Views of Santorini 🇬🇷🌅

Santorini is one of those places where you think, I’ve seen a million pictures. I know what it looks like.No, you don’t. 😂 When you actually stand there and see the white cave houses spilling down the cliffs, the blue domes, the caldera and that ridiculous Aegean blue below you, it really is breathtaking. It’s one of the most beautiful places we’ve ever been.

It’s also crowded, expensive, steep, full of stairs and, at certain times of day, absolutely PACKED with people trying to take the exact same picture. 😂 But I still think everyone should see Santorini at least once. My biggest advice is not to turn it into a checklist. Stay somewhere beautiful if you can, enjoy the views you paid for, eat fabulous food, drink the local wine, get out on the water and give yourself time to actually enjoy where you are.

Getting to Santorini ✈️⛴️

You can fly into Santorini or arrive by ferry. If you’re flying from Athens, check the baggage allowance on the island flight because it may be much smaller than your international allowance. If you’re taking the ferry, rolling luggage is your best friend. The ferry itself can be very comfortable, but boarding and unloading can feel like everyone has suddenly entered The Amazing Race: Greece Edition. 😂

Santorini adds another challenge: the cliffs. The ferry port is at the bottom of the caldera, and getting up involves a steep, winding road. I would arrange transportation with your hotel ahead of time instead of arriving with luggage and hoping for the best. If you’re staying in Oia, ask exactly where the driver can leave you and whether the hotel provides luggage assistance. A lot of Oia is pedestrian-only, and that gorgeous cave hotel you booked may be down 57 stairs. This is NOT where you want to discover your suitcase weighs as much as you do. 😂

Oia 🤍💙

Oia is the Santorini you’ve been picturing your entire life. Whitewashed cave houses, blue-domed churches, tiny pedestrian streets, boutiques, restaurants, flowers spilling over white walls and that incredible caldera below you. It’s absolutely gorgeous.

It is also VERY popular. When the cruise ships arrive, the little pedestrian lanes can become packed. People are lining up for particular photo spots, standing on walls and taking approximately 400 pictures of themselves in a flowing dress. 😂 This is one of the reasons I really like staying in Oia rather than only visiting it for a few hours. Early in the morning and later in the evening, it has a completely different feeling. Get up, have coffee and wander before everyone arrives. When the crowds get crazy, go back to your beautiful hotel and enjoy it. Then come back out later.

Where You Stay in Oia REALLY Matters 🌅

One thing I didn’t fully understand before staying there is that not every Oia view is the same. If you want the iconic postcard view with the caldera, blue domes, cave houses and cliffs, look along the caldera side. If your priority is the actual sunset, look toward the western or sunset side of Oia. A caldera view does NOT automatically mean you have a sunset view, so ask before spending a fortune on the room.

If you want something quieter and usually less expensive, look around Finikia, just outside the busiest part of Oia. If you want to be down by the water and seafood restaurants, there’s Ammoudi Bay, but remember what goes down eventually has to come back up. 😂

Santorini is one place where I would actually contact a hotel before booking an expensive room and ask very specific questions: Is the terrace private? Can tourists walk directly in front of it? Is this a direct caldera view? Can we see the sunset from our room? How many stairs are there? Where does a taxi drop us off? Do you help with luggage? These questions sound ridiculous until you arrive. Then they suddenly become VERY important. 😂

Where We Stayed — Art Maisons Oia ❤️

We stayed at Art Maisons in Oia, and it was AMAZING. The views were honestly unbeatable. This was one of those places where I finally understood what you’re paying for in Santorini. We could sit peacefully looking out over this incredible landscape while people outside the hotel were practically hanging off walls trying to get the same view for a picture. 😂

That's what I loved about staying somewhere special in Oia. We could go out, shop, wander around and experience all the craziness, but then we could escape from it and enjoy Santorini privately.

One of my favorite things was the sunset arrangement through their sister property. Oia sunsets are famous, which means EVERYONE wants to see them. People start staking out spots, squeezing into little streets and holding their phones over one another's heads. Meanwhile, we had access to a private sunset area at the sister hotel. We were sitting peacefully watching one of the most famous sunsets in the world while everyone outside was fighting for a spot.

