Greece

September 1st, 2022-Departure

At the airport terminal of an international flight one runs into all sorts of different cultures. The beauty, habits, and rituals are unlike our everyday lives, and that’s simply wonderful. That must always be kept in mind when certain aromas, obtrusive behaviors, or non-midwestern norms inevitably come across your eyes, ears, and olfactory. However, the level of volume individuals choose to either FaceTime or watch YouTube at does not seem to vary between the international terminal or a Spirit Airlines terminal, so keep that in mind.

An individual traveling can take one of two roads. The first of which can be asking those who may be interpreted as disruptive to kindly utilize their headphones that Apple so kindly provides to every customer upon receipt of any and every iPhone. I have never chosen this specific route; however, I can’t imagine it going particularly well regardless of language barrier or not, people are not using their Air Pods for one reason and one reason alone, they don’t want to, so be prepared for any and all varieties of response to your request. The second option is to keep to oneself and avoid any and all sorts of horrifically uncomfortable scenarios that could in fact haunt you for the duration of the 14 hour flight you are about to embark upon. It’s your call, but I go with the former, ten out of ten times.

September 2nd, 2022-The Flight, Chicago to Istanbul, Istanbul to Athens

The only real take away from this series of flights was my brilliant maneuver to deter individuals from impeding upon your personal space while you are in the middle seat…in economy…of an 11.5h flight. Depending on the schematics of the airflow, if one puts their fan on high it inherently blasts the cold, crisp, glorious circulated air on not only yourself, but those next to you as well. This inevitably leads your too close for comfort companions to burrow themselves deeply into their own seat and their own (maybe washed?) airline provided blankets, keeping any limb infringements upon your general vicinity, far and away! I have dubbed it, the Freeze Out, patent pending.


Another plight of the middle class that was bestowed upon me was the misfortune of a certain individual who decided they wanted to start playing the in-flight games, provided to them by the lowest of quality touch sensitive screens, thanks Turkish Airlines! (You’ll hear more about how they’re my favorite later). When I finally began to drift off into the sweet lull of slumber I started to feel a tap tap tap upon my head. Chalking it up to the individual merely choosing which mediocre blockbuster they were going to watch next, I decided the annoyance would pass. However, that simply was not the case. A few minutes passed and I decided a contempt filled glare was warranted. Damn, my hostile gaze had no effect. More tapping took place. Two or three more glares followed, yet to no avail. Eventually I decided sleep was not in my future so I…started playing in-flight games on that less than responsive touch screen myself. Luckily for me and my conscious however, no one occupied the seat ahead of me.

September 2nd, 2022-Athens, Greece: The Parthenon

The crazy thing about historical landmarks one visits without a tour guide is they’re simply just that–historical landmarks. Sure a certain level of ooh’s and ahh’s are warranted and rightly expelled, (much less the oof’s upon the ascent of the acropolis), however, the majority of historical landmarks go observed without fully absorbing what they truly meant to the world. That is why I will recommend one to get a tour guide or app of some sort to aid in your understanding and comprehension of the historical gravity of the site you are viewing. The fact that it is thousands of years older than anything I have ever come close to seeing makes it special in of itself. Having said that, we loved it, even without proper education and guidance, and it is an absolute must while you’re in Athens.

On top of the fact that my wife and I are not the biggest proponents of guided tours and consider ourselves burdened by the time commitment to those always seemingly far too long extracurriculars, we necessitated an expedited visit to the Parthenon due mainly in part to the fact that we had a ferry to catch at 2pm, and we were uncomfortable on navigating there with our luggage. Long story short, it turns out it is far easier than we had predicted as far as navigating to the port. Spoiler alert: you just go in the direction of the Aegean sea.

A Note for My Readers

Periodically I will depart from the main storyline that is our adventure abroad and will unload a slew of helpful “how-to’s,” for travel, that actual “tips and tricks to travel,” portion that I so boldly advertised. I have dubbed these “Drew’s How-To’s.” If you wish to read a slightly less verbose portion of these tales and are interested in simply getting answers for your questions on which airline to fly (not Turkish!), how to navigate the Greek ferry system, or best places to stay, this section is for you! If you wish to simply read for the comedic and entertainment value I bring to your screen, feel free to skip over these snooze filled sections! If you are interested in both, then you’ve hit the jackpot!. Mazel Tov!

Drew's How To's: Luggage Storage for a quick trip to the Parthenon

If you ever find yourselves in a similar predicament as us and want to see the Parthenon with yourselves still straddled to your luggage, there is a lovely Greek family who watches your luggage just a stone's throw away from the acropolis, you can find them here).

