Oia, Santorini
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4 Days In Santorini Itinerary: Your Ultimate Guide

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We’ve visited Santorini a couple of times, with our longest trip lasting a whole two weeks. In other words, we know the island pretty well! We also know that most people won’t want to spend 14 days doing a deep dive, which is why we’ve prepared a tight 4 days in Santorini itinerary that covers our fav experiences.

Of course, you must see the iconic views over the blue domes and whitewashed houses of Oia, but Santorini has a lot more to offer than just that. The submerged volcano that created the island has had a huge impact on the landscape and the culture, with black sand beaches and extensive vineyards to explore.

Our itinerary for Santorini takes in everything from seafood restaurants to the best places to spend the golden hour around sunset. It might be the modern architecture that has captured the world’s imagination, but we haven’t overlooked the prehistoric ruins nor the Venetian heritage of the island in this succinct guide.

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4 Days In Santorini Itinerary: Overview

Santorini Itinerary Map

Here is a little summary what you can visit in 4 days. We reccommend renting a car in Santorini at least for the last day.

DAY 1 📍 Oia
DAY 2 📍 Imerovigli & Wine Tour
DAY 3 📍 Fira & Sunset Cruise
DAY 4 📍 South Santorini

Day 1: Oia

Oia is a must-see on any Santorini Itinerary.

We’ve started our Santorini Greece itinerary at the most well-known place on the island: Oia. This clifftop village, with its whitewashed houses topped with bright blue domes, is famous all over the globe and provides plenty of opportunities for avid shutterbugs like us to immortalise that perfect holiday snap.

📍Morning Stroll & Photos

Blue-dome church in Oia.
Panagia Akathistos.

We always try to beat the crowds in the Cyclades by starting our days early. Particularly when exploring popular towns, we’ve found the mornings (pre-9am) are the best time to soak in the ambiance and get some fab pics.

Start at the Panagia Akathistos, a modern but distinctively designed church with 5 domes and a bell tower with 6 bells. From here, walk towards the Church of Agios Nikolaos, which hangs above the ruins of the old Venetian castle. 

Blogger Mal in Oia during 4 day itinerary Santorini.
Blogger Mal in Oia during Santorini Greece itinerary.

There are several iconic Oia viewpoints along the way where you can capture multiple azure domes popping out above the pure-white buildings set against the backdrop of the glittering sea. Only a small queue of people were trying to snap a pic when we stopped by in the morning, but it was a lot busier when we passed through again later in the day.

Blogger Mal in Oia near Kastro Houses.
Blogger Robin visiting Oia as part of Santorini road trip.

Continue on towards the Kastro Houses, another iconic Instagram spot that’s famous for having (shock, horror) orange buildings instead of the usual white! It might sound strange, but once you get there, you’ll see why it’s so popular. They really stick out like a (very attractive) sore thumb. It’s also possible to stay inside this upmarket hotel – but for quite a steep price.

Keep working your way around the hill face, and you’ll come face to face with the Oia windmills, picturesquely standing out against the sky.

📍Maritime Museum 

Maritime Museum in Oia.
Maritime Museum in Oia.

Once you’ve finished the little photo tour, it’s time for the history portion of our 4 days in Santorini itinerary. The Maritime Museum has an interesting mishmash of objects that cover the island’s seafaring past, accompanied by a handful of boards in English and Greek that give an overview of the essential details.

Santorini was one of the many Greek colonies that flourished in the BC era, back when it was known as Thera. Changing hands many times over the years, it functioned as a base of Aegean operations for the Byzantines, the Venetians, and the Ottomans before eventually reverting to the Greeks.

As a testament to that history, ship figureheads, nautical charts, model boats, naval uniforms, and loads of other items are crammed into the two-floor museum, which occupies a former home. 

📍Ammoudi Bay 

Ammoudi Bay is a must-see on 4 day Santorini itinerary.

Not far from the Maritime Museum are the Oia Steps, which wind downwards into the Santorini caldera. We found the hike quite steep but not overly difficult. Maybe bring a hat, though, if the day is sunny!

