The Perfect 5-Day Santorini Itinerary

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I’m sharing all the deets of our 5- day Santorini itinerary in today’s Santorini travel guide!

Santorini is one of the most Instagrammable places on earth (just peep my 20 Instagrammable spots in Santorini guide here!), and it’s also one of the dreamiest places I’ve ever been to.

The caldera-shaped island is naturally stunning, with dramatic cliffs overlooking a turquoise sea. It’s legit heaven on earth.

But there’s more to Santorini than just great views: there are also lots of things to do here that go beyond just admiring the view from your balcony or hotel room (even though it’s so stunning and we spent hours doing that too!).

Pssst, heading to Santorini? Don’t miss these travel guides to help you plan your trip!

The Best Santorini Views: Top Can’t Miss Spots

Santorini Sightseeing: Top 20 Things to Do in Santorini

Airbnb Santorini: Iconic Places to Book

So if you’re planning a trip to Santorini soon, here’s what I’d recommend for five days in this island paradise.

Book some of my favorite things to do in Santorini through GetYourGuide below!

First, a few general Santorini travel tips…

Where to Stay in Santorini

Oia is the iconic spot you’ve seen all over Santorini blog posts and Lonely Planet books. So if you’re looking for that quintessential Santorini experience, you might want to book a hotel here.

Since Oia is the most popular town, it’s also the most expensive.

Fira, the next town over, also has beautiful caldera views and more budget-friendly options.

How many days should I spend in Santorini?

There are so many incredible Greek islands to visit and while Santorini is obviously one of the most popular ones (if not the most popular), you have a lot of options.

We were considering splitting our time between Santorini and another island but ultimately decided to spend all of our time in Santorini and come back another time to visit other islands.

We actually had six full days in Santorini and I was a little worried it’d be too much time and we might get bored. This ended up being so far from the truth—we were able to have the perfect mix of just relaxing by the pool and enjoying our incredible hotel and the views from there, as well as going out and exploring Santorini.

I’m so glad we decided to spend the full six days here because two or three days just wouldn’t have been enough!

Do I need to rent a car in Santorini?

This depends on where you’re staying and what your plans are, but in general, you don’t need a rental car every day during your time in Santorini.

It’s pretty easy to rent a car just for a day or two when you want to get around the island and explore more.

On other days, you can easily walk around Oia or take a cab to a neighboring town.

What time of year should I visit Santorini?

Shoulder season is the best time to visit Santorini. During peak summer months like July and August, the temperatures get pretty hot—I just Googled averages for July/August and it said 84 degrees Fahrenheit, but I honestly don’t think that’s accurate.

Summertime is also when there will be more crowds, both from people staying on the island for vacation and from cruise ships that drop off thousands of people during the day.

I would say late September or early October are the best times to visit Santorini. The weather will still be nice and warm and you’ll have thinner crowds.

Starting around late October, many restaurants and shops will close for the winter and open back up again when the weather starts to warm up in the spring.

Do I need travel insurance for Greece?

Travelers to Greece are not legally required to have travel insurance. It’s always a good idea to have some form of travel insurance though. I personally have the American Express Gold card, which is the best credit card for travel IMO as it gives you 4x points on dining, travel, and groceries, as well as travel coverage.

You can sign up for the American Express Gold card and get 90,000 bonus points when you spend $4k in the first six months through my referral link here! Their typical bonus program is 60k points when you sign up but right now they’re doing an extra 30k points. For reference, I used my 60k points to book a roundtrip flight to the Maldives!

Alright, let’s get into this five-day Santorini Itinerary!

5-Day Santorini Itinerary

Santorini Itinerary: Day 1

Explore Oia

Start out by exploring famous Oia—just strolling around will give you plenty of magical scenes to obsess and wonder over.

The main streets of Oia are narrow and can get crowded, especially during peak travel season and during the afternoon after the cruise ships have added thousands more tourists to the island.

So either explore Oia in the morning or just be prepared for some areas to get crowded.

You’ll definitely want to see and get a photo of Oia’s famous blue domes.

There are so many incredible spots in Oia to take some seriously wanderlusty pics. Be sure to read my 20 Santorini Instagram Spots post here—it gives you Google Maps pins and exact locations for the best photo spots.

Lunch at Pitogyros

Once you’ve worked up an appetite strolling the cobblestone streets and getting epic photos in Oia, head to Pitogyros for an insanely delicious gyro at a super affordable price.

This spot is cheap and delicious, which is definitely welcome in Oia where you get price gouged a bit at most restaurants.

