8 Days in Santorini & Mykonos Greece

Santorini & Mykonos, where do I even start?

I can’t put their beauty into words.

It’s 100% true what others say about Greece’s most popular islands, you can’t describe them in words or pictures or videos, you just need to see them with your own eyes to truly appreciate their beauty.

This was my first international trip across the pond.


Disclaimer: This post contains affiliate links. If you book or buy something through these links, I earn a small commission (at no extra cost to you).


The thought of going to Greece came into perspective in late summer of 2017 and almost one year later, that idea became a reality. I remember it like it was yesterday. As I was sitting with my girlfriend Amanda on a perfect summer’s night on her porch, we were discussing our must-hit destinations to travel to. Greece was a top three choice for both of us, along with Thailand and Costa Rica.


After countless hours of researching and deciding on the specific areas of Greece to visit, we decided on Athens, Santorini and Mykonos. Santorini and Mykonos are a top choice for many travelers because of the famous Caldera in Santorini and the beaches (and party’s) in Mykonos. The islands have a lot more to offer than just those two examples and I’ll talk about them in more detail in the paragraphs to come.

Planning the pursuit of happiness...

I booked our first flight to make sure we were on our way to our destination months before our scheduled departure date.

Usually you can find the best prices around 80 days out to a European destination from the US using sites such as SkyScanner.

Our round-trip airfare ended up being about $715, which is not a bad price, but not budget friendly either. A price I was willing to pay for multiple flights and destinations.

Our flight path would be from Chicago (ORD) to Philadelphia (PHL) to Athens (ATH) on the way there. And Athens (ATH) to Madrid (MAD) to Chicago (ORD) on the way back. With only one-stop there and one stop back, we were sure there was little room for delay.

Next up, we had to book our connecting flights to the island of Santorini and a ferry boat to Mykonos.

Then, another connecting flight from Mykonos to Athens. We chose to use Ryanair because of its cheap prices ($105 RT that included priority boarding, carry-on, checked bags) and short flight times.

We could’ve booked a ferry from Athens to Santorini, but it would’ve taken around 8.5 hours, not the time we wanted to sacrifice.


Ferry Hopper


We used ferryhopper.com to book the ferry from Santorini to Mykonos. The cost was $151.35 for two people and the cruise would take around 2hrs and 20minutes. After the main transportation was booked, we then looked into hotels, hostels, apartments and Airbnb’s. We ended up staying in a combination of almost all those options besides a hostel.

Traveling as a couple, a shared-room hostel just wasn’t going to be our thing this time around. There was a lot of research and time spent on finding the right hotels at the right locations wile keeping budget in mind. And as you know, location, location, location!

I use AirBnb to find many of my accommodations while traveling. Use the link below if you’re interested in saving $25 off your next stay on one of the most trusted travel sites.

The first place I ended up booking was an apartment near the Athens city center, about a half mile from the Acropolis. The Airbnb was called “Comfy Home in Vibrant Neighborhood”. Check out my YouTube room tour of this apartment and let me know what you think in the comments section of the video on YouTube.

Let’s start from the beginning of our trip, now that everything was booked, and we were ready for takeoff…

Day 1 - Leaving Chicago & The USA Behind

The day our flight was scheduled to leave, it was raining in Chicago. We were just dropped off at the gate of O’Hare International Airport by my sister and we then found out at the ticket counter that the plane was going to be delayed. We were told that the plane could not take off at the scheduled time because of the approaching storms.

However, when we were told it was going to be delayed two hours, we immediately realized we would miss our connecting flight in Philadelphia. No bueno!! We quickly asked the ticket counter associate to see if there was another connecting flight. There wasn’t another flight going to Philadelphia…until tomorrow. With a little bit of luck and a lot of patience, the lady at the counter was able to find us a flight to London later that day that had a connecting flight to Athens the next day.

So, instead of gambling on our plane to get fixed, we chose to re-book and head to London. We had about a half of day to kill before the London flight, so we headed over to the nearby shopping mall to kill some time.

We arrived back at the airport via Uber to head through security and wait at our gate. The original plan was to get into Athens around 9am 24hrs later and visit the Acropolis, Parthenon, Plaka and local taverns to eat, drink, etc. Unfortunately, that didn’t happen, so we missed our entire day in Athens. After what felt like the longest delay ever, we boarded our overnight red eye to London around 11pm Chicago time.

I slept for most of the flight and woke up just before landing in London. It was the next morning now and we arrived in anticipation. Our flight for Athens was in a few hours and we had time to kill again. There is not a lot to do so I wrote an article for the blog titled “Top 10 Carry-On Items”. Check it out!


Landing in Athens, Greece


We ended up getting into Athens International Airport (ATH) “Eleutherius Venizelos” around 7:45pm and by the time we grabbed our luggage and hoped in the taxi to our Airbnb apartment, it was around 9pm. We found a local place to eat near the apartment that served us some souvlaki, homemade fries and a tall glass of Mythos (popular Greek beer). The souvlaki was tender, moist and had just the right amount of seasoning.

It was my first experience in Greece and right away I noticed a huge language barrier. Most of the conversation at the restaurant was based on pointing at the menu and making hand puppets, it was hilarious. Our original waiter, bless his soul. had to grab somebody else from the pub who understood English so they could take our order.

After dinner we mustered up the energy to take a walk to the Acropolis, so we could at least see it from the outside. It was dark and we were super tired but how could we go to Athens and not get a glimpse of it, it’s one of the most famous landmarks in the world. Plus, we needed to walk off all that food we just had.

