Gliding through the sunset in Santorini

In Santorini, Greece, some of the most unforgettable vacation moments unfold after the sun goes down. 

Austin Raymond was organizing a romantic escape from D.C. with his fiancé, and the enchanting Greek island of Santorini topped his list of dream destinations. Enjoying a sail on the Mediterranean while sipping wine as the sun dipped below the horizon? Booking the trip was the easiest choice he’d ever made (second only to his proposal, of course). During their stay, the couple was captivated by the sunset excursions and the island’s hidden beauty that emerged after dark. Here’s Austin’s perspective on their unforgettable journey:

What led you to choose Santorini for your ideal getaway?

We were looking for a vibrant, romantic, and picturesque location to unwind. Santorini met all our criteria. We spent a week in the cliffside village of Imerovigli and then in the northern town of Oia, renowned for its iconic blue-domed houses.

What was your initial reaction upon arriving on the island?

I was amazed by the sheer height of the island! The cliffs soar 300 feet above the sea, rising steeply. It used to be a volcano that collapsed, and you can definitely see the evidence of that.

What nighttime adventures did you experience, and what stood out as a highlight?

We explored three vineyards with some other friendly travelers and quickly made new friends. We savored wine and snacks while discovering how the grapes thrive on the dry, windy cliffs, even enjoying some fresh off the vine!

What can you tell us about the food and overall atmosphere?

Sunsets and olives! I’m usually hit or miss with olives, but in Santorini, they are rich and tasty. Plus, you come to Santorini for the sunsets. At a cliffside vineyard, we experienced a stunning sunset over the caldera volcano crater. After dark, we lingered at the vineyard, watching the towns light up. We connected with new friends over more wine and spent the night sharing travel tales.

Did you venture out onto the Mediterranean Sea?

One evening, we boarded a spacious catamaran and sailed into the heart of the caldera, where the water was warm enough for swimming and snorkeling. It was quite salty, allowing us to effortlessly float around. Afterward, we anchored in a cove to savor fresh seafood and soak in the tranquil night. 

Did the stunning views end with the sunset? 

Witnessing the sunset from the water was breathtaking, but the moonlight was absolutely mesmerizing! The island fell into darkness, and the moon cast a soft teal glow on the water. You could really appreciate the vastness of the cliffs and the twinkling lights of the towns. 

My fiancé remarked how the night sky blended seamlessly into the sea, creating the illusion that we were sailing into outer space. It was one of the most stunning views of the entire trip.

So, was the best sightseeing experience of the trip during the night?

Absolutely! On our last night, as we walked home along the steep path, we paused on a cliff to gaze at the expansive ocean and the twinkling lights of Oia. It was breathtaking.