Drew's How To's: Navigating the Ferry System (For Greek Island Hopping)

Greece has a ton of beautiful islands. You can go island hopping via plane or ferry. Prior to doing so, my wife did her research and all the bloggers say, ferry is the way to go. It’s relatively easy. You can download the app Ferry Hopper and you would type in which islands you want to head and when. There was a somewhat outrageous ticket price we paid for a series of 4 maybe 5 ferries ($800, about $400 per person), primarily because along with cars these ferries also tote human cargo, and comfortably too! A couple important lessons we learned throughout our journeys that are VERY important to note!

1.) You must download the tickets from the ferry hopper app for each person and then once you download them and have the QR code, that’s all you need! You do NOT need to wait in a 37 minute line, in the direct sun, on an 89 degree day, to show the Ferry ticket office your QR code so that you have a printed out version of your ticket (I see why our very friendly cab driver told us to do this, a lot of countries do necessitate physical copies i.e. Turkish Airline plane tickets etc… however, avoid the swass and sun poisoning and download the actual ticket upon your phone prior to leaving a wifi free zone.

2.) The most veteran move a traveler can do is, and I can not stress this enough… ASK WHICH GATE AND WHERE SAID GATE IS THAT YOUR FERRY IS LEAVING FROM. We will get into the details later but spoiler alert: this will prevent you from missing any and all ferries that may in fact be stationed at a HIDDEN GATE!

3.) Remember how I said that all the bloggers recommend taking the ferries? And NOT the planes? I’m unsure why. Ferries get canceled… FREQUENTLY! Due to high winds and choppy waters, that happen OFTEN in the Greek Islands! You know what don’t get canceled frequently even with high winds?! Sky Express flights! An airline that consists of little airplanes that have 20 rows of people in them that make Spirit Airlines look and feel like luxury! And guess what, those airplanes, that don’t tend to get canceled, they’re only $10-$20 more per person. To guarantee yourselves getting from island to island, and NOT losing an entire deposit on an Air BnB? I’d pay more every single time. But who am I ?

4.) The ferries are nice. You have nice leather seats. You can take a nap. You can buy food (pretty decent) and drinks (alcoholic if you're not prone to sea sickness). You can even stand atop the ferry and watch the beautiful scenery fly by. You will have assigned seats, and just because someone isn’t sitting next to you from the first island to the second island, does not mean someone won’t sit next to you during the second island to the third island (the ferries tend to hit at least 4-5 at a time). Some journeys are longer than others so bring a book, bring a card game, bring a journal, it’s a good time to slow down and regroup during (what tends to be in our case) a very hectic, jam packed trip.



September 2nd, 2022-Our First Night In Santorini

After a nearly five hour ferry from Athens to Santorini we finally arrived. The beauty, the awe, the wonder of this amazing island was sadly completely under the veil of darkness by the time we had reached port. We did have the privilege of watching the indescribable Santorini sunset however… but, our view was slightly obstructed in large part by the fact that we watched it through a splash filled nearly translucent ferry window that just shy of a baker's dozen of tourists were blocking. There would be more sunsets we told ourselves.

I’ve always told my wife of a dream I’ve had. You know when you’re at the airport and you’re coming down the escalator with your luggage? Tired, dreary from travel, burdened with pure exhaustion, and you see the slew of suited individuals bearing signs with names upon them and you so desperately look to see if you happen to come across your name? Even though you know DAMN well you arranged no such overindulgence of luxury transport? Well, my dream came true! My AirBnB host had suggested I arrange transport from the port to their location primarily due in part to the fact that cabs are difficult to come across on the islands, especially at that time, so I took them up on that (will reveal further logistical details in the next Drew’s How-To’s). And boy I’ll tell ya, when we herded out like cattle off that ferry and my gaze was bestowed upon the friendliest Greek man I’d seen in the last few hours, we were elated! Best decision ever.

When we arrived at the AirBnB which was spectacularly stunning (further details in Drew’s How-To’s), our host’s host (unclear of his title), Themis, was waiting for us. He greeted us with “You’re Welcome,” (the second Greek to greet us with this, which I found odd yet slightly comforting?). Themis was a kind, warm, welcoming individual. He showed us around our room, how to operate the hot tub, and mentioned, if we needed to book any day trips or reservations for dinner, he was our guy. We inquired further. Themis, the beautiful Grecian angel that he was, booked us a yacht cruise of Santorini, for what he told us was 20 euro more per person, but the yacht itself had a 16 person max capacity. Which, trust me, is what you want. Some of those cruises have 24, 30, even 40 people squished onto them.

