Four Days in Santorini

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One of the most romantic and desired locations in the world, Santorini is a bucket list destinations. Because we were here during our second wedding anniversary, we celebrated in style while experiencing the other unique island activities!

Logistics:

Although there are many, many great hotels, here is where and why we stayed at certain places during our stay. I consulted a fantastic website, Santorini Dave, for help on everything in Santorini!

By Public Transportation

From either the airport, port, or any of the hillside villages, there are cheap public transportation options to reach city center. 

While I am not an expert (see Santorini Dave’s website), there are cheap buses from the main entry points and villages to Fira, where connections can take you to the rest of the island. Each ride generally costs €2 and is the nicest public bus you will see in Europe! The buses are former coaches and even have AC!

For ferries, I used Ferryhopper.com to plan and buy our tickets. The website and app are very easy and allows mobile tickets so you don't have to worry about printing.

By Private Taxi

Every hotel will offer a private transfer or taxi to any point of the island. While it is really nice, the cost quickly adds up as these are not cheap rides! Usually, it costs anywhere from €30-50!

By Private Hire

While we did not hire a car, we saw plenty of people who hired ATVs, scooters, or cars. There appeared to be more rental places than people! I would ask the hotel for any recommendations because most of the shops are not typical American car rental companies.

Lodging

Wow, there are an overwhelming number of options on Santorini. From posh boutique hotels to “cheaper” hotels, there are possibly too many options. I would start by choosing your village if you want a “classic” Santorini experience: Fira (the capital and hub of Santorini), Oia (sunset paradise), or Immergivil (boutique hotel heaven). Because we were only there for a few nights, we first began in Immergivili and then went to Oia once our friends Kelly and Sarah joined us.

After researching for an hour or two, I finally gave up and went with two hotels that either I followed on Instagram or came recommended by a friend. I couldn’t take the overwhelming number of choices and decisions! In the end, we learned there is no “bad” view and even if you pay for the private and super lush hotel room, you won’t have absolute privacy.

Cocoon Suites

In Immergivil, we chose Cocoon Suites for their classic Honeymoon Suite. With a gorgeous views of the caldera, our room came with our own cave suite, pool, and fantastic cave bathroom. Our bed was extremely comfortable and one of the more unique rooms we have visited! At sunset, we were greeted by fantastic views from our pool. In the morning, we were greeted with a huge breakfast buffet with all of our favorite selections.

While we enjoyed every second, we are very curious why people pay this much for almost no privacy. We had constant views of our neighbors and visa versa. For over $400/night, I would expect a little bit more. However, the views are absolutely incredible and room is so unique so I get “why” people come here for romance!

Cocoon Suites

Chelidonia Traditional Villas & Luxury Suites

Once our friends arrived, we changed hotels to Oia. Seen in all Santorini postcards, Oia is picturesque regardless of the hotel’s location. While I would recommend the famous caldera view, we saw plenty of nice hotels with a “normal” incredible sea view. Our hotel was Chelidonia Traditional Villas & Luxury Suites, located in the heart of Oia. From the start, we had the best service on possibly any trip! We asked questions from hiring taxi to where MF could buy nail polish and the family run hotel provided an answer. For the service alone, I recommend this hotel!

Compared to Cocoon Suites, we had a more traditional cave villa with our own kitchen, outside patio, and two bedrooms. While our beds were a little uncomfortable, we enjoyed every other aspect! Every morning, they provided a picnic basket full of tasty treats like fresh fruits, bread, jam, honey, orange juice, and coffee. We noticed they had more “normal” luxury suites located further down the cliff. While we were jealous of their pool, we were satisfied with our cave villa!

Travel Tip: For the Greek islands, I relied on booking.com because Santorini Dave said most hotels are listed on this site.

Food & Drinks

While restaurants in Santorini may be overpriced, the quality is superb if you search in the right places! We could have eaten at many places, but we tried the recommended spots and again, highly recommend each of these restaurants.

Metaxi Mas: Listed first for a reason, our favorite restaurant isn’t located near any of the major cities. While we took a taxi and sketchy nighttime walk to reach this great taverna, the food was absolutely amazing! For our appetizer, we had a wonderful honey and sesame seeds feta cheese! For our main, we split pork fillets covered in feta cheese. Wow, that meal was fantastic! 

Pitagyro: Possibly our most visited restaurant in Santorini, this gyro shop is off the main street and perfect to help your budget. We did both eat in and takeaway and enjoyed every bite! I highly recommend the pork gyro pita!

