Two Week Greek Island Vacation

Wow! What an absolutely amazing vacation we just had in the Greek Islands. Greece has been on our bucket list to visit as a couple for as long as I can remember, and we finally decided that 2023 was the year that we make it happen! Everything was literally perfect, and I credit that to the extensive research I did ahead of time to make sure we hit all the best spots and did all the best activities. We would do the entire trip over if we could, and I really recommend our itinerary to anyone who is looking to book such a trip. It would be perfect for a nice vacation, an adventurous honeymoon, or even as part of a longer trip (although I did feel like 12 days was plenty!)

This time of year (first two weeks of September) in Greece are picture perfect. Every single day we had 80F and sunshine, the water has warmed up all summer so it is perfect for swimming, and the skies were blue every day. We only had one sprinkle of rain and that was on day 1 in Athens. I swear traveling after Labor Day each year is the BEST time to travel. Kids are back in school so the crowds are way less than July and August, but there are still people there, and the weather is absolutely phenomenal! We plan all our trips this time frame!

Be sure to check out my three part Instagram Highlights titled ‘Greece’ so you can see everything that we did in pictures and videos!! Pure magic.

I had so many requests on Instagram to share where we stayed, what we did, and just overall HOW we planned it, so I’m diving in. Now note, we planned this entire trip ourselves with the help of recommendations from friends and family, but we never used a travel agent or any outside help for planning purposes. We really love to plan our own vacations because although it may take a lot more time and effort to make sure everything makes sense and we are staying in the best places/doing the best things, we feel like you can really customize your trip to make it exactly how you want.

How to plan a two week vacation

There are a few key things I like to think about when planning out vacations in new cities:

• Ask everyone you know for recs. I asked family, friends, Instagram, etc for their best recommendations for each city. I compiled a big list and then went on and individually researched each recommendation.
• Research where to stay – try to find places that are NOT touristy, places where locals stay, near areas with good food, and are popular among people your age.
• Use AirBnB to save money. Hotels were nearly double the price and with AirBnB you can be EXTREMELY picky and find the best location, tons of space in an apartment, and read thousands of honest reviews. We save so much money by using AirBnB and always have stayed in places that are incredible.
• Plan major activities for each city. Do not plan to just ‘walk around + explore’. This is boring and never works, so I highly recommend booking at least 1 activity per day. These can include historical tours, walking tours, food tours, classes, etc. Plan for 1-2 a day.
• Plan at least 2-3 hours of rest every day. No one wants to be overtired and you need to recharge. Don’t plan back to back to back.
• Plan meals ahead of time. Food is one of the MAJOR reasons why we travel, and we are huge foodies so take this with a grain of salt. There are so many touristy restaurants in many of these major cities, trying to usher you in, usually around tourist attractions. Please stay away from them. Do your research!!! Study bloggers who live in the area of the city you are going, use websites like Bon Appetit and Conde Naste. Make reservations ahead of time.
• Once all of the above is done, plan logistics. I put Tom in charge of all logistics, so he had to plan all planes, trains, and automobiles and booked everything ahead of time with flexibility when we needed it.

DAY ONE IN ATHENS

We flew from Newark to Athens on the Sunday of Labor Day Weekend – we often fly out of Newark instead of Philly because the prices are just that much better and this was exactly the situation this time. We left around midnight and arrived at 4:00pm on Monday. Athens was really only a quick pit-stop at the beginning of our trip because we actually planned to head out the next day on a 10am flight to Santorini! I had heard mixed reviews about Athens and basically took away that we only really needed 1 full day there, so we had half a day when we landed and then on the back end of our trip, we had another half day before we headed out. Honestly, this was plenty of time.

After landing, we grabbed a taxi (soo easy – we originally were going to do the train but realized that there were so many taxis with door to door service and it wasn’t much more $) and headed to A for Athens hotel, which is where we stayed. It is in Monastiraki Square which is a great location to place yourself for a night! They also have an incredible bar on top that has a great view of the Acropolis.

We immediately redeemed our ‘free drink’ ticket from the hotel at the rooftop bar! A free glass of wine, don’t mind if we do. Little did we know that this glass of white wine would be the first of MANY – we drank so much white wine!! After we finished that, we walked across the street to 360 Cocktail Bar which I had gotten a lot of recommendations for to grab a drink at. There is an incredible view of the Acropolis, but sadly, it was a little cloudy when we got there so we sat inside at the bar instead. I had one of the best (and most expensive lol) margaritas of my life there! It’s a spicy margarita and pretty popular, so make sure you try it.

