Santorini

Greece is already a dream destination, but Santorini takes the cake. The views, the sunsets over the caldera, and the white and blue buildings built into dramatic cliffs are gorgeous.

Santorini Island used to be known as Strongili (which means round in Greek). A giant volcanic eruption in 1500 BC caused the middle of the island to sink, and earthquakes destroyed most of the island.

The island has been a center of trade, home to pirates, and had many different owners until most of the inhabitants left after an earthquake in 1956. Today, Santorini is a bustling tourist destination thanks to development work that started back in the 70’s.

STAY in FIRA

In Santorini, my favorite place to stay is Fira (also called Thira). Kavalari Hotel is in a prime location and built into the cliffs. The hotel has caldera views, a friendly staff, and most of the rooms have balconies.

The hotel entrance and lobby is at the top of the cliffs. Kavalari Hotel has staff that will help bring your bags down the many stairs to your room.

The hotel’s Greek breakfast comes with this lovely view.

Breakfast included juice, coffee, pastries, cheese, vegetables and fruit bowls.

It was worth the extra cash to stay in a hotel with a caldera view. Kavalari Hotel is conveniently located on a relatively flat area of the island filled with shops, bars and restaurants.

Fira is not nearly as expensive as Oia, has a lively night-life scene, and with the relatively flat walking paths, is much more friendly for your knees.

I loved waking up to this view of the sandy cliffs every morning.

The balconies are “semi private” but that is because they’re all connected by a winding walking path for guests to get from the top to bottom of the hotel.

There are plenty of outdoor terraces not connected to any room that guests can enjoy.

The top and bottom of the hotel are closed to non-guests.

The property used to be a captain’s house. There are 18 different rooms, and some (like the one we stayed in) are cave rooms.

I recommend booking directly through the hotel - we got a complimentary upgrade upon arrival!

STAY in OIA

We broke our trip up and stayed in both Fira and Oia. Oia is THE spot to see the sunset, but it also draws the crowds, tourists and cruise ships. All those people aside, the architecture around every corner is stunning.

Oia Mares Villas is at the tip of Santorini. It is more expensive than the Fira hotel, but an iconic spot - so splurge for a night or two and treat yourself.

Oia has never ending stairs, and even when you get to Oia Mare Villas, the stairs do not stop.

Just be mentally prepared, wear good shoes, and get the hotel’s help in moving your bags.

The hotel has a pool overlooking the cliffs, which is exactly what I was looking for in an Oia hotel.

The property is above Amoudi Bay, the old port of Oia.

The white and colorful buildings facing the water never got old.

This is the view from our balcony.

There are also plenty of lounge options to watch the sunset (away from the crowds)

The hotel is situated in the cliffs, but it is about halfway down, so it is not the highest point in Oia.

The hotel has cave rooms, and even a cave-like shower. Our room had a small terrace too.

My flight back to Athens was super early, so I didn’t get to experience the real breakfast, but the front desk did make us a to go tray the night before.

I still can’t believe this was our view walking out of the room.

DO

Santorini is surrounded by colorful land coming out from the sea - if you go on a tour around the island, you can see the white, black, and red cliffs for yourself.

My favorite activity of the trip was a caldera cruise around the island with Caldera Yachting.

Kavalari Hotel helped arrange it (and even got us a discount!). The tour included hotel pick up and drop off. The catamaran took off from Amoudi Bay and sailed around the island.

The semi-private catamaran held 10 other people.

It was a fun experience and a great way to see the entire island from the water. There are many options for routes, stops and time of day for the boat tours including afternoon, happy hour or sunset cruises.

Our tour had an open bar and included a Greek dinner that was cooked on the catamaran.

This was my favorite and most memorable meal in Santorini.

While I thought watching the sunset from a balcony or cliffs of Santorini, it’s equally impressive from a boat.

DRINK

We stumbled onto this small shop for happy hour. Santorini is known for its windmills.

From any vantage point, it’s a great view.

Here’s our happy hour spot from near the windmill.

I made sure to take advantage of the balcony in Fira and the wine that came with the room.

Franco’s Bar in Fira is a fun spot for coffee, breakfast, or happy hour. It is a short walk from Kavalari Hotel.

I cannot get over the white buildings set into the cliffs of Santorini.

DO

For some cardio, walk down the few hundred steps to The Old Harbor. Keep your eyes peeled for the donkeys that go up and down the steps too. They tend to take up the whole sidewalk, so stay away from any narrow spots when you see them approaching.

Here’s what you can see from halfway down the stairs.

Above, is Fira (for scale).

Amoudi Bay is at the tip of Santorini in Oia, and filled with water front restaurants.

The hotels and buildings look tiny from the bay, and shows off how vast the cliffs of Oia really are.