Two Days in Santorini: Gem of the Cyclades

Santorini is a destination that needs no introduction.

One of the most renowned islands in the world, it is quite simply a breathtaking place—with whitewashed villages tumbling toward the sea and cobalt waters scintillating under the Aegean sun.

Considering its beauty, it comes as no surprise that the Greek island is a magnet for Instagrammers and honeymooners. Millions of tourists flock to its shores every year in search of the perfect white and blue backdrop.

Although I often pride myself in straying away from the crowds, I could’t resist adding Santorini to my Greece itinerary. I’d fallen prey to the lure of powdered sugar villages and sapphire seas.

And I and wanted to see it all for myself.

 

SANTORINI GREECE: AN OVERVIEW

Santorini is the most famous of Greece’s jewel-like Cycladic islands. It consists of two inhabited islands: Santorini (also known as Thera) and Therasia (accessible by ferry from Oia).

Santorini’s unique geography dates back to 1600 BC, when the Minoan eruption decimated the island and carved out a massive caldera that collapsed partially under water. The volcanic eruption was one of the largest natural disasters in human history. Its effects were so far-reaching, that mentions of the explosion can be found in literature from around the world—from Egypt to China.

Some even go as far as to suggest that Santorini could be the sunken city of Atlantis.

Today, visitors flock to Santorini in droves. They are drawn to the Greek island for its chic shopping, posh hotels, and humming nightlife.

But despite the appeal of Santorini’s human-engineered attractions, its stunning caldera remains the primary draw.

 

HOW TO SPEND 2 DAYS IN SANTORINI

While the idyllic Greek island packs a lot of punch, touring Santorini in two days is quite manageable. The island—though world-renowned and historically significant—is small and easy to navigate.

Dan and I traveled to Santorini with my parents and baby Elio, who was 9 months old at the time. Even with a squirmy infant who napped twice a day, we were able to fit the island’s highlights into a two day itinerary.

Of course, many travelers will want to spend extra time soaking in the island’s exquisite panoramas. I imagine it would be easy to lose track of time in some of the lavish hotels with their infinity pools and caldera views.

But each day on Santorini comes with a high price tag. So my family and I chose to spend our extra vacation days on the quieter, cheaper islands of Naxos, Paros and Milos instead.

 

DAY 1: HIKING AND SUNSETS

Santorini’s mountainous topography means that you don’t have to go far to get stunning aerial views over the Aegean’s sparkling waters. The plethora of lofty vantage points–coupled with an absence of view-obstructing trees–ensures that the island’s 360 degree panoramas are always photo-worthy.

On our first day in Santorini, we took on the island’s most renowned hike. The route connects multiple scenic tourist towns and encompasses striking views of the caldera.

• THE HIKE FROM FIRA TO OIA

The six mile walk from Fira to Oia is, without a doubt, my favorite Santorini activity. The hike follows the caldera’s rim between two beautiful whitewashed towns and boasts the island’s best views. It is an absolute must-do, as long as you’re willing to lace up your walking shoes.

The hike begins in Fira, Santorini’s urban hub. It hugs the cliffside along the city’s western edge–passing alongside blue-domed churches, bougainvillea-clad doorways and opulent luxury hotels. The walking path is a mix of paved pedestrian streets and dirt hiking trails. It is a hilly trek with little shade.

The trail isn’t always well marked, but as long as you keep the water to your left, you’ll eventually come across the official path.

For its first two kilometers, the trail consists of a well-trodden cobblestone walkway. It cuts through the northern end of Fira and its adjacent towns of Firostefani and Imerovigli. In Imerovigli, whitewashed homes give way to rugged and desolate terrain.

Travelers with a little extra time and energy may want to add a detour to Skaros Rock. The promontory is accessible from Imerovigli. Reaching the rock requires an additional hour of hiking, roundtrip.

A small snack shack lies at about the half way point between Fira and Oia. We stopped there for a small bite to eat, before continuing onward. Past the snack bar, the path continues up a dirt track to a small church. Then, it descends into Oia with jaw-dropping views of the cobalt sea.

My family and I spent the entire morning hiking between Santorini’s two main tourist hubs. Traveling in the hot sun with a newly walking baby required lots of breaks.

