Whimsical, romantic and divine luxury are what comes to mind when I think of Santorini. This unique place on earth has been one of my dream vacations for as long as I can remember. Considering it’s one of the world’s top travel destinations, it seems like I’m not the only one.
I could give you an itemized list of where to go, but frankly, there’s just too many amazing options. And Isn’t half the fun finding your own favorites? 🙂
Instead, I’m going to map out the island for you and give you some basic info that will help you better plan your trip!


» If you envision your Santorini trip waking up to a crystal blue ocean view and having a cliffside pool to dip in, you will need to book accommodations in Fira, Imerovigli or Oia. These are the famous cliffside towns with caldera views.


» If you have no clue what the caldera is (I didn’t), here’s a quick lesson. Santorini is an active volcano, thousands of years ago part of the volcano collapsed into the sea. What was once an O-shaped island now looks like a backwards C. The caldera is the collapsed side of the island on the West Coast between Fira, Imergovilgi, and Oia.

The caldera side of Fira

» One of the most popular things to do in Santorini is to “walk the caldera”. The cobblestone path stretches between towns with stunning views of the volcano, sea, and of course adorable tiny white homes and blue domed churches built into the cliffs.

Everywhere you turn you will find the cutest little doorways!
Little restaurants and shops line the caldera path. (This one in Fira)

» While Santorini certainly has unique and picturesque beaches, you won’t be anywhere near the sea if you’re staying in any of the towns on the caldera; you’re way up a massive cliff.

» In Fira, Firostefani, Imerovigli and Oia, you will find the best luxury hotels. Even MORE important than the room is the pool and its views. That is why Santorini is known for some of the most stunning pools!img_0528

» Everything on the caldera side of the island is more expensive, from accommodations, shopping, and especially the food; the beautiful view comes with a price tag!

Niki is one of the ocean front caldera restaurants in the heart of Fira. I had to try the eggplant dip!


Niki Restaurant is pricey, but the food is delicious and the portions are big too!

» If you’re debating between taking the ferry from Athens or flying, flying Aegean is super convenient. The flight is just under an hour and cheap. Compared to other cheap European airlines like Ryan Air and Easy Jet, Aegean is my favorite. Where as most cheap airlines don’t give you anything for free, Aegean gives out cookies, candy, and a hand wipe on short flights.

» It’s important I forewarn you about the airport in Santorini. For this incredible destination, the airport is in need of some major help! It’s small, dirty (the bathrooms were always out of something), people practically piled on top of each other, and it’s completely unorganized. Leaving in the middle of the day was a mess, there are just way too many tourists for the small airport. So just plan enough time when traveling through, since you will most likely be waiting in a line out the door!

» If you are traveling to the Greek Islands for Ibiza style nightlife, then Mykonos is your best bet.

» Fira is the capital; it has the most shopping, restaurants, nightlife and the donkeys! If you’re going out late night, it will be in Fira, there are many options for clubs and bars.

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» Below Fira is the Old Port, you can either get from top to bottom by the cable car or the donkeys. (I personally felt so sorry for the donkeys hauling people up and down the switchbacks in the extreme summer heat).

» Firostefani and Imerovigli are great options to stay to avoid the crowds, they are a little more seclusive and yet very close to the action in Fira and Oia.

» Let’s talk about Oia! It’s the MOST photographed area of the island and is the best vantage point to view one of the world’s most famous sunsets. Like Fira, it is very touristy, catching the sunset here you will be amongst the crowds. Get there early to snag a spot to view it, the sunset is worth the praise!

Sunset in Oia
The cutest clocktower in Oia

» Santorini may not be famous for its beaches,  but they are uniquely beautiful in their own right. Don’t expect pristine white sand beaches; the volcanic beaches are amidst more natural settings with pebbles for sand in some cases. Most of the beaches are in the Eastern and Southern parts of the island. The most popular include The Red Sand Beach, Kamari Beach, and Perissa Beach. Some are only accessible by boat or short hike.

One of the beaches we visited on our Yacht tour

» While Amoudi Bay, the bay down the hill from Oia, is not a beach, it’s a great spot to go swimming and cliff jumping!

Amoudi Bay is a hidden gem in Santorini; adorable little restaurants line the water.

» Kamari, Perivolos, and Perissa are towns at sea level, they don’t have the outstanding volcanic views, but are very charming and walkable to the beaches.

» If you want to see all of Santorini, get to the hard to reach beaches, hot springs, lighthouses, and go swimming all in one day, do a yacht tour!

The natural hot spring we visited on our Yacht tour

» We booked a tour with the Santorini Yachting Club, and whereas other boats were filled to the brim with passengers (40+), we booked a smaller tour with a cool and calm, 15 people. It was perfection! Not only did we have plenty of space, food, and alcohol, but we got to know every person on board. I was so impressed with the authentic Greek bbq lunch; it tasted like a delicious home cooked meal. To top it all off, the toured ended with a front row seat to the sunset (without any crowds).

Greek BBQ prepared right on the water!
There is a reason Santorini is famous for its sunsets!


» Other activities not to be missed, wine tasting and hiking! Although the wine in Santorini doesn’t even compare to that of France and Italy, they take pride in their volcanic creation. There’s a few wineries across the island, and they even offer wine tasting tours.  As for hiking, there are many different paths to choose from, but arguably the best is the hike from Fira to Oia.


One of my favorite Greek dishes, Chicken Souvlaki
I could live on this! Greek feta and kalamata olives, you can find it almost everywhere!


» Transportation is something you should consider beforehand. You’ll need to either rent a car, ATV, set up private shuttles, take the public bus or take taxis. ATV’s are a great mode of transportation during the day (and fun activity to go off-roading), you will constantly see people zipping by on them.

» Our experience taking the public bus didn’t pan out so well. We waited at the bus stop to head to Oia for the sunset; it was already 15 minutes late when a private shuttle came by offering everyone at the stop a ride for 5 euro’s each.

» After the sunset we got dinner and then stopped at a bar for drinks. When we walked out to the main square to catch the bus back to Fira, we realized we had missed the last one. Since we were going to have to pay for a taxi regardless, we decided to make the most of it and have another drink at the bar. After the one(ish) drink more, we went back out to the square only to find out all the taxies were now gone for the night.

The cutest bookstore in Oia!
Little house in Oia

» If you hear people saying Greek’s have their own sense of time, it’s very true! Greek time is leisurely and not always accurate to what’s posted.

» Fortunately, Greeks are also some of the friendliest people, and when a lady closing up shop saw the two of us trying to figure out how to get back to Fira, she instructed the chef just getting off work to give us a ride. He didn’t speak a word of English, had to stop a few times to ask other locals where our hotel was, and then didn’t want to accept a tip. We were so thankful for his kindness!

Sunset in Oia



Hope this helps give you a better idea of what your trip to Santorini will look like. If I didn’t cover anything, feel free to ask below!



Jenny Habdas
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