How I Spent Four Days in Santorini—A Trip to Remember!
Four Days in Santorini
I spent four days in Santorini the end of May and absolutely loved it! It was a wonderful amount of time for a leisurely pace to explore the island!
Santorini is dreamy and worth visiting whether it’s for solo travel, with a friend like I did, or for a romantic getaway. With its stunning views of the caldera, dramatic cliffs, black sand beaches, and charming towns, Santorini is a dream! Here’s how I spent four days in Santorini with a friend, exploring this beautiful island!
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Four Days in Santorini | My Itinerary
When I travel, I plan ahead and book any tours or important experiences to ensure I don’t miss them. Then I research various things to do and keep them in mind and wing it. Some people like to plan moment by moment, but I like more of an outline, so I can pivot as needed.
With that in mind, here is how my friend and I spent four days in Santorini.
DAY ONE | South Santorini on an ATV
Before arriving in Santorini, my friend and I spent a day and a half in Athens. I had read you don’t need more than two days in Athens, and I can confirm that is true! We flew direct from Athens to Santorini, and the journey was smooth!
The flight out of Athens was late afternoon so we landed in Santorini when it was dark. We just grabbed a taxi to take us to our Airbnb in the southern part of the island. It’s not the cheapest option, but it was the easiest and we split the fare. Since we were friends traveling, we saved a little money and stayed near Perivolos Beach instead of in Oia (pronounced ee-uh).
Breakfast at Perivolos Beach
So we’re picking up our first of four days in Santorini in the morning after we enjoyed a good night’s sleep in our Airbnb. We strolled a block to the beach for breakfast to a place recommended by our host. We ended up loving it and eating there every morning.
The breakfast place is on the black sand beach, Perivolos Beach, so we enjoyed the view as well. After breakfast, our host graciously helped us rent some ATVs to explore the island.
Exploring Akrotiri on an ATV
The ATVs proved to be fun way to explore the island, and since the island wasn’t super busy yet, it worked out well! With our first day in Santorini, we started by exploring the southern part of the island.
First up, we headed to Akrotiri Lighthouse, but made some picture stops on the way. The lighthouse isn’t one you climb, but the area is beautiful with its dramatic cliffs! It was fun to walk around, and take in the scenery of the area.
Being on the island the end of May was perfect as there was some people around, but it was much quieter overall. Especially on the southern portion of the island, it felt very quiet!
We ended up eating lunch at a quiet restaurant in this part of the island. We were the only customers, if that gives you an indication of how quiet it was in this part of the island during our visit! It was charming but the food wasn’t special. Either way, we enjoyed the experience!
Red Beach
After the lighthouse, we hopped on the ATVs and made our way to Red Beach. You’ll know you’re getting close to the lookout when you pass the charming Saint Nicolas Church. Follow that small road around until you get to the Red Beach lookout.
My friend and I didn’t hike down to Red Beach. Being from Florida, we weren’t in Santorini for beach days, but loved seeing the diversity and dramatic beauty of this island. So we simply walked to the lookout for photos.
However, if you do want to visit the beach, the common two ways are hiking down or a boat tour to the beach. If you hike down, be sure to take everything you need as there are minimal offerings on this beach.
Kamari Beach
After Red Beach, we made our way to Kamari Beach to relax for a bit and check out that area. It has a cute lineup of restaurants and shops. We purchased some Turkish cotton style towels from the store here and then used them to lounge on the beach. However, it wasn’t comfortable as this black “sand” beach is more like black small rocks.
It’s a cute area to relax at for a couple hours, which is what we did before calling it a day.
Extra Stops in South Santorini to Consider
White Beach
White Beach is harder to access and the most common and recommended way to see it is by boat. However, if you’re feeling adventurous, there is said to be a trail near to Kampia Beach.
Akrotiri Archeological Site
Not too far from Red Beach is the Akrotiri Archeological Site! My friend and I weren’t interested at the time, but if I was to visit Santorini again, I’d probably include a visit.
If you’re into history, this will be a worthwhile stop for you!
South Santorini Tours
My friend and I did a self tour on the ATVs, but if that isn’t for you, here are some top rated tours to consider!