Candouni: Sharing a fried saganaki cheese to start, we dug in and enjoyed the fresh cheese. For our mains, I had a tasty pork fillets with an apricot and plum reduction sauce while MF ordered the slow roasted lamb. The portions were the perfect size and we thoroughly enjoyed every bite! Not a bad way to begin our group trip!

Elias Grill in Kamari: While we may have been starving after our diving, Elias was a great local cheap eat off the notorious beach walk in Kamari. I ordered the meat plate and could not manage to finish it. It is a close second to Pitagyro, losing only because we did not like the fries as much.

Lotia Gelato: Near the Oia bus station, this hidden gelato shop has to be in my top 3 gelato shops in the world. I ordered banana and chocolate scoops and each flavor was freshly made that morning and had real banana and chocolate chips! 

Too Many, Too Few Days

While on our list, we ran out of time and room in our stomachs for these places, but they all looked amazing so they are worthy of a shout-out!

Vineyart: Off the beaten track, Vinoart is our hotel manager’s favorite bar and restaurant in OIa. Filled with local art and wine, it is perfect for a chill evening.

Click here for our Greece Google map pins for all of our hard research of the top food and drink spots!

Activities

There are loads of activities in Santorini although I think the best one includes a pool or beach to escape the Greek heat! 

In Oia:

  •  Wine Tour: On both trips, we have really enjoyed our wine tours, but we decided to do our own wine tastings at restaurants. I highly recommend Santos Winery below.
  • Main Street: Running through town, the main street has food, souvenir, and boutique shops. I recommend walking down at night rather than noon!

Outside Oia:

While we could lounge or enjoy Oia, we explored the other famous sights around the island. 

  • Navy’s Waterworld: As the only 5 star PADI resort, Navy’s offers two tank dives either shore or boat. We dove two great locations via onshore and swam on an underwater volcano!
  • Kamari Beach: Located next to Navy’s Waterworld, Kamari Beach has plenty of restaurants and offers the unique black sand for half the price of the highly rated and more famous black sand beaches mentioned below. Plus, it has better access via bus from Fira or Oia.
  • Perissa black sand beaches: Famous for the volcanic black sand, Perssia offers sun beds and more posh restaurants. Kelly and Sara went here for the day and loved it! There are plenty of sun beds and restaurants so take your pick! In high season, it may be best to reserve ahead of time.

Sunset Locations:

We asked our lovely hotel manager how to structure our sunset locations for our three nights. Just make sure to stay at your location for the afterglow that is about 20-30 minutes after the sun disappears. Here are his personal recommendations!

  • Oia: Possibly one of the most famous sunset locations in the world, Oia sunsets are crowded, yet spectacular. We chose to walk down a few steps towards Amoudi Bay rather than join the horde on top of the castle ruins. Bring a bottle of wine and settle down for the show! 
  • Akrotiri Lighthouse: Located on the opposite side of Oia, the lighthouse is a rocky and barren, but usually full of people. We decided against the lighthouse since we didn’t have a car and the winds were rough on our days.
  • Pyrgros Castle: Perched high in the middle of the island, Pyrgos Castle is a perfect location. We had the entire castle to ourselves!
  • Santo Winery: Near Pyrgos, Santos Winery offers spectacular views of the island and sunsets in addition to tasty wine! I wish we had one more night because we would have been here!
  • Sunset Cruise: Originally, we wanted to be on the ocean, but we noticed the boats sailed off as soon as the sun disappears. While scenic, you might miss on the afterglow!

Fixed Costs:

While Santorini certainly did not fit into our trip budget as nicely as other locations, we knew this was a once in a lifetime opportunity!

Onto Santorini

Beginning in the dark hours, we began our trip to Santorini by taking the Athens metro from Monastiraki to Piraeaus. Once in the port, we were surrounded by  huge ships and no clue where to look for ours! Thankfully, we found big signs located in a few places in the metro station and in the port stating that our ferry was leaving from E9. If only MF believed me the first time I found the sign!

Travel Tip: The Monastiraki metro stop is the perfect place to stay if you're about to go ferryhopping from Athens sightseeing. Just be prepared for madness at the port!

Despite the 5-6 hour ferry that stopped at 5-6 different islands, the ferry was all right. Compared to our expectations, the ferry ride was rather smooth and not bumpy so I considered that a huge win. Before we realized, we arrived in Santorini to the chaos that is their port. Thankfully, I pre-arranged a taxi with Cocoon Suites so we merely looked for our driver holding a sign with our name and away we went!

Is this Paradise?

