2-Day Santorini Itinerary (+ Options For 3-5 Days)

Summary: In this post, I’m sharing an example 2-5 day Santorini itinerary along with advice about when to visit Santorini, how many days to spend on Santorini, and more.

Disclaimer: Some of the links in this post are affiliate links which just means I make a small commission if you purchase from them with no additional cost to you!

Santorini is such an interesting place for me. On one hand, it’s one of the most beautiful places I’ve ever visited with its white-washed buildings, picturesque sunsets, and blooming flowers everywhere. On the other hand, it’s a place I ended up stranded due to catching Covid-19 when we still had to test negative to come back to the United States.

I can look back on that time now and appreciate the experience, but it certainly wasn’t fun while I was living it.

Even with that unfavorable situation, Santorini remains a place that I’ll continue to travel back to because even though it’s a relatively small island, there’s a lot to do and see!

The Best Time to Visit Santorini

Santorini’s peak season is the summer months and into September. I visited in April and would highly suggest April or May as the best times to visit Santorini. The sunset viewing spots certainly got crowded, but for the most part, the crowds weren’t to bad.

I’ll give more advice about how to avoid crowds at sunset below!

The weather was also perfect for me. I don’t like hot summer weather and in April, it was still a bit chilly in the morning and warmed up by mid-day. It was warm enough to spend time on the water, but not unbearably hot.

How Many Days to Spend on Santorini

When considering how many days to spend on Santorini, you need to consider what you want the vibe of your trip to be. When people visit Santorini, sometimes they are Greek Island hopping and sometimes they want to spend a relaxing week in a beautiful place.

If you’re island hopping, I’d recommend spending at least 2-3 days on Santorini so you can see some of the more popular, touristy towns, but also have time to explore some lesser-known areas.

If Santorini is your main destination for your trip, you could easily spend a full week here. Doing this will allow you to have slower days and enjoy the island without rushing through each activity. Lately, I’ve found a lot of joy in slower travel, so this is what I’d opt for.

However, I know there are a lot of places to see in this world, and some of us have limited PTO to take, so this 2-day Santorini itinerary will allow you to see a lot of the island in a short period of time.

What is Santorini Known For?

Santorini has a few iconic attributes. Aesthetically, the tourist areas are known for the white-washed buildings, cobblestone walkways, blue-domed churches, and blooming flowers everywhere. This part of Santorini is built around a caldera, giving it its half moon shape.

The caldera was formed after Santorini’s underwater volcano erupted and completely changed the shape of what used to be a round island. This underwater volcano is another iconic feature of Santorini and the caldera is one of the most beautiful parts of Santorini as all of the white-washed buildings are built into the side of it.

Santorini is also said to have the best sunsets in the world. I don’t know if I fully agree with this, but I do love the culture around sunsets on Santorini. Everyone stops what their doing this time of day to find a spot to watch the sunset. It’s one of my favorite traditions I’ve witnessed when traveling because it’s a practice of finding so much joy in this thing that happens every day that we might usually take for granted.

2-Day Santorini Itinerary

Day 1: Explore Oia, Catamaran Tour

If you’re anything like me, you’re going to want to explore the gorgeous streets of Santorini right away. I’d suggest spending your first day exploring the town of Oia.

As you’re wandering through white-washed buildings and cobblestone alleyways, you’ll see a lot of souvenir shops selling linen, blue and white-themed items, shoes, and more. There are also a lot of beautiful, quaint restaurants. I’d carve out some time and just walk, shop, and eat where your heart takes you!

The next activity on your first day is a Catamaran Tour. Here is the link to the exact tour that I did and loved. It is a shared group experience, so you’ll likely meet other travelers. It also includes an open bar and a guide to show you around while you’re sailing. We even dropped the anchor in the middle of the sea and got to swim to one of the beaches. It was truly an amazing experience!

