.  Not that anyone said anything to me along those lines (everyone was crazy polite and good sports), but I was so paranoid that it was going bad and was starting to feel a smidge of anxiety.  It was tougher to get to than I think we expected, and when we got there it was pretty crowded and there was nowhere to put our stuff or sit.  We basically stripped down on the path, shoved our belongings to the side and jumped in the water, lol.  I was actually apprehensive about the water situation since you jump right into deep water.  But again, I felt some sense of responsibility for this activity so there was no way I could weenie out of this one.  So in I went, before I gave myself a chance to get nervous.

This was taken on the way back, and was one of the flatter areas, but you get the idea.
Don’t fall.
The water was fairly deep, so we found a slimy rock to rest on.
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My brave husband.  I did not participate.

Fun fact: this swimming area was actually featured in the movie “Sisterhood of the Traveling Pants”.  They were there on a mission in Santorini to find the pants or something?  Idk.  I didn’t know this when we went, but I’m glad that I DID end up getting in the water because I would have been deeply embarrassed to have been too scared to experience something that a group of teenage girls who believe in magical pants managed.  Go me!

Source:                                    That whacky sisterhood.  See the same jumping platform?

For dinner that night, we decided to stay relatively close to our apartment since we were very, very tired.  We ended up at Floga, based on a recommendation from our apartment managers.  Floga was basically right outside the gate of our apartment, I’m pretty sure it was a 60 second walk, door to door.

It is ridiculously hard to get a group pic where everyone is smiling and looking at the camera
Salad with prosciutto, cashews, dried tomatoes, dried figs and sesame crusted goat cheese.
Tagliatelle with Filet Mignon Julienne
Not sure what this one is, might have been a special of the day?  Nothing from the menu is ringing a bell.
Spaghetti with Shrimps
Risotto with “fruits of the sea”

Our meal was excellent (the salad and the risotto were especially good), but overall I don’t know that I’d go out of my way to go to Floga if I wasn’t as close as we were.  No ragrets or anything, but I’m glad we didn’t travel far to dine there.

We spent the rest of the night hanging out and talking on our super amazing patio until bed time!

The next morning we woke up on the early side to partake in one of the activities I was most excited for.  The Oia-Fira hike.  There is a trail that runs from Oia to Fira (or Fira to Oia depending on where you are coming from) and is said to have exceptional caldera views.  The total hike is about 5.5 miles and takes 2-3 hours (depending on your pace, more  if you stop a lot).  We had a hard time finding the trail entrance (it’s not marked super well),  but I’ve read that it’s easier to find if you are coming from Fira, which is apparently the more common route.  The trail head just kind of branches off from the main road in Oia.

Some tips for the hike:

  • Do not wear sandals.  Do not.  The hike is kind of tough at certain points.  Portions are very gravelly and along a cliff with no guard rail.
  • Bring some water.  You do stop through a few towns but we didn’t see a lot of easy convenience type stores where you could easily grab something.  We all carried backpacks with water and a few snacks.
  • If you would like to read up on the sites you are seeing this site has a good description.  Of course, it describes the trail from Fira-Oia so I had to read backwards.
  • Charge your camera so it doesn’t die on you mid-hike.  Also, remember to pack your charger in general so you don’t have to track down an electronics store in Fira so that you are able to take photos for the rest of your trip. Go me!
  • If I were to do it again I might cab or bus to Fira and take it from that direction.  It would have been much easier to navigate, and we would have ended on a nice downhill rather than starting our trek on a steep uphill climb.  We also started facing the sun, and if you hiked from Fira, the sun would be at your back.

After our hike, right outside of Fira, we stopped at Pirouni for some lunch.  We were hungry and THIRSTY.  We hadn’t seen/read a lot about this restaurant beforehand, and just kind of picked it because it was recommended by my app and we were starving, but we had a wonderful experience.  For one of the only times during this trip, we ordered multiples of the same dish (because it sounded amazing).  The dips that came with the bread were really good, olive tapenade and tzatziki.  We also ordered some Santorini salads and Lamb Souvlaki.  The dessert is a mystery, something chocolatey and nutty, but was delicious and served to every table!  We also had some wine/beer for rehydration purposes.  Both our meal and the service here were really great! 10/10.