- Akrotiri: Guided Horseback Riding Day Trip to a Beach
- Archaeological bus tour to Akrotiri excavations & Red beach
- Private Cultural Villages Sightseeing & Akrotiri Excavations
DAY TWO | Santorini Caldera Cruise
Pickup
One tour that my friend and I pre-booked was a Santorini Caldera cruise! We booked this tour to see the volcano, Thirassia and the hot springs and got the stunning Santorini caldera views as well. The one we chose was inexpensive, and it ended up being a great value for the price.
We booked the options with pickup and dropoff so we were picked up from our Airbnb accommodations near Perivolos Beach. After gathering a few others in the area, we were taken to the Thira port. Even the drive offered stunning views as we were driven down the winding road to the port.
Upon arrival to the docks, we were ushered to this old style, small wooden ship and it wasn’t long before we were setting sail. Of course, we weren’t going too far, but we did pass big cruise ships and plenty of other boats.
Volcano
Our first stop is the volcano! It was suggested that you bring proper footwear for the hike, but I never got the memo. I did the hike in my havaianas flip flops! The trail was clearly marked and while there were moments we had to navigate some rocks, the climb isn’t bad, but it is very dusty!
It didn’t take long to make it to the top and once our group made it, the guide began to explain the history of the volcano and the area as a whole! Santorini is the result of the explosion from around 1600 BC, which also created the stunning caldera! While the volcano hasn’t erupted since 1950, it’s still considered active.
After walking around with the guide, we were eventually given the chance to explore and take photos, with a general timeline of when we had to be back on the boat. From the volcano, we headed to the hot springs.
Hot Springs
While I missed the memo on the shoes for the hike, I didn’t miss the memo when it came to choosing an old swimsuit as it could get discolored. The water in the hot springs area was brown and it was also advised not to wear jewelry due to the sulfur. Something worth keeping in mind if you choose to do this tour or a similar one!
The boat was a bit away from the hot springs area, so it required jumping into the cold Aegean Sea! Those of us planning on swimming in the hot springs took turns jumping in. The water did get warmer the closer to the hot springs we swam, but I wouldn’t call them “hot” overall!
So my friend and I swam in the “warmer than the sea,” but not quite “hot” hot springs for a while, before heading back to the boat. I was ready to get dry and was very happy it was a sunny day on our tour!
Thirassia
After everyone returned to the boat, we were taken to Thirassia for lunch. The price of lunch is not included, but the port of Thirassia was very cute with enough restaurants to accommodate a few boat tours. To explore the island more, you can climb the stairs, which would take about 20 to 30 minutes.
My friend and I were happy to relax after we had lunch and enjoy the views from the docks. There wasn’t really enough time to do both the climb and have lunch. While I can’t speak to Thirassia as a whole, the port was charming and I loved taking in the views of Santorini from there!
Oia Sunset
Originally when I booked the tour, I had imagined watching the sunset from the boat. However, that wasn’t quite the case. It was most likely my misunderstanding as an Oia sunset would be from Oia.
After Thirassia, we were taken to Oia’s port (Amoudi Bay Port). On arrival, we were told we could enjoy exploring Oia, watch the sunset, then instructed to meet the bus in the parking lot after sunset.
We disembarked, and noticed the incredible amount of stairs that lay between us and Oia! There are two ways to get to Oia from the Amoudi Bay Port. One is to walk up the stairs and the other is to ride on a donkey! Whichever you choose, the journey will take some time, but it’s worth it.
Once in Oia, my friend loved walking around, taking photos and just admiring the stunning views! There are also some cute shops in Oia and plenty of restaurants as well! We had plenty of time to enjoy and explore Oia, which was wonderful!
When it was closer to the sunset time, we made our way to the area to watch. While our four days in Santorini in May never felt crowded, the Oia sunset was crowded! It was definitely an Instagram vs reality kind of moment. Even though we shared the sunset with hundreds of strangers, the views are so stunning and dreamy!
Dropoff
Once the sun set, we made our way to the parking lot. Since we weren’t really sure how to get there, we headed back to the bus as soon as the sun disappeared. The parking lot ended up being very close and easy to find which were happy about after the long day. At the end of our second day of our four days in Santorini, we were a happy tired and ready to get back to the Airbnb.