Just around the corner of the Plaka, which is a narrow cobblestone village near the city center, we could do nothing but stand and admire the Acropolis. There was something about the calm breeze and quiet streets that really made it special, even at night. Even though we couldn’t go inside, the positives were that there were no crowds to fight or the sun beating down on us. The negative was that we couldn’t go inside the Acropolis because it was closed for the day.

After aimlessly walking the Plaka streets, we eventually headed home for the night.

Day 2 - Flying from Athens to Santorini

We got roughly three or four hours of sleep before we had to catch our flight to Santorini, Greece at 7am.

Getting to the plane was a marathon though. ATH recently went through some renovations and let’s just say it’s a long walk. Don’t be surprised if you’re winded when you finally get to the gate.

It was cool that we got to go on the tarmac to board the plane. I’ve never been on the runway before and it brought a new perspective to boarding a flight, I felt like a rockstar!

It was a short fifty minute flight from Athens Greece to Santorini Greece. You couldn’t tell you were in paradise upon landing, it kind of looked like a baron desert. The airport is on the East side of the island and in the middle of nowhere, surrounded by sand, rocks and rubbish. We grabbed our luggage and scampered out of the small airport to hop on a bus for a few euros to the town of Fira.

Still tired from traveling the day before, we were dropped off a block away from Main Street. As we made our way up the long and steep hill of Mitropoleos, our checked bags pounded the cobblestone street as we went. Making it that much tougher of a climb to the top.



Fear not though as we were in for a delightful treat. I was awe-struck by the incredible view of the Santorini caldera, it’s astounding. The fresh ocean breeze coming of the Aaegan Sea, the smell of fresh buiscuits and coldcuts, it took my breathe away!



As we gazed in awe and stood there with out bags still in our hand, we didn’t but all notice our hotel was merely 15ft away. I was too busy being trigger happy with my camera as I kept firing away as many photos as I could.


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We sat and pondered about how we made it this far in the last two chaotic days, but we didn’t even notice our hotel, The Kavalari Hotel, was 20ft away from where we were standing. We couldn’t have picked a better location in Fira!! We were eager to check-in to our hotel and start navigating. Our check-in time was at 2pm and it was only around 9am but we were able to drop off our bags at the front desk for them to hold.



Pro Tip: Water is your friend, stay hydrated!



There was not much of an agenda for the day and we just wanted to take it easy before our hike to Oia later in the afternoon. We walked in and out of quite a few Santorini shops while taking a break to enjoy the beautiful views. A smoothie and an omelet sounded good, so we stopped shopping to eat. One of the best things about island life is that nobody is in a rush. It’s always “island time” and you really get a sense of that when you sit down at a local restaurant or cafe. Americans would classify the service as very slow, but it’s just the way the Greek culture operates. R-E-L-A-X-E



After getting lost in the narrow alleyways and peeking around every corner, it was time to officially check in to our first hotel of the trip. The check-in process was a breeze and before we knew it the hotel staff was carrying our luggage to our room. The sun really beats you up and as we learned, if you don’t drink a lot of fluid, you will get burnt out very fast. It didn’t help that we only had a little over a two hour slumber the night before.



I woke up from my nap refreshed and ready to go. I grabbed my camera and a few bottles of water and threw them in my backpack. Currently I am using a Sony A5000 mirrorless camera. It’s been a great camera to take pictures and also vlog on, I highly recommend it if your looking to get into vlogging without breaking the budget. Get it on Amazon here!



As we made our way up and down the numerous sets of stairs and down narrow village pathways, we could only stop what seemed liked every 10ft to take a photo or two. The hike was supposed to take roughly four hours, but we were way off the pace because of the heat and we made a few unexpected stops for more photos.



One of those stops was at Skaros Rock. Skaros Rock is one of the more famous locations in Santorini due to its large rock form shaped by the volcano blast dating back to 68,000 B.C. It has since been shaped by earthquakes and erosion. The best part about climbing to the top was looking back up at all the cave houses lined up on top of the caldera, such a site to see.


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As we continued our journey in and out of the shade, up and down roads and dirt paths, we started to run out of water and became hungry very quickly. The heat really started to take a toll on us and we found a corner convenient store just in time. Side-tracked, but now with some water and snacks we continued further to later realize that we weren’t going to make it to Oia for sunset. So, instead, we ended up at hotel Cilla. With an outside restaurant and bar to sit down at, we enjoy our first glass of  wine just before our first Santorini sunset! I would be lying if I didn’t say that taking the famous Fira to Oia hike is a terrible idea in the late afternoon, it’s just too hot. Don’t do it!



You’ve never experienced a sunset until you’ve seen a Santorini sunset, they are so beautiful. The sun looks so big and it feels so close, there is nothing like seeing it duck under the Aegean Sea. The sky is so vibrant, and the amount of colors are unlike anything I’ve ever seen anywhere else in the world. One sunset down and many more to go! We took a nice walk along the caldera edge to a bust stop that would take us back to Main Street. We didn’t waste any time getting to bed and recovering from the last few days. We were finally able to get a good night’s rest.

Day 3 - Boat Tour Excursion in Santorini Greece

Sleeping felt so good and waking up and walking out to the balcony was pure bliss. We stumbled around our room to find our shoes and made our way down the narrow steps to the hotel terrace to be served a homemade breakfast. Breakfast was included with our stay and was pleasantly tasty. As we discussed our plans for the day and finished up breakfast, we made our way back to the room to get ready.