We walked around Fira for a good while afterwards, there are so many shops!  We were on the hunt for some jewelry, and I found a really pretty sapphire necklace based on the Greek meander (symbolizes eternal life, love and friendship) that my mother-in-law so generously bought for me!  I love it and have worn it tons of times already.

Fira was very crowded from all of the cruise ships, we all commented that we were glad we decided to stay in Oia.  We debated staying in Fira and had heard that it was much bigger, so we were somewhat concerned that we wouldn’t find as much to do in Oia.  However, we thought Oia was a great size and actually probably would have been overwhelmed by Fira.

We debated taking a cable car down to the Fira port, but the line was verrry long so we skipped it in favor of more walking around.  We ended up stopping at a wine bar for a while too and enjoying some Santorini wine and  snacks.

 We attempted to take a cab back to Oia and waited at the cab station for about 20 minutes.  No cabs were really coming or going (not sure why) so we abandoned ship and decided to take a bus.  The bus was less than €2 per person and was easy peasy!  It was a little anxiety-inducing to be barreling around on a big bus on these little roads, but overall I’d definitely recommend trying to take the bus back and forth.

We got back and showered and ready fairly early that evening, because we had super important SUNSET plans!  Arguably the most popular activity in Oia is to watch the sunset, because Oia is on the tip of the island and there are no obstructions to the gorgeous sunset view.  However, because of this popularity it can get very crowded in the popular spots.  We wanted to head there early to secure a good spot.  We got there around 5 for the 7:30ish sunset.  We split up to scope out spots, Nick and I went to the ever-popular old Byzantine castle lookout and managed to get one person’s worth of space in a far corner.  But Bob was the MVP of spot-scouting and got a wide spot right around the famous three bells, which served as a great backdrop for all of our pictures.

We stopped in a store and grabbed some beers along the way.  We got four tall boys for our crew, but the guys decided not to drink since there were no bathrooms around.  H-oookay, Debbie and I will just take those off your hands then!  This made for a really fun “tailgating” experience for her and I.  The pictures are insanely beautiful, so I will just let them speak for themselves.  This night was on the cloudy end of the spectrum, but we still got some amazing shots!



You can kind of tell in the pictures of us above, but it was so, so crowded out.  It was still an awesome experience that I think everyone should do once, but I definitely got annoyed with people shoving and sticking their cameras right in my view.  Also, I hate crowds of people as a general rule, so eh.  I’m glad we did it, but we agreed we would make other arrangements for the next night.

The less glamorous perspective.

Due to aforementioned tailgating, the rest of the night has some holes in it for me.  We went to dinner at Strogili, where I was ENTHUSED to find BURRATTA.  So I ordered that as my dinner.  A ball of cheese was my dinner.  And it was awesome.

Our group also had the Santorini salad and….some other stuff that I don’t remember.  Overall, we thought the restaurant was a little overpriced and just ok.  But individually, my drunk ass was on cloud nine with my ball of cheese.

I originally planned to recap all of our time in Santorini in one post, but I think I will break it up now!  It’s getting pretty wordy and I guess I just love all of the Santorini pics too much to pare them down.

Next up in Travel: Santorini Days 3-4

This post is part of the Travel Tuesday link-up!  Thanks for hosting, Courtney and Lauren!


4 thoughts on “Santorini Days 1&2

  1. Awwwww I’d love to visit Santorini too one day! Seems like the most beautiful place on earth – and does it ever rain there??? One question though, how did you find your apartment again? All these houses look so similar, haha 🙂

    Liked by 1 person

    1. It didn’t rain any of the days that we were there! And in fact, when we went on a wine tour our guide said it hardly ever rains and the grapes get moisture from dew at night.

      We kind of lucked into this apartment, we booked relatively late and we needed a place for four people, which can be hard to find on AirBnB. So that narrowed down our choices quite a bit! Here is a link to our place if you are interested 🙂


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