Good morning! I’m writing this to you from the sky. I’m off on an adventure, heading to market in New York for a high-level brand transformation project that Long Weekend is working on. We are in the process of helping a national retailer reimagine & enliven their product assortment & in-store experience.
Today I’m kicking off the first in what will be a series of (inconvenient) Island Guides… I’ve felt conflicted about writing this one. About starting this series at all. This piece speaks to a lot of what I feel around intentional travel, the dissonance between wanting to share openly, and also wanting to respect where you’ve been and what you love about a place.
My friend Kim put it perfectly:
“There’s a loss of intimacy, meaning, and curiosity. The openness and wonder that once defined travel have been replaced by checklists and photo ops.”
I feel that tension all the time.
A small example: I felt a ping of excitement when Le Sirenuse announced their new beach club in Nerano and, almost simultaneously, a ping of regret. Because the rooms above Lo Scoglio, my favorite off-season hideaway, may soon be less affordable & less available.
That’s the thing about travel. It’s ephemeral.
A return visit is never the same — even if time stands still, even if you never tell a soul about a place.
So why share at all?
Because I believe in sharing. I care deeply about it. I want to encourage more of it.
I love traveling from my sofa. I love reading about other people’s journeys—- not to replicate them, but to feel what they unlocked. Monica & Marissa are a couple travel favorites right now, and of course the OG Club Yolo. Yes, sometimes I look up the places they mention. But I rarely feel the need to repeat an itinerary. It’s not about that. It’s about feeling the wonder through their writing.
It’s about tuning my energy to openness. To curiosity.
From that place, I want to start offering small windows into some of the islands (and occasionally mainland places) I’ve been lucky enough to experience.
Not a guide. Not a checklist.
A tight edit, and a loose itinerary:
How it felt to be there
Something I loved
Something I noticed
Something I carried home
Yes, you could be inspired to plan a visit, but it’s not meant to be a comprehensive travel guide…yet (tell me if that’s what you desire and we can talk; I always have a Google map on the ready). But for now, this is something else.
This is a roadmap of desire.
A chance for me to wind the clock back and notice the thread in the places I’m drawn to. To enjoy past journeys. To share the adventure. Because it’s only once we’ve arrived somewhere that we can see where we’ve been heading all along.
[Editor’s note: I did book a trip to Folegandros because of Monica’s newsletter… sometimes you just need to give into the yearning and go take a look for yourself].
It’s very clear to me now: I have a thing for islands. Difficult islands. Today we are starting on one of the first ones I had the pleasure of visiting. From Hydra I didn’t know what stretched in front of me. Only where I was.
So with this new little window into a place, a tight edit and loose itinerary, my intention is to inspire you to perhaps think differently about journeys of your own. To get lost in wonder. And perhaps to travel not to collect places, but to let them quietly rearrange you.
Hydra is small, just under fifty square kilometers, but its gravitational pull has always been outsized. Set in the Saronic Gulf, south of Athens, it sits between the mainland and the open Aegean, long positioned as a crossroads.
In the 18th and 19th centuries, Hydra’s shipowners built fortunes and helped fund Greece’s War of Independence, leaving behind the stone mansions that still line the harbor. Later, the island drew artists in search of clarity and constraint. Leonard Cohen wrote here. Henry Miller passed through. Painters like Brice Marden and Panagiotis Tetsis found a rhythm that let their work breathe.
With no cars and no appetite for hurry, Hydra has always protected its lineage. Maritime, artistic, human.
This is a place that feels out of the way, it’s an island that asks something of you.
To arrive here on the ferry is to shift rhythms entirely from the mainland. The harbor hums, but without automobiles. Boat, donkey and on-foot are the means of transport here. Life is social, the town ebbs and flows with summer visitors joining and leaving (and sometimes returning… the gravitational pull here for those who love it is strong). The protected harbor forms a nucleus for daily life. From there, worn stone steps twist and climb the hills upwards, making for great glutes and plenty of ways to get a little lost.
Hydra isn’t for everyone.
If you’re looking for luxury and frictionless, full-service travel, this isn’t your place.
But if you’re willing to slow down and let the island lead, welcome.
My time there was deeply soulful and wildly spontaneous. I lured my friend Anthony over for a few days (he’s a frequent returner now). I spent long days alone, sitting by the sea with questions that felt too big to answer anywhere else. Some questions are so deep they require dropping into an island like this.
I made unexpected friends. Josh, who runs the Hydra Book Club. Fellow adventurers Bill, Michael and Amy, who return every summer. On my final night, I dined at a long table for 20. Serenaded by a neighbor’s violin, surrounded by new friends, overwhelmed by the grace of Hydra. Needing to say a proper goodbye, I slipped away alone to my favorite swimming spot. I peeled off my dress and dipped into the dark quiet sea one last time, washing off the heat of summer and sealing my admiration for this inconveniently perfect island.
Peel Me a Lotus (Charmian Clift’s lyrical account of her early years on Hydra)
Hot Milk (a sun-soaked Deborah Levy classic)
All found at Hydra Book Club (thanks Josh!)
A glass wine carafe from the hardware store, the same one used by my favorite proprietress at Ostria
90% bathing suits, 10% skinny dips
Pack flats. There’s no need for heels on Hydra’s cobblestones… i recommend a barefoot nighttime stroll to feel the suns warmth still radiating on the stone
Endless sardines at Ostria
A perfect pasta at Il Casta
Lunch at To Pefkaki, swimming between courses
Dinner in Kamini at Pirofani, or Kodylenias for sunset
1821 is the spot for evening socializing
Pirate Bar in the port
Hydronetta for aperitivo, swimming, and my favorite late-night dip spot
Everywhere!! The best places aren’t necessarily the coziest… but just getting to the sea as often as possible anywhere you can. Everyone seems to find their own ‘favorite’
A classic is Avlaki Beach for postcard-worthy rock slabs full of sunbathers
I bounce between a low-key historic home rental & the lovely Mandraki Beach Resort if you want something more secluded and restorative.
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