Once we arrived at Cocoon Suites, I wondered is this paradise? We arrived at a perfect little cave suite, with a luxurious bed complete with a stunning view of the caldera from our private pool. Although our neighbors could see us and visa versa, we did not mind as we knew we found a little slice of paradise. 

After we changed into our bathing suits, we chilled and did not move. We ordered a tasty lunch via room service of a chicken club sandwich and greek salad. For the rest of the afternoon, we baked in the Greek sun and alternated between the chair and the pool. Although I think MF hogged the pool….

One Win and One Fail

During sunset, we had front row seats to one of the most spectacular natural events in the world - a Santorini sunset. Immediately, I set up the GoPro, iPhone, and Nikon Camera to attempt to capture the picture.

iPhone Sunset

GoPro Sunset

However, I don’t think the pictures do it justice especially the afterglow. I guess I see why people flock here for a romantic getaway….

After a major win, I attempted to feed my bride on our two year anniversary. We originally wanted to order souvlaki via room service, but the hotel sold out of the dish. Thus, I searched this tiny village for any takeaway as there was no way I was getting MF to walk up and down stairs for food! I ended up with a terrible takeaway that I wish I didnt get… Oh well! At least the bed was extremely comfortable! MF even took pictures of the bed and sheets brand for future use!

From One Paradise to Another

On our first full day in Santorini, we switched from a morning paradise to another paradise as we welcomed our friends, Kelly and Sara from London.

One Night is Not Enough

Because we only had one night at Cocoon Suites, I woke up at sunrise to take pictures! Although I did not last that long because the thought of climbing stairs that early sounded awful and the bed was that comfortable!

Once our appointed breakfast time arrived, the kind bellboy/handyman/person who did everything, delivered our huge breakfast. Last night, we ordered everything from yogurt parfaits, croissants, cereal, and scrambled eggs with prosciutto. Unsurprisingly, everything was delicious and we didn’t even have to leave our balcony! Now I see why people stay at the luxury suites… 

Before heading off to the next paradise, we attempted to take great photos using my iPhone but ultimately failed. Either we looked huge in the water or we just looked awkward! Thus, while we failed at great photos, we enjoyed the pool until the very last moment. 

Onto Oia

After a quick transfer to Cheldonia, we were welcomed with open arms by the hotel manager who spent at least 20 minutes telling us the top tips and suggestions both in Oia and the island. Armed with useful information, we went to our traditional villa and ate our Pitagyro gyros and planned our Santorini stay. With COVID, most things don’t require advanced booking longer than 1-2 days so it is really easy to travel at the last minute!

An Oia Sunset

While I had seen Oia sunsets via other traveler’s pictures, I could not wait to see it in person. Deemed one of the most beautiful events, we all were very excited! Our hotel suggested grabbing a bottle of local Santorini wine and going to the stairs that lead to Amoudi Bay rather than join the hordes of people on top of the abandoned church.

Sunset from Oia

When we arrived at the stairs around 6:30pm, we were the only group on the ledge until 15-20 minutes before sunset when there was a crowd. As soon as the sun set at 7:40pm, the crowd disappeared and missed the afterglow. Thinking we saw the afterglow, we left around 7:50pm but sadly missed the best part that appeared at 8:00pm.

First Oia sunset

Travel Tip: Stay until the sky gets dark to avoid missing the entire show! Chances are you will be alone!

Candouni

While Candouni was not recommended by our hotel manager, Candouni was recommmended on Sara’s trip. Thus, we headed there in an attempt to grab a table as we were warned that reservations were likely needed as they recently started live Greek music. Thankfully, we nabbed an inside table where we could still hear the enchanting Greek music.

For our first meal in Santorini, we feasted! A family run restaurant, Candouni has tasty treats throughout the menu. Sharing a fried saganski cheese to start, we dug in and enjoyed the fresh cheese. For our mains, I had a tasty pork fillets with an apricot and plum reduction sauce while MF ordered the slow roasted lamb. The portions were the perfect size and we thoroughly enjoyed every bite! Not a bad way to begin our group trip!

Seeing the Other Side

Unlike most tourists, our first real day on Santorini was spent underneath the sea and on the beach in the lesser known Santorini villages.

Photo Mission

Like most amateur and real photographers in Oia, I woke up about 15-30 minutes before sunrise and hit the village. At this time and probably due to COVID, the village is empty and the morning golden hour is perfect! On my first day, I went to the most famous photo spot in Greece (most likely!) before attempting to find the quieter spots. While most people like the famous spot, I found a terrific view of the iconic blue domes just on the other side. 

Travel Tip: Use common sense when taking pictures in Santorini. I found several people to be distasteful when they climbed over walls and on top of homes or churches. If there was a rope blocking an entrance or doorway, I usually checked to make sure I wouldn’t be breaking any privacy. 

