Last time I was at a resort was 30 years ago in Bahamas. Needless to say I don’t remember much other than the way the cleaning lady made the bed and how I enjoyed my first English muffin with butter. So it was a very different experience from the types of vacations I’m used to.

Cuba was always my first choice in Caribbean destinations. The cars, the history, the sea, the contempt for their closest neighbour. Not to mention being able to see how socialism can actually succeed in a North American setting (yes I said succeed—at least on some levels). I figured the beaches would be great anywhere, but at least Cuba has other stuff going for it too.

Turns out I got to spend a lot of time by the pool working on my tan. It’s a nice tan but…

I think I get the whole point of going to a resort. It’s supposed to be relaxing and chilled out. No worries, just hang out and do what you want. But to me that felt more like a jail. Don’t get me wrong, it was a really fucking nice jail… but still.

It’s not like there was a shortage of things to do. There were excursions to different islands, deep sea fishing, SCUBA lessons, day trips to Havana and Varaderro, scooter rentals, kayaks, jeep trips into the forests… pretty much anything that you could ask for was there. But after spending as much money as we did to just get there, it was hard to justify spending a couple hundred extra to take a boat to see a better island with a better beach and better snorkeling. So I tried sitting by the pool. The beach was nice, but the pool is where we all ended up.

The day trip to Havana completely soured me on leaving the resort on any organized excursions. There was so much potential, but so little of it was realized. The architecture was uber cool. I adore urban decay. I could have spent all day with a camera and a bottle of water. Our tour guide babysat us through all the tourist traps—having to contend with people selling everything from cigars to charlie to on-the-fly caricatures drawn as you’re walking by. People walking into your pictures and asking for money. People with no hands begging for a change. Guaranteed if you make eye contact with a local they will be asking you for something. Entirely unenjoyable. The cigar factory tour would have been a lot easier to digest if it didn’t feel like a 30-minute infomercial for the cigar shop next door.

The resort was nice. The wedding was perfect. The food was actually quite good (if you chose correctly). The service was hit and miss. I’m sure if consistently tipped well it’d be more of a hit, but even then I’m not so sure. We tipped the cleaning lady well and she did a good job. Not exceptional, but better than usual. I get the impression that at that class of hotel that the service staff have worked their way through the crappy places to get there, and it’s almost like a retirement for them. They’ve already proven themselves and now it’s the gravy train.

The watersport rentals were pretty much useless. A half hour in a sea kayak isn’t anywhere near long enough, plus all the interesting stuff is outside their boundaries—although I’m sure if you tipped well enough they’d look past their self-imposed restrictions and you could do what you want. The music was the biggest pain in the ass. Every morning at 10:30 they’d play one of the two CDs they had very loudly. Then someone would come on the mic and speak some incomprehensible hybrid of French, Spanish and English, trying to get people to come dance. Annoying.

The best thing was having everyone there. That’s what made it for me. Being able to go out for lunch or breakfast at any time and running into friends is the best. There was always someone who’s up for doing the same things as you… even if it is just hanging by the pool.

I really needed to experience a vacation like that. It’s a good feeling to not have to do anything. To be able to get up when you want, and to do what you want. It was an awesome destination. But I don’t want a destination—I want a journey. I want to actually do something. Not something that comes in a box.

I want challenges and solutions. I want stories and misadventures. I want to be forced to have to communicate with someone I don’t share a language with. I want to be stuffed on a stinky bus to some village with a bunch of locals. I want to accidentally end up on the wrong end of a train, heading to some place I need a visa to get into. I want to sleep in a train station of a place I’ve never heard of. I want to spend four days in bed with explosive [ahem] stomach issues so I can be forced to read the first book I’ve read in years. Those are things that happened on my other vacations, and that’s what was missing in Cuba.

When our plane was diverted to Havana most of the people with us were aggravated and stressed out. I left there wishing more things happened. Things were too smooth, too predictable.

I guess it’s kinda like life. Either try and control change or revel in it. I choose the latter.