We Accidentally Stayed at Our Grail Hotel
Sometimes, the hotel you didn’t know you were chasing finds you first.
Most of us who care about travel in the way we do have a dream hotel—a grail property that sits firmly at the top of the ‘wants list’, patiently waiting for the day we finally make it. Or for when we finally hit the lotto. (We’re still holding out hope!)
Let’s just say that both of us have many grail hotels on our list. And given our line of work, sometimes, we’re lucky to hit a special kind of lotto: having a grail stay fall, unplanned, right in our laps. Call it a perk of the job! Call it unfair! Call it whatever you will—we’re thankful as ever and we’re here to share about it.
Enter: Castello di Vicarello—a property that wasn’t on our grail list but damn well should’ve been. The reasons why aren’t immediately obvious…
Castello is tucked in the rolling hills of southern Tuscany—about two hours from Florence and an hour from the coast. It feels perfectly remote, removed from just about everything. And as a result: supremely unbothered by trends.
Originally constructed in the 12th-century, the castle was carefully restored over multiple decades by one family that still operates it today. Just nine suites are spread across multiple stone buildings, creating a stay that feels distinctly private and personal. (With one major addition in the works!)
There are two pools (one with a cinematic infinity edge), lush gardens with both flowers and organic produce, and common spaces that make you feel more like you’re lounging in a friend’s exceedingly well-decorated home than a hotel. Oh, and the food is sublime, to put it mildly.
But listen—as much as we talk about the usual markers that make a great hotel, the best experiences are never built with a checklist. The best stays feel like something. They linger. They’re experiences that you’ll never forget.
Sometimes story and personal connection take over everything else—and this was one of those times.
So here are just a few things we won’t soon forget about our stay at Castello di Vicarello. What made them special? They were personal. Unrepeatable. Impossible to fit into any kind of template. And really, that’s the whole point!
Curated Objects & Design Direction // every room at Castello has its own distinct character and design POV. The owners spent years in Indonesia working in silk and furniture exports, and that background shows in the furniture, objects, and every quiet detail. Piles of vintage books and magazines, sculptural bathtubs, busts of men and bronze statues of boar. Nothing here feels templated. We haven’t seen anything quite like it.
Consistent & Considered Service // with just nine suites, you see the same staff every day. This kind of continuity matters. We visited early in the season as the team was still working through little service quirks and nailing it all down—but it actually made the experience feel all the more human. Less overpolished, more personal. There was honest heart behind every interaction and it stuck with us.
Familial Pride You Can Feel // we stayed in the Villa Chiesina, once the family’s home during the decades-long restoration. We shared dinner with the parents and their eldest son, who now runs the wine operation on site (among many other things). We saw the family on the grounds each day. In the gardens. At breakfast. A consistent presence that was never performative. And how could we forget Uva—not a hotel dog but the family dog. She became family to us right away, even if that was a bit performative in the pursuit of treats. The point? Familial pride like this is enduring.
Last thing: a quick shoutout to our lovely PR partners (thanks, E & K!) who opened the door for this stay! As we said: our days on property will not be soon forgotten.
See more photographs from our stay below! And let us know about your grail stay…
That’s all for today. If you made it this far—we sincerely thank you for your support. Why not drop us a line in the comments and say hello? We’ll be responding to all of them. And if you like what you’re reading, please hit the heart (<3) on this post to show others that it’s worth subscribing.
As always, smooth skies to the lot of you!
Great photography as always. I aspire to make travel photography like you guys do. Would love a behind the scenes post about your travel gear.
Adding to the list!