There are around 280 steps to get to Ammoudi Bay, a narrow slice of houses with a small port. There are a handful of restaurants here where you can eat some delicious seafood. We dined at the Dimitris Ammoudi Tavern, but to be honest, all the places here had similar menus and vibes. Just pick whichever one has the best seating available out by the lapping waves!

If you walk left along the coast from the restaurants, you’ll come to a small beach where you can take a plunge into the sapphire-blue waters and cool off.

📍Sunset At Oia Castle

Suset in Oia.
A sunset spot just below Oia Castle.

Finish off the first day of your 4 day Santorini itinerary with sunset views from Oia Castle. It tends to get super busy here during the golden hour, so make sure you turn up early with some refreshments to nab a prime spot. 

Don’t worry if that sounds like too much effort. We found a small path just under the castle, by the lower ruins, where there are equally gorgeous views but far fewer people camping out. In fact, when we went on our first night, there was no one there at all!

Day 2: Imerovigli + Wine Tour

About half an hour’s drive south from Oia, Imerovigli is a slightly quieter clifftop town. It’s at a higher altitude and offers a better panorama of the caldera, but it’s also not quite as photo friendly as Oia. It’s still pretty though!

The second place to visit on our 4-day Santorini itinerary, Imerovigli can be reached from Oia by car or by the convenient local bus. A route runs every half hour to an hour (depending on the time of day) from Oia to Santorini’s capital, Fira, stopping off in Imerovigli along the way.

Imerovigli is a must-see on any Santorini 4 day itinerary.

📍Church of the Resurrection of the Lord

The Church of the Resurrection of the Lord (aka the Blue Dome of Imerovigli) has the best viewpoint in town. From this vantage, you can see the cliffside houses at their most beautiful, with a perfect blend of architecture, sea, sky, and the rocky curve of the caldera.

This is actually where Mal splashed out to do a ‘flying dress’ photoshoot. You know, those cool portraits where the wind catches a silk dress, making it flutter dramatically in the breeze? It’s pricey, we can tell you! But it’s a once-in-a-lifetime experience that makes for an unforgettable souvenir – and a cool story.

📍Saint John’s Chapel

Blogger Mal in Imerovigli.

Our 4 days in Santorini itinerary is filled with fantastic photo opportunities – it’s one of the reasons people come to the island, after all! 

Another great place to capture a holiday snap is at Saint John’s Chapel, a short stroll along the cliff road from the Church of the Resurrection of the Lord. It’s right on the edge of the town, with nothing between the building and the sea except the ruins of the Skaros Venetian Fortress.

There’s often a queue here to walk along the roof of the church and get the perfect holiday memento. As with Oia, the best way to beat the crowds is to visit early!

📍Skaros Venetian Fortress

Blogger Mal in Imerovigli, near Skaros.

Skaros Rock is a striking natural promontory. Created by volcanic activity associated with the caldera many millennia ago, it’s one of the most memorable natural features in our 4 days in Santorini Itinerary. 

Jutting out into the sea, it’s easy to see, even today, after centuries of erosion, why the various civilizations that ruled Santorini thought this spot was a perfect place for a castle.

A whole fortified settlement actually grew up around the rock, with homes, shops, and monasteries, making Skaros the capital of Santorini. After a particularly devastating earthquake in the 1600s, however, the residents decided they’d had enough of precarious living and began to move to more stable ground! Around a century later, the site was almost completely abandoned.

Today, there’s nothing but a few scattered bricks left to indicate that anybody ever lived on Skaros Rock at all! Still, it’s a scenic locale to take enjoy a short hike and take a selfie.

📍Church Mother of Lord Theoskepasti

Blogger Mal in Imerovigli.

While you’re on Skaros Rock, don’t forget to climb down to Theoskepasti Church. A relatively new building, it’s hard to imagine that it’s a very practical place to go for worship, but it is attractively positioned so that it faces out to sea.

The track to the church is mildly strenuous, but the views are worth it. It’s a great place to watch the sunset, snuggled up with that special someone.

📍Wine Tour

Bloggers Mal and Robin on a wine tour in Santorini.

Wine is a key constituent of any 4 day Santorini itinerary. They’ve been making wine here for at least 3,000 years, rebuilding and regrowing over the millennia after devastating volcanic eruptions and destabilising earthquakes.