Since it was now dark and we had a long day, we rested on the ride back and crashed that night!
Check out the 1-Day Boat Trip: Santorini Volcano, Thirassia & Oia Sunset
DAY THREE | Fira and Cliff Jumping
After our long day, we enjoyed a good night’s sleep before having breakfast at our favorite place! We ended up having breakfast there during all four days in Santorini. The owner was a sweet older Greek man. He explained that he works long hours during tourist season, but in the winter he returns to Athens and studies languages. This adorable Greek restaurant owner knew ten languages!
Fira
Once we finished breakfast, we rented ATVs again, but this time to explore the northern half of the island. We started by heading to Fira. This capital town in Santorini also has cute shops, maze like streets and is perched on the cliffs offering stunning views.
The parking was easy to find and we made our way into town. After we explored for a bit, we walked for a while on the Fira to Oia trail. It’s not what you’d think of when you think of a trail. There was no dirt or trees, at least in the Fira part that we walked. Rather, the walk was more of the same winding streets you experience in Oia and Fira.
We didn’t do much of the hike, but the views are amazing and I definitely think it’s worth doing! If you’re up for all of it, I think the two to three hours would be well spent and it’s something I’d plan to do if I ever get to return to this dreamy island! The part we did was beautiful, so I definitely recommend at least part of it!
Fira to Oia Road
We headed back to our ATVs and began our journey to Oia. I’m not afraid of heights, but I soon learned my friend was afraid. The fastest way to get from Fira to Oia is on a main road high on a cliff. I’d watch to see if cars were behind us and then pull over when possible to let them pass.
The road does have guardrails, but I was distracted and enamored with the breathtaking views! My friend, however, was not. She was very scared! To be fair, I can understand why! The road is on the side of cliff after all! The lane heading to Fira from Oia was next to rock and our lane had a guardrail because it was a steep drop!
When my friend was ready, we would continue on the road and anytime there was room to pull over, we did. This allowed my friend to catch her breath and let the cars pass. If you’re afraid of heights, consider avoiding this road!
Cliff Jumping Amoudi Bay
One thing I had read about was the cliff jump at Amoudi Bay! I was so excited to do this, but it ended up being the most overcast day. Either way, we got to Oia, then continued driving past the parking lot until we were on a small road going down and to the left towards Amoudi Bay.
There was a small parking lot, and with ATVs we had no issue finding a place to park them. It was a short walk and we could now see the charming Amoudi Bay! If you’ve seen Sisterhood of the Traveling Pants then you’ve seen Amoudi Bay! It’s an adorable little bay lined with seafood restaurants right on the water. It gives authentic fishing village and it’s worth visiting for a meal at least once in your four days in Santorini.
To get to the cliff, you will need to walk by all the restaurants. When I was there, the path eventually seemed to end and I had to navigate some rocks. My friend had enough adventure with the drive to Oia, so she chose to wait by these rocks.
I continued on and navigated some of the rocks before the path reappeared. As I walked around the corner, I saw some local kids jumping off a real cliff. I didn’t want to interrupt their fun, so I continued on to where I saw some tourists in the distance.
Swimming to the Cliff
The area dead ends and thankfully there were several tourists in the area to give me the lay of the land. I met a couple from Melbourne, Australia and another couple from Florida. They pointed out where the cliff is and explained there will be a rope ladder once I swim across the small channel.
I asked if the water was cold and the couple from Melbourne said it wasn’t bad, but the couple from Florida confirmed my fears, it was cold (for us anyway)! After organizing my waterproof phone case, I jumped in the water and immediately gasped! It was SO COLD!
With the weather being overcast and breezy, the water currents looked intimidating. I had watched someone swimming and they were easily moving through the water, so I figured I’d be good. Once I started swimming, I realized the current wasn’t bad all and I easily made it to the ladder.
The climb up the rope ladder was easy, but I’m not used to being barefoot anymore so the walk proved more difficult. The rocky path was one thing, but eventually the path becomes this beautifully decorated walkway with rocks and shells. I made my way gingerly to the concrete cliff, which thankfully was smooth.