We had a few hours to kill before our caldera boat tour, so we took a stroll again through the Santorini alleyways and stopped at the one with the best view overlooking the Aegean Sea for some much-needed cocktails! Afterwards we grabbed a couple of gyros to go and headed back to get ready for our excursion.


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Pro Tip: Bars with a view are more expensive so be prepared to pay premium prices.



Everything seems to be an adventure in Greece, after all we were in another country and couldn’t speak the language in the least bit. So, even finding the bus stop to get picked up for our boat tour was challenging. It was only a few blocks away but not having precise walking directions and not many people who speak English, it was harder to find then it should’ve been. The morning streets of Santorini were already bustling, and you could feel the energy starting to pick up for the day. We finally found “the old hospital” and while we almost got hit by a car, we held our invitation in the sky and looked for our bus. We noticed somebody shouting “Aphrodite, APHRODITE” and we knew that was our ride. The tour was $84.96 per person and includes dinner.



It was a short 20min ride from our bus stop to the port of Athinios, the main port in Santorini. We got off the bus and stood right in line to board The Aphrodite. The ship was beautiful. It’s rustic appeal, golden wood stained bow, double decker and bustling sails were something I’ve never experienced before, a real and genuine sailing boat.



We boarded the ship and quickly looked for the best spot on the boat to get a seat. Early bird gets the worm and we didn’t want to be stuck in the hot sun, so we chose a covered spot on the first floor near the back of the ship. Most importantly, it was right next to the bar! Ha! We figured we would have a great view of the ship and our surrounds and we sailed the Aegean Sea and boy, were we right. We happened to forget sunblock because I was more worried about my camera equipment, silly me, so staying covered all day was crucial. The ship left the port and we had a wonderful view of the caldera and the white and blue domes of Santorini as we looked back on the island.



Our first destination was the famous volcano of Santorini! After 20 minutes of sailing, we reached Nea Kameni’s jetty. We got off the ship and paid the 2.5euro/ per person (they dont except US cash) as an entrance fee to walk to the top. The walk to the top was a bit strenuous as it was very hot and the elevation changes that I could feel in my lungs. We stopped to take a few pictures on the way up and to catch our breathe. As we got higher and higher, the view become more spectacular. Once we reached the top, we had some fun taking epic photos of the landscape. We made our way to the volcano’s ridge and listened to our guide that explained everything about the history and the geology of the volcano.



As we embarked again to our boat for the next stop, we grabbed a drink or two before setting sail to the hot springs. The small island of Palea Kameni where the famous hot springs are located on the west side or the island were a bit popular with other ships and groups of tourists in the area. It was a bit crowded and felt un-natural to experience this place. The best part was jumping off the ship into the ocean. It was a good 12ft plung and it was so refreshing! The water was colder here until you got to the hot springs, which were more like warm springs. The water was dark, brown and murky and you couldn’t see the bottom or what you were swimming in. the waters are mixed with mud that they are full of sulfur, iron and other metals coming from the volcano and it’s said that they are very good for the skin, rheumatism, arthritis and other physical pains. I’m not so sure about that, but science is science, right? This was a quick stop and by the time we swam from the boat to the springs, we heard the ship horn to swim on back and we were off to our next location, Thirasia.



We pulled into the cove of Ormos Korfou and anchored. Again, we were offered to jump off the boat and we wasted no time jumping into the deep blue sea. I had never seen water so blue in my life, it was crystal clear and a very dark blue color. It’s hard to explain but the photos do a little bit of justice. We swam and took some GoPro shots before climbing up the ladder and getting rinsed off by the crew. The crew was adventurous and funny, the trip wouldn’t have been the same without them.



As we dried off and listened to the dinner bell ringing, we grabbed a plate and got in line. Dinner on Board consisted of a tasteful Greek buffet; pork, chicken, rice, baked potatoes, Greek salad, tzatziki sauce, bread, seasonal fruit and an included glass or local wine. The food was very good, and I waited for everybody to eat and the lines to die down before going back to see what was left for round 2. Full and feeling good, we walked around the ship to get a view of different angels. At this point we have disembarked and were setting sail to Oia for the sunset. The warm light cast brilliant shadows along the caldera and surrounding islands. Golden hour was upon us and everything looked straight out of a fairytale. As the sun dives to the sea in the northernmost part of the island, we settled in at a great spot to watch the sunset. This was an unforgettable experience as the Caldera and the village of Oia turned into gold. The tour could’ve not concluded any better as the sun set and we made our way back to the port.


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When we docked back at the port, there was some confusion about which shuttle bus to board. Overall the drivers were very unorganized, and we just wanted to make sure we were heading the right way. As English-speaking tourists, it was hard to communicate and figure out where we needed to be going with the bus drivers. Long story short, we made it back to our bus stop safely, albeit dropped off in a sketchy area a few blocks from the main street.




My final thoughts; I highly recommend doing a boat tour during your stay in Santorini. While most of the tours are the same, it’s important to read the fine details and make sure everything you want is included. A big deciding factor for me was deciding on this specific boat, I wanted an older sailing ship as opposed to a catamaran. Make sure to read reviews thoroughly so you know what you are paying for.