We grabbed ours to go and just sat on some steps, but they do have some outdoor seating if you’re willing to wait for a table.

Hotel/Pool time

After lunch, we went back to the Mystique to cool off at the pool and just marvel at the incredible views. We literally felt like we’d died and gone to heaven.

Ammoudi Bay for Sunset and Dinner

Once we’d relaxed poolside for a bit and the heat of the day was starting to wear off, we were ready to head back out and walk through the streets of Oia again, this time on our way to Ammoudi Bay.

To get to Ammoudi Bay, you have to walk through the main street of Oia and then down a lot of very steep cobblestone steps.

I was ill-prepared for this and not wearing the right shoes for these steps. They’re oddly shaped (slanted downwards, long, and steep) and they’re slick—I almost ate it several times in my sandals.

You can also take a cab to Ammoudi Bay but the walk and the steps (though a bit treacherous) really is beautiful.

Once you make it down to Amoudi Bay, take some time to just stroll around and admire the stunning view. The water is so turquoise and beautiful and the little restaurants are set against the red cliffs of Santorini.

There are a lot of inviting-looking fish tavernas at Ammoudi Bay, but Ammoudi Fish Tavern is the iconic spot here.

So iconic that when you make reservations, you have to pay a $20 deposit (that then gets deducted from your bill when you dine here).

It’s definitely a pricey spot but the seafood is so fresh and awesome, and you really can’t beat the views.

You’ll be able to see why everyone raves about this place—it’s truly beautiful!

Pro-tip, when I booked the reservation online I told them we were celebrating our anniversary and asked for a table with a nice view. When we arrived the host was kinda teasing me (we noticed during our trip to Greece that a lot of the men have a funny sense of humor and like to pull your leg a bit) and asked if it was me who requested the best seat in the house.

I was a little confused but played along, and he literally gave us the best seat in the house—we were seated in a corner table at the very edge of the platform that juts out into the ocean.

The views were truly epic and we had such an unforgettable night here.

Santorini Itinerary: Day 2

For your second day in Santorini, book a food and wine tour or take a cooking class!

We enjoyed such awesome food in Santorini, and experiencing their food is an amazing way to spend an afternoon, while learning all about local cuisine and culture. Here are a few different options for a foodie day in Santorini:

Santorini Food & Wine Tour: This is a perfect option if you love wine and want to try some of the best wines on the island—you’ll visit wineries and taste different varieties of local white wines before heading back into Fira, where they’ll treat you with traditional Greek dishes like calamari salad or octopus salad (with feta!).

You can book this wine tasting tour here.

Santorini Cooking Class: If you love cooking classes, this one is for you! In this class, which takes place at a restaurant, you’ll sample wines and learn how to cook Greek food with a professional chef.

Olive Oil Tasting: For those who want to learn more about the olive oil-making process, check out this tour where you get to go down into their caves to sample honey and olive oil.

Go on a Sunset Sail from Oia

You can’t go to Santorini and not do a sunset cruise from Oia!

It’s a great way to get a different view of the island, and they’re available most nights. They’re also easy to book since there are many companies in Oia that offer them. You’ll need to make sure that you have reservations before you go out on your sail.

Book your sunset sail below:

What to bring: Your camera (of course) plus sunscreen and a hat. Wear a swimsuit underneath your clothes so you can take a dip.

We booked this boat tour through GetYourGuide and it was great. They took us around the island to the “hot springs” (it was more like “slightly warmer than the rest of the cold water” springs) and the red beach.

They also cooked up a delicious Greek dinner for us on the boat.

We didn’t have the best sunset that night because it was a bit cloudy, but I’m sure they get some pretty epic Santorini sunset views out on the water.

I definitely wished I had brought a warm sweatshirt to wear on the way back—things got chilly and windy as we made our way back in.

Santorini Itinerary: Day 3

Road Trip around Santorini

You absolutely have to spend one day renting a car and driving around the island to explore other towns!

Below, I’ve created a little Santorini road trip itinerary for you. Oia is the starting point but you can of course take this itinerary and make it your own based on where you’re staying.

Visit the charming town of Megalochori

We started out by driving 30-minutes south of Oia to the small and charming town of Megalochori.

The town is known for its beautiful seaside architecture and cobbled streets. It’s so much quieter than Oia and was a welcome reprieve from the crowded streets there.

I loved Meglochori so much that I wrote up this Megalochori Santorini post with more deets on this charming town and what to do there. A few highlights include the Megalochori Bell Tower, the Underground Caves, and the all-white Saints Anárgyri Holy Orthodox Church.

