2 Days in Santorini Itinerary

I think Santorini is a bucket list destination for most people who have a seen a movie or ad with those stunning white-faced houses cascading down the cliffs into the Aegean Sea, and I have to say it did not disappoint!

I only got a chance to spend about two days in Santorini (closer to 36 hours after a delayed ferry) but that was certainly enough time to fall in love with island, and the Greek Islands in general! I’d love to make it back for a longer trip in the future, but two days gives you enough time to see the highlights!\

Disclaimer: This article contains some links where I earn commission through booking. There is no extra cost to you, and I only recommend things I’ve used and love or places I’ve stayed and enjoyed!

How I Got There & Where I Stayed

Getting There

Santorini is one of the Cyclades islands in the Aegean sea, putting it among the more Southern Greek Islands. Santorini, given its popularity, does have it’s own airport and is also accessible via ferry.

I was coming from Athens and opted to take the ferry to Santorini, but to fly back to Athens (en route to Rome) Truthfully, I wish I just flew both ways. The flight was super quick and really convenient, but I had decided I wanted the experience of taking the ferry and seeing a few others Greek islands on the way to Santorini, since there are several stops between Athens & Santorini.

The Athens ferries actually leave out of a port in Piraeus, a town about 30 minutes from Athens. Piraeus is accessible by public transport or taxi, but I had a 6am ferry and wanted to make sure I had a confirmed, safe transport for that early + being alone, so I used Welcome Pickups to schedule a ride. I highly recommend their services, the prices are comparable to taking a taxi, but booking a guaranteed ride ahead of time that’s trackable in an app brings a lot of peace of mind to early morning and late night transfers!

I had an image in my mind of sitting on a ferry enjoying a cocktail and some stunning views, but these ferries are built much more for function than luxury. They’re large catamarans with rows of seats similar to a movie theatre, and storage racks for large luggage downstairs (you can keep a carry on with your valuables with you at your seat.)

They do have a bar serving coffee, snacks and drinks, but the line was super long throughout most of the trip and it was such a rough day on the water the boat was rocking too much to really enjoy a coffee or any cocktail. Luckily, I don’t get seasick, because many people were sick throughout the trip.

In terms of the views, there really were some stunning views, and before the trip got too rough you could venture up to the outdoor roof deck. Although, it was insanely windy and a bit chilly it was worth it for the views! From the seats downstairs views would be better if you managed to snag a window seat, but most of the seats are in the middle and a bit farther away from the windows!

Due to the weather the ferry was delayed, so it took about two hours longer than it said originally to get from Athens to Santorini (6ish hours instead of 4) which was fine, but I had really limited time in Santorini, so I should have considered flying to cut down on travel time. But overall, if you’re starting your island hopping somewhere closer to Athens than Santorini (like Mykonos or Naxos) I would recommend the ferry. If you’re going straight to Santorini, I’d recommend flying to save time.

Where I Stayed

I really wanted a hotel with one of those quintessential Santorini views, but I also didn’t want to spend a ton of money if I could avoid it. So I opted for a five star hotel a little south of Fira. Fira, Imperovigli & Oia are some of the most popular areas of Santorini to stay, making them a bit more expensive for nicer hotels.

I decided I was ok with walking or taking the local busses (which were super convenient and located about a 3 minute walk from my hotel) to get a nicer hotel with a view! The hotel also had parking, but I opted not to rent a car.

I stayed at the Apeiron Blue, a four star hotel that had just been redone and reopened under new management. I could not recommend it enough. The rooms were small, but well stocked and clean with nice renovated bathrooms, and all had direct access to the upper deck with the stunning pool (pictured below.)

There was plenty of seating for lounging on the deck and they offered drink service. Down on the lower deck there was a second pool, an infinity pool with stunning Aegean views + a poolside bar. The hotel also had a restaurant and bar with amazing sunset views, and a full-service breakfast was included. It was so much food I almost felt bad and wanted to tell them to give me less so it wouldn’t go to waste!