We were hungry, the spinach pies on the ferry were waning quickly through our digestive tracts. Unfortunately we were saddled with few options for a nicer dinner due to our late arrival however, we made the most of it. The food at our chosen place to dine was lackluster at best, and most assuredly expensive, but no more than you’d pay for a meal of similar quality in a West Loop facility attempting the latest song and dance at being “trendy.” Bottle of wine, Greek salad, 2 seafood based entrees, 118 euro. But you know what we DID get that you don’t get in the West Loop? (Besides the swarms of investment banker bro’s and thousands of dollars of lip injections) A beautiful view of the lit up Caldera and the Aegean sea. Oh, and the sweet comings and goings of wily old feral cats and pups alike. One even was able to weasel its way into obtaining an entire bone of some sorts. To say that he was the clear winner of the night would be an understatement. Yes, we were in fact on vacation in a country unfamiliar to our own. How wonderful.


Rather than stay out and fork over the euros for more wine at an establishment with less than stellar service (to be ONE HUNDRED, this was the ONLY restaurant in Greece in which we felt like we had bad service. I do realize others have established ideas of what is good and bad service, and most Americans prepare themselves for bad service abroad. Greece especially gets a bad rep, but being completely transparent, every restaurant we went to, besides this one had very good service) we decided to get a bottle from a market, and indulge in the luxury that was our hot tub. Sadly, the hot tube wasn’t necessarily HOT, it was more so a luke-warm tub, but we indulged in feeling bougie nonetheless.

September 3rd, 2022-A day In Santorini

The next morning we woke up relatively nauseated and headache forward. I assume that was in large part because we steeped ourselves like a couple of tea bags whilst consuming little to no water and replacing that intake with 2 bottles of red instead. Coincidentally enough, we slept through the night quite well and remained free of jet lag.

The best aspect to our AirBnB was that although it was not on the Caldera itself, it was literally a three minute walk from it. It just happened to be on the other side of the island, sunrise facing. And it was easily half the price of the Caldera options. Something all the bloggers were correct about was the move to wake up early so you can get pictures of the Caldera without the streets being flooded with a flurry of fumbling fools feigning joy for their photos (yes, I’m absolutely going to push the limits of alliteration within the confines of this comedic travel blog). We indulged in the treat of being alone to take our very own Instagram pictures, to discover what wonder we captured feel free to give me the follow @Youroldpaldrew. Kidding… kind of. After pushing our iCloud memory to the brink of overflowing, we returned to the room where the FREE Greek breakfast was included! An immaculate omelet paired with delicious pastries and fresh orange juice, absolutely hit the spot. If my wife ever had any doubts that I had gone rogue with my AirBnB decisions, that breakfast alone reassured her mindset. As soon as we were finished, our van to our Caldera Yacht tour arrived.

September 3rd, 2022-Caldera Yacht Tours

Our trust in Themis had been rattled a bit after he had recommended that less than spectacular meal on the Caldera the night previous, so there were some reservations regarding the yacht tour. However, after we stepped our first steps on the ship that we were going to spend the day on, our faith was restored. The yacht was large, the staff were friendly, and we were only 2 of 16 people on it. On top of that, those that we were joined by really made our trip that much more memorable. (I have a theory that the slight price differential of 20 euro per ticket probably played a factor in keeping the group free of undesirables). We met a lovely (parent age) couple from Chicago (actually Arlington Heights, but we weren’t about to be THOSE people) who we talked to initially. When we set sail my wife and I scored absolute primo seats. They were slightly difficult to get onto (see pictures below-we flailed and flopped our way on, it wasn’t pretty but we did it). There happened to be room for two couples and wouldn’t you know it, an amazing couple from Switzerland (our age) joined us. These two delightful individuals were on their honeymoon. We had great conversations comparing lifestyles of work life balance, how weddings differ in Europe than the states (they don’t have bridesmaids and groomsmen, who would have known?!), and sharing stories of what life was like during the pandemic. They were the prime example of perfect individuals to meet and make friends with on a vacation. Folks who you learn from, share laughter with, and who are able to open up your eyes to a different way of living.