After drinks, we wanted to get our first authentic Greek meal so we went to Efcharis for dinner and it was perfect. Truly authentic, cheap, amazing Greek food – we knew it was good when the place was packed with locals. Tom and I got a massive plate of meats and dips, along with a few appetizers, dessert and a bottle of wine all for $42. If you’re looking for a quick + delicious authentic meal in Athens, you must check it out!

With vibes extremely high, we decided to round out our night with a drink at the top of A for Athens. The view was absolutely spectacular and we were really so excited for an incredible trip to Greece!

DAY TWO – TRAVEL TO SANTORINI

An early morning flight had us leaving Athens pretty early. We headed to the airport, hopped on a flight, and got to Santorini an hour later. It was such a quick and easy flight! We arranged with our hotel (Charisma Suites) to pick us up from the airport because we quickly realized that having private transfers in Santorini is necessary. Any time we needed a car in Santorini, we arranged it with our hotel the day before or morning before and they were absolutely amazing with making sure we had rides.

They picked us up and took us directly to our hotel, Charisma Suites, which was an absolute treat to stay at. If you remember from our Italy trip, we typically like to stay in AirBnB’s when we travel, but after doing a bunch of research I quickly realized that most people stay in boutique hotels in Santorini. So off I went to the research land to check out hotels! We ended up using our Chase Sapphire points to book this hotel, so it made it ‘free’ for us. I always love saving up my points and using them on big trips!

Charisma Suites was an absolutely gorgeous hotel, it is based in Oia, which I personally think is the best place to stay on the island. Most hotels in Oia tend to be more expensive than Fira, but I found that Fira was more cheesy/touristy, although honestly, they both are touristy. Oia just felt classier and nicer. The hotel was built into the cliffs in Oia, and each room was like its own cave. The staff was extremely attentive, and they greeted us with fruits and a bottle of wine upon arrival. We had the most gorgeous room with a cliff-side view that was truly just breathtaking, and included in the hotel feel was a full gourmet room service style breakfast every day. You choose the day before what you want from their list of over 60 things (and you could choose them all if you wanted to!). It was epic to wake up to our delicious breakfast every single day and eat it outside on our balcony.

The hotel has two pools and the largest pool in Oia – it’s truly SPECTACULAR. And each pool has a bar, so if you choose to relax and spend some time out on the chaise loungers, you can sip aperol spritz and overlook the most gorgeous view.

As far as transportation, they were able to book us all of our rides whenever we needed to go anywhere. There are only 50 taxis on the entire island so I wouldn’t rely on getting a taxi…you definitely need to communicate with your hotel and this is another reason why a hotel is better than an AirBnB here. We absolutely loved our stay at Charisma Suites and would highly recommend it to anyone!

One thing to note about Santorini – it is FULL of steps. It reminded me a lot of Positano because sheesh!! So many steps, your calves will be screaming!

On our first day in Santorini, we walked around to grab lunch and explore for a while because that’s what we like to do anytime we get to a new location. It helps us to get our bearings for the area. A quick stop at the famous Pitagyros for lunch (yum!) and some more exploring lead us back to our hotel for an afternoon swim and relaxation. Tom loves pools and he will always go in! I read my book and sipped on a glass of wine…perfection.

We got ready for our first dinner in Santorini which was at Sunset Ammoudi. I made the reservation a month in advance, so definitely be sure that you do that if you want any good meals in Santorini! Sunset Ammoudi is at the bottom of the big hill, and while you can get a ride to the bottom and back up to the top, Tom and I are always looking for ways to stay active so we opted to walk down (and walk back up after dinner!). Its definitely very challenging and steep though, and there is a lot of donkey poop, so plan accordingly.

