I’ve been thinking lately about the hotels that left the strongest impressions on me. They aren’t always the fanciest or most expensive places I’ve visited, but they stick in my memory for different reasons. Some were part of “once-in-a-lifetime” trips, others were so unique that they simply couldn’t be forgotten. A hotel doesn’t have to be luxurious or famous to be memorable — any place can turn out to be special once you experience it for yourself.
Here, in no particular order, are eleven (well, now twelve!) of my most memorable hotel stays:
Disney’s Contemporary Resort
There’s no denying that I’m a Disney fan. Heck, I live in Orlando because of it.
When I was growing up, the coolest thing ever was staying at the Contemporary on a trip to Disney World. Come on — the monorail goes right through the hotel!
The view from the top of the building wasn’t that bad either.
The Contemporary Hotel also holds a special place in my heart because it’s where we stayed when I proposed to my wife, Sharon.
Awwwwwww.
(Note from Sharon: he didn’t mention that he proposed while we were on the Haunted Mansion attraction [because he knew it was my favorite ride].
He popped the question as we went through the ballroom scene — and then I COULDN’T SEE MY ENGAGEMENT RING UNTIL THE RIDE WAS OVER!)
Hotel Taiseikan
What makes the Taiseikan Ryokan in Hakone one of the most memorable hotels for me is that it was the setting for one of my most embarrassing travel mistakes. It was also the first place (no, make that the only place) I ever stayed where I couldn’t find the bathroom in the room.
Ignoring those things, it was still one of the most amazing experiences I’ve had while traveling. It was my first trip to Japan, so staying somewhere off the major tourist path — and being in a place that was so, well, Japanese — was fascinating.
Being treated like a special guest (we were assigned the room featured in the brochure!) made our two nights here something I’ll never forget. I still remember small details, like watching part of the movie Taxi with Jimmy Fallon, dubbed in French with Japanese subtitles, on the tiny TV in our room.
Casablanca Hotel
The Casablanca Hotel isn’t some exotic getaway; it’s smack dab in the middle of Times Square. I found it years ago while searching for hotels on TripAdvisor. It’s been well over fifteen years since we stayed there.
The reason we haven’t returned isn’t a bad one — well, not for the hotel, anyway. You see, it was rated the number one hotel in New York on TripAdvisor for years and years (currently, it sits at #3), and they price the rooms accordingly. We just happened to get in before they got famous.
The hotel itself is fascinating. It’s just steps from Broadway, yet it somehow feels like a quiet oasis. The rooms are small, but the theming makes it feel more exotic than cramped.
I’d gladly stay there again to see if it lives up to my memories, but I’m not willing to pay upwards of $500 a night. I’m glad they’re doing well, though, and I’m happy we got to stay there when we did.
South of the Border Motor Inn
When creating this list, I aimed to recall places that left an indelible impression on me. While some of the locations have a special meaning or are tied to a specific event, this hotel is… not one of them.
It’s memorable for entirely different reasons.
It’s unique compared to the other places we usually stay. Also, I will never forget the overpowering scent of PineSol that hit us the moment we walked into the room.
From our stay at the hotel to our dinner at the Peddler Steakhouse (located inside a building shaped like a sombrero), I’ll never forget the night we spent at South of the Border.
Hyatt Regency Danang Resort & Spa
Switching gears, I’m going to a hotel that’s memorable because it blew away our expectations. I don’t know exactly what I was expecting the Hyatt Regency in Danang to look like, but it wasn’t this.
Our room was beautifully designed, with an extra-large bathroom and a patio that overlooked the huge pool area.
Our stays in Hanoi and Saigon were pretty much what I expected — big cities are big cities, no matter where in the world you are.
But getting to see a different side of Vietnam was a true highlight of this part of our trip to Southeast Asia.
L’Enfant Plaza Hotel
In my mind, this hotel will always be the Loews L’Enfant Plaza. As a kid, it was one of the first “fancy” hotels I ever stayed at. Until then, it had always been hotels, motels, and Holiday Inns — but now, I was in a massive hotel in Washington, D.C., just steps away from the Air and Space Museum.
The only way we could ever afford to stay here was by using a coupon from the Entertainment book. Not only did we receive a discounted room, but they also upgraded us to a suite.
I still have a picture from that trip — my dad, feet up on the table, making himself right at home.
I was embarrassed at the time (and honestly, I still am a little), but looking at it now, after losing him this year, it’s one of those memories I’m so grateful to have.
The hotel has since reopened as the Hilton Washington D.C. National Mall The Wharf. I’d love to go back someday to see what they did to the place.
The Don CeSar
I’ll remember our stay at The Don CeSar on St. Pete Beach for many reasons. One of them is that Sharon had been talking about the place since we lived in Tampa — over 20 years ago.