The first place we sailed by and took in was the red rock beach. From there we saw the white beach, and then we got to deboard and jump into the “hot springs.” This excursion necessitated a forboding warning that pregnant, breastfeeding, and those with skin sensitivities should avoid entry into the water. This was due to the fact that this area contained excessive levels of magnesium, copper, and sulfur. Oh, and those wearing white bathing suits were suggested to avoid entry as well, unless they wanted their suit to change to a lovely red hue. When we entered the water it wasn’t necessarily “hot” per say (much like our hot tub actually), it was more so sporadic areas of warmth in the water that came and went. Much like when your friends (totally never you) pee in the pool. Regardless, we still had a fun time. Following that, we sailed a bit further and eventually dropped anchor (love that term) just outside an island mountain village that had a population of 350 people. Main purpose of this stop? To indulge in some absolutely delicious lunch provided by the yacht staff. Chicken, shrimp, mussels, and the BEST sausages I have had in a long time! The Swiss friends of ours and I went back for seconds even. More wine was poured and more beers were cracked open and we stopped at a final location, just outside the Caldera, where we swam for about an hour.

Soaking in the Caldera from the water was an absolute treat. You really have a different understanding of the feat that it is to build such beautiful buildings upon less than ideal terrain. Our time swimming was filled with laughter, attempted back flips, and new friendships. A couple (parent age) from Vegas who were on a THREE month cruise, a lovely couple from England with the most delightful British accents, one couple from the states who also happened to get married in NOLA (like us), a very fun gay couple (maybe? Never heard any label placed). One of the men said we may have recognized his friend, (we did not), and that would be because he was THE face of Match.com. Excuse me sir, do we look like an old enough couple to have met on Match.com? Rude (kidding, they were great).

Lastly there were two Asian women (close to our age) on the boat who weren’t as social as the others. I couldn’t tell whether it was us all unknowingly being racially bias towards folks who “looked more like us,” and “talked more like us,” and that’s why they didn’t conversate as much, or whether they simply preferred to keep to themselves, which would be totally fine, I get that! Overall, the decision to get the 20 euro more yacht tour was definitely an unforgettable moment of our trip that we couldn’t recommend more.

As our ship began to dock, I shot a message to our guy Themis, thanking him for a great recommendation and booking. I then propositioned, did he have any idea where we could get a reservation on the Caldera for the sunset? He said, he had the exact spot, and to be there at 7:30pm. We were stoked.

September 3rd, 2022-The Andromeda Villas

We were so stoked in fact that we left around 6pm to get pre dinner cocktails on the Caldera. Who wouldn’t want a lovely sunsetting view with an (you had to figure) overly priced cocktail? The thing about the Caldera is, the majority of the restaurants are associated with hotels. And if you don’t have a reservation at that hotel, you generally aren’t allowed to sit on their beautiful patio. Which is understandable, that’s how they keep it regulated and not too overcrowded. Due to this stipulation, our choice of pre game beveraginos was severely limited. We came across a bar that was open to the public, the drinks were definitely expensive, but we knew that coming into it. During the ordering process somewhere things got lost in translation and instead of ending up with their house red, we ended up with their house sherry, which was NOT a top choice by either of us. We had to plug the nose and put that one back. It was not at all delicious. To add insult to injury we bore witness to a really terrible situation. (Going into this, my wife warned me, Greece can be incredibly racist, specifically towards black people). In the middle of attempting to guzzle down wine that was far too sweet for anyone’s palate, we saw a beautiful French man, who happened to be black, come in with his white female partner. As they were merely setting their bags down at the table they chose to dine at, the bartender immediately begins to shout, instructing them they MUST go to the bar and order, there’s only one person working and you absolutely must go there to order, now! The accosted man responds incredibly politely, apologizes, and lets the bartender know they were just setting their bags down. The bartender seemed to not accept this, and the black man and his partner left, good choice. My wife and I looked at each other like, this bartender is hostile, and clearly bias because he didn’t react this way to anyone else who had come, let’s chug this awful drink and bounce! We did as such, and got out of there.