We didn’t mind at all though. The slower pace allowed us to enjoy the scenery all the more.

• OIA SUNSET

It is almost impossible to decouple Oia from the fiery sunsets with which it is often associated. Viewing the sunset in Oia is consistently regarded as a top Santorini activity. For this reason, I’ve decided to add sunset-viewing to my suggested itinerary.

Full disclosure though: we didn’t actually see the sunset. At least not in the sense that we saw the sun dipping below the water. The crowds were simply too intense and we didn’t feel like pushing through throngs of people in order to catch a selfie-stick-obstructed view of orangey sky. Especially with a 9 month old baby in tow.

However, for those who don’t mind being shoved by the masses, I’m told the sunset views are spectacular. My parents went out to see the sunset while Dan and I were rocking Elio to sleep. They gave it two thumbs up.

• OIA AT NIGHT

On our first evening in Santorini, after we put Elio to bed, Dan and I headed out for a moonlit stroll around town. We climbed up to the castle, then made our way down the long chain of steps to Ammoudi Bay—a waterfront area that houses the town’s finest seafood restaurants. In complete solitude, we relished the illuminated views of Greece’s most picturesque town.

After the day trippers and cruise ship tourists leave, a certain magic descends upon Oia. We found that wandering the deserted streets of town was somewhat akin to visiting Venice after dark.

Oia is considered by some to be the most beautiful village in the world. And in the evening lamplight glow, it wasn’t difficult for us to see why. The whitewashed town—rebuilt to its current glory after a devastating earthquake in 1956 all but obliterated most of the original buildings—looks like something out of a fairy tale.

 

DAY 2: THE REST OF THE ISLAND

While the walk from Fira to Oia gave us a perfect overview of Santorini’s offerings, our second day on the island allowed us to stray away from the main tourism hubs.

On day two of our itinerary, we stopped by Pyrgos, the Profitis Ilias Monastery, Kamari Beach, and Red Beach.

• PYRGOS

Pyrgos is Santorini’s former capital. The idyllic town sits perched atop a hill, in the shadow of the island’s tallest mountain. In all directions, it boasts magnificent views.

A castle lies at the center of Pyrgos. From the castle, the whitewashed village tumbles downhill toward the sea. The town reminded me of a Middle Eastern medina, with its kasbah-like fortification and twisting narrow alleyways.

Yet, while Pyrgos is full of charm and aesthetic appeal, its hinterland location has spared it the extravagant hotels and infinity pools that adorn the covers of tourist brochures. Pyrgos is not swamped by throngs of sunset chasers and Instagrammers. Nor is it the first stop for cruise ship tourists and day trippers. The city’s charm strikes a different chord: one that feels more authentic, less picture-perfect.

Unlike Fira, Immerovigli and Oia, we didn’t find it difficult to imagine locals living amongst the mix of hotels, restaurants and shops. In fact, it wasn’t until my family and I visited Pyrgos that we felt like we were in an actual town.

Because, if I’m being quite honest, the main towns of Fira and Oia made us feel a bit like we were in Disneyland.

• PROPHITIS ILIAS MONASTERY

Built atop the highest point on Santorini, the Monastery of Profitis Ilias (Prophet Elijah) stands tall. Offering all-encompassing views over the entire island, the monastic sanctuary is well worth visiting.

• KAMARI BEACH

Kamari Beach is a testament to Santorini’s volcanic past. Its stretch of ebony sand is one of the largest on the island. The beach lies southeast of Fira, adjacent to its namesake town—a popular resort area that is home to some of the island’s more reasonably priced accommodations.

While Kamari isn’t likely to make a list of best Greek beaches, we found it to be a great place to visit with kids. It is a great place to relax and one of the top places to go snorkeling in Santorini. Elio loved playing in the fine black sand, and we enjoyed soaking in the shallow waters.

• RED BEACH

Santorini’s most unique and iconic beach lies tucked behind a soaring bluff. On an island that is not particularly known for its sandy shores, Red Beach stands out as a visually stunning exception–though perhaps one that is best admired from a distance.

A rocky footpath connects the famous beach with a nearby parking area.

Exercise caution when visiting Red Beach. The area is prone to rock slides and technically off-limits. The warning signs do not dissuade throngs of daily visitors, however.