Day 4 - ATV adventure across Santorini

The next day started off much like the first, with a traditional Greek breakfast on the veranda overlooking the cruise ships and Aegean Sea. You are absolutely paying for the view at The Kavalari Hotel and its worth every penny. The morning dew on the blue topped domes, a slight ocean breeze, the sun peeking from behind the Caldera, birds chirping, restaurant owners cleaning up before the breakfast rush, store owners sweeping their entry ways; and this was what we could see from breakfast. It was one of my favorite parts of the day at this location. It was just perfect.



After breakfast we went to the front counter to rent an ATV for the day. The staff at the hotel was most accommodating and quickly attended to our needs, I can’t thank them enough for their hospitality.



Traveler Tip: I would not recommend renting an ATV if you are not an experienced rider. The traffic in Santorini is INSANE and it’s very dangerous.  Also, if you have two people and are sharing an ATV, make sure to get a 300cc or higher engine.



We signed the paperwork and our ATV was waiting just steps outside of our hotel. We packed the included luggage rack on the back of the ATV with beach towels, extra water and my camera equipment, I dialed in the GPS directions and off we went! Vroom vroom!

Our destination for today was Ammoudi Bay at the northern most tip of the island. I will prefix this by saying this was my absolute favorite place in Santorini! We took off from the Fira and navigated through the Santorini countryside on mostly the East side of the island. This side of the island is very different than the caldera side. It mostly consists of fields, bungalows, wide open roads, few people and lower elevation. Basically, the opposite of the sea side cliffs on the densely populated West side, its considered country living on the island. As we made our way to Ammoudi bay we were diving in and out of the huge rolling hills (which were more like mountains) of Santorini. The drive on the ATV was incredible and I’m so glad we chose to “ride” this one out instead of being in a car or bus.

We were able to see so much of the landscape and cover a lot of ground quickly. Finding the bay proved to be a little difficult using GPS as the GPS only brought us so far. Luckily, I did my research beforehand and recognized some landmarks at which to turn at. There were some signs but only every so often down the road, so it wasn’t crystal clear. What was crystal clear though, was the water in the bay, oh my god. Eventually we made it and parked on the hilly slope near the bay. rocky bend to find the swimming hole. The bay was stunning and a must-see. Down below were sailboats, restaurants, along with locals and tourists alike taking in a fresh seafood meal and the sights and sounds the bay had to offer.

Birds chirping, waves washing ashore, bustling wait staff and hanging octopus. We grabbed our things and headed on a short hike through the sea-side restaurants and around the bend. We must’ve stopped every 15-20ft to take in the view of the bay, the volcano or boats going by in the distance. Finding a spot to put our things in the bay proved to be a little challenging as the volcano rocks jetted, zigedg and zagged. Something like these water shoes HERE would have been very helpful! Climbing up a few of the boulders and neatly tucked away from most of the crowd, we stashed our things in a place we felt it wouldn’t get stolen. We changed into our bathing suites and made our way to the water.

One drawback of the beautiful bay was that the water was freezing. I found this odd, as this was the end of summer, the first week in September to be exact. There was a spot where everybody was jumping or climbing in the water and we made our way, albeit very slowly. The water was so cold it was shocking at first, it felt like my bones froze and at that instance I knew how Jack felt when he jumped off the Titanic. I might be exaggerating a little bit, but it did take a little while to get used to it. We stopped wasting time looking at each other’s frozen faces and blue lips and slowly crawled off the rocks in the water. We started swimming away from shore and before we knew it, we didn’t even realize we were cold anymore. Equipped with no life jackets and flotation devices, our destiny was right in front of us nearly at nearly 50 meters ahead.

There is a famous little church nestled on the side of the cliff stationed offshore. Locals and tourists alike dive off the cliff side into the sea, which is about a 25ft drop or so. After I arrived at the base of the cliff to make the climb up the wall of century old lava, I gave the look over to Amanda to see if she was going to join me. She thought about it for a second and she just wasn’t sure about taking the plunge. No worries I said, wouldn’t want a great trip to turn into a bad trip and risk getting hurt, plus I needed somebody to film my jump anyways. The GoPro Session really came in handy here! Ha!

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I had to be careful climbing up to the top because the rocks were covered in seaweed, algae and water, this wasn’t a man-made set of stairs. Once I was at the top looking back at the caldera and looking down at Amanda, it was totally worth it. The view was incredible, and I couldn’t wait to jump off the edge. I don’t really have a fear of heights, but I do have a slight form of vertigo. I knew the key to making the jump was to look at the edge quick and decide on my launch point and then step back a few feet, run and jump out. And that’s just what I did! I stepped back, took two and half steps forward, took a deep breath and belted out a rebel yell as I hung in the air for what felt like forever. I hit the water hard and tried to not panic but I didn’t realize how far down I had sunk into the ocean and came up coughing and out of breath. My ears had popped bad and my head started hurting a little bit.

I wanted to jump again but thought it was best to not chance it. I found another way up, the concrete dock on the side of the cliff was an easier route for Amanda to get a view for herself.

What a moment! Although I still couldn’t convince her to jump off the cliff, she did jump…off the dock, not the cliff. Next time, babeee! We jumped back in the water for a little bit longer, taking in the beautiful views and wading in the ocean. There weren’t many people out this far from the shore, so it was like we were there alone, and it was awesome. Before we got tired of swimming, we thought it was smart to head back to shore and check on our stuff. After we swam back, we didn’t stay too much longer because more adventure awaited. So, we picked up our belongings (which were not stolen, yay!) and headed back to the ATV.

The ATV seat was hot as the sun and we had to use our beach towel, so we could sit. As the bay got smaller and smaller in our rear-view mirror, we sped up the inclined street.

