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Not Your Typical Trip to Santorini

Luxury Meets Meaning and Authenticity on the Greek Islands

Our stunning view

It seems there are two categories of travelers: tourists happy with tourist experiences, content to anonymously eat at a restaurant at Fisherman’s wharf or spend an afternoon schlepping around Times Square, and tourists craving something less cookie-cutter.

I fall mostly into the latter. It’s my favorite thing to connect with a place and its people, to meet locals and hear their stories, see their homes through their eyes, and eat at their beloved local spots.

So it was the most incredible surprise when my partner and I went to Santorini, Greece — an island with a capital T for tourist and found ourselves at the Iconic Santorini, a cave hotel nestled into the cliff above Fira, identical to a sight you can easily muster up in your imagination when you think of the Greek islands.

We were greeted by the receptionist/hotel manager as if by a close friend welcoming us to her home. We were offered drinks with traditional ingredients of the island while we sat and chatted about ourselves, our plans for our time there, and the property. 

We were told that there were no set menus for room service — just call and ask for what you’d like, the manager instructed. And breakfast — an elegant surprise of a feast each morning — would be served every day at the time of our choice on our private table outside our room. There weren’t any set menus at the restaurant, either. Each day the chef would head to the market and then prepare whatever was fresh into the best meals we would eat on our entire trip. Never have I ever been a fan of hotel food (in fact, quite the contrary) but this wowed us. It was as if we had arrived at the home of a very friendly and doting host, careful to attend to our every need, make sure we were comfortable, happy, well fed, experiencing the best of what the area had to offer — and most of all, make us feel right at home.

Our private breakfast table

So often when I travel I feel anonymous. Another American tourist in a slew of tourists, washing in and out of whatever hotel in whatever city as I make my way through nearby attractions. I am just another credit card to swipe and another bed to make after I check out. In travel hot spots there are seemingly endless seas of us, swarming about without any real connection to the place or to the people.

This was different. We felt seen, we were known. And so we connected — with the place, with the people, and our fellow travelers, too. Yes, it was a luxury property and the hotel staff was tasked with making us feel well attended to. And, no, we weren’t actually staying at a friend’s house. But this was personal and real. It was luxury meets meaning and comfort and a warm sense of authentic familiarity.

On the last day of our trip, we ate a perfect chicken souvlaki at the pool overlooking the glittering Aegean sea and toasted our Mythos beer to an experience beyond our expectations — lavish and deluxe but also intimate and dear. I guess I really am that other kind of traveler.

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