Sunset Ammoudi was gorgeous and delicious! You truly cannot beat the view of the caldera, you’re down right on the crystal clear water and it’s stunning. As the night gets darker they turn on lights in the water and all over, and its a beautiful place to be. As far as dinner goes, we split a bottle of wine, got the Greek salad (quick note – we got a Greek salad every single night of vacation. It’s incredible and a guaranteed way to get in more veggies each day) and we got the famous Lobster pasta. It’s expensive but boy is it incredible! It’s all over their Instagram and if you go and you like lobster, you have got to get it – worth every penny and we were both so full! After dinner, we walked back up the hill and out to the lookout to overlook the absolutely gorgeous view of the island. Definitely go to this at night!

In typical Erin and Tom fashion, we rounded out the night with gelato from Solo Gelato – it was perfect and I even ran into an ELW follower there! Perfect day and night!

DAY THREE – SANTORINI

This was our major adventure/hike day! We woke up to our beautiful breakfast spread on our little patio and were in awe of all the delicious food. We got all fueled up not really knowing what was ahead for us. We were told that we needed to hike from Fira to Oia for the most incredible views in a hike ever and so that was our plan for the day.

Our hotel driver was able to drop us off in Fira, where we basically realized we just have to start walking north towards Oia. There were a few signs directing the hike but it definitely was easy to get confused so just make sure you map out a plan before you go. People had said to plan for about 4 hours for the hike, so we got started at 10am so that we would have some down time once we got home before we needed to go to dinner.

The hike was absolutely beautiful, and at most points its really just a trail you are walking, but there are definitely some times that are pretty steep and you really had to use your legs! We also chose to go out to Skaros Rock which is another 30 min STEEP hike. Like think stairmaster for 30 minutes straight, we were cooking and were absolutely drenched in sweat after Skaros, but the views were the best of the whole island so I highly recommend doing it if you’re in good shape. We kind of just stumbled upon it but it was awesome! There were some other steep parts to the hike and we walked so much!! I think I had over 20k steps by 2pm.

We eventually got back to Oia and were absolutely sweaty messes and very tired. 7.5 miles later!! I knew our calves were going to be absolutely wrecked because we already had sore calves from walking up and down all the steps in Santorini, so after this hike it is going to be brutal!!

We got back around 3pm since we did Skaros Rock and we decided to head down to the pool to hang for a little while with drinks and swimming. It was the perfect day to hang by the pool after we were so tired. We stayed for a few hours before showering up for drinks and dinner.

I was very excited for our drink spot tonight – PK’s Cocktail Bar in Fira. I had gotten so many recommendations for it and it looked like such a gorgeous spot overlooking the water at sunset. This is a must if you’re ever in Santorini. Our hotel dropped us off there and we had the most beautiful sunset at PK’s – the drinks were also to die for. Perfect way to start a fun night!

Our hotel driver told us that we were very close to a taxi stand in Fira so that would be the easiest way for us to get to dinner and they were right! It was super easy to just grab a taxi and head to our dinner spot.

Dinner this night was the one I was most excited for. A few of you had recommended Metaxi Mas and after reading the reviews and hearing the description, I knew it was going to be the perfect dinner place for us. Authentic, delicious food that locals love, tucked away on the island not close. to anything else so you must drive there. The food rivaled some of the best restaurants here in Philly and everything was absolutely phenomenal!! It was the cutest setting, too, we sat outside with other locals and travelers alike. I cannot speak more highly of this place and tell you that you must go here for dinner if you are traveling to Santorini!!

The restaurant called a taxi for us on the way home and we ended our night there!

DAY FOUR – SANTORINI

The next day we woke up to our breakfast on the patio and got ready for our Catamaran Sailing Cruise. Part of traveling to Greece is all about enjoying the beautiful beaches and waters and I knew that we needed to get on at least two boat trips so we could see the beauty of the waters and the islands!! Per usual, I did so much research on finding the best catamaran cruise with the most amount of fun and I think I nailed it! We booked this one through Viator about two months before our trip. It was a 6 hour boat day with lunch and drinks included and we definitely took advantage of everything they had to offer!

The tour picked us up and dropped us off, too and that was amazing and made it very convenient. We got on the boat with 6 other couples and had an absolute day. Many of the couples were the same age as us so we ended up becoming friends with a bunch of them (we even had mutual friends!). The boat stopped in three different spots, docking at one of them for lunch, and at each spot we were able to jump in the water and take advantage of the floaties and swim time. Some of us jumped off the top deck of the captains area and it was a far jump, but so much fun!! I felt fearless this trip and didn’t want to miss out on any adventure.