We quickly realized we were low on gas, like really low…so we pulled over to look at our next destination and navigation plans. We must’ve looked in duress because we had a few people stop and ask if we were OK and I said we were fine but needed some gas. I asked where the nearest gas station was and many did not know (dang tourists). Our worst fear set in as we were told it was back in town. We frantically checked our phone, comparing our GPS maps with gas stations we had Googled. Go figure, the nearest gas station was miles away. I don’t know how we made it, but we did eventually make it to the next gas station running on fumes. Once our tank was full, we could only help but notice that we were starving and needed to eat asap. Does the phrase HANGRY mean anything to you?!

We were back in Fira and on Main Street to stop at a local  gyro place. The gyro and fries here were OK but I would wait it out next time for a more authentic place had we have not been so hungry. Our stomach full and a couple of hours of daylight left, we headed to our hotel for the next two nights. This was an epic adventure in its own. The trip was only about 5min or so, but we took some questionable roads up and around the caldera, which on an ATV, seemed more like a mountain. Luckily, we blended in with all the other crazies on the road. I think renting an ATV is the most popular way to get around on Santorini. With dirt in our teeth and sand in our hair and riding down a couple of sidewalk/alleyways later, we found our next hotel, Kalestesia Suites! The suites are located in Akrotiri, which is in the southern part of the island. We wanted a change of scenery and a different perspective so heading to the southern part of the caldera was in the plans.

We checked in, got changed, freshened up and headed right back out the door to catch the sunset at the infamous Akrotiri Lighthouse. Although there were a ton of people there, it was worth it. Such a beautiful location on the edge of the southern caldera, surrounded by the warm tones of golden hour.

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As the sun set and the day turned to night, we headed back towards town but stopped at a local restaurant for some dinner. I have to admit on this trip I’ve had some of the best food I’ve ever experienced, each meal was so exciting to try something new. For those wondering or doing their research, the restaurant was called “Good Heart”. They are a traditional Greek restaurant and not the kind of touristy trap you would fine in some of the more popular towns. I had my first Crazy “Yellow” Donkey beer here as I’ve been wanting to try it since I first arrived. Crazy Donkey is well marketed on Santorin, as that’s the local brewery. After dinner we enjoyed our suite hot tub and gazed at the stars under the moonlight until we couldn’t keep our eyes open any longer.

Day 5 – Horseback Riding to Eros Beach

The next morning I woke up early to catch the sunrise off of our balcony and do some drone photography with my DJI Mavic Pro. We had a perfect location to view the sunrise rising from just on the other side of the hilltops. I was able to take some time lapse shots, you can view the video here!. Amanda and I enjoyed a beautiful made to order breakfast on the veranda of our hotel overlooking the ocean and bay. Our breakfast consisted of a veggie omelet, fresh fruit, tea, orange juice and hash browns. SO good!

Our main adventure for the day was a horseback ride to Eros beach. Around 9:15am a car picked us up from our hotel and brought us back to the riding stable. The stable was a small one in the heart of Akrotiri call Santorini Horse Riding. We stood in a room to get the shakedown of what was going to unfold, grabbed our gear and saddled up. I got the clumsy horse of the bunch or maybe she had too much to drink the night before but she was a bit clumsy. For what it’s worth, everything was fine and I managed but the horse seemed to stumble a lot. Better than Amanda’s horse though, it wouldn’t stop pooping!! And of course she was in front of me. What a view…

Luckily for you, you can skip the next couple of paragraphs and watch a video instead. I had my GoPro on and you can see the horseback adventure for yourself by clicking here.

We left Santorini Horse Riding and immediately hit the first trail. We walked past local farms and made our way through the sandy and rocky hills to the ocean. Getting to the ocean was a feeling of eureka! It was gorgeous and so refreshing. It was really hot out and if I had to guess the temperature, I would bet it was close to 90 degrees. I had only been on a horse a handle-full of times and this was the first time I rode a horse through water. It was really beautiful and I tried to enjoy every second in the moment. We stopped for a few photos and my only complaint was that we didn’t have enough time to take everything in. We took a slightly alternative route back but eventually came back to the same trail that led right to the stable. By the end of the ride I felt like a pro and I was ready to take the next step of my horse-riding career.

We had a great time and I would highly recommend this company if you are looking to do some riding in Santorini. While we did get to trot here and there, I believe we didn’t do it enough. When you ride in a group like we did, you can only go as fast as your weakest rider. The tour was meant for first timers and experienced riders alike. Amanda has been riding since she was 10 years old so she was ready to canter her way through the fields. Maybe next time!

The tour concluded with them dropping us back off at our hotel mid-afternoon. We had some time to kill before our dinner plans so we stopped at a few pottery and souvenir shops along the road and headed further south to check out Red Rock beach. Red rock was a short 15 minute drive from our hotel but we did have to make a couple of U-turns to find the correct roads. We specifically picked this hotel in the southern part of the island to make use of the location to see what it had to offer. The southern part of Santorini is just as beautiful but a lot less crowded. You’ll want to rent a car or have a means of transportation though because it’s not very walking friendly, things are too far apart to waste time walking around.

Our stay was short at Red Rock beach but we wanted to make sure we saw it if we didn’t get a chance to before we left the island. The views from the cliff are a sight to see. The sun beats off the red rocks and creates these beautiful colors in the water. It’s amazing how it just drops off and all the clay is exposed from years of decay. We snapped a few photos and headed back down to the trail to the parking lot, hopped in our 5-speed fiesta and made our way back to the hotel to get ready for our night out on the town.