There is an option for a morning cruise that includes lunch, or a sunset cruise that includes dinner. We did the morning cruise and the food was surprisingly good! The full sail is 5-6 hours long and it includes hotel transfer if needed.

If you end up choosing the morning catamaran tour, then find a spot that faces west to watch the sunset in Oia this evening! This area gets extremely crowded, so if you want a specific location, I’d arrive 1-2 hours before sunset.

Pro Tip: I always suggest making dinner or drink reservations at a restaurant around sunset time so you have a guaranteed place to sit and watch.

Finding a Sunset spot in Oia

Day 2: Explore Fira, Santorini Old Port, Local Shopping

The second day we will be exploring the town of Fira. It’s just as beautiful as Oia and you’ll see very similar white-washed buildings, cobblestone walkways, shops to pop in, and restaurants to eat at.

At some point during the day, make your way down to Santorini’s Old Port. This port is where cruise ships stop to let cruisers off at Fira (via ferries to and from the actual cruise ships), and where some boat tours leave from.

You have the option of taking the cable car to and from the Old Port for a small fee, or hiking down. Keep in mind the hike is quite steep! You’ll also see donkey rides taking people to and from the Old Port. Personally, I wouldn’t support this as it gets quite hot and those donkeys are going up and down all day.

You can also make your way to the Three Bells of Fira which is an iconic blue-domed church that every tourist will be trying to get a picture of, but it is quite beautiful!

Blue Dome Church on Santorini

Just like the day before, you’ll notice the entire town stops to watch the sunset. We really enjoyed having cocktails at PK Cocktail Bar in Fira while watching the sunset. I’d recommend making a reservation, or arriving very early because it fills up as soon as the sun starts to go down.

Sunset view from PK Cocktail Bar

3-5 Day Santorini Itinerary

If you’re going to be in Santorini longer than two days, I’ve outlined additional days below to add to your 2-day Santorini itinerary.

Day 3: Rent ATVs to Explore Lesser-Known Areas

While Fira and Oia are the two most popular and touristy towns on Santorini, they are a very small portion of the island. There is a lot of Santorini left to see and explore, and what better way to do that than on ATVs?

You can rent ATVs from companies like Rent Me, Fresh Rent, or Freedom Rentals.

Another options is to sign up for a group tour that will guide you to different areas on ATVs. There are full-day tour options, or tours that last just 3-4 hours. Most can include hotel transfer and meals while you’re out.

Day 4: Santorini Volcano Hike

I mentioned earlier in this post that Santorini’s crescent shape was formed from volcano eruptions. A popular activity is to hike right to the heart of that volcano on Nea Kameni! This is a small, crater island that you can see from Santorini. You’ve probably seen it if you’ve been watching the sunset each night!

You’ll need to take a tour boat or a catamaran cruise to get to this island, and once you’re there, the Nea Kameni hike is just over 1.5 miles long and takes 1-2 hours to complete. There are tours you can sign up for while you’re in Santorini, or you can book them online ahead of time.

Some of the volcano tours even stop in the same area where we anchored on the catamaran tour, so you could double up and just do one boat tour for both activities.

The boats all seem to leave from the Old Port in Fira (mentioned on day 2 of this 2-day Santorini itinerary).

Day 5: Santorini Winery Tour

If you’re lucky enough to be in Santorini for 5 full days, first of all, I’m envious! Secondly, you can do a tour that I really wanted to take, but didn’t get the chance to: A Santorini Winery Tour!

I actually booked and paid for this tour, but then got incredibly sick during our stay and ended up not taking it. All the more reason to go back, though, right?

There are several wine tours around Santorini, but this specific one picks you up at your hotel and takes you to three different wineries, where you’ll taste up to four different wines at each location! You’ll get to spend the day exploring parts of Santorini that not everyone gets to see.

Read More About Greece

I hope this 2-day Santorini itinerary helped you plan the perfect trip to this gorgeous island! While you’re curious about Greece, I have a couple more blog posts you might want to check out:

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