I’ve been dreaming of wandering the dreamy streets of Santorini since I first saw the Sisterhood of the Travelling Pants movie over ten years ago! If you’ve seen it you’ll know what I’m talking about it, if you haven’t seen it then you need to take care of that. Perfect girls night movie! While there are so many people who rave about Santorini, there are also a lot who think it’s too busy and too expensive.
So I wasn’t quite sure how I would feel about it. The last thing anyone wants is a holiday that just ends up being stressful. But I am very happy to report that Jase and I both absolutely loved Santorini, it really does feel like walking around in a dream land. The buildings are too cute, the blue ocean views are unreal and the sunsets are magical. We definitely could have had a more stressful time, but we figured out the perfect things to do and ways to spend our time that made for a really relaxing time on the island and that is what I want to share with you in this post! So here it is, my guide to Santorini…
A Relaxed Guide to Santorini: The Dreamy Greek Island
When to go
If there is one big thing you can do to ensure your stay is more relaxing than hectic it would be to go in the shoulder season. I would totally avoid June, July and August. It’s not just the visitors staying on the island that make up the crowds, but some days over 5000 people pour in from the daily cruise ships that dock in Fira. Keep an eye on the daily cruise ships docking on this website and plan your days to avoid the crowds as much as possible. We went in early September and were able to avoid the crowds but after getting a tip from locals that October is still nice and warm, I would recommend October. I’ve also heard May is nice, but the water may still be a little cool to swim in.
Keep in mind that the Santorini airport is tiny… like one baggage carousel tiny. So be sure to get to the airport with more time than usual so you don’t miss your flight home. When there are multiple flights leaving it can get pretty crazy and crowded.
How long to visit
We had four full days in Santorini with two days either side for traveling. I felt like this was a perfect amount of time to take things easy and still see quite a lot. However I could have easily spent another day or two there. We didn’t get around to seeing Fira or a few other spots on my list. If you are short on time I would say two or three full days would still work, you would just have to be more selective with what you do.
How to get Around
The villages on Santorini are car-free and quite small, so very walkable. However there are lots of hilly areas which some people may struggle with. If you would prefer to stay away from the hills then take care to book accommodation that is easy to access. In between the villages you can catch buses or hire a buggy or car, which makes it really easy to explore the whole island. We opted for a car over a buggy because it just seemed like a more comfortable and safe option. Also I didn’t love the idea of wearing a helmet in the heat and not being able to escape the sun – I know, sounding very princessey!
A little tip we learnt – if you just hire a car for one day (which is all you need to see lots of the island), and you have an early departing flight, then hire the car for the day before you leave as your rental is valid for 24 hours. You can pick the car up from the village and then drop it off at the airport the next day and you avoid paying for a taxi. We used Vazeos Car Rental and found their customer service was amazing and very easy going.
Where to Stay
The two main villages to stay in on Santorini are Fira (the capital and where the daily cruise ships dock) and Oia (famous for the picturesque streets and sunsets). We decided on Oia because of how pretty it is. But it is also the most expensive place on the island to stay. Because this trip had been a dream for so long we decided to really enjoy it and book accommodation in the heart of Oia with views of the ocean. We also planned to have a relaxing time and hang out on our balcony quite a bit, so for us it was worth splurging more than we normally would on our accommodation.
It was also so nice to walk out the door and be in the prettiest area on the island. The traditional cave we decided to stay in – Roses Cave – is 300 years old and one of the original houses in the village, which has been dug into the side of the hill facing the ocean. This ‘hill’ is actually the inside ring of the mouth of the volcano (known as the caldera) that makes up the island – since the last major eruption (in about 1600 BC) the middle of the volcano has been flooded by the ocean creating the most amazing blue views.
I think our stay at Roses Cave will be one that will stand out in our memories for a lifetime, we could have sat on that balcony and stared out at the ocean views all day long, and in fact we spent the hottest part of our days (between 1pm – 5pm it’s really too hot to be out on the streets, even in September) there everyday. Rose (the owner of the cave) was also really helpful when we arrived and gave us all the local tips on where to go, what to do and most importantly the best places to eat!
Things to do
Wander the streets of Oia
We spent a lot of time in Oia because it was the main area we wanted to explore and also where we were staying. I cannot recommend enough to get up to see sunrise across the village. If you leave at around 6.30am you will catch the magical golden lighting and experience the cute alleyways in peace. It’s also the perfect time to get photos without crowds. There are so many iconic spots to discover in Oia, and it’s so small that if you wander around you will find them! But if there is any specific spots you like in my photos feel free to ask me for more details in the comments below.