I assessed the jump and took some photos from this view! It was beautiful and I was taking it all in. There was a sailboat in the bay and suddenly I heard someone yell, “just do it!” I put my phone in video mode, took a couple deep breaths and ran and jumped off the platform!
Once I came up from the water, the sailboat people were clapping. Since I had to do this by myself, I really appreciated that simple gesture. I swam back across the small channel and to the starting point. After drying off, I made the walk back to the rocks, where my friend was waiting.
Early Seafood Dinner
While in the area, we stopped for a seafood meal in the charming Amoudi Bay (sometimes spelled at Ammoudi Bay). Since we were there earlier, we had no issues getting a table, but if you plan to eat during prime dinner times, you might need a reservation.
The table we got was right next to the water and the meal was good. Though, I never loved the way Greeks prepared fish. I know I’m partial, but I prefer the flavors used in Barbados. I’ll take a fish cutter from my birthplace any day!
While the fish preparation was just okay to me, the setting was stellar! Amoudi Bay is so incredibly charming and cute!
The Return Drive
As we were heading out of Oia, I suggested we ask if there was a return option on a different road. My friend really hated the journey to Oia, so we stopped and asked for directions. In all honesty, the return on that road wouldn’t be as easy. Since it borders the cliff, it makes it impossible to pull over when cars appear behind you. Plus I like exploring new places, so we found the long way back to the Airbnb!
We headed down to sea level and drove through the farmlands of Santorini. The drive was longer, but a beautiful change of pace! We made some stops along the way to take pictures and really enjoy the experience. The traffic was almost non-existent which also made the drive on our ATVs feel safer!
The sun was setting and we still had a ways to go, but we did manage to make it back before it was completely dark.
Dinner at Perissa Beach
Once safely back at the Airbnb, we cleaned up and then walked to Perissa Beach to find a spot for dinner. Similar to Perívolos Beach, there are restaurants lining the black sand beach. Overall, it was a little more lively in Perissa, but still much quieter than in Oia.
DAY FOUR | Relaxing on a Black Sand Beach
Our last day in Santorini was spent relaxing. We started the day at our favorite breakfast spot and then made our way to the lounge chairs of the same restaurant because they are free to the customers.
Since it was so quiet, we felt like we had the beach to ourselves. There were a few other tourists around, but mostly it was quiet! My friend and I enjoyed relaxing, getting a little sun though it wasn’t that strong or hot, and reading. It was a perfect end to our four days in Santorini!
Our flight to London the next day was super early in the morning! We ended up going out with our Airbnb host, so not much sleep was had. However, our relaxing day made up for it!
Additional Ideas for Your Four Days in Santorini
Skaros Rock
If you enjoy hiking, the Skaros Rock Hike is another good one to consider! It won’t take as long as the Fira to Oia walk and proper footwear is even more important. While I saw the Skaros Rock, I never did the hike. However, it looks beautiful and could be a fun way to spend an hour or so.
Visit a Winery
If you enjoy wine, then consider visiting a winery during your four days in Santorini. The below experience sounds dreamy and has over 1,300 five star reviews!
Book the Santorini Wine Adventure with 12 Wine Tastings, Tapas and Sunset
Customizable Tour
If renting a car or ATV doesn’t sound appealing, consider a customizable tour! You’ll get to see and experience what you want and hitting all or most of your major spots in one day will give you more time to relax during your four days in Santorini.
Book the Santorini: Private Customizable Car Tour with a Local Guide
Catamaran Cruise
Consider enjoying a relaxing afternoon on the water and enjoy the stunning views of Santorini from the Sea! The below tour includes stops at Red Beach and White Beach, which will be beautiful to see from the boat. You’ll also enjoy a delicious meal and have time to relax!
Book the Santorini: Catamaran Tour with BBQ Meal and Unlimited Drinks
Profitis Ilias
My friend and I never visited this highest point in Santorini during our four days on the island. Our Airbnb hosts told us the road is windy and steep and after our Fira to Oia drive my friend was not interested.
While driving is an option, it’s not the only option as some choose to hike by starting at nearby villages like Pyrgos! If you do drive, head to the monastery called Moni Profiti Ilia. From there, it’s a short walk to the top.