Sunrise

Either way, the photo mission was a grand success. I now know why people flock to Oia for stunning pictures!

Scuba via Navy's Waterworld

Located on the “other” Santorini coast (non-caldera), Navy Waterworld is five minutes from the beach and perfect for diving! We hopped in the dive car and headed to our dive spot located inside the caldera. Compared to other days, we had an incredibly windy day so the outside waters were rough but the underwater visibility and conditions were fine. We were going on an underwater volcano!

Scuba location

On our first dive, we were going to the famous “Lion’s Face” or Simba, an unique rock structure shaped like a lion. Thankfully, I got a few great GoPro pictures and it was really exciting!

For our second dive, it was a shallow dive called the cleaning station. Situated on a flat sandbank, if you hold your hands very steady, the fish would “clean” your hands by biting all of them. It was very cool!!!

Black Sand Paradise

Similar to our first volcanic trip to Hawaii, we were determined after a long morning of scuba to layout on the black sand beaches! But first, we went for traditional Greek souvlaki lunch! Our scuba guide recommended Elias Grill on the beach and it was a great choice! Ordering with my eyes, I had the huge plate of pork gyro meat while MF had the “slimmer” pork gyro pita. Boy it was tasty after a long morning!

Afterwards, we went into a food coma on the black sand beach. We napped, read, and enjoyed what was left of the Greek afternoon sun!

Sunset in Pygros

Compared to our first Santorini sunset experience, we went to a very small village of Pygros, about 30 minutes from Oia. Recommended by our hotel, the castle at the top of the hill offers unparalleled views of the caldera, surrounding villages, and most importantly, the sunset!

Similar to my morning photo mission, I went on my own to the castle ruins to set up the cameras while the girls drank at the popular Franco restaurant. While it was windy and cold by myself on the castle ruins, I think I had great pictures!

Castle Sunset

Metaxi Mas

While we thought Metaxi Mas was within the Pygros village, it turns out the restaurant was down a very narrow pathway in the nearby village. Because we saw the sunset afterglow, it meant we were walking down in the pitch dark! As I told the group, our walk was building character and emptying our stomachs!

However, Metaxi Mas is entirely worth a creepy, dark walk and whatever else it takes people to get there! One of the highest rated restaurants on the island, it is a neat hole in the wall with great views and an amazing atmosphere with large outdoor patios on a traditional Greek villa estate. For our appetizer, we had a wonderful honey and sesame seeds feta cheese! For our main, we split pork fillets covered in feta cheese. Wow, that meal was fantastic! The melted feta cheese combined with olive oil and oregano over tender pork fillets is a terrific dish that I definitely want to recreate! If only…

In typical Greek fashion, we were served homemade raspberry cheesecake. Yum! We definitely enjoyed it!!

Travel Tip: Even in COVID times, we had to book a reservation in advance. Regardless of the wait or distance, I highly recommend Metaxi Mas!!!!

Sailing and Hiking

On our final full day in Santorini, we wanted to be incredibly active from the ocean to land! 

A Sailing Cruise

One of the Santorini bucket list items is a sailing cruise around the island. Preferably, we wanted sunset, but the spots were completely booked so we went with a morning/afternoon cruise and I think it was the best “worst case” scenario! First of all, we had only 8 other people on our 55 person boat. Secondly, we had perfect swimming and laying out conditions! Lastly, we had much more fun because it enabled us to do a sunset hike!

Hot Springs

Sailing at 9:30am, we first went to the “hot” springs located off the new caldera. Initially, we were very excited to test the warm Aegean waters, but after we jumped into the cold water, we could not find any! Regardless, we had a great first swim here even if we failed to find any warmth!

Red Beach

After sailing for 30 minutes, we arrived at our next destination of red beach. Famous for sulfur colored red cliffs and red sand, the beach is currently closed for visitors due to landslide risks. Or so we were told… Our crew told us that people still illegally reach the beach and it is very dangerous. I am glad we chose to responsibly see the famous Red Beach rather than walk to it!

For our swim, we were annoyingly told to stay behind the boat which meant we couldn’t have any good views. Other than that, the snorkeling was subpar as it was a flat sandy bottom with no fish. 

White Beach

For our last and final stop, we went to famous white beach! With a very small beachfront and surrounded by white cliffs, this beach is much preferable to red beach or perhaps any Santorini beach because it is very hidden and private. Similar to Red Beach, we were told to swim from the back so we were blocked from these awesome views so we stayed on our yacht for some sun!

