Derika and I just returned from an amazing vacation in Santorini.  We went for 10 days to celebrate our 10-year anniversary and our 3-year wedding anniversary. I can’t believe how quickly the time has gone…10 Years!  Santorini has been on both of our bucket lists for over 10 years now and I can tell you that it was worth the wait. We decided instead of island hopping that we would just relax and spend the whole time in Santorini. I did want to go and check out the other islands, but there is something so nice about arriving to a travel destination that you know you are going to be at for an extended period of time. It gives you some time to relax, and really get comfortable with your surroundings.

Instead of doing one huge post to cover all of the amazing things that we did over the 10 days, I thought that I would break it down into a few posts.  Below you will find a quick overview of my “9 Must Do Adventures in Santorini.” Make sure to click on the photos, because each section has its very own gallery with captions. 🙂


1. Take a Sunset Sailing Tour

Our actual anniversary is 4th of July, which happened while we were in Santorini, so I wanted to do something special for that day. When we travel I never really book any adventures in advance. I usually just research the heck out of a location, and make a list of all of the things that I would like to do. This way the vacation can happen organically, and when we are looking for something to do we can just refer to my handy-dandy list. Since I wanted the day of our anniversary to be a little special, I decided to book a sunset catamaran sailing adventure. This was one of two things that I planned in advance for our whole vacation. It was also the only day on the island that we experienced gale-force winds and white cap waves…go figure!

To my surprise they still put us on the catamaran…the waves were insane, but we had an amazing time aside from trying to avoid the puke slopping over the side of the boat from seasick passengers. I tend to get a little seasick, so I planned ahead and we were wearing Sea-Bands…if you are prone to motion sickness, I highly highly recommend these! The sunset boat ride consisted of swimming at a White Sand Beach (which you can only access by boat), swimming at Red Sand Beach (where we snorkeled and they fed us a veg-friendly Greek themed dinner), and we stopped at a volcano in the caldera to take a dip in the hot springs.  Our final stop was right outside of a town called Oia, where we watched one of the best sunsets of our whole trip! I splurged on the semi-private sailing tour and I would highly recommend it.


2. Go to Perissa for a Day of Fun at the Black Sand Beach

We ended up going to Perissa and Perivolas (these two beaches are connected) twice during our stay on the island. We fell in love with the miles of comfy beach chairs with cocktail and food service, the amazing black sand beach, the Mediterranean sea, cute shops where I bought my first romper, the endless rows of the most amazing open air restaurants that I have ever seen (with some of the best food that we had during our whole trip), and all of this was easily accessible by bus…Winning!


3. Open Air Cinema in Kamari

The second thing that I planned in advance while we were in Santorini was to go see a movie at the Open Air Cinema in Kamari. Before our trip I stalked their website and just decided to go for it. A movie with cocktails under the stars is my kind of evening! This hidden gem should be high on your list if you have a free evening in Santorini. Buy your tickets ahead of time online, and they will let you into the theater first, so that you have your pick of the seats. All of the movies are shown in English with Greek subtitles, and you can see the list of movies that are playing ahead of time online. Enjoy your movie under the stars, while shipping local wine and munching on buttery popcorn. It is soooo magical and the perfect way to end a long day at the Kamari Beach.


4. Sunset in Oia

Oia is known for its amazing sunsets and let me tell you that it did not disappoint. I would recommend making reservations at one of the cliff side restaurants so that you can enjoy your meal over a lovely sunset. This is one tip that I wish I had known in advance. However, as we were bumbling around Oia trying to get away from the sunset crowds, we got lucky and found a cozy bar right next to the Golden Sunset Villas (right near the windmill) with a great view and pitchers of sangria to enjoy with the sunset. Not a bad way to watch one of the best sunsets of your life!


5. Visit Some Wineries

Santorini has grapes growing all over the island. We were there just before crush, so we got to see the actual grapes growing on the vine…so neat! They weave the vines into little baskets and the grapes actually grow really close to the ground and not on grape trellises like they do in the US. We rented a car for one day with the goal to hit a few wineries and to see what other cool nooks and crannies we could find on the island. Stay tuned for a full write-up on some of our favorite wineries and tasty beverage spots on the island.


6. Rent a Car or ATV and Zip Around the Island

Usually when we travel to a different country we always rent a car so that we have the freedom to zip around as we please. However, the public transportation was so easy in Santorini, that we took advantage of it the whole trip. We decided to rent a car for one day, so that we could hit some of the wineries that were on our list and discover other parts of the island that were not accessible by bus. Over the course of the day, we found some amazing local cherries, drove up to the top of some mountains to enjoy the amazing views, ate lunch on the opposite side of the caldera overlooking the town that we were staying in and went swimming at some secret beaches… I highly recommend zipping around on your own for at least one day.


