Sailing past sunset in Santorini

In Santorini, Greece, some of the best vacation experiences happen after sunset. 

Austin Raymond was planning a romantic getaway from D.C. with his fiancé and the Greek island of Santorini was at the top of his list of dream destinations. Sailing on the Mediterranean and sipping wine while watching the sun set? Booking the trip was the easiest decision he’d ever made (next to proposing, of course). While there, the couple was blown away by the sunset excursions and the island’s unexpected beauty that came out after dark. Here’s Austin’s take on their once-in-a-lifetime trip:

How did you decide on Santorini for your dream vacation?

We wanted a fun, romantic, beautiful location to destress. Santorini checked all the boxes. We spent a week in the cliffside village of Imerovigli and then the northern town of Oia—famous for the blue-domed homes.

Oia may be the most picturesque part of the island.

What was your first impression when you stepped onto the island?

I couldn’t believe how tall the island was! The cliffs are 300 feet high, rising straight from the sea. It used to be a volcano that collapsed, and you can totally tell.

What after-dark excursions did you do and what stands out as a top moment?

We visited three vineyards with some other outgoing people and quickly made friends. We shared wine and snacks, and got to see how the grapes grow on the arid and windy cliffs, and even ate some right off the vine!

Santorini’s spiraled vines.

What about the food and overall vibe?

Sunsets and olives! I’m usually 50/50 on olives, but on Santorini they’re meaty and delicious. And you go to Santorini for the sunsets. At a cliffside vineyard, we caught a magnificent sunset over the caldera volcano crater. After dark, we stayed on the vineyard and watched the lights come on in the towns. We met new people over more wine and stayed up late trading travel stories.

Did you get out on the Mediterranean water?

We went on a large catamaran one night and sailed into the middle of the caldera, where the water was warm enough for swimming and snorkeling. It was super salty, so you could just float around. We sailed into a cove after to eat seafood and enjoy the calm night. 

Did the views end with the sunset? 

Seeing the sunset from the water was beautiful, but the moon was incredible! The island got very dark and the moon reflected off the water in a light teal glow. You could see how massive the cliffs are and the tiny speckled lights of the towns. 

My fiancé pointed out how the night sky bled into the sea, and it looked like we were sailing into outer space. One of the best views of the entire trip.

Santorini’s nighttime skyline.

So the best sightseeing of the trip was at night?

Yes! Even on our final night as we walked home up the steep path, we stopped on top of a cliff to look at the vast ocean and the little lights of Oia. It was incredible.