If you’re traveling without a car, you can visit Red Beach as part of a boat tour around Santorini. Most boat tours include pit stops at Red Beach and White Beach (a strip of sand that we did not visit because it is only accessible by water).

 

WHERE TO STAY IN SANTORINI

Santorini has no shortage of wonderful places to stay. These accommodations range from small apartments to luxurious villas.

While Santorini isn’t exactly a haven for budget travelers, decent cheap accommodation does exist. Most of the wallet-friendly options are located near the island’s sandy beaches, away from the main whitewashed towns. Notable exceptions are the Bedspot Hostel in Fira and the Central Hostel in Oia.

For travelers seeking mid-range accommodation, the hotels in Pyrgos offer a taste of opulence at a more palatable price point. Among them, are the Voreina Gallery Suites and Nova Luxury Suites.

And if you’re looking for a splurge, Santorini certainly has you covered. Just outside of Imerovigli, the Nobu Hotel offers some of the caldera’s best views with a side of delectable food. Also notable for its 5 star elegance is the Perivolas in Oia—a beautiful property with front row seats to the town’s famous sunset.

During our two day Santorini trip, we opted for a place that could accommodate a family of five. We found an AirBnb just outside of Oia. It was the perfect fit for our family and an affordable option.

I’m not going to lie though, a twang of jealousy hit me every time I passed the opulent hotels with their infinity pools and drop-dead views.

 

ISLAND HOPPING FROM SANTORINI

Santorini is a hub of travel in Greece and a perfect launching pad for multi-island adventures. The island is well-connected to Athens, as well as to the other Cycladic islands of Ios, Naxos, Paros, Milos and Crete. We spent two days in Santorini before continuing on to Naxos. Boat tickets were easy to secure, even during high season.

Numerous ferry companies make the journey between Santorini and its surrounding islands. You can find details and timetables at Ferryhopper.com

If you’re traveling from Athens to Santorini, you can choose to either take a ferry or fly. Flights take less than an hour and cost as little as $50 roundtrip.

 

TRAVELING SANTORINI WITH A BABY

Santorini isn’t exactly a typical destination for travelers with babies in tow. The Greek island caters to honeymooners, cruise ship tourists, and luxury-seekers.

Prior to setting foot on the island, I had multiple people tell me that I should look elsewhere if I wanted to bring the baby. The island is difficult to navigate by stroller and extremely hilly. It isn’t exactly the type of place where I could plop Elio on the beach and watch him play in the sand.

I’m happy we decided to travel to Santorini with a baby anyways. Visiting Santorini with kids can be incredibly rewarding. Elio handled the trip like a champ, and our Ergobaby got a lot of usage.

We quickly learned that carriers trump strollers on Santorini. So you may as well leave the stroller at home, unless you have the extra space to bring a versatile all-terrain stroller like the Guava Roam Crossover.

We brought a lot of baby gear on our trip, including our travel crib and travel car seat. If you don’t want to lug a million pounds of baby gear with you, I recommend renting the equipment you’ll need when you arrive. A quick Internet search led me to Santorini Travel Tots—a website that rents out the necessities.

 

WHEN TO VISIT SANTORINI

July and August are peak travel months in Santorini. I would advise against exploring the island during these busy months if at all possible. Santorini is notoriously crowded during the summer. While Greece is one of the best places to visit in June, I would suggest traveling to Santorini during the shoulder months of May and October. Even September remains high season.

When we visited in September, the crowds of tourists were so intense that we felt like a herd of cattle being corralled into a pen through a single doorway. I can’t even imagine what it would have been like had we decided to travel to the island during the two months prior.

If I were to visit again, I would choose May or October.

 

****

Before traveling to Santorini, I knew to expect the crowds and over-tourism. I kept my expectations in check, realizing full well that the images I’d seen online were often heavily curated and filtered.

Yet the island’s white-washed villages, dangling on the edge of the iconic caldera, still managed to take my breath away. As did its precipitous cliffs and its scintillating waters and its lofty viewpoints.

Put simply, no matter how crowded and expensive and overhyped Santorini is, the idyllic Greek island is still 1000% worth visiting.

 

________________________

DID YOU ENJOY THIS POST ON THINGS TO DO IN SANTORINI? PIN IT!