Drive to Pyrgos – Explore the Town and Have Lunch at Kantouni

Hop over just a 6-minute drive east to the nearby town of Pyrgos.

We popped into Kantouni to put our name in for lunch—it’s a popular spot and there was about a 40-minute wait, so this gave us the perfect amount of time to walk around the town a bit.

Expect to climb a lot of steps as you explore Pyrgos. We made our way up to Theotokaki – The Assumption of the Mother of Lord Holy Orthodox Church, which is known for its beautiful architecture.

We used Google Maps as our guide but we also just kind of got lost along the small streets and stairways and snapped a ton of photos along the way.

Lunch at Kantouni

After visiting the church, head back down to Kantouni for lunch. You’ll see a lot of locals hanging out here as well (always a good sign!). The food here is absolutely delicious and super reasonably priced!

Highly recommend getting the grilled octopus—it was some of the best octopus we had on the island (and like, maybe ever) and I think it was like 12 Euros for a generous serving.

They also had this amazing Cretan dish that was SO decadent and amazing. It was like a fried dough stuffed with meat and yummy things and an insane, creamy cheesy sauce on top. Ughhh so good!!

Ancient Thira

After lunch, we made our way to the Ancient Thira Archaeological Site. This is the oldest part of Santorini and was once its main town before being buried by volcanic ash in 1500 BC.

Today, it’s a UNESCO World Heritage Site where you can visit the remains of this prehistoric city that thrived during the Minoan period. This ancient civilization flourished on Santorini between 3100 and 1400 BC and it’s interesting to learn about their culture as well as how they lived here thousands of years ago.

Ancient Thira is basically on top of a mountain, so to get up there you’ll have to drive up some narrow, steep switchbacks.

I’d also recommend bringing good shoes or even hiking boots for this visit. I didn’t realize that it’s pretty rocky with lots of loose gravel and steep steps, and I was wearing sandals. At some point, I had to stop and just wait for Omied as he went up ahead to explore by himself because I was worried about spraining my ankle and ruining the rest of the trip.

Santorini Brewing Company

Y’all know I’m not into beer, but Omied is a craft brew fiend. So of course, being the loving wife I am, I made sure we had time to stop at Santorini Brewing Company so he could do a tasting.

This is a great stop for those who want to sample some local brews and see how the brewing process works. The brewery itself offers tours of its facilities as well as tastings in their tasting room and deck outside.

You can also buy bottles here to enjoy at your hotel later.

Windmills + Santa Irini Bakery

I wanted to be sure to visit this bakery where you pay by weight and load up your bags with cookies and pastries!

This is a spot I saw on a lot of travel guides and I’ll be honest, the cookies weren’t anything amazing. Don’t get me wrong, they were good and we enjoyed them, and had fun picking out a bunch to try. I think they just got a little hyped up for me lol.

On our way there we happened to spot these windmills up on a hillside and had to stop and snap some pics. They were super cool and apparently windmills in Santorini used to be used to grind flour and housed bakeries as well.

If you wanted to visit the black sand beach in Perissa, this would be the time to do it. We ended up skipping and heading back up north to Fira so we could catch the sunset!

Visit Fira – Watch the Sunset from Franco’s Bar and Have Dinner at Parea Tavern

To round out your evening, head back up north to Fira, the capital of Santorini, to catch the sunset and enjoy dinner! We walked around and visited the Three Bells of Fira for some golden hour photos, and then made our way over to Franco’s Bar.

Franco’s has such gorgeous views of the caldera and it’s a really popular spot for sunset, so it doesn’t hurt to get there early. We had drinks and apps here and soaked up those gorgeous views.

After sunset, we walked down to Parea Tavern for dinner. This restaurant has a lot of Greek classics and their moussaka was to die for!

Santorini Itinerary: Day 4

Wine tasting at Domaine Sigalas

You can’t miss a visit to Domaine Sigalas, a small winery with a tasting room in Oia. They’re known for their high quality and unique blends, and several locals told us it’s the best wine and place for wine tasting on Santorini—they weren’t wrong!

Definitely indulge in the food and wine lunch pairing here—you absolutely won’t regret it. You’ll get a tour of the vineyard and learn about the vines and growing grapes in this area of the world. It’s so different than what I’m used to in Napa!

The vines are groomed to be round and low to the ground, known as “koulouri” or circular, which helps protect them from the strong wind.

We tried a lot of different Greek wines when we were out at restaurants and Domaine Sigalas‘ wines were hands down the best. Their lunch pairing was fantastic—each dish was delicious and paired so well with the wines we were tasting.