But the main reason is that we love old hotels that have a real sense of history. The Don CeSar is a unique place, and not just because of the bright pink paint. The hotel has a fascinating history — it opened in 1928 as a playground for the rich and famous and was later acquired by the U.S. Army to serve as a convalescent center during World War II.
I’m not saying that I’d pay what it costs to stay there again, but I’m really glad we stayed when we did. In 2024, Hurricane Milton caused massive damage to the St. Pete and Tampa areas, including significant damage to the Don CeSar itself. The hotel was closed for many months and has only recently reopened to guests, with a “breaking-in” phase expected to last until at least May.
Tokyo DisneySea Hotel Miracosta
With my love of Disney and Japan, staying at Tokyo Disneyland was a must during our trip. I have to say that the Miracosta Hotel at Tokyo DisneySea is the best-themed Disney hotel anywhere in the world. Everything about it is perfect.
It also helps that it’s located inside Tokyo DisneySea, which, as far as I’m concerned, is the best Disney park anywhere.
From the lobby ceiling, which depicts each of the park’s themed lands, to the fountain outside the entrance, everything is just beautifully designed. Every little detail feels intentional, immersive, and perfect.
Glacier Park Lodge
While I’ve stayed in several National Park hotels — including ones in Yosemite and the Grand Canyon — Glacier Park Lodge is the one that’s stuck with me the most. It’s a fantastic building that dates back to 1913.
Now, if you’re looking for luxury accommodations, this isn’t the place for you.
It also helps if you aren’t creeped out by hallways that are very reminiscent of a certain movie.
But of course, you don’t come here to stay in the room.
You come because of what’s waiting right outside your door.
Portmeirion Village — Wales
While my actual room wasn’t anything particularly special, it almost didn’t matter. Waking up inside this colorful, whimsical village — with its winding paths, vibrant architecture, and dreamlike setting — was unforgettable.
It’s one thing to visit Portmeirion for the day, but experiencing it after the day visitors have left, when everything grows quieter and more magical, makes it a memory I’ll always cherish.
Our Most Memorable Hotels
I mentioned earlier that this list isn’t in any particular order — except for the two hotels I’m about to mention.
Out of all the places we’ve stayed, these are the ones we are certain to revisit someday.
They aren’t just memorable — they’re our all-time favorites.
Grand Hyatt Kauai
The moment I set foot in the Grand Hyatt Kauai, I knew it had to be added to my list of memorable hotels. We stayed here for three nights in a club room, which happened to be one floor below the former Presidential Suite. Not too bad for a regular booking!
View from our balcony at the Grand Hyatt Kauai
We loved everything about the property. While we’re usually not “resort hotel” people, we happily made an exception here and spent the better part of the day just relaxing around the pools.
I can’t say enough good things about this property — from the beach views, to the sound of the ocean outside our patio doors, to the excellent restaurants, multiple pools, and friendly staff.
And of course, it doesn’t hurt that it’s on Kauai — one of the most beautiful places in the world.
Hotel Goldener Hirsch
The Hotel Goldener Hirsch in Salzburg is one of the most incredible places I’ve ever stayed. It’s where we stayed when we visited several of the filming locations for The Sound of Music.
Our first visit was so fantastic that we knew we had to return. Fortunately, our trips ended up bookending a total renovation of the hotel, and for our second stay, they upgraded us to one of their beautiful suites.
From the moment you walk inside, the charm of the place just envelopes you. After the renovation, they retained many of the little details — including real room keys at the front desk, even though the locks are now RFID-enabled.
Even the bar area, with its slightly cheesy but completely charming decor, feels authentic and perfect.
It looks a little strange in pictures, but this place is pure magic. The furniture has all been refurbished, but it still smells like it’s been there for a hundred years — in the best way possible.
Finally, there’s the view from the windows. If you’re a fan of The Sound of Music, you’ll recognize it immediately from the song My Favorite Things.
Top it all off with the best hotel concierges we’ve ever encountered, and you have a place I’ll never forget — and hope to visit again.
Final Thought
Putting this list together brought back so many memories — some funny, some emotional, and all unforgettable.
It reminded me that traveling isn’t just about checking places off a list or finding the biggest suite or the fanciest pool. It’s about the moments you collect along the way. It’s about finding magic in a perfectly timed proposal, a once-in-a-lifetime view, an unexpectedly charming hotel, or even something as simple (and memorable) as laughing at a photo you didn’t know would mean so much years later.
It also made me realize that you never know when the places you visit will change — or when life itself will shift in ways you couldn’t have seen coming. Some hotels get renovated. Some weather the storm, literally. Some memories become even more precious with time.
A hotel doesn’t have to be perfect to be unforgettable.
The most memorable places are those that become an integral part of your story.
Here’s to making more memories, finding more surprises, and always remembering why we travel in the first place.
Happy travels.
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