Scuba!

While we were at White Beach, the crew cooked us a rather tasty and simple souvlaki meal! They grilled fresh chicken skewers and vegetables with a tasty Greek salad. Yummy! We all were definitely surprised by the tasty lunch as we had low expectations for a large boat kitchen.

Afterwards, we lounged on the boat, soaking in the warm sunshine and Aegean sea spray as we sailed to the port.

It’s the Hike

For our last Santorini sunset, we decided to do the famous Fira-Oia hike along the island’s rim on the caldera side. Offering superb views throughout the hike, we were very excited - although part of us dreaded the heat and the long walk! From Oia, we took a bus to Fira, where we decided to skip 30 minutes of the trail by taking another bus to Immergivil. From there, we were lost and eventually found the path! 

Immergivil to Hills

From Immergivil to the hills, we had amazing views. We could see to the far left side of the island to the far right eventual destination of Oia. Combined with the descending sun, the caldera hike was perfect! 

Eventually, we made it to the shaded hills and it was a little bit easier although we faced more direct uphill walks and fading light. At this point, we were not taking a lot of pictures as we just had to get close to Oia so we would not be walking back in the pitch dark. I think the girls were scarred from last night’s adventure to dinner….

To Oia

With 3-4 minutes remaining in the sunset show, we made it to the scenic Oia overlook! Perched above Oia, there is a beautiful Greek Orthodox church with perfect views of the sunset over the village. With no crowds, we had the sunset all to ourselves!

Despite our rough appearance, we marched straight to Pirogyros and sat down for a delicious souvalki dinner. Perfect for carb loading after a 6-7 mile walk, our large plates or tubs of gyro meat was a great ending to a great day!

Jumping off Santorini

Before jumping to Milos, we had one final morning in Santorini where we took fabulous pictures and jumped off cliffs into the sea!

Professional Pictures

Rather than a final photo mission, we hired Nikola via AirBnB for professional pictures for our two year wedding anniversary. For once, it felt nice to not take the pictures and just enjoy the scenery as we posed awkwardly in the city. With COVID, it felt like we had the entire village to ourselves whereas normally the village would be very busy!

We began our professional hour by the windmills and had terrific photos there by ourselves. Afterwards, we went to the castle and had solo shots of the famous Oia sunset location. We then walked along main street taking photos along the path and in side alleys. For our final location, we went to my “secret” location so it validated by earlier photo missions! Surprisingly, we did not go to the (in)famous popular location, but I am glad as there were crowds and we wanted something different!

Jumping in Amoudi Bay

Located 270 stairs down from our hotel, Amoudi Bay is a quiet part of Oia partly because it requires 270 stairs up and down and partly because there are only 4-5 restaurants. However, it has one of the best kept secrets in Santorini. Around the bend is St Nicholas’ Church and a perfect spot for cliff jumping!

https://youtu.be/Mr4GNFKIK4M

After a quick swim to the island, we proceeded to jump 10 or so meters multiple times! I jumped four times, while MF jumped three times. I win! 
After our swim, we took the lazy way back to Oia… We called a taxi to the very top! We didn’t want to get hot and tired before our ferry trip to Milos later that day. Despite looking forward to our island hopping trip, we were very sad to leave Santorini!

The UnChartered Summary

Alluring Santorini is perfect for romance, adventure, and relaxation. With delicious food, amazing hotel and village views, and plenty of activities, we loved exploring every corner of the volcanic island. For us, we hit the bucket list and achieved perfect photos, sailed in the caldera, and saw the famous Santorini sunset.

  • While we liked our private taxis and transfers, the costs quickly added up! In hindsight, we should have utilized the excellent bus service for save money. I would recommend a private taxi once you arrive on the island as arrivals can be hectic, then switch to buses!
  • Between Oia and Immergivili, we preferred Oia because it has a village feel combined with amazing sunsets. Immergivili is slightly more better for couples and romance. 
  • At Chelidonia Suites, we had the PERFECT concierge experience. The kind hotel staff organised our dinners, activities, taxis, and much more! They had the best customer service and it easily made our Santorini trip!
  • Before splurging on a high end hotel, if privacy is key, you will have to pay a lot of money. Otherwise, you will be surrounded by neighbors and strangers with a bird’s eye view into our hotel space. While we did not mind it, we could easily people watch into rooms that cost thousands of dollars. Compared to other honeymoon destinations, I wouldn’t say this is my preferred spot unless you are willing to spend. 
  • Our favorite meal is still Metaxi Mas. While it is a trek to reach from Oia, the food and atmosphere is worth it!

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