The day went by so quickly and we were definitely all feeling a little buzzed by the end, it truly was a great time! They dropped us off back at our hotel where we napped for a little, showered, and got ready for drinks and dinner with our friends that we made on the boat!

We met them for drinks at Strogili (Aperol Spritz #5 of the trip for me! Haha) and then headed off to Elinikon for dinner. Both were perfect for the setting and the food at Elinikon was delicious! Best Baklava of our entire trip. Also highly recommend the honey sesame feta donuts. As insane as they sound! Perfect day!

DAY FIVE – PAROS

We woke up the next morning to another amazing spread, cleaned up our room, got our bags together and left them at the front desk before spending the rest of the morning in Santorini. We walked around a bit before we had to leave to head to the port for our 2pm ferry to Paros. Our hotel arranged a driver to take us there, so we headed out at about noon.

I recommend leaving plenty of time to get to the ferry. It was about 30 minutes away from our hotel, but there is only one road going into the ferry port and its packed with traffic, so be sure to leave an extra hour because you never know! We made it to the port and sat at a cafe and grabbed an aperol spritz.

Now as far as the ferries go, I had seen some really awful Tiktoks about how sick people are getting from the ferries. The boats are really small and the Greek Islands are notoriously extremely windy, which often times makes the boat rides really rocky and many people get very sick. I am one of those people who gets really sea sick, so I prepped myself and got nausea sea wristbands on amazon, along with these nausea patches for behind the ears, and I brought and took Bonine before the trips.

Luckily, we had a day with calm waters and the two hour trip was so easy! A breeze and nothing like Tiktok….

Once we got to Paros, we went straight to our AirBnB in Naoussa to check in. This was hands down, the most majestic AirBnB we have ever stayed in. The location is a two minute walk from downtown Naoussa, basically right downtown, but slightly away from where any loud noise would be. I had done MUCH research on where to stay in Paros..either a hotel or an AirBnB and I went back and forth until I found this incredible AirBnB with absolutely outstanding reviews and a perfect location. Also – Naoussa is the best place to stay when coming to Paros! It has the most activity and it’s really to easy to get around the island by car or ATV.

The owner Christos went above and beyond our entire stay. From several months out, he helped us book transportation from the ferry port to the home, he helped us make dinner reservations, and he was in constant communication with us. The place was GORGEOUS!!!! Right on the water where you catch the most beautiful sunsets on the front patio. It was super clean (which is a top priority for me) and overall just felt like a five star hotel. This was our favorite AirBnB!! Book this if you’re going to Paros.

We got settled in and then went to walk around and explore the town, which is what we always like to do when we first get somewhere. Paros was wayyyyy calmer and less touristy than Santorini and I immediately liked it so, SO, so much more. It was way cuter and had more charming vibes, although don’t get me wrong, Santorini is gorgeous and just incredible with everything being built into the side of the cliff. But Paros was more my speed and I loved the windy alley ways with beautiful pink florals against the white buildings.

We enjoyed sunset on our patio with an aperol spritz and headed to our dinner location at the popular Sigi Ikthios. We booked a reservation at 7:30 pm here but quickly realized that we were going to be one of the only ones at the restaurant so asked if we could push to 8pm. Turns out that in Paros, people actually eat closer to 9/9:30 – lesson learned for future and que me calling all of our reservations to push them back. This restaurant was in the middle of several popular restaurants and it was good – delicious, fresh food that we enjoyed (still on the Greek salad every night) but we also got fresh fish, fresh tzatziki, risotto and some fresh bread. Delicious! Looking back, our meals in Paros were top notch! But this would rank last – not for being bad, just strictly because we ate so many good meals.

After dinner, we grabbed a drink at Sante Cocktail bar which was recommended by a lot of you! Absolutely adorable vibes, outside seating, and a large list of incredible cocktails. Highly recommend coming here before or after dinner. And because I’m ridiculous, I decided we also needed dessert – we had seen people walking around with mini donut hole looking things and turns out there was a huge line around the corner for these Loukoumades which are Greek donut holes that are soaked in honey. You can get them with melted white and milk chocolate on top, and WOW!!! I’m normally a gelato after dinner type of girl, but I knew I’d be getting these again. An absolute must! We went to Loukoumades to Paradosiako – it’s famous and you’ll see it!