We felt like celebrities in a VIP section. 😂

That experience changed how I look at hotel prices in Santorini. Sometimes you aren’t just paying for the room. You’re paying for the view, privacy and access, and in Oia those things can make a huge difference.

The Santorini Sunset 🌅

Yes, the sunset really is THAT beautiful, but figure out where you’re going to watch it before sunset. Don’t casually wander out five minutes beforehand expecting to find a private little wall with an unobstructed view and a waiter handing you wine. 😂

If your hotel has a private sunset area, USE IT. If you’re making a dinner reservation specifically for sunset, ask whether your actual table has the view. And if you've paid for an incredible room or terrace with a sunset view, buy a bottle of wine and stay there! You don't need to leave your gorgeous hotel to stand shoulder-to-shoulder with hundreds of strangers because someone online told you there was one particular spot where you’re supposed to watch the sunset.

Ammoudi Bay 🐟🌊

We ate down at Ammoudi Bay, and it’s beautiful. It sits right at the water underneath Oia, with seafood restaurants along the waterfront and those dramatic cliffs towering above you. I definitely think it’s worth seeing and having a meal down there.

However, DO NOT look at the map and think, “Oh, we’ll just walk.” 😂 There are hundreds of steep, uneven stone steps between Oia and Ammoudi. They can be slippery, and you may also encounter plenty of donkey mess along the way. Arrange transportation when possible. Your knees, shoes and nose will thank me.

PLEASE Don’t Ride the Donkeys 🫏❤️

This is one of my biggest Santorini rules: please don’t ride the donkeys. Aside from the concerns about the animals working these steep routes, you’re dealing with uneven stone stairs, crowds, animals and all the mess that comes along with them. There are other ways to get around, so use them.

And definitely don’t walk those routes in inappropriate shoes. Greece already gives you enough opportunities to test your balance without adding a donkey to the situation. 😂

Santorini From a Cruise 🚢

If you’re visiting Santorini on a cruise, plan ahead because Santorini is not necessarily one of those ports where you casually step off the ship and you're standing in Oia. Cruise passengers generally tender ashore, and getting from the water up to the towns can take time—especially when several ships are there at once.

Know where your tender or excursion is leaving you, how you're getting to Oia and how you're getting BACK. If you can arrange transportation ahead of time through your cruise, excursion or a reputable local provider, I would. Most importantly, leave yourself plenty of time to return to the ship. This isn't where I would say, “We'll figure out a taxi later.” Later may involve thousands of other cruise passengers who had exactly the same idea. 😂

If you only have a few hours, don't try to see the entire island. I'd rather spend a wonderful few hours really experiencing Oia than spend the whole day sitting in traffic trying to check six towns off a list.

Get on a Catamaran ⛵

If you’re staying for more than a day, I HIGHLY recommend a catamaran tour. It was one of our favorite things we did. Santorini looks completely different from the water, and it really gives you a sense of how enormous and dramatic the caldera is and how crazy it is that these beautiful white villages are sitting way up on those cliffs.

Depending on the trip you choose, you can swim, see different parts of the volcanic landscape, eat and drink onboard and spend a good part of the day on the Aegean. It’s also a wonderful break from the crowds in Oia.

Santorini Isn’t Where I’d Go JUST for the Beaches 🏖️

Santorini absolutely has beaches, and they're really interesting because of the island's volcanic geology. You’ll find dark and black volcanic beaches, including areas around Perissa and Kamari, and the landscape looks completely different from the beaches on Naxos or Paros.

But if I only had a couple of days on Santorini, I personally wouldn’t spend one of them lying on the beach all day. Naxos and Paros are where I want to spend entire days at beautiful beaches. Santorini is where I want to experience the cliffs, villages, caldera, wine, food and views. If you have plenty of time, absolutely explore the beaches because they're another completely different side of Greece. I just wouldn't sacrifice Oia or a catamaran day for one if my time were limited.