You’ve probably heard of the famous Oia sunsets you can see from the castle area – and it is something you can’t miss! But to get a good spot at the castle you probably need to arrive two hours before sunset. We avoided this by booking dinner at a restaurant with the same sunset views, so we watched it in peace and quiet with a table full of amazing Greek food. I’ll let you know the name of the restaurant below. Oh and don’t forget to take a walk once the sun has gone down, the view from the castle at night is magical. The whole village is lit up.
Sail around the island
The perfect relaxing way to see the whole island – and another way to catch sunset without the crowds. We did our sunset cruise with Caldera Yachting because they take smaller groups for a more personal experience. Our yacht was gorgeous and the dinner they cooked us was so yummy! Just make sure if you want to swim in the thermal springs you visit on the cruise, don’t wear light coloured swimmers because the sulfur in the water will turn them yellow.
Visit a winery (or two)
As I mentioned earlier we hired a car for one of our days on the island. One of the stops we made was to Santo Wines Winery for a tasting. There are plenty to choose from on the island but this is the one we ended up at. The views are amazing and the wine was just as good. I really loved the sparkling white and sparkling rosé – had to try them all to know that though!
Explore one of the quieter villages
As much as I adored Oia I also wanted to see one of the more peaceful and untouched villages on the island. We didn’t have time to see them all so I picked Pyrgos because I had heard that it was really pretty as well as being the former capital, perched atop the centre of the island with amazing ocean views. It was the perfect place to stop for lunch! This was another one of our stops the day we hired a car.
Relax at one of the colourful beaches
On our sail around the island we learnt about all the colourful beaches on Santorini. There’s black beach, red beach and white beach. Black Beach or Perissa Beach is said to be the best for swimming and blue water so it’s the one we decided to visit this one. And it did not disappoint, it was actually so nice and quiet. We rented beach chairs for EUR10 (yes I found pink ones!!!). read our books and swam in the sea for the afternoon.
Places to Eat
There are so many cute cafes and beautiful restaurants to eat at on Santorini. We had most of our meals in Oia and here is my recommendation list:
- Post-sunrise breakfast at Vitrin Cafe Creperie: This cafe is in the cutest spot and you can sit upstairs with incredible views over the ocean. They have a menu full of delicious crepes.
- Breakfast with a blue view at Terpsi N Oia: With a perfect view of the iconic blue domes in Oia this was such a beautiful spot to start the day.
- Greek breakfast at Skiza Cafe: Another cute spot with amazing views, loved the Greek breakfast full of local produce. The coffee was not so good though.
- Blissful gelato at Lolita’s Gelato: The coconut gelato is a winner!
- Cheap and delish lunch at Pito Gyros: It’s true that Santorini isn’t the cheapest holiday you’ll ever take, so it’s good to find some more affordable meals and this place is perfect for a souvlaki or gyros. They even use traditional charcoal grills.
- Sunny lunch at Ammoudi Fish Taverna: We didn’t actually get to do this but it was on my list, go have a yummy seafood lunch by the sea at the port below Oia – You’ll work it off walking back up the stairs to the main part of town.
- Cosy dinner at Roka: Roka doesn’t boast the same view as many of the restaurants in Oia but it has the cutest courtyard with a cosy atmosphere and the food is really good.
- Sunset dinner at Elinikon: This is the restaurant we booked to see that famous Oia sunset near the castle, and our view on the rooftop was perfect. The traditional Greek mezze food was also amazing and more affordable that some of the fancier restaurants with views.
So yes Santorini is a popular place to visit and does get really busy during the summer months, but for good reason. It is absolutely stunning. And if you are a little more strategic about when you visit and how you spend your days you can avoid those crazy crowds and have a perfectly relaxing time on this dreamy island.
LIKE MY OUTFITS?
You can see more details about my outfits and exactly what I packed for Santorini here, you can also shop these items and support Jayde Archives at the same time by using some of the affiliate links below:
- Basic Tee
- Detail Top (sold out, similar here)
- White Romper (you could swap this out for a dress if you prefer)
- Pink Romper
- Pink Midi Dress (old, similar here)
- Denim Skirt
- Hair Bow (old)
- Hair Scarf
- Denim Jacket
- Sweater (old, similar here)
- Plain Swimmers
- Patterned Swimmers (old, similar here) (no I didn’t really need two pairs, but I wanted to embrace the last bit of summer)
- Straw Hat
- Leather Sandals (from Marrakech markets, similar here)
- Trekking Sandals (perfect for days with lots of walking)
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