Go for sunrise or sunset, but definitely try to avoid the hot midday sun!
Food Tours
You certainly don’t have to do a food tour during your four days in Santorini! There will be plenty of times for meals, desserts and coffee to give you a good indication of Santorini’s Greek food scene. However, if you enjoy a food tour and hearing more about the culinary scene of a destination, they are fun and informative!
I very much enjoyed the Little Havana food and walking tour I did in Miami and it really made the area come to life! So if a food tour in Santorini interests you, the below two are highly rated and worth considering.
Check out Fira: Guided Foodie Walking Tour with Tastings or
Santorini: Sunset Walking Tour with Local Food and Drinks
ATV or Horseback Ride
Now renting an ATV and exploring on your own may not interest you, but you can do an organized tour on ATVs! Of course, if you’d rather a more chill horseback riding experience, that is also an option in Santorini!
Check out Santorini Horse Riding to Black Sandy Beach or
Santorini ATV-Quad Experience Tour Transportation
Weather & Best Time to Visit Santorini
If you’ve been around here at all, you know I LOVE a shoulder season! Santorini is one destination I can’t recommend the shoulder months enough! You will get less crowds, beautiful weather and cheaper accommodations!
My four days in Santorini was in late May and while there were definitely people around, it still felt rather quiet! For my three days in Mykonos, I visited in late September and early October and again loved the weather, fewer crowds and cheaper hotel options! As an example, my friend and I stayed on the beach in Mykonos for one night. We paid $100 USD in early October, but I checked the price for that stay in July and it cost over $300!
The weather is cooler during the shoulder months, so that is something to consider if you want a beach vacation. However, it’s still warm enough to relax on the beach, but also pleasant for exploring!
Peak Season (June–August) 🌞
- Weather: Hot, sunny, and dry (average temps: 26–30°C / 79–86°F)
- Pros: Best beach weather, vibrant nightlife, all restaurants/shops open
- Cons: Very crowded, expensive hotels, high tourist traffic
Shoulder Season (April–May & September–October) 🌅
- Weather: Warm and pleasant (average temps: 18–26°C / 64–79°F)
- Pros: Fewer crowds, great weather, lower prices, still great for swimming in late summer/early fall
- Cons: Some seasonal businesses may still be closed in April
Low Season (November–March) 🍂
- Weather: Mild but cooler (average temps: 12–18°C / 54–64°F)
- Pros: No crowds, lower prices, local experience
- Cons: Some hotels, restaurants, and ferries shut down, weather can be rainy and windy
Where to Stay in Santorini
The dreamiest place to stay in Santorini is Oia, followed by Fira! You will have that side of cliff, stunning views kind of experience! The prices will be higher as a result, but if you’re visiting for a special occasion it will be worth it! If you do stay in either of these places, consider that you will likely be navigating stairs and maze like streets, but that will be part of the charm!
Since I went with a friend, we stayed near one of the black sand beaches in the southern part of the island. We were still able to visit both Oia and Fira, but enjoyed a quieter end of the island and cheaper prices.
If you plan to use the bus system, consider staying in Fira as that is the main bus stop on the island. If you stay somewhere else, you will be changing buses in Fira.
Art Maisons Luxury Santorini Hotels Aspaki & Oia Castle | Luxury | Oia
Athina Luxury Suites | 5 Star Hotel | Fira
Astra Suites | 4 Star Hotel | Imerovigli (10 minute drive to Fira and 23 minute drive to Oia)
Hotel Sunny Villas | Mid-Range | Imerovigli (8 minute drive to Fira and 21 minute drive to Oia)
Villa Kavallaris & Apartments Santorini | Budget | Mesaria (8 minute drive to Fira)
Asterias Mini Coastal Apartments | Budget | Perivolos (17 minute drive to Fira)
Four Days in Santorini
I hope my Santorini itinerary was helpful as you plan your trip! Not everyone will spend four days in Santorini, but this dreamy Greek island is worth it, in my opinion! Of course, I’ve enjoyed all the islands in Greece I’ve had the pleasure of visiting. Although, none had the stunning and dramatic beauty of Santorini!
Hope you have the best trip and love breathtaking Santorini as much as I did!
