The 5 Hotels I Think About Most

Stays with staying power

Arriving at Monteverdi Tuscany.

I have been quite fortunate to stay at some incredible hotels in my adult life. More often than not these stays haven’t cost me anything as I’ve typically been the guest of an automaker or on some occasions, the hotel. In my early years of traveling the whole “it’s been taken care of” element really colored my overall opinion of the experience. Just about any decent accommodations suddenly seem excellent when the room is free and incidentals are covered too.

The longer I stayed in the game, the more discerning I became. I became acutely aware of the details that set one hotel apart from another. At every property I visited I eventually started putting myself in the shoes of someone who was paying their own way. The shine wears off pretty quick when you consider the financial outlay that some of these places require. On the surface, great hotels appear to be plentiful everywhere. There’s always a new design forward, wellness centered, F&B-team-led concept having a moment. Upon closer inspection many of these fade from memory into the great mess of mediocrity that’s prevalent not only in hotels, but the whole world of hospitality. It’s understandable too. This shit ain’t easy to pull off, let alone sustain year after year. With that in mind, here are 5 hotels that I think have nailed what I call “The Three Esses”, Service, Setting, and Sleep.

Monteverdi Tuscany - Castiglioncello del Trinoro, Italy

Megan and I visited on our honeymoon in October of 2022. I think I’ve brought up Monteverdi at least once a month since then. It is the total package. Fairytale location, dedicated staff, incredible spa, and a dining program that’s worth the trip on its own. The village of Castiglioncello del Trinoro only has a handful of full time residents. One visit to Monteverdi Tuscany and you’ll wish you were one of them, with the caveat that you get unlimited spa days.

The Peninsula Tokyo - Tokyo, Japan

An obvious choice? Perhaps, but that doesn’t make it any less deserving. Hands down the most attentive and detail oriented service I’ve ever experienced. Some might say the property is in need of modernization, I disagree. I prefer my spa bathroom experience to be button operated instead of via a glitchy tablet. Same goes for the powered blinds for my floor to ceiling windows. A fax machine in the room? Charming. There are other 5 Star hotels in Tokyo I’ve yet to stay at, but from what I can tell they’re short on the character The Peninsula is deeply imbued with. Location overlooking both Hibiya Park and the Imperial Palace is unreal. For more on both the hotel and nearby destinations I enjoyed, check out this story I did for Cool Hunting.

7132 Hotel - Vals, Switzerland

The photo above is the view from the patio where I had breakfast. Underneath that grass is one of the best geothermal spas in the world designed by Peter Zumthor. I’ve stayed in a few hotels in Switzerland and Austria that I categorize as “Bond Hotels” as they could easily have been a location in a 007 film. I plan to elaborate on those properties in another newsletter. With regard to 7132, it is like being transported to another planet where food’s flavor is more intense and everybody sleeps soundly. My visit was brief, but impactful. The drive in, the arrival ceremony, the views. In a country with no shortage of fine hotels, 7132 deservingly stands out.

Wickaninnish Inn - Tofino, British Columbia

When I think of Wickaninnish Inn I hear the sound of waves crashing against rocks outside my room. I can pretty much taste the salt spray from standing on Chesterman Beach and feel the warmth of the sun going down over the North Pacific. Vancouver Island as a whole is a special place and Tofino a standout destination. A few nights at “The Wick” and it’s easy to understand why. The place is steeped in local culture and is ultimately the result of decades of a family dreaming, planning and finally, acting. To call it a labor-of-love would be an understatement. Since opening in 1996, The Wick has been recognized for its exceptional hospitality(it was added to the Relais & Châteaux family only a year after opening) for both overnight guests and dining guests alike. A few days here is like being on the frontier of another planet where all your senses are just a bit sharper. On top of all of that, I had one(or two…) of the best Negroni’s I’ve had in my life at their bar.

Le Vieux Castillon - Castillon-du-Gard, France

Above is probably the best of the very few photos I took while staying at Le Vieux Castillon. Rarely do I ever look back on a visit to a hotel only to find that I didn’t take enough photos. That this is the case with Le Vieux speaks volumes about the sort of experience you have on property. It’s one of those places that doesn’t demand your complete attention so much as it puts you in a state of mind where you can’t help but to be present. Being perched on top of a hill overlooking the valley of Gardon, where the Provencal winds of summer warm you as soon as you step out of the pool, might have something to do with that. Utterly relaxing, deeply charming and with a non-corporate current of authenticity running through it, Le Vieux is truly a hidden gem.

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That’s It, That’s All.