Drink the Local Wine 🍷

Santorini wine is absolutely something you should experience. The island has volcanic soil and is especially famous for Assyrtiko, a crisp white grape variety. Even the vineyards look different. Because of the wind, the vines are traditionally trained low to the ground in basket-like shapes instead of growing in the tall rows we’re used to seeing.

Do a winery visit if you have time, but at the very least, order the local wine. You're sitting on a volcanic island overlooking the Aegean. This is not the moment to order the exact same wine you drink at home. 😂

Shopping in Oia 🛍️

Leave yourself plenty of time to wander and shop. Oia has beautiful little boutiques hidden throughout the pedestrian lanes selling jewelry, linen, clothes, artwork, ceramics, leather goods and Greek-made pieces. I always prefer finding something made by a Greek artist or designer rather than buying a generic souvenir.

And yes, I'm going to say it again: WEAR FLAT SHOES. 😂 I don't care how fabulous the flowing Santorini dress looks with heels. Oia has stairs, marble, uneven surfaces and hills everywhere. The ancient Greeks apparently did not consult us when designing the streets around our vacation outfits.

Eating in Santorini 🍽️🍅

Santorini is one place where I absolutely think you should have at least one meal where the view is part of dinner. You're in Santorini. You're allowed to pay a little extra to sit somewhere beautiful and stare at the caldera. But if you're booking somewhere because of a gorgeous photo online, specifically ask for a table with the view. A restaurant can technically have a caldera view while your particular table has an excellent view of another person's head. 😂

Eat seafood, local cheeses and fresh produce, and try Santorini fava, one of the island's traditional foods. Drink the local wine and, obviously, order the Greek salad because I will never stop talking about Greek tomatoes. They taste like fruit, and Greece will unfortunately ruin tomatoes at home for you forever. 😂🍅

And slow down at dinner. Greeks aren't trying to turn your table over every 45 minutes. Dinner isn't something you need to hurry through so you can get to your next activity. Dinner IS the activity. Sit, share food, have wine and enjoy where you are.

Don’t Over-Schedule Santorini ❤️

This may be my biggest advice about Santorini: if you spent a fortune on a beautiful hotel, USE THE HOTEL.

If you booked a cave suite with a private terrace, plunge pool and ridiculous caldera view, you don't need to leave at 7 AM and come back at midnight because you're terrified you're missing something. You're already sitting in one of the most beautiful places in the world.

Have breakfast. Drink coffee on the terrace. Swim. Read. Open some wine. Take approximately 600 pictures of the exact same view because somehow every picture feels necessary. 😂 Take a nap. Then wander back into Oia later when the crowds start changing.

Sometimes sitting on your terrace looking over the caldera IS the thing you came to Santorini to do.

My Perfect Santorini Day 🌅

I would get up early enough to wander around Oia before the biggest crowds arrive. Have coffee, take pictures and shop while the streets are quieter. When the cruise crowds start filling the lanes, go back to your hotel, have lunch, swim, relax and TAKE THE NAP. 😂 Greece has taught me that fighting the afternoon nap is completely unnecessary.

Then get dressed and head back out later. Have dinner somewhere beautiful, drink Santorini wine and watch the sunset from somewhere you've planned in advance rather than fighting 900 people for six inches of wall. Another day, do the catamaran and see the island from the water. If you have more time, add a winery, Ammoudi Bay and maybe one of the volcanic beaches.

You don't need 14 tours and 27 reservations.

Santorini doesn't need that much help being impressive.

Why I Love Santorini ❤️🇬🇷

Santorini is crowded. It's expensive. There are stairs EVERYWHERE. Someone will probably be taking 47 pictures directly in front of you. You’ll question every shoe you packed. 😂 And then you'll sit somewhere on that enormous cliff as the light starts changing, with white villages glowing against the deep blue Aegean, and you'll understand exactly why everyone comes. It’s stunning!!!

It really is THAT beautiful.

Naxos is somewhere I want you to stay and live a little. Paros is somewhere I want you to beach, nap, shop, eat and play.

Santorini is somewhere I want you to slow down, look around and think, “I cannot believe this is actually real.”

Because pictures really don't do it justice. 🇬🇷🌅❤️