Although the volcano has been a destructive force on Santorini, it’s also gifted the island a unique terroir. For wine connoisseurs, that means the opportunity to sample unusual vintages.

For such a small place, there are quite a few wineries and wine tours to choose from, with options for most budgets. The fanciest ones boast a professional sommelier as a guide, who will take you through the most famous local grapes, like Assyrtiko, Nykteri, Athiri, and Aidani.

We pretty much went middle of the road with the tour we chose, sampling a whopping 12 wines across 3 wineries. There happened to be only a couple of other people on the trip with us, but the experience is capped anyway at 10 people. 

Honestly, we loved every moment of it and would definitely recommend it to our friends – and our readers, obviously!

If you want to do the whole thing on your own, it’s possible to self-organise winery stops as part of a Santorini road trip. The downside, of course, is that someone will have to spit rather than swallow – the blood alcohol limit on the island is the same as everywhere else in Greece: 0.05%.

Day 3: Fira + Sunset Cruise

Fira is the island capital and an essential stop off on any itinerary for Santorini. It’s here that we experienced some of the best shopping and nightlife, but also the most impressive churches.

This city is a great place to base yourself, as it’s quite centrally located, meaning that only short trips are required to the north, east, and south coasts.

📍Museum of Prehistoric Thera

Museum of Prehistoric Thera.

Humans have been living in Santorini since at least the fifth millennium BCE. Archaeological objects unearthed at the prehistoric city of Akrotiri showcase a rich cultural heritage that has produced some truly gorgeous pieces of pottery, jewellery, and art.

You can visit Akrotiri – we’ve included it on day 4 of our 4 day itinerary Santorini – but it’s at the Museum of Prehistoric Thera that you’ll find the most impressive items that have been excavated so far. We especially liked the vivid frescoes, but the prettily painted crockery is wonderfully well preserved.

To be honest, this is probably the best museum we checked out on our trip, which is why we definitely recommend a visit. It’s not very large and can easily be slotted into a full day of Fira activities.

📍Stroll The Fira Promenade 

A promenade in Fira.

From the museum, head past the fabulous, all-white Orthodox Metropolitan Church to Ipapantis Street. This promenade begins with views out over the caldera, before transforming into an alleyway packed with shops selling an intriguing mix of mementoes that make for perfect souvenirs of your 4 days in Santorini itinerary. 

Ipapantis is particularly famous for gold jewellery, but it doesn’t come cheap! Instead, you may prefer more affordable handcrafted items – or of course the classic fridge magnet!

📍Cathedral of Saint John the Baptist

Blogger Mal in Fira on itinerary for Santorini.
Fira

A complete contrast to the whitewashed Metropolitan Church with its copious arches, the Catholic Cathedral of Saint John the Baptist is a colourfully painted affair that stands out a mile from the other buildings in Fira. We were particularly enamoured of it clocktower, but the whole place has been wonderfully restored following the earthquake of 1956. 

After having seen quite a few blue-domed, white-walled churches during the course of our Santorini 4 days itinerary, the pastel prettiness of the Cathedral of Saint John the Baptist adds a nice bit of variety.

📍Church of Agios Stylianos

Is 4 days enough in Santorini to visit Fira?

The Church of Agios Stylianos is just around the corned from the Cathedral of Saint John the Baptist and is painted in a similarly colourful style. It’s a beautiful photo spot where you can get the church and the natural scenery in one gorgeous snapshot.

If you wander a bit further up the street past the church, you can actually get an amazing view of the whole downtown area.

📍Three Bells Of Fira

View of Imerovigli
Fira

For more of a classic Santorini photo op, head to the viewpoint above the Three Bells of Fira. This is another point on our 4 days in Santorini Itinerary where you can enjoy an incredible view od the caldera and a quint church.

What’s distinctive about this particular panorama is that the church has a trio of bells on its roof, which stand out sharply in snapshots.

📍Sunset Cruise

A sunset cruise is a must-do on any Santorini itinerary 4 days.
Bloggers Mal and Robin on a sunset cruise in Santorini.