DAY SIX – SECOND DAY IN PAROS

We started the second day by getting breakfast at Almond which is a breakfast cafe that focuses on more health food but had rave reviews so we went and got a delicious breakfast! Smoothie bowls, yogurt & granola bowls, and avocado toast with eggs. It was perfect.

We picked up our ATV from Motorland ATV – Tom had called them two weeks prior and reserved our ATV, althought plenty of people just showed up day of and got one. We had planned a beach hopping day, so we hopped on our ATV and headed out to our first stop.

Kalogeros Beach – we knew we only wanted to stay about an hour at each spot, so we planned three. Kalogeros was our first spot and was the coolest! They have rock down on the far right side of the beach that when wet, turns into a natural clay that you can use to put all over your body and make a ‘mask’ – this was so fun! Tom and I both lathered up with our clay masks and then washed them off in the ocean. It was so cool to see how smooth it really left your skin.

Golden Beach – this was our next stop! It’s a popular windsurfing area because it’s on the windier side of the island. The water is so clear it’s really amazing! We swam, lounged, and just took time to relax at this stop. It reminded me of a Jersey beach, just a lot warmer and clearer.

Kolimbithres Beach – this was our last stop! This beach is basically a ton of rock formations that you can spread out and lay on. It’s really cool and you’ll see people laying all over. Tom loved exploring all of the different rocks and cliffs here. It was pretty busy!

We headed home after our beach exploring day so we could shower up and get ready for our next adventure, Moraitis Winery!

We walked over to the most popular winery on the island and truly had the best time sitting outside, getting a wine flight, followed by a glass of wine, and playing cards. There were a bunch of other couples and people there doing the same and it was a perfect way to spend a late afternoon.

The Moraitis Winery had absolutely delicious wines – Greece is actually known for their wine (mostly their whites) and Tom and I seriously crushed tons of white wine while we were there! Delicious!

Since we had time to kill before our dinner reservation, we grabbed another drink at a really cool cocktail bar called Stilvi. It doesn’t open until 7pm, but its so cool inside and a great place to grab a drink! We loved it so much we actually came back another night. Wonderful drinks!

After drinks, we went to Gemeni for dinner which was highly recommended. They write their menus by hand, which I absolutely loved! The whole place was packed so I definitely recommend making a reservation ahead of time – sign of a good restaurant! We got tzatziki, Greek salad, Mousakka, and fish. Everything was out of this world delicious!! Highly recommend.

After dinner we walked to get gelato at S. Cream and then went home. So good and perfect night!

DAY 7 – THIRD DAY IN PAROS

On our third day, we woke up and went to Ragoussis Bakery, which ended up being our favorite breakfast of the trip. The bakery is HUGE and filled with amazing baked goods, literally hundreds of different options of freshly baked baked goods. We were in absolute heaven and could not decide what to get!

They also serve regular breakfast, so we both got some combination of eggs and toast, and I also got a yogurt and granola bowl because the yogurt in Greece is just next level. To finish it off, we got the famous orange cake, which Ragoussis is known for (I did some research ahead of time). OMG, it was to die for! You must get a slice if you go. They even serve freshly squeezed OJ – you literally watch them squeeze it!

After breakfast, we took our ATV to Lefkes, which is another popular village in Paros. It really was so majestic and beautiful, super small, but the white houses with the pink flowers were amazing. We had fun exploring and shopping for a couple of hours before grabbing an afternoon coffee.

We had scheduled a cooking class at 3pm, so after spending time in Lefkes, we drove over to the area the class was in. I saw this cooking class on Tiktok and after reading the rave reviews online, I knew we had to book it! Everyone said the experience is very authentic and truly incredible. It was lead by Maria, a local older woman who has lived in Paros her whole life. She grew up cooking and all of the recipes that she shared were either hers or her families.

We were with several other couples, but Maria and her team truly got everyone involved in the cooking! We each had a role and they did a great job incorporating all of us. OH! Also, they continually refill the wine and want you to have a ton of fun! There is Greek music playing the vibes were so high, everyone was having a ball!

For the cooking class, we made spanakopita, a Greek quinoa salad, seabream with lemon, stuffed grape leaves, mousakka and baklava! It was amazing how much we learned and how delicious the food was….I would highly suggest this activity to anyone who is going to Paros. At the end, we all did a typical Greek dance!! It was so fun.

