One thing that helps is location. We've been staying at the Movie Colony Hotel for the past few visits and even though it could use a little re-fresh, it seems to suit us: private terrace, quiet guests, no trendy party people. Yeah, we met some hipster industry types by the pool this time around, but everyone seemed really down to earth there.
It made me realize that I don't need to keep justifying our hotel choice to certain design snobs or other folks who might give a sh*t about where we stayed. (I guess I came to this conclusion about the weekend because I feel like I'm at a crossroads with my career as well--to be a snob, or not to be a snob. That is the question.) Being welcomed back to the Movie Colony--and to the same familiar room, no less--was more than just nice. It was reassuring. And I think most parts of life and design should be reassuring, welcoming, and unpretentious.
It helped to hear from a local friend that trendy hotspots like the Ace were in dire need of freshening too. At Ye Olde Dayjobbe, I've seen how commercial projects begin to wear down after just a year of being open to the public, so I understand and have a certain level of tolerance for normal wear and tear and what a process it can be to keep things looking new. Luckily my partner can also be pretty easy about accomodations, having grown up on cheap and cheerful family roadtrip holidays and the like. For both of us, vacations and getaways are about the experiences and time spent together, for better or worse. Hotels and/or resorts are only a fraction of that experience. Personally, I think you can always find the memorable, positive experiences no matter where you go or stay:
(Reading apartamento by the pool...)
(Having wine and a chat on our private terrace under the Bougainvillea flowers...)