Day 1:

Boat Tour of the Caldera

Exploring Santorini by boat is one of my top recommendations! There are tons of great cruise options, but most of them have similar itineraries. I’d recommend a half day tour, like this one, so you have the afternoon to relax poolside at your hotel! This tour leaves from Santorini Old Harbor and allows you to visit:

• The Santorini Volcano – wander around the volcano’s ridge
• Palea Kameni – soak in Santorini’s infamous hot springs
• Thirassia – visit a small island, mostly untouched by tourism. Explore the quaint towns, grab lunch and enjoy some stunning views of Santorini!

Sunset at Santo Wines

Later that evening I decided to head over to Santo Wines, which was pretty close to my hotel, for some wine tasting and some sunset views! They offer winery tours, wine tastings and a restaurant that serves their wines as well as local food. You can book all three separately on their site.

I did a wine tasting and stuck around for some sunset views. Santorini is known for their white wines, and the crisp, refreshing white wine varieties were perfect since the temperatures were so high. I’d definitely recommend adding Santo to your list for the views as well as the wines!

Day 2:

Hike From Fira to Oia

After a lot of research I decided my day 2 plan would start with the infamous hike from Fira to Oia. This would give me time to explore the three most popular cities in Santorini; Fira, Imperovigli & Oia. The hike itself is about six miles, but that doesn’t include wandering through the various towns and exploring, so you’ll end up walking quite a bit more than that.

There’s no real dedicated path, but it’s easy to follow as long as you keep the Caldera at your left the whole time and keep walking you’ll eventually end up in Oia! A lot of it is flat, easy walking, but there is a hillier, rockier stretch as you get closer to Oia from Imperovigili. It gets hot midday, so make sure you pack water, sunscreen, etc!

Fira is the busiest area of Santorini and is a great place for souvenir shopping & for the late night bar scene. It’s also offers the most variety of accommodations and is your best bet if you’re looking for the cheapest and most conveniently located option in Santorini. I spent about half an hour exploring the narrow pathways cutting every which way through Fira before heading towards the small village of Firostefani and the famous Three Bells of Fira.

The next town you’ll come to is Imperovigli, another cute town with endless little paths and cutoffs to explore. Imperovigli is a bit more low key than Fira and tends to be more of a go-to spot for honeymooners and couples looking more for views & relaxing than nightlife.

As you continue to make your way North you’ll leave Imperovigli and keep heading toward Oia. This is certainly the longest and most “hiking” part of the journey with the least to see. It’s a decent uphill stretch on a rocky, dirt path. Eventually, you’ll come to Panagia church, and the view back is pretty incredible.

The trail begins to descend into Oia and you’ll soon be hit with those quintessential Santorini views (like the ones below & above) I cannot say enough how impressive this view is. I must have taken 500 pictures on the last stretch of this hike and then another 500 more when finally making it to Oia in general.

Like the other towns, Oia is filled with wandering paths that lead to a variety of shops and restaurants. There is plenty to explore & tons of places to reward all your hard work with a glass of wine or a cocktail with some of the worlds most famous views! Also, make sure to venture all the way up to the infamous windmill.

Lunch in Amoudi Bay

If you’re up for more walking (and a LOT of stairs) you can get to the charming Amoudi Bay via a set of stairs in Oia. There are about 300 long, rocky steps winding down the into Amoudi Bay. This is where you’ll see the donkeys you can ride up and down. I opted to walk (and almost got slightly trampled by a rogue donkey with a terrified child on it!) and going down wasn’t too bad.

Coming up was much more of struggle after the ten + miles of walking my iPhone told me I’d already done that day. At the bottom there are several delicious restaurants known for the seafood and Aegean views. It’s a great spot to grab lunch after a long day!

Sunset in Oia

I had to make sure to catch the infamous Oia sunset during my short trip, so I headed back to Oia (this time via the local busses) later that day to make sure to grab a spot for the sunset. I was there during October, which is considered shoulder season in Santorini and it was packed, like actually hard to find a spot to see packed and get pictures without a ton of other people in them.

Luckily, I had heard this from others and did a ton of research and found the perfect spot from She Wanders Abroad. This article has a ton of detail, but I recommend following her instructions for spot #2. I did it and got some amazing photos despite all the crowds!

Another option I would have considered if I had one more night in Santorini would be to catch the sunset on a catamaran cruise. There are tons of options, but some of the better ones include a full afternoon with a volcano tour, hot springs, open bar & ending off the coast of Oia for those perfect sunset views!