Oh Santorini, how do we even begin to describe this beautiful place…

When you think of Santorini, or Thira as the Greeks say – you probably think romance, honeymooners and blue & white houses. All of this is absolutely true but there is so much more to this stunning little island…


Getting There


By Boat – After our whirlwind Athens weekend, we hopped on board the Blue Star Ferry ($40/each) and headed for the jewel of the Cyclades. We were both really looking forward to a week of sunshine and relaxation.  We chose the Blue Star line over the other slightly faster options because the ships are huge and you are allowed to freely move around the outdoor decks – fresh air is very important to us on a long boat trip! The 8 hour trip was very pleasant. It ended up feeling like a mini cruise ship, complete with bars, a restaurant and plenty of space to lounge around. If you plan to sleep on board, I recommend paying the extra €5 for the assigned airplane style seats. (Don’t worry, they have plenty of legroom!) That way you don’t have to worry about someone snagging your cozy spot if you get up to go to the restaurant or bathroom. We went for the cheapest seats, (unassigned) since we were happy to just sit wherever and get some work done. The people watching on the top deck was excellent. We also loved that unobstructed view of Santorini from the water as we finally approached it!


By Plane – Obviously, you can also fly to Santorini and skip the 8 hour ferry ride all together. Aegean Air has multiple daily flights from Athens directly there and plenty of other airlines offer flights from other European hubs. EasyJet and JetAirFly were just two of the budget airlines we noticed at the airport on our way out.


Where to Stay


There are 2 main towns on the caldera side of the island (these are the cliff front houses overlooking the volcano), Oia and Fira (the capital). The beach side has 2 main towns too, Perissa and Kamari, and is generally much more affordable.
After doing some quick research, we knew we wanted at least 5 nights on the Caldera side. It was our first time here, so we wanted the crazy postcard views!  We decided to stay in Imerovigli, a small village between Oia and Fira. We wanted the gorgeous views without the cruise ship and tour group traffic! And we couldn’t have been happier with our choice. Watching the sunset from our balcony each night was one of the highlights of our trip. Imerovigli is also the highest point on the Caldera which made the views even more epic.
We spent 4 nights in Kamari Beach afterwards, due to some travel plans changing and having a little extra time on the island. We figured we should get a feel for the beach side too! We found this great little studio on AirBnB. We highly recommend the beach towns if you’re on a budget, you can still wander over to the Caldera side to explore, without paying the inflated rates to sleep there!


sunshine from balcony imerovigli

dogs looking at oia santorini


couple walking in Oia santorini


Oia at night santorini


What to Do


As I mentioned before, some of our favorite times were spent sipping on some local wine and enjoying the view from our balcony. Santorini is a great place to slow down and take it all in. The natural beauty of this island is absolutely breath taking!


Hike – We spent one morning hiking along the cliff top from Imerovigli up to Oia and highly recommend it! Just make sure to wear good walking shoes, the volcanic ashy terrain is not the easiest to deal with! It’s quite a long walk, but the views are well worth the effort… Make sure to bring water and sunscreen, there isn’t a whole lot of shade up on the cliffs. If you are staying in Fira you can even hike all the way from there, it’s a great way to see all the smaller towns along the Caldera.  If you get tired, don’t worry there are plenty of nice little Cafes and Tavernas you can stop in for refreshments along the way. We walked to Oia and had a delicious lunch at Thalami then took the bus back to Imerovigli. If you are hardcore, you can walk back the way you came 🙂


hike to oia santorini


We also hiked up to the top of Stavos Rock, our balcony in Imerovigli was directly across from it. It is crazy how your height perception changes! Looking out, we didn’t realize how high up on the caldera we really were… Lets just say, climbing up to the top of the rock isn’t for people afraid of heights! Also, don’t forget to walk all the way down the path, there is an amazing little church tucked away behind the rock.


top of stavros rock, santorini.


Drink Wine – Santorini is very well known for it’s wine, the volcanic soil makes for excellent grape growing. A visit to a vineyard was definitely in order!  There are tons of wineries to choose from, but after reading some reviews and asking around we chose Sigalas. It’s a little out of the way and unique because it’s on the Northern part of the island, close to Oia. We noticed that most of the vineyards were further south. The wine at Sigalas was excellent! They have a couple of options for wine tasting, the complete line – 13 wines including four sweet varieties, or you can taste all but the sweet wines. We opted for the 2nd option, although the sommelier did give us a taste of his favorite sweet wine on our way out. It was an overall amazing experience, the wine was delicious, the staff really friendly and knowledgeable, and the whole place was beautiful!  People even have their wedding receptions here.. It’s obvious why! I recommend going close to sunset, watching the vineyard changing colors while sipping away is unforgettable.


Sigalas winery wine tasting


cheers at sigalas winery


Drive Around the Island – Make sure you rent an ATV or car for a day or two. It’s really fun to drive around and explore some of the more remote areas and beaches! We were so happy to have a car for a couple of days and skip the public transportation… There are buses in Santorini, but they are always very, very crowded and sometimes run late or leave early. The island life is super easygoing but as such can be slightly disorganized! We rented a car (50 euros for 2 days) because the evenings were still slightly too cold for an ATV to be enjoyable. Although the ATV looked like more fun 🙂 Definitely buy the extra insurance, the drivers here are pretty crazy!