This is about when the fun started to turn when another couple we were with started getting upset because their ferry for the next day got cancelled due to high winds…

We started checking our ferry to Milos for the following night and it seemed okay for a while, until it eventually got cancelled and with only one ferry leaving Paros to Milos every day, that meant we would need to stay an extra night in Paros. We were worried because we already only had two days and Milos, and we weren’t sure if it would even be worth it to go, but we just had to wait to see how the weather was.

Our AirBnB host let us know that the ferries RARELY get cancelled (as they typically go even if the wind is bad) but apparently these winds were almost hurricane force winds (out at sea – mind you, the islands were so stunning and perfect weather so we never experienced it).

As far as finding another AirBnB, we didn’t need to because the people who were coming in to take our spot for the AirBnB couldn’t make it on their ferry, so we got very lucky and could keep all of our stuff and stay an extra night! We were worried we would need to find a hotel.

After figuring all of that craziness out, we went out to grab a drink downtown and then came back to bed. It was a long, but great day!

DAY 8 – FOURTH DAY IN PAROS

We woke up on our fourth day in Paros feeling much better about our plans but hoping that the wind would calm down for tomorrow’s new noon ferry from Paros to Milos. It was still showing really windy days so we were a little worried!

But we put our worry aside, grabbed breakfast again at Ragoussis (yum), and headed over to Monastiri Beach club via our ATV for a total chill beach club day. This is one of my favorite things to do when it comes to Europe, as you may remember our beach club day in the South of France last year. I always schedule one full day at a beach club, I reserve the chairs ahead of time, and totally just relax, read, and hang out all day, drinking aperol spritz and ordering from their beach club menu!

We picked this for our last day because we were supposed to take a ferry at 7pm, but since that was cancelled, we would now head back to our AirBnB afterwards instead of to the ferry port. But Monastiri Beach Club did have bathrooms and showers in case we needed to freshen up before our ferry.

We spent all day here and it was a dream. The water was crystal clear, super comfortable temperature, very calm, and we loved going in and out of the water. We ordered burger and fries and a chicken club, and several different aperol spritzes throughout the day. We ended up staying here until about 5pm when we headed back to shower and get ready to go out!

I think it was all a blessing in disguise because there was another restaurant that I really wanted to go to on the island of Paros, but with only having three nights and one night was a cooking class, I didn’t think we would make it, but turns out that we were able to!

Dinner was at Siparos, which ended up being our absolutely FAVORITE restaurant in Paros. Wow. It’s off the beaten path so you will need to get a taxi or ride your ATV but we wanted to have a few beverages and wanted to be safe, so taxi it was! We asked our AirBnB host for the name of a taxi and he helped us arrange it! Nice!

Dinner was so incredible…we got to pick out our own fish, we had the best tzatziki, Greek salad (of course, lol), fresh octopus that was caught that day, and they filleted the fish right in front of us!. Plus we had these little ice creams wrapped in phyllo dough for dessert.

We ended the night with one more drink back at Stilvi because Tom really wanted to go back! And then we got donuts again, LOL. Such a great day!!!

DAY 9 – PAROS TO MILOS

The next day we grabbed another breakfast, at you guessed it, Ragoussis. It was just so delicious and so close to our place that we knew it would be perfect, so why not! After breakfast, we grabbed our stuff and headed to the port via taxi. Our ferry ended up not being cancelled – woohoo!

With the wind being as bad as it was, the ferry ride was TERRIBLE!! This was the ferry rides that everyone on Tiktok was talking about…absolute rocky and i would say 30% of the ship was throwing up, the bathrooms were packed and all I heard was throw-up noises. NOT GREAT! I had loaded myself up on my nausea pills and patches and I was one of the only ones not seasick! I swear, prep yourself and you’ll be fine. I always get sick… so this was a miracle. Tom wasn’t feeling so great but he didn’t get sick.

We eventually made it, grabbed a quick lunch at Gyros of Milos (our favorite gyro of the trip – wow!), rented a car, and headed to our AirBnB. We had to cancel our ATV reservation because of the delay in our trip and we would need a car as a place to keep our bags the next day, so we literally walked up to a few rental car places in hopes of them having an extra car, and we got lucky! I don’t suggest this though, definitely make a reservation in advance.

