What is the Best Hotel You Have Ever Stayed At?

nice view

Not a room view, but in the city of one of my top three hotels

Back when I was willing to spend more money, and spent less time thinking about long-term financial goals, I had some pretty good vacations.  Traveling is something I enjoy, and back in the day I actually did quite a bit of it.  Whether or not I should have is another question, but we’ll leave that one alone!

I’ve said this a few times here before, so forgive me if I’m repeating – but I’ve been to 47 of the 50 states, 6 provinces in Canada, and traveled to a few locales in Europe and Asia.  While there are plenty of people that have done a lot more traveling than that, I think my list is fairly robust all things considered.

However, with family responsibilities and financial needs, I don’t travel that much anymore.  Priorities change in life, and at this point in life I think traveling is overrated, at least when taken in the context of other responsibilities at the moment.  The last trip I took was to the Financial Blogger Conference in St. Louis, which was a just a 5 hour drive from here in suburban Chicago.   It was a great time, though it would hardly qualify as an exotic trip.

What got me thinking about traveling?  Well, of all things it was news about the Winter Olympics in Sochi, and hotels there.  Specifically, it was the apparent fiasco that has resulted from many hotel rooms not being up to standard, per widespread reports by journalists.  Yes, some of these folks reporting from Sochi were even tweeting remarkable pictures of their environs there, based on this article in the Washington Post.

Some of things noted included, in different individual reports at different places:

  • Water that wasn’t drinkable
  • No heating or internet
  • Elevator broken
  • Water that contains “something very dangerous”
  • Stray dogs wandering in and out of rooms

Seriously, stray dogs?

It sure didn’t seem like those people staying there were reporting back that these were the finest luxury accommodations they’ve ever had.

Thankfully, not all hotels around the globe are like that.  While I’ve stayed in a few that disappointed, most have been at least passable.  Some were actually really good.  A few have been outstanding.

Thinking it through, there were a handful that would make the cut as the best I’ve stayed at, for various reasons.  Here is a totally independent view of my 3 favorites:

Hotel Villa Franca – Positano, Italy

The views from this place were incredible.  Overlooking the Mediterranean Sea, this place was perched relatively high up to also allow for views of the village.  This is a village which is essentially built in the hills extending down the coast.  If you don’t know much about it, this summary on Wikipedia gives a sense of what the village looks like.

The big thing about staying at this hotel was not only its location in the village, but also the ambiance there.  Just a super relaxing place with great views and accessible to all the neat things to experience in that great community to visit.  The selling point to me was the atmosphere, which was amazing during that summer visit.

Mandarin Oriental, San Francisco

Maybe I have a thing for hilly communities by the water :)  Anyway, I’m a huge fan of visiting San Francisco, but have almost always stayed with people I know.  On one occasion, however, I had the opportunity to stay in an upscale hotel there, and it was a great visit.

When you’re in a city as expensive as San Francisco, you don’t always get a lot for your money.  This place wasn’t exactly inexpensive, but it was fantastic.  A totally different experience than the Italian hotel I referenced, this one was like a retreat in the middle of the city.  Really nice rooms, and outstanding service.  The best part was having incredible views of the city.

Four Seasons, Chicago

Okay, so we live in Chicago.  However, this was an ultra-rare hotel stay in town that we had the opportunity to take.

It was outstanding.  The location is as good as it gets, right by the Magnificent Mile off Michigan Avenue.  In other words, close to the best (in my view) restaurants in the U.S. between the coasts, and excellent shopping and entertainment.  The hotel itself was plush, with luxurious rooms and great service.  The health club was actually pretty good too.

Just a winning experience all around, and a real treat to stay there.

Bottom Line – while I now operate on a more realistic and practical budget, which means very little traveling, I do appreciate those past experiences.  When it comes to hotels, there really are some that can be more than a few steps above the norm.  And they won’t have people live tweeting pictures back as the journalists did while visiting the Olympics :)

My Questions for You

Have you ever stayed in any really nice hotels, that really appealed to you for whatever reason?

What was your favorite, and why?


  1. says

    We really loved the Hard Rock Hotel Chicago (we stayed in a suite on our wedding night and it was AWESOME). We’ve stayed at the Four Seasons too when we’ve done staycations and liked it too.

    Our ultimate favorite was our hotel in DC. It was such a random find for $90 a night, but it was so unique. Big room, good view, old school touches, and great service.

    • Squirrelers says

      Sometimes those random $90 type of places can be great diamonds in the rough, I know what you mean. I stayed at one in the Carmel/Monterrey area of California that was around that price range and a total deal.

  2. says

    47 out of 50 states?!
    That’s quite a feat.
    Me, I’ve stayed at plenty of five-star hotels, traveling as I’ve done for work for the last 25-odd years. One of the better ones was in Oman, a hotel that was refurbished specifically for a Gulf States summit. And, there’s nothing like room service

  3. says

    Best hotel I ever stayed at was in Beijing (don’t exactly remember the name). Their all you can eat breakfast was amazing. Here in the States, the all you can eat breakfast amounts to bread, butter, and cereal. There – it’s like a 20 course meal.

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