We spent a very leisurely afternoon here and loved every minute of it!

Sunset at Oia castle

I was pretty buzzed after our wine pairing, so we relaxed at the pool at our hotel during the late afternoon. After that, we were ready to head out again!

Oia Castle is known for being one of the most popular spots in Oia (and all of Santorini) to watch the sunset.

Since it’s such a famous spot, if you want to have space to sit down you’ll need to arrive early. I think we got there 1.5 hours before sunset and we just barely managed to get a spot to sit!

Elements for Dinner

Elements was a recommendation that a very friendly and sweet server at the Mystique gave us (shout out to Dorota!), and it was one of our favorite meals during our trip!

The restaurant is at the hotel Canaves Oia, and the setting is absolutely stunning. While they don’t have caldera views (they’re on the other side of the island), they do have ocean views and just a really lovely ambiance.

The menu features Mediterranean and modern European cuisine with Greek touches. And their cocktails were absolutely out of this world.

You can book reservations online.

Santorini Itinerary: Day 5

Book a Flying Dress Shoot

If you’re extra and you know it…book a flying dress photoshoot! It’s seriously so much fun and the pictures turned out epic.

We used the one of me and Omied for our holiday card last year and I’m telling you guys, I have never received so many texts and questions over a holiday card before, lol!

This shoot was so much fun and I love how the photos turned out. Where else are you going to shoot an epic, ridiculous large dress (that an assistant throws up in the air for you to give that “flying” look) with an incredible backdrop??

Book a flying dress photoshoot below:

Explore Imerovigli

I purposefully left Imerovigli off of the road trip itinerary, since I knew we’d be spending a full afternoon there on another day. We rented a car for this day but afterward realized it would have been relatively the same price and easier to just get a cab from Oia!

Or if you’re looking for an Oia hike, the path from Oia to Imerovigli is a popular hike that will take about 2.5 hours to complete.

Once we got to Imerovigli, we walked around the town for a bit and stopped at Imerovigli’s famous photo spot, Church of the Resurrection of the Lord.

Let’s Eat

We grabbed gyros at Let’s Eat for a cheap lunch spot. Their gyros were good but not as good as Pitogyro’s in Oia.

If you’re ok with something more expensive for lunch, Vigla Restaurant & Cafe has great reviews.

But we wanted something quick and casual to fuel us up for our next activity…

Hike to Skaros Rock

We hiked down to Skaros Rock for some amazing views. It’s a moderately challenging hike and takes around 40 minutes to an hour roundtrip, depending on how much you stop to enjoy the views and take photos.

It’s not a long hike but it’s steep, so you’ll definitely work up a sweat on the way back up.

Once you get to Skaros Rock, you can also continue down more steps to Panagia Theoskepasti Chapel. We didn’t continue on because we were tired lol, but it looked beautiful!

Armeni Bay for Dinner

We freshened up after our hike and relaxed at the hotel for a bit, and then walked down to Armeni Bay.

Armeni Bay is next to Ammoudi Bay, and it’s definitely quieter and less well-known. Again, you’ll have to face a lot of steep, slick steps on your walk down there.

We had a delicious seafood dinner at Armeni Restaurant. The ambiance is simple and the restaurant is open-air, right by the water.

It’s just very chill and all the servers are friendly and super helpful. We loved this spot!

The icing on the cake was, after dinner, the restaurant coordinates a small boat that will pick you up from the dock and take you over to Ammoudi Bay, where they’ll have a cab waiting for you.

The boat ride over to Ammoudi is one of those surreal moments that I’ll never forget. The moon was shining so bright, the stars were out, and Oia looked like a fairy tale on the cliffs. It was so serene I literally almost asked the driver if we could just ride around on the boat with him while he picked up other passengers and went back and forth, haha!

Also, if you don’t want to walk down to Armeni Bay from Oia, you can get to the restaurant using this method as well. You can give Armeni Restaurant a call or have your hotel help coordinate, but you can take a cab to Ammoudi and get picked up by boat to get to Armeni.

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That’s my super in-depth 5-day Santorini itinerary! We absolutely loved our time here and would love to come back again someday. Santorini is just other-worldly!

If you’re heading to Santorini and hit up any of my recs from this Santorini itinerary, please tag me in a Story, @wtfab on Instagram, I’d love to see what you get up to!

Loved this Santorini itinerary? Don’t miss my other Santorini guides here!

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Megalochori Santorini: Discover This Charming Town

Santorini Sightseeing: Top 20 Things to Do in Santorini

Top 20 Santorini Instagram Spots

Mystique Santorini Review