Santo Wines was another 15 minute short trip from our hotel, I told you Kalastesia was in a good location! Santo ones is one of the most prestigious wineries on the island. We had a reservation booked for an hour before sunset, that would give us plenty of time to take in the views, order a flight of wine, an entree and a delicious dessert. So, we did just that! We order a flight of 10 wines and a pork tenderloin dish with golden roasted potatoes. The wines were OK in our opinion, we really only liked a few of them, mostly the white wines. The pork tenderloin and the potatoes though, were phenomenal! The pork was tender, full of flavor and hit the spot, not to mention the presentation was 5-star quality. We splurged on some dessert which consisted of strawberry ice cream and two warm dark chocolate brownies. Yummm!

However, the best part was our table next to a waist high glass window on the edge of the balcony of the restaurant. The best sunsets in the world must be in Santorini, I swear. The sun is so big, bright and full, I’ve never seen it like this in my existence. As we quickly took some golden hour photos and enjoyed every second before the sun set behind the horizon, the setting was something out of a fairy tale. Everything the light touched was so stunning looking and with 180 panoramic views, this was the place to be! Absolutely incredible, you must go…

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Feeling good and ready to mingle after our wine flight, we were ready for our next adventure of the night. We headed back to Fira to find a few bars and check out the local dance clubs. We didn’t have any luck at any dance clubs but maybe we weren’t looking in the right area or we didn’t want to pay an arm and a leg for a cover. Let me know in the comments below if you have some suggestions.

We took a stroll down the famous alleyways of Thira and found a local Irish pub called Murphy’s that we could hear from what seemed like a block away.


Bumpin’ – when the club’s so loud that you can’t help but dance and join the party!

There was no cover and everybody looked like they were having a great time so we stopped in, grabbed a few drinks and sang and danced the night away. After Murphy’s we headed to another hot spot right in the heart of the caldera nightlife called Tropical Bar. This bar didn’t close until the wee morning hours but we had to be up at a decent time but made it until around 3am partying with the locals and meeting other travelers from Denmark and Germany. The best part of this bar was the balcony for viewing the Fira skyline. After meeting our new friends and getting pretty tired as the hours ticked by, we called it a night and headed back to Kalestesia.

Day 6 - The Hangover & Sailing to Mykonos Greece

Waking up the next morning was a little rough, if you know what I mean. No complaints though, YOLO right?! Between my tech gear and all my clothes, I had to quickly throw everything in my suitcase and backpack to make our way to the Athinios Dock. The Sea Jet Champion 2 was going to take us to Mykonos, our next destination. The sea jet was more affordable then taking another quick flight. The cost for the two of us came out to be 133.60E, which is roughly $151 US dollars. Not only was the ferry cheaper but it was another way to see the islands and sail the Aegean Sea. The views leaving Santorini and coming into Mykonos were fantastic and very enjoyable from the rooftop observation deck.

We made a quick stop at Naxos Greece to pick up passengers and then were docking in Mykonos in no time. The ride was not too bumpy as the waves and ocean were tolerable that day. Overall the trek took about 2 hours and 15 minutes. Stay tuned for my video review of the Sea Jet Champion 2 coming soon.

We grabbed our bags and stepped off the ferry to meet our shuttle bus driver to take us to the rental car agency. We gave the Fiat Panda a once over and make sure everything was all good.

Pro Tip: Always take pictures or videos of the rental car before you drive away. That way, if there is any damage, you will not be charged when you bring it back.

If you’re keeping track of our expenses, check out my article breaking down the cost of our trip. This is our second rental car. Most rental cars in Europe are manual, so be sure you rent in advanced if you need to book an automatic but expect to pay more.

After navigating the narrow and curvy roads of downtown Mykonos and heading south to the beaches, we made it to Votsalaki Boutique Resort next to Paradise Beach. This place was something out of a Hollywood movie. Infinity pool, ocean views, personal bartenders and right next to the beach. The price to stay here is steep but in our opinion, it was well worth it. Read in detail all about the Votsalaki Resort here!

Since we had ourselves a long day and night the day before, we decided to take is easier today after our boat ride here. The first thing we did after throwing our bags down and getting changed was hitting that infinity pool. I’ve never been in an infinity pool and it didn’t disappoint. It was so relaxing floating on my giant popsicle floaty and looking out into the ocean with a drink in my hand. This was life and it couldn’t get any better in this moment. Complete relaxation and miles and miles away from home and work. My favorite cocktail had to be the Zombie dust , which was the special of the day. We ordered a bacon, pepperoni and BBQ pizza and it was the BEST pizza I had ever have. Oh my god, you don’t even understand. So good, like, so…so….GOOD!

After a couple hours of pure bliss, we got ready to head to Little Venice to catch the sunset. Parking is very limited in the area and we didn’t want to get our bumper smashed, pay a ridiculous parking fee or worse, get towed.

Pro Tip: Get to Little Venice hours before the sunset. Parking is very limited.