A sunset cruise is a romantic way to end the third day of your itinerary for Santorini. 

We decided to do this to celebrate Mal’s birthday, opting for a 5-hour boat ride that left from Vlychada Marina on the south coast – although we were picked up from our Fira hotel.

Our catamaran took us on a tour of all the coastal island highlights, including Red Beach, White Beach, and Mesa Pigadia Beach, with stops to enjoy a spot of snorkelling or swimming. We also got to hop in the hot springs at Palea Kameni, which are heated by the Santorini volcano!

The open bar and delicious dinner were, of course, fab, but it was watching the sunset from the deck while anchored in Ammoudi Bay that was our absolute fav part of the experience. 

Day 4: Heading South 

After three days of seeing the island’s trio of picturesque clifftop towns, the last day of our Santorini Greece itinerary is all about getting a different perspective of what this place is all about. This part of the trip is easiest if you rent a car, but it’s also doable by bus – as long as you do plenty of preplanning!

📍Vlychada

Blogger Mal on Vlychada Beach.

Vlychada is a curious little fishing village that is home to Santorini’s largest marina – as well as its one and only tomato museum! Easily one of the quirkiest places we visited on the island, the museum is housed in a former tomato factory, where you can sample different kinds of tomato-based products.

The habitation is probably most famous though as being home to a black sand beach, another feature created by the volcano. We found it a little rough underfoot, but it’s pretty cool as something to check out. Plus, it’s not as commercial as most beaches on the Cycladic archipelago.

Hemmed in by cliffs, it was one of the more dramatic natural phenomena we saw and certainly worthwhile squeezing into Santorini in 4 days.

📍Red Beach 

Blogger Mal on Red Beach.

A bit further west along the southern coastline, Red Beach gets its name from its terracotta-coloured cliffs, which made us feel a bit like we were visiting Mars! 

We drove here as part of our Santorini road trip, paying to leave our rental vehicle in a nearby car park and hiking down to the rocky shore. It’s also possible to reach the cove by boat. 

There’s a café here if you want a meal or a drink, though we brought our own since we weren’t sure about the hours outside peak season.

📍Akrotiri

Blogger Mal in Akrotiri.
Akrotiri

We’ve already talked a little bit about the amazing items that continue to be unearthed in the prehistoric city of Akrotiri, but for history buffs there’s nothing better than checking it out first hand! 

A bit like Pompeii but a heck of a lot older, Akrotiri was preserved in volcanic ash in the 16th century BCE, which is why so much of the Minoan city has survived intact. 

For anybody who likes their ancient artefacts, this is an unmissable stop on our 4 days in Santorini Itinerary. To be honest, we’re not entirely sure why it hasn’t already been added to the list of UNESCO World Heritage Sites!

📍Akrotiri Lighthouse

Right on the westernmost edge of Santorini, the Akrotiri Lighthouse is perched on a rocky promontory that stretches out like a finger into the Aegean Sea. It’s a beautiful place to watch the sun as it sets on the western horizon.

We found the lighthouse itself only minorly interesting – it’s really the natural scenery that you’re coming for here! There’s a rather good restaurant called Giorgaros with classic Greek fare where you can sit and enjoy lunch or dinner if you want to stick around. 

The Akrotiri Lighthouse is not accessible by public transport that we could see, so this is only something to add to a Santorini road trip itinerary. Parking does get crowded, particularly around sunset, so turn up early to make sure you get a space.

📍Megalochori

Blogger Mal in Megalochori.
Blogger Mal in Megalochori.

If you haven’t yet had your fill of whitewashed towns, Metalochori is a lesser visited but still stunning example of the model. It doesn’t have the same glorious panoramas as Oia, Imerovigli, or Fira, but it’s also a quieter place to get lost in authentically local alleyways that lack the polish and paint of more famous Santorini settlements.

The most memorable feature for us was probably the church belltower with its 6 bells, although the underground storage caves from yesteryear are also a pretty cool feature.

Megalochori isn’t a major highlight of our 4 day itinerary Santorini, but it’s a convenient place to pop in as you make your way from Akrotiri to Pyrgos.