Due to our premature departure from cocktail hour, we arrived to our reservation about 30min early and arrived at the restaurant after some sleuthing about looking for the place, with another couple, older, slightly older than our parents’ age, clearly Americans. We just exude that vibe, you know? We happened to approach the hostess and explained we were a bit early for our 7:30pm reservation, she immediately responds with, “oh, you’re with Themis?” we responded “why, yes!” and we were immediately sat in the most perfect seats, right at the edge, completely unobstructed view of the most amazing sunset I’ve seen in a long time. I can’t speak more highly of Themis and this Air BnB, seriously! However, there was one little problem. As we sat, I happened to hear the older woman of the couple let out a little peep of sorts. Then I heard (the patio for dining was quite small, I promise I was not eavesdropping) that her and her (now) husband, had put money down for a deposit for their wedding reception to be here and then COVID happened and they weren’t able to get that money back so they chose to come and spend what they had put down. Oh, and their reservation was for 7pm. Having easily heard all these transactions, my wife and I looked at each other and knew what had to be done, we offered them our amazing seats. We reinforced it wasn’t a big deal, because it seriously wasn’t (we had already obtained prime IG photos let’s be real). They returned with the fact that they didn’t mind either, it’s not a problem what so ever, then after the battle of nice gestures, we relinquished our kindness and overtook the location. This led to the rest of the night being… quite lovely actually!

We talked with one another back and forth, asking what each other did, asking where one another lived, and yet when food arrived or when there was a necessary moment for silence or private conversation that took place effortlessly. Towards the end of their meal they realized there was no way they were able to spend all $350 of their deposit. They asked if they could buy us a bottle, we respectfully declined we were pretty well served at the moment, and then a pretty cool moment took place. They were able to convince the server to take the remaining $150 or so and give it to the staff, either via a tip or via buying food from the restaurant, for them. It really was a great dinner. My wife and I noted too, had this exact same scenario played out in the United States there would have been far different outcomes. They never would have let us sit 30min early, the couple NEVER would have let a millennial couple take THEIR seats, and there’s no way they wouldn’t have spent all that money on themselves instead of help the staff. It’s moments and interactions like this that really only come your way on international travel. I know that may come off as pretentious and uppity but, it’s true. Those who are experienced in international travel know that you have to be willing to go with the flow, you have to be kind to others, and lastly, you always have to show respect to those who’s country you’re in!

Oh, and this food? This food was pretty damn good. It remained expensive, $3 more than the previous night’s spot, but as stated earlier no more expensive than a dinner in West Loop and far better environment. When we left we remembered that the cleaning staff had unfortunately taken our wine glasses (actually all our glasses) and we had no vessel to partake in more of the country’s finest wines. So, we did the next best thing and headed to the market and got mini bottles of twist off wine. They weren’t great but, they weren’t great in Greece. That’s about all you can ask for. We indulged in the luke warm tub one more time and called it a night.

September 4th, 2022-Departure from Santorini

We were able to sleep well again and woke up just in time for another fantastic breakfast. We had an awkward amount of time left on the island before our transport (arranged by Themis again! Literally THE man!) was to arrive. Instead of lounge around we took the mini walk to Fira from Oia, took some lovely pictures, then quickly turned back around.

Apparently ferries tend to be notoriously late (if you are not at the originating port). This ferry was no different. As one waits on the Santorini port, there are plenty of options available for one to sit and obtain reprieve from the beating sun, however that all comes at a cost, low quality food and beverage for excruciatingly high prices. So, instead we found a sliver of shade under a tree in the parking lot, and hung out with a local who was organizing rides for ferry goers.

Drew's How-To's: The Best Air BnB Experience In Santorini

As I had stated In the narrative, this Air BnB experience was great, the location was great, and I couldn't speak more highly of It. The exact Air BnB we stayed In you can find here. As mentioned too, this location was great because the nightly rate Is far cheaper than staying on the actual Caldera Itself. However, It Is seriously a three or four minute walk from the hotel to the Caldera. Pictures of the actual room on the link are accurate, It Is quite nice and well kept. The hot tub looks over the ridge and gets the sunrise view, but within your picture will be a parking lot, not the sexiest thing In the world, but easily angled out of any IG photos. The breakfast Included Is worth the booking alone. Very good. And obviously, as mentioned, Themis, the guy who made ALL of our reservations was a gift from the Gods, old and new. If you have the opportunity to go to Santorini, I couldn't recommend this stay any more.

Drew's How-To's: The Best Yacht Cruise In Santorini

One of the best experiences we had In Greece was most assuredly the day cruise we had with Caldera Yachting. As mentioned In the blog, It was about 20 euro more than the "average" day cruises, but the small group size couldn't be highlighted enough. Sharing a big catamaran with only 14 other people was really nice. When the bar was open, It STAYED open. They had one of the best light sippers of a white wine I've ever had. The food they cooked for lunch was amazing, and vegetarian/pescatarian friendly. The staff were friendly, outgoing, and welcoming. And the 5 hour time frame was perfect for a not-so-early morning start and left you with the rest of the later afternoon and evening to do what you want.