Watch the Sunset –Enjoying the sunsets every night was the highlight of our trip. The elevation and the architecture of the white caldera homes is what makes this place really special. Every night, tourists gather at the edge of Oia to watch the sunset. It is VERY packed but worth seeing it from there at least once. The best places on the island to view sunsets are Oia and Imerovigli. We felt that the sunset from Imerovigli was more special, not because we were staying there, but because it was much more peaceful and serene. Also, since Imerogvigli is the highest point on the caldera side, the views are spectacular!

Imerovigli sunset santorini


windmill sunset oia


Other Stuff

Unfortunately we had a few days when the weather wasn’t cooperating.. Had we been luckier with more sunshine, we would have loved to go scuba diving! Santorini has a couple of amazing wrecks that even beginner divers can visit. The visibility wasn’t the best and the water was sadly too cold for these Floridians to enjoy. We found a wonderful dive shop in Oia, and we will definitely go out with them next time we are here! (hopefully in the late-summer so the water has a chance to warm up :))

Another popular activity, that we skipped, is a boat ride out to the volcano and hot springs. There are many options for getting out on the water… In each of the towns you will find shops offering everything from sunset cruises on luxury catamarans complete with champagne and dinner (90 euros +), to a full-day out on a big traditional-looking boat with snorkeling and a barbecue lunch (40 euros), to a quick island tour on a speed boat (20 Euros). We heard a lot of different opinions from people we met along the way. The general consensus was that the Hot Springs were still slightly too chilly to swim in (they are more like lukewarm springs) but seeing Santorini from the sea and getting close to the volcano made the boat rides well worth it and also, the catamaran cruises are awesome and romantic.

Dining in Santorini

The island is littered with restaurants, especially on the caldera side. The views from Oia and Imerovigli mean that you will be paying a premium for your meal. To find a more budget friendly option, head towards Fira and look for restaurants that are just off the caldera. Most of them still have some kind of a view, but are at a greater discount. Often times you will find them advertising a 2 person special for €30 or so which includes salad, main course, dessert and wine! Beach side, there are also plenty of places to try. Our rule of thumb was to look for the crowds, you can’t go wrong!

fish dinner fira santorini

One of our favorite spots was this awesome little coffee shop called Meteor Cafe in Oia. It’s along the path towards the ruins near the last fork in the street. The prices are high, but the atmosphere is incredible! Be sure to step out on the balcony for a pic.

Meteor Cafe Oia Santorini

girl meteor cafe oia santorini

Another spot we loved was, Why Not Souvlaki. This place is great, we enjoyed several 3 euro gyros in our time on the island. Cheap food and beer. It’s a hole in the wall, located in Firostefani, they also have a cute little garden area you can sit in to enjoy your meal.

In Imerovigli, check out Avocado for lunch or dinner. Everything we tried here was delicious, the Greek Burger was our favorite.

We enjoyed a tasty thai meal at Kiwi in Kamari. The food was a little overpriced (they charge extra for everything, even rice…) but still good if you’re craving it.

Interesting Spots You Shouldn’t Miss

Atlantis Books

While walking around in Oia, we stumbled across Atlantis Books. Located in the center of town, it is very quaint and wonderfully decorated. The story behind the origin of the bookstore is awesome. In short, it was founded by a couple of friends who fell in love with Santorini and moved there after finishing University and started selling books, and the rest is history… Be sure to pickup their Guide to Santorini and check out the great collection of books, ranging from a first edition of The Great Gatsby to beautiful copies of all your favorite classics. If only we had more room in our suitcase! Definitely worth stopping in.

Atlantis bookstore exterior santorini


Atlantis bookstore santorini

Akrotiri Ruins

Be sure to drive down to Akrotiri on the south side of the island. The ruins are amazing! The settlement was destroyed by a volcanic eruption in 1627 BC and is very well preserved, it might even be the origin of Plato’s legend of Atlantis.


Akrotiri ruins santorini

Red Beach

A visit to the Red Beach can be done while heading to Akrotiri. They are right next to eachother… This beach is very unique in that the sand is red and the volcanic rock has been carved out against the backdrop. It is quite a sight! Wear decent shoes, the sand gets very hot and it is a short but rocky walk down to the beach from the parking place/bus spot.

red beach panorama santorini

Red beach rocks santorini

Stavros Rock

As we already mentioned, a hike up here is a must! This imposing rock cannot be missed from Imerovigli. It dominates the view from the town and is such an incredible backdrop. When you are in Imerovigli, the scope of how tall it really is is skewed. When you look at the rock from Oia, it will blow your mind as to high out of the water it really is!

Imerovigli sunset from balcony

Black Beach

There are several black beaches on the island, Perissa and Kamari are both nice spots to check out. There’s a lot going on in these towns and plenty of beachfront bars and restaurants. Rent a chair and enjoy!

If you have an opportunity to visit Santorini, don’t miss it! Yes, this place is super romantic and a big honeymoon destination.. But it can also be enjoyed on a budget, alone or with friends! The locals are very friendly and there is always plenty going on. We can’t wait for our next visit! Leave us a comment if this makes you want to go 🙂

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Working Wayfarers is run by Daisy & Nenad. We are two millennials living life to the fullest. We share pics of our favorite destinations and some great tips and insights about living life unplugged. Click here to learn more about us!

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