📍Pyrgos

Blogger Robin in Pyrgos during 4 days in Santorini.
Blogger Mal in Pyrgos.

What we liked about Pyrgos – and why we’ve included it on our 4 days in Santorini itinerary – is that it’s situated in the interior of the island, away from the coast. That means the views are completely different from everywhere else you’re likely to visit.

From hangouts like Franco’s Cafe, you can look out on the entire island rolling out beneath you. Pyrgos is, by the way, the highest village on Santorini!

Blogger Robinek in Pyrgos.
Pyrgos is a must-visit on all Santorini road trips.

There’s not anything specific we’d recommend seeing here, it’s more just about getting lost down the higgledy-piggledy streets and drinking cocktails on rooftops!

📍Santo Winery

Blogger Mal at Santo Winery as part of 4 days in Santorini Itinerary.

End the day and our Santorini 4 day itinerary at Santo Wine. This winery is on the outskirts of Pyrgos, less than half an hour from the town centre on foot.

Hovering over the sea, it has stunning views of the caldera, which pair nicely with a glass of the sweet house Vinsanto or a dry white made from 100% Assyrtiko.

You can come to Santo just for a tour of the vineyard and a wine flight of up to 8 wines. We chose to come here for drinks AND dinner, which was magical. The food is pricey, but we felt like the combo of quality ingredients and spectacular views justified the bill. 

Best Places To Stay In Santorini

Blogger Mal staying in Santorini Virginia's Cave Studios.

📍Oia ➡️ Oia is the best option for first-time travellers since it’s the most iconic town in Santorini. 🌟 TOP PICK (We stayed here! 🥰) 📍 Virginia’s Cave Villas ➡️ CHECK RATES

📍Fira ➡️ Fira is a little more budget-friendly; it boasts good nightlife and dining options. 🌟 TOP PICK📍 Deluxe Hotel Santorini ➡️ CHECK RATES

📍Kamari ➡️ A great location for families and beach goers, it is also very affordable. 🌟 TOP PICK📍 Santa Elena ➡️ CHECK RATES

4 Days In Santorini Itinerary: FAQs

Where to stay in Santorini?

Oia is the best place to stay overall. It’s the most beautiful town on Santorini, with plenty of places to eat, drink, and stay. The downside is that it’s filled with tourists and expensive. 

Fira is the capital, has good nightlife, and stays alive even in the off season. Imerovigli is relatively quiet and relaxed, with luxurious suites with private pools that make for a great romantic getaway.  Kamari is a solid bet for families, since it’s quite flat and has plenty of modern amenities, as well as a sizable beach.

How many days in Santorini is enough?

For a complete Santorini itinerary, 4 days is just about right. That gave us enough time to explore the pretty towns, snap way too many photos, sample the local wine, and still have a little time left over to chill out on the beach.

Is 4 days in Santorini too much?

Seeing Santorini in 4 days means you don’t have to rush from town to town. You could feasibly stay just two days if all you want is to snap a few pics in Oia and go on a wine tour, but it would mean just feasting on the bare bones of what the island has to offer.

Do I need a car in Santorini?

A Santorini road trip does make it easier to see more in less time. The island is very small, so it doesn’t take long to drive from one end to the other. On the other hand, hiring a car is an additional expense, and there are buses that connect most of the places we’ve mentioned in his post.

Is Santorini expensive?

There’s no way around it, Santorini is expensive. Oia is probably the priciest part of the island, but most of the accommodations and restaurants we encountered were on the more expensive end of the scale compared to other places in the Cyclades island group.

What is the least crowded month in Santorini?

The least crowded month in Santorini is probably either January or February, when the weather is cooler. If you want warm weather without the crazy crowds of July and August, we’d recommend embarking on our 4 days in Santorini itinerary in either May-June or September-October.

4 Days In Santorini: The Wrap-Up

If you follow our 4 days in Santorini itinerary, you’re guaranteed to see all the major attractions. Even though the island is undeniably touristy, it’s also incredibly beautiful and unique. With its numerous pretty churches, fruitful vineyards, and dramatic cliffs, it’s guaranteed to provide plenty of unforgettable photo ops!

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