We finally found a place to park but by then it was too late and we unfortunate missed most of the sunset. We got to see the final minutes from the parking lot and it wasn’t the worst but it wasn’t very romantic either. Walking along the boardwalk that runs along Little Venice’s bay was gorgeous at night. The sea side restaurants and bars were gleaming and in full swing for the dinner rush. Romantic table settings and a perfect backdrop could be had at almost every restaurant. While the seaside places were a bit more expensive because of the view, we chose to stop at an Italian restaurant near the center of town that was more affordable called D’Angelo’s Italian Mediterranean Cuisine. As much as we wanted to sit seaside (you couldn’t see a ton at night), this place did not disappoint! Probably the best bruschetta I’ve had in my life and pasta dishes that would make your grandma’s knees weak. We didn’t have any room after dinner for dessert but we had to walk off those carbs.

Little Venice is magical at night. The quaint shops, the vibrant restaurants, the sea side bar escapes, all as energetic ambiance fills the air. Strolling in and out of alleyways looking for the best-looking ice cream was high priority for the night. We finally walked off our dinner and were ready to commit!

After grabbing some of the best gelato I’ve ever had, we continued to stroll along the lakefront and did a little bit of window shopping and people watching. If you’re keeping track and a foodie like me, you probably realized by now that today was food paradise for me. So many top choices and everything was so amazing. Doesn’t everything seems more amazing when you’re away from home?! Ha

Day 7

The next morning we got up bright and early to catch the sunrise off of our balcony suite. It was a beautiful sunrise and the location of the hotel is spectacular. Check out my time lapse video of the Paradise Beach bay.

After the sunrise, we hoped in the Panda and headed back to Little Venice for a quick photo shoot to see the city during the day. We learned quickly in Santorini that it gets so hot during the middle of the day that you don’t want to be outside or you get tired super quickly.

Our first stop was the famous windmills. A symbol of Mykonos’ rich past, the island’s windmills represented one of the earliest manufacturing units in Greece, showing the locals’ great use of innovation in their effort to harness the enormous power of the wind to grind local agricultural such as wheat and barley. It is said that there used to be 28 windmills all over the island, 10 out of which were located in the Kato Mili complex. Most of the windmills were built by the Venetians in the 16th century, but their construction continued into the early 20th century and renovations to the windmills are a constant work in progress.

It was great being there so early in the morning while the rest of the town was still nursing those Jager bombs from the night before. If you were not aware, Mykonos is considered a “party island” and most clubs and bars are open until about the time we got back into town. As we were strolling past with our water and breakfast bars, the club doors were swinging open and folks were just coming out. I was honestly shocked, Greeks like to party, hard!

We continued down the narrow alleys and found a spot to eat called “Crepaland”.  Crepaland is a popular European breakfast destination. We wanted to try a couple things off of their menu so we ordered an egg burrito crepe and a delicious waffle topped with chocolate ice cream, fresh whipped cream and a caramel drizzle. Desert for breakfast, sign me up!

We left Little Venice with our stomach full and headed to a private beach not too far from town. A quick 10min drive along the coast and down a very sketch dirt road, that seemed it was leading to nowhere, we found a parking spot. Today was definitely a beach day, as we ended up at three different beaches. This one is seldom talked about and not very big, but it was beautiful. It’s secluded and not easy to find so there were only a few locals besides us. Did I mention it’s a topless beach? I mean, you always have a choice to keep clothing on, but it was optional here. We are talking about woman and men…some things I would’ve rather not seen.

Well now that that’s out of the way, the beach itself was sandy bottom and pristine. The views were spectacular of the Aegean Sea and you could see plenty of ships,  boats and jet skis flying by in the distance. I went snorkeling for a bit but didn’t find much. I think the lack of coral and seaweed around the beach leaves the fish nowhere to hide so they don’t come close enough to the shore. There were minnows and other really small fish but that was about it. Nonetheless it was still refreshing to get out of the hot sun while Amanda worked on her tan lines. I felt the beach was too small to get the drone up in the air so I didn’t bother. On to the next beach!

The next beach was called Elia. The drive made me appreciate the Mykonos landscape, curvy roads and the hustle and bustle of local towns as we passed by. Parking was super tight near the beach and I was thankful that our Fiat Panda was not much bigger than a smart car. I became a parallel parking champ by the end of the day! Our parking situation was as close as it gets to being a disaster. We had about 8ft on a very steep hill to grab the last spot.

Most people fear driving in another country, but I look at it as a challenge. In America, things are so structured and organized, mostly because of the governmental laws and dense population. It is a bit crazy getting around but its organized chaos and predictable. If somebody is going too slow, they are going to get passed, no doubt about it. If somebody is going too fast, people will move over and get out of the way. There is a uniqueness to driving in Greece and much throughout the country that just makes more sense than what I am used to in the states. I like it, not to mention the curvy roads that make me feel like I’m back on the race track.

Anyhow, back to the beach! This beach was full of people, locals and tourists alike. Most had umbrellas for shade and beach towels to sit on, as there were not a lot of chair options. The bay was a little windy, but beautiful. The water was a deep turquoise and very clear, which made a good experience for snorkeling. The ocean floor was mostly rocks and coral for the first 15-20ft. You have to walk carefully or swim over giant slabs of rock/coral to find the sandy bottom and the gradual decent into the deeper waters led me about 75ft from shore. The boats passing and the tide made swimming difficult and I got tired quickly. I would consider myself a good swimmer but I’m not Michael Phelps. I was able to wade a little bit but then decides to head in to rest and catch some rays.

I was able to get some good GoPro footage here to include in my vlogs and you can see the beach and atmosphere in the video below. Last but not least on the Mykonos beach bucket list, Pinky Beach. I’m not going to lie, the only reason I knew about this beach was because of Instagram and the only reason we stopped here on our tour was because…. they have a famous swing on the beach, overlooking the ocean and it’s the perfect spot for some candid beach portraits. Check it out!

