lonesome roads

the art of self-romance in santorini

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Right now, I’m sitting in the middle of one of the most romantic destinations in the world, and I’m totally alone. Let’s be honest, this could be really weird.

This dude is solo and loving life (and Sunday’s parade).

The solo survival plan

I love super-romantic destinations and hotels, in a way that probably seems odd for a super-independent, very single solo traveler. This is not just because I love a good bathtub and for some reason, romantic hotels have that game on lockdown.

But romance is also associated with coziness, charm, and decadence. All things I adore. If I avoided places like beautiful and historic Santorini, my Burgundy chateau, or Paris, all filled with honeymooners and the occasional and exciting people having affairs, my life would be less beautiful.

I would not have peeped these views, and that’s a shame.

So what do I recommend for the solo traveler stranded on an island (literal, in my case, but sometimes metaphorical) full of couples taking pictures of themselves making out for their instagrams?

Here’s my 5-step guide.

1. Make friends

While a place full of twosomes can seem like an unfriendly place, there are loads of very sociable couples who come out of hiding from their romance lairs occasionally. After all, you can only spend so much time gazing into each other’s eyes.

Watching a beautiful sunset alone at a swank bar? Strike up a convo about how time-lapse photos work with the couple next to you and see if they’re feeing chatty (they were, and they were so lovely! Got a bunch of book recommendations).

Bond over becoming insta-famous with the friendly Australian girls on your catamaran cruise where you’re the only single person, and chat up the pair of friends from DC too, and the hilarious honeymooning couples. The free-flowing wine helps!

New friends!

2. Shamelessly people-watch

This is one of my all-time favorite activities, and it’s even better in famously romantic places. You would not believe how many couples get in wonderfully petty fights on the steps of Santorini or lost in the twisting Paris alleys.

As a single person in these places, you can often feel a little invisible. Use this to your advantage and get some free but priceless entertainment.

3. Treat your own damn self

Luxury, decadence, and pampering are not limited to the honeymooners. While a couple’s massage is out of the question, how else can you treat yourself well on your trip?

Buy that pricey catamaran cruise for yourself. Order room service and eat breakfast in your enormous, comfy bed. Eat baklava on your adorable pool deck while petting the hotel dog, Milo, and planning how to get out of Santorini when the ferry to Crete suddenly stops running (a live view of my life today). Read in bed for three hours. Treat yo’self.

4. Lean into the solitude

That sulking couple I mentioned earlier fighting on the steps? They probably just planned a 150-person wedding and flew through the night to get to Santorini, where they spent a ton of cash and feel like they have to have the perfect honeymoon (and show all this on Instagram). Quelle stress.

But you? You’re free and footloose. No jet-lag induced arguments, no pressure, no rules. Do whatever you want, even if what you want would seem lame to another person (personally, my favorite is reading the new translation of the Odyssey in bed at 6:30 am when I have insomnia).

Throw yourself fully into that freedom. Into the inherent awkwardness too occasionally, but into the hours of the days that belong entirely to you.

5. Flirt. Shamelessly.

So you’re the only solo person on a sunset cruise in the crystal-clear waters of the Aegean Sea, which is staffed by gorgeous people who want nothing more than to bring you spaghetti and wine.


Those honeymooners and the young parents can’t smile winningly and guiltlessly at every beautiful person they see. You can. And you’re on vacation! This is precious and should not be wasted. Live your best life!

Romance for one

If you skip going to places where you will be surrounded by couples, you’ll miss out on so much beauty. Don’t wait until you’re on your own honeymoon to see these beautiful places.

Just acknowledge those occasional awkward moments (and laugh at yourself a little), take in the scenery and people, and eat a waffle in bed.

You’re deserving of lovely moments when you’re solo, too.

2 Replies to “the art of self-romance in santorini”

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