Our AirBnB was in Mandrakia and it was BEAUTIFUL!!! Literally the most peaceful and remote location, right near the popular restaurant Medusa. This AirBnB was SPOTLESS, super clean and they had welcome snacks waiting for us. It was truly so beautiful and high tech – the owners were so so nice and easy to get ahold of – it was perfect. I wish we were staying longer than just 24 hours! Highly recommend this AirBnB if you are in Milos.

After checking in, we headed to Sarakiniko beach, which is alternatively called Moon Beach. It is the coolest beach, lots of cliffs and ultimately it looks like you’re on the face of the moon. We hung out here for a while, explored, and while the water was too rough to get in, it was so cool to see! We checked out the town of Plaka on our way home and it was really cute. Such a small, little town, I loved imagining that I lived there. We were trying to cram as much as possible into one day since we only had like 30 hours in Milos!

The one meal I really couldn’t wait for was O! Hamos! in Milos. Its a farm-to-table family owned restaurant that is arguably the most popular restaurant in Milos. There are no reservations, and expect a wait, but they have a little spot across the street where you can get drinks.

The meal was one of the most incredible meals we had while we were in Greece. Everything is either grown on their farm or lived on their farm. The whole menu is handwritten and everything is so cheap compared to America. We got a pitcher of wine, Greek salad, Tzatziki, Saganaki, fried meatballs, and pork shoulder. WOW WOW WOW!!! All so delicious. Then we got two desserts to split! The orange cake with chocolate and the pudding – incredible!

DAY 10 – MILOS

Now for my very favorite day of the entire trip. The whole reason why I didn’t want to miss out on our Milos part of the trip was all for this day. We had a 9 hour boat day tour planned with Oneiro Boat Tours that several of you had recommended to me and told me NOT to miss out on. Well, I totally understand why! This boat tour took us all throughout the island of Milos to the most beautiful water areas and beaches. Milos had hands down the BEST beaches of all the islands we went to, the water was so sparkling crystal clear, and I’ll share a bunch of unedited photos below so you can see the water!

But the best part about the boat? CAPTAIN ELIAS!!! He is the most precious, sweetest, proud captain that I’ve ever been on a boat with. He is a native of Milos and knows everything there is to know about the island. He takes you on a 9 hour boat cruise around the island, stopping at the most beautiful places for swims, relaxation, and incredible facts. At each spot, Elias got OFF the boat with all of us and took us to secret caves, showed us the best snorkel spots, passionately telling us everything we would ever need to know. My favorite part was when he literally said, OK – in the water!! He dove in and took us to a small cave that is tucked away under the rock formations and he had to use a flashlight to get us there! It wasn’t for the faint of heart or those with claustrophobia (you could stay back with the other people on board), but it was the absolute highlight. He had us seeing all the different colors in the dark cave with the amazing flashlight, and then would shine it down into the crystal clear water. This was the CLEAREST water I have ever seen – and mostly that is because of the white rock underneath. In order to get out of the cave we had to fit our head in this tiny little cave and hold our breath if a wave came! It was just incredible.

During the 9 hour boat day, the crew provided a delicious lunch with octopus, pasta, greek salad, endless wine, bread, and tons of snacks. They even gave us nuts and ouzo throughout the day! It was pure magic, we really didn’t want to get off the boat.

Huge thank you to Elias and his team at Oneiro sailing. This was hands down the best part of our trip!!!

After the boat, we quickly booked it to the airport where we needed to catch a 7:10pm flight back to Athens. It was a tight turnaround, but we made it.

Once we arrived, we went to our hotel and then grabbed a quick bite at Ella, then got some gelato (last one!) and went to bed. We were exhausted after that day!

DAY 11 – ATHENS TO NEWARK

We had to leave for the airport at 2pm, so we had half a day to explore Athens a little more, but we decided that instead of doing anything touristy, we were gonna shop a little! When aborad, right? We had a fun day shopping and I walked away with a few goodies!

We headed to the airport, hopped on the plane, and landed in Newark 10 hours later.

The trip was absolutely amazing, and I hope that some of you are able to copy this itinerary and experience the beauty of Greece.

Happy Traveling!