After the days beach tour we stopped back at our resort to rest up, take a break from the sun and get ready to go out for the night. Our destination was set for the popular 180 Sunset Bar. We navigated through windy city streets and almost missed our turn. There was a tiny sign on the side of the road, but the side road didn’t look promising. We made our way a few blocks are were still confused. How does such a popular place not have solid directions, signs or somebody directing traffic?

Finally, we made it to a parking lot and somebody was there directing traffic to park. The attendant didn’t speak any English, but we thought we were in the right spot. We asked a few others in the parking lot if they knew where we were and they confirmed, 180 Sunset Bar! YES!

The bar and restaurant is truly a unique and one of a kind experience. The 180 views (hence the name) are incredible, and the atmosphere has some super chill vibes to it. It was a good mixture of locals and tourists, but mostly Instagrammers trying to get that money sunset shot (guilty! ha). The drinks were very original, and the food was surprisingly good, although expensive.

We tried to hold off on food until after the bar but the drinks made us hungry and the atmosphere made us stay longer than anticipated. Which was a good thing! We ordered some sliders and enjoyed cocktails overlooking Little Venice and Port of Mykonos. Drinks averaged around $16 and food options were around $20-30. This is not a spot for the budget minded traveler but it is well worth it for the experience. I believe in experiences, and this was worth the price of admission and then some. Our night ended with lots of laughter and there was nothing more fitting than being at 180 Sunset Bar. Another great day in the books!

Day 8

Our last day saw us traveling to a lesser known destination called Fokos Beach. Not many visitors to the island know about this particular beach because its off the beaten path, literally. The twists and turns of the narrow Mykonos suburb streets took us eventually to a road that ended and gravel began. We went a couple of miles down the dirt and gravel road until we met a few Billy goats playing on the side of a cliff. I tried my best to get their attention and talk back with a series of specialty goat calls (total sarcasm by the way).

Once the road ended and we couldn’t drive anymore, we found a spot to park and grabbed our things to explore the beach. The beach was completely vacant and we had paradise all to ourselves. It was around 9am so we weren’t surprised but that was the plan all along, get there early and get a good spot! A 1/2/ mile stretch of perfectly white sand all to ourselves! The small bay is nestled between a few mountains (hills?) and is gorgeous.

I decided to fly my drone while there were less people out and Amanda wanted to get some sun while taking in a view of explorers on horses riding along the beach. If you didn’t know already, Amanda LOVES horses! The drone flight was somewhat successful and you can see some clips on my YouTube channel. I say somewhere because it was very windy along the coast and I kept losing signal. Rather than lose my drone, I decided to pull up and land before disaster struck.

It wasn’t long before we were joined by a few other nude beach go-ers. Did I say we were nude? Because…. we weren’t, don’t worry ;). But yet again, clothing was totally optional at this place, something to keep in mind for your planned travels.

The bay was a little hard to swim because of the wind so we didn’t swim a lot here. We mostly used the water to cool off for 5min or so and that was about it. You couldn’t hear much chatter along the beach besides the waves crashing and it was a perfect ending to a great adventure in Mykonos. I always like to end on a beach day to get some much-needed relaxation time and wind down before getting on the plane. Technically this was not our last day on our trip, but it was the last day in Mykonos before our big travel day home the following day.

We left the beach with a golden tan and sand in places we didn’t want it, but sadly, it was time to head to the airport. But, before we did so we stopped at a local place to grab some lunch. It was called Mykonos Oregano Cook & Grill and it was delicious. I had a Mythos draft beer, fresh garlic bread and a rice and prime beef with sweet pepper dish. It might have been my favorite meal of the trip! Amanda had stuffed chicken and rice, also very delicious!

After lunch we headed to the airport to take our Ryanair flight from Mykonos to Athens. The plan ticket was around $105 including priority boarding and one checked bag. Not a terrible price, but not cheap either. However, this was the most efficient way to get from Mykonos to Athens. We could’ve done another boat charter but it would’ve taken at least triple the amount of time.

In Athens, we would be staying overnight at a breathtaking seaside escape in Porto Rafti. Watch my video room tour of this apartment HERE. The bright holiday apartment was right along the ocean and was just a 25 minute ride to the airport. Because we were taking a very early flight out in the morning it was important that we had somewhere close by to stay. The apartment fit the bill perfectly as it had great views, comfy accommodations and was just a block away from quite a few restaurants.

We had a quick dip in the ocean before we got ready to head to dinner. Greece is a foodies dream and we had another great meal at Barco Cafe Bar Restaurant. Listed at number 6 on TripAdvisor’s top Porto Rafti restaurants, this Greek Pub and grill has plenty of delightful options, it was hard to choose. Ultimately, I went with the grilled chicken and sautéed vegetable medley entree.

Exhausted from our travels, we retired to bed to wake up in a few hours for the long flight back home. The flight to Madrid was scheduled for 4:50am and once we arrived in Madrid, we had a four-hour layover. Going home is never fun and a lengthy layover made me re-think even going home. I really wanted to explore Madrid and Spain! Luckily our flight wasn’t delayed leaving Madrid and we made it back to Chicago around 2pm (CST).

Our time in Greece was bittersweet and I can’t wait to come back to visit more of the islands.

Enjoy the full video from our trip below!

Total Trip Cost: $$$

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