7. Eat Like A Local

Before our trip I was a little nervous about the vegetarian food options on the island. I was hoping that I would be able to eat more than just salads and Greek yogurt (even though I was really excited about trying the Greek yogurt). To my excitement I was pleasantly surprised with the vegetarian and the non-vegetarian options that the island had to offer. I did eat my fair share of salads, but the salads were jam-packed with some of the best tomatoes that I have ever had (sorry California), homemade feta cheese, and a boatload of other amazing veggies. I was just glad that I was not eating iceberg lettuce the whole time. Some of my favorite things I ate on the island was a fava dip, a lovely dish similar to hummus that is made from yellow split peas and olive oil and topped with capers and red onions. I also fell in love with Veggie Gyros, basically a Greek version of the California burrito and the Santorini Salad that was a salad packed with a ton of tomatoes, veggies, capers, feta cheese and topped with olive oil. For more info on the places that we ate at on our trip check out my ‘Eat and Drink in Santorini’ post.


8. Hike to Oia

So this recommendation needs to come with a disclaimer…all of the things I read about Santorini before our trip recommended that we stroll from a town called Fira to a town called Oia, to see the best views on the island. So on our third day of our vacation when we were debating on what to get into that day, I decided that it would be the best day to check the Fira to Oia stroll off our list. Going into this adventure I was picturing a lovely stroll through cliff side towns that would eventually land us in Oia, where we would hang out for the day and catch a sunset in the evening. Sounds amazing right??  What ended up happening, is that the “stroll” started out the way that it was described, but then took a drastic turn and became a full on hike, during the hottest part of the day, up and down huge hills with random spray painted rocks that were very few and far between directing our adventure.

I bet at this point you are wondering why I am recommending this adventure! So here’s the deal… If I had known that it was a full-blown hike before I took Derika on this adventure, I think that we would have been mentally prepared. The day before we spent the whole time drinking and eating rich foods…not the type of meal you want to start a hike off with. I like to hike, especially if the views are amazing and there is a tasty beverage waiting for me at the end. This hike totally had all of these things going for it, just know that it is a decent hike that will make you sweaty and you will get sunburned in weird places. It will take you a minimum of 2.5 hours with no breaks. So plan to do this in the morning or late afternoon (not during the hottest part of the day, like we did) and pack your water, your sunscreen, your hiking shoes, your camera and your sense of adventure! Yay! On this HIKE you will see some of the most amazing views, and you can reward yourself with a frosty unicorn beer and swimming in Amoudi Bay afterward.


9. Eat and Swim in Amoudi Bay

After our adventurous hike to Oia, we were hot, thirsty and hungry.  We stopped off at a cute cafe to enjoy some fruit ice, basically a Greek Slurpee and then headed off to downtown Oia to do some shopping.  Our main goal was to shop our way to Amoudi Bay in Oia , because I read a ton about the amazing seafood and the possibility of a swimming hole. We eventually found the bay, but we were shocked that we would have to trek down 300 slippery steps that were covered in donkey poop. I wanted to cry a little bit, but I wanted to swim more. So down we went in our sandals. You can hire donkeys to take you up and down the steps (because the stairs are that epic…hence the donkey poop on the stairs,) but I felt bad for them so we didn’t. We did not slip to our death, but we came close and we had to negotiate our way around some very moody donkeys at the bottom of the steps. Putting all of this aside, it was soooooo worth it! Derika claims that she enjoyed some of the best mussels of her life, and we also found the local swimming hole, which made me ALL of the happy! To find the swimming hole… when you get to the bottom of the treacherous stairs, make a left, walk through all of the open-air restaurants and follow the small trickle of people heading off around the cliff. You will be rewarded with a great place to go swimming and a huge cliff to jump off of!


Whew!  Now I want to go back….

If you are thinking of going to Santorini on your next travel adventure, stop thinking and just go. It was just as beautiful as all of the pictures and it lived up to all of my expectations and then some. If you are looking for a great place to stay, check out Ira Hotel (get a room with a caldera view).  It is located in a cute town called Firostefani just outside of Fira, and it is walking distance to everything you could possibly need.


6 thoughts on “9 Must Do Adventures in Santorini

  1. Lexi

    Hi! I just wanted to say thank you for posting tips about Santorini. I found your blog before my recent trip and many of your under-the-radar suggestions ended up being highlights of my whole vacation (Perissa, Tranquilo, Open Air Cinema). So, many thanks for the inspiration and great suggestions! 🙂

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