You could spend a week or more in Santorini exploring the island or kicking back to watch the sunsets. A weekend is a good amount of time to get a taste of what the island has to offer.

From the dreamy blue domes and white villages clinging to the cliffs of the caldera to the dormant volcano, mud baths and turquoise coves.

Here’s how to spend a weekend in Santorini.



Peak is July and August so you’ll be fighting the crowds if you go in these dates. We’d normally recommend late spring/early summer when the island still holds its greenery or early autumn.

The first two weeks of September are great and when the sea is at its warmest but bear in mind, by the third week the island starts to shut down with reduced ferries, restaurants and pretty much everything.




Picking the right place with uninterrupted sunsets views on the caldera should be the aim here. Though it’s not the be all and end all as there are plenty of spots to catch the famous views avoiding the biggest crowds on the island.

Oia (for the sunsets)

Last time we were in Santorini we stayed in Finikia just outside Oia which is where you see all the pictures of the caldera and sunsets. It’s well worth getting a place with sunset views to avoid the crowds up on the main view points. And it means you can spend some time just admiring the views by your pool or in your hot tub with a glass of wine in hand. However, it’s not the only place to stay. 


Thira/Fira (for the buzz)

Fira is the largest town on the island and absolutely buzzing. You’ll find the largest selection of cafés, restaurants and shops here as well as the Archaeological Museum of Thira and the Museum of Prehistoric Thira. 

This is where the parties are and the town looks over the caldera and the volcanic islands of Palaia Kameni and Nea Kameni.


Imerovigli (to escape)

Imerovigli is perhaps the lesser known and quieter option, still on the caldera with the views you came for. Known as the balcony of the Aegean it’s the highest town on Santorini, right next to Fira. 


Emborio (local experience)

One to consider if you want to experience a more local way of life. You’ll find the town deserted in the day as all the locals head to the more commercialised towns for work, making it a great spot for pictures without the crowds.



Hands down the best thing we did in Santorini was ditching our bags and heading straight down to the winery. There are plenty of great wineries to chose from on Santorini so we’ve put together a few of our favourites so you can take your pick:


Domaine Sigalas (local feel)

We were staying up in Oia and actually walked down to Sigalas. Depending on where you’re staying it was a half hour stroll through tumble down shepherd shacks to a lovely little terrace to try some wine and nibbles. A great way to kick off your stay.


Venetsanos (dramatic views)

Venetsanos has the big views, perched on one of the most dramatic locations on Santorini, built into the cliff in 1947 on a rocky terrace with the stunning caldera below.


Gaia (close to the airport)

Gaia is on the sea line not far from the airport in a idyllic setting on the black sand beach. It’s a beach bum vibe and they even age some of their wines under the sea.
Tastings start from €8


Estate Argyros (oldest vines)

Find some of the oldest vines on the island. Originally trading from an old caravan in Episkopi Gonia, there’s now a pretty stunning winery in its place with vines that date back to the 1850s.
Tastings start from €15



The route from Fira to Oia captures the vast majority of the best photo spots you see in all the guide books. We did it in reverse and loved it. You’ll want to bring some water with you as there’s not many cafés on the way and have some trainers or the like but the walk is not too taxing.

It’s a great way to spend some time admiring the views and being out in the open. Was one of the best things we did on Santorini and only takes a few hours (3-5 hours) depending on how fast you walk/how many photos you take.

It’s not the easiest route to find the starting point, just make sure you’re heading to the caldera side rather than down the road linking the towns.


If you can watch this from where you’re staying then you’re winning. We’d would recommend avoiding the most popular spots as you’ll find it hard to get a decent picture without the crowds spoiling the view.

Sunsets from Akrotiri Lighthouse

One of the best spots to watch the sunset. It’s not crowd less but there’s far more space here and you won’t be bumping elbows with bus loads of tourists.

The lighthouse is called ‘Faros’ by the locals and seemingly changes colour as the sun goes down. (Though it is actually white). It looks spectacular as the sun sets and well worth the detour.


Or sail a yacht or a private charter. Depending on what sort of experience you’re after. You can catch more than the sunset as well with stops at the red beach, volcanic hot springs the lighthouse or even a hike to the sunken volcanic crater that formed Santorini.

Ammoudi Bay is where to head to catch a boat and watch the sunset from the sea and watch the light dance on the caldera cliffside.



There are heaps of great places to eat on Santorini and it’s not just the big name restaurants you should head to. Here are a couple of our favourites.


Fresh fish at Ammoudi fish tavern

If fresh fish is what you love, then this is the place to head. You may even find said and octopus hanging up to dry outside some of the taverns right on the water. Great for lunch or dinner and you might just spot some cliff jumpers whilst you’re there.


Lunch at Salt and Pepper

This one’s in Fira, the main town. You’ll probably have to book. Everything is great and it won’t cost you the earth. A fab lunch spot that pulls out all the stops and beats some of the big name restaurants in many respects.


Affordable fish at To Psaraki

Making a name for itself as quite possibly the best seafood taverna for your money on the island overlooking the islands main fishing port. Daily specials and wine by the litre keep it affordable or there are far more fancy dishes to try.


Greek music at Santorini Mou

This was our surprise find on Santorini. On our walk back from watching the sunset and where we fell in love with Saganaki (with the feta and tomatoes) as a post dinner snack. The live music is hilarious making it a place we kept coming back to throughout our stay.



If you’ve got a bit more time in the Cyclades then hitting a few other islands is a great idea. Mykonos is the obvious choice but the lesser visited Milos would be our choice.

It might be a little harder/longer to get to but it’s well worth it if you’re up for a little exploration. From a beach that feels like you’re on the moon, to abandoned sulphur mines that are other worldly. Ancient theatres to hidden catacombs. Food baked in the sand and caves off the coastline. This is the Greece that needs no itinerary. An escape to a slower pace of life.

But for now we’re heading back to Santorini.



There’s an airport on the island with direct flights from London with BA as well as numerous indirect routes. Santorini Airport (JTR) is 6km outside Thira(Fira) and taking a taxi or getting picked up by your villa owner (if possible) are the best ways to get you to your accommodation.

You can also arrive by boat, ferry or catamaran from another island such as nearby Mykonos if you’re planning a little island hopping adventure. The ferry takes around 2 hours from Mykonos.


For your next swanky escape.