2 Days in Santorini – Sunsets, Wine & Almost Getting Trampled by a Donkey

For one of my first ever solo trips I decided to head to Santorini! Honeymoon for one? It did not even occur to me almost everyone visiting would be couples, but honestly I loved it & mornings staring out past whitewashed houses over the caldera are some of my favorite travel memories ever. I combined this trip with a bunch of other places, so I only spent 2 days in Santorini.

You could easily spend more time in Santorini, but there are also so many other stunning Greek Islands to see, and 2 days is enough to see the highlights below is my ultimate 2 day itinerary! With some of my favorite embarrassing travel memories (like almost getting taken out by a rogue donkey in Oia & being told I couldn’t have a table for 1 at a restaurant & being adopted by a couple who overhead)

If you have a bit more time see my Santorini Travel Guide.

Santorini does get crazy crowded, and thousands of people visit from cruise ships daily, so it’s critical to plan around the crowds where you can to have the best experience! All my suggestions for where to stay and when to visit are included at the bottom of this article!

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!

Day 1: Boat Tour & Santo Wines

Boat Tour of the Caldera

Exploring Santorini by boat is one of my top recommendations! It offers some of the best views of stunning Oia and the Santorini coastline. 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 recommend heading over to Santo Wines 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. Sunset is absolutely unreal here. 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, Lunch in Amoudi & Sunset in Oia

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!

Stop 1: Fira

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.

Stop 2: Imperovigli

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) 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! You could also make a reservation at a restaurant with views for sunset.

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!

When to Visit Santorini

Summer is by far the most popular time to visit Greece, but personally it’s not my favorite. July and August will bring the most crowds, highest prices and super hot temperatures. Santorini is small and crowded even during the shoulder season, but summer is insane.

For the best experience I highly recommend fall. I love October, the sea is still warm and temps were plenty high enough for me. It’s crowded, but less so than summer. September is also good, warmer, but busier. Things start to close in November, so you’ll need to plan more carefully.

Spring is also lovely, although the ocean won’t be as warm. I’ve visited Greece in early April and some things may not be open or things are just opening. Later April, May and June are all lovely!

Getting to Santorini

Santorini is one of the Cyclades islands in the Aegean sea, and it is a bit farther South than other popular Cyclade islands like Mykonos, Paros & Naxos. Santorin does have it’s own airport and is also accessible via ferry.

TLDR: If you’re coming from Athens I recommend flying, if you’re coming from another nearby island, like Mykonos, the ferry may be better. The flight is less than an hourl the ferry says 4 hours from Athens, but can take much longer.

I was coming from Athens (see my Athens Travel Guide here) 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 to Stay in Santorini

There are tons of acommodation options in Santorini, and it can be a bit overhwelming to decide where to stay. There are 3 main towns many people stay in – Oia, Fira and Imperovigli & then tons of options across the rest of the island.

There are many lovelt resorts spread around the island, and a few popular resort areas on the east coast of Santorini. If you stay outside of one of the main towns, you’ll likely want to rent a car depending on how much you want to leave the resort. There are busses to get around, but they can be unreliable and crowded. The busses also require you to transfer at Fira to get anywhere, so you’ll spend a lot of time going to and from FIra.

Here’s a break down of each area:

Stayig in Oia

Oia is the most iconic town in Santorini (picture windmills, whitewashed houses and sunsets) and is a must-see on any Santorini trip.

Pros: Best for sunsets, most picturesque & popular area of Santorini, statying there allows you to explore early and late before and after the crowds

Cons: Expensive, super crowded (this is where all day tourists go essentially), not a lot of area for parking if you rent a car

Staying in Fira

Pros: Best for nightlife, cheaper hotels and restaurants, good home base for exploring the rest of the island (all the busses to anywhere on the island depart from Fira)

Cons: Crowded, can be a bit loud due to nightlife

Staying in Imperovigli

Pros: quiet, romantic, picturesque, best for honeymooners!

Cons: can be a bit too quiet if you’re looking for nightlife

Where I Stayed – Apeiron Blue Santorini

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 four star hotel a little south of Fira.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

I decided I was ok with walking or taking the local busses (which were 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 as I was only there for 2 days and sticking to the areas accessible by bus.

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!

Getting Around Santorini

Santorini is small in some ways, but big in others. Depending on where you want to go and what you want to see you may be travelling around more than if you plan to mostly hang at your resort. ALso, if you’re booking guided tours you likely don’t need a car!

I personally would use a combination of busses, taxis/private transfer, and guided tours vs. having to deal with having a car, but it’s really dependent on your preference.

Rental Cars

If you like to explore on your own, and are hoping to explore the south and east sides of Santorini you may want to rent a car on your trip to Santorini. Definitely book in advance, particularly in summer. One thing to be aware of is parking. You’ll need to make sure your hotel offers parking, which can be tricky in Oia, Fira and Imperovigli.

Busses

Santorini has a series of public busses that can take you to all major areas of the island. All busses transfer and leave from FIra, so to get from one place to another you almost always need to transfer through Fira. I took the busses and they were fine. They ran late in my experiece and were a bit crowded.

The schedule and routes can be found here!

Private Transfer & Taxis

There are taxis on Santorini, altough there’s a limited number, so you may need to wait a while, especially when it’s busy (ie leaving Oia after sunset) I used private transfers to book transport to my hotel & the airport just to be safe. (Santorini was one of my first solo trips!) I always use 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!

Santorini Travel Map

Exploring More of Greece?

Check out some of my other popular Greek posts

• Ultimate Greece Itinerary (5, 7, 10 and 14 days)
• Mykonos Travel Guide
• Crete Travel Guide