What I Learned from the Worst Vacation of My Life

Summer is just around the corner and people are eagerly gearing up for another vacation season full of fabulous food and frolicking fun in the sun with friends and family.

With that in mind, I thought it would be a kick to relive the worst vacation of my entire life. It’s certainly a vacation I’ll never forget.

In fact, even though it was 20 long years ago, I still remember it like it was yesterday. As a surprise, my girlfriend, B.H. — before Honeybee — had purchased one of those ridiculously-priced travel package deals to the Bahamas.

And, boy, was she ever proud of the bargain she got. And who could blame her? The package included a romantic “cruise” to our destination in Freeport, and seven days and six nights of lodging at a local “resort” that had a very exotic-sounding name like “Palm Gardens” — or something to that effect — all for the low price of $199.

That’s roughly the equivalent of just $300 today.

Of course, the airfare wasn’t included, and neither was our food, but we didn’t care because it seemed like we got the deal of a lifetime. And being young and naive, I never bothered to consider how anyone could ever offer such a “fabulous” vacation for two at such a bargain-basement price.

In retrospect, I should have.

Our romantic “cruise” was a basically a five-hour ride on a glorified fishing boat owned by some two-bit operation trying to pass itself off as a cruise ship; a Royal Caribbean luxury liner it wasn’t.

Still, my excitement level rose as we rolled into port. As we were walking off the boat, the sun went behind the clouds. And the rain began to fall. Actually, it poured so hard that the drops stung as they hit my skin.

When our cab driver stopped at our “resort hotel” I thought he had made a mistake because he parked in front of a dilapidated old apartment building in a run-down part of town. Unfortunately for us, he was at the right address.

And that’s when the cold reality of what we got ourselves into hit us both square in the face: The real mistake was my girlfriend’s dubious decision to buy such an incredibly cheap vacation package in the first place.

Once we got out of the taxi, things went from bad to worse.

Our room was sparsely furnished with an old lumpy couch in the front room, a small table and several chairs in the small kitchen, and a very uncomfortable — and squeaky — double bed and chest of drawers in the bedroom. The place was filthy too.

Not only that, but we were at least a couple miles from the beach, which was very inconvenient to say the least.

On the second day we looked into staying at the only real resort in the vicinity that we could afford, but it was booked.

Meanwhile, the rain continued to come and go in waves. The sun never came out.

On the third day, completely dejected and with the rain still falling, we decided to cut our trip short and head home.

Looking back, I learned some really valuable lessons from that trip from hell. The biggest lesson, of course, is to always do your research before embarking on a vacation to a new destination.  In particular, you should be sure to focus on these four key points:

1.  Be weather-wise. We went to the Bahamas in late September, which just so happens to be the heart of the rainy season there. If we had known that ahead of time, we could have at least mentally prepared ourselves accordingly – if not canceled the trip outright.

2.  Carefully vet your lodging location. If we had at least been staying at a legitimate resort in a nicer part of the Bahamas, it would have a lot easier to make lemonade out of lemons, so to speak.

3.  Don’t under-budget. Being just out of college at the time, my girlfriend and I were on a tight budget. The thing is, it was so tight that it prevented us from rectifying the unfortunate lodging situation we found ourselves in once we got there.

4.  Be especially wary of incredible deals. Yes, it’s cliche. But it’s true just the same. If you see an incredible vacation package offered that seems too good to be true, it probably is. If you don’t believe me, ask my ex-girlfriend.

Photo Credit: Nigel Morris

9 comments to What I Learned from the Worst Vacation of My Life

  • :) i noticed the ad for Pure Michigan and thought I’d add my home town to the commercial. lol
    Charlevoix Michigan

  • I remember this story from 2010 apparently. It always popped to my head when the fax machine at my old job would spit out another page that said “Fabulous One Week Caribbean Vacation – Just $299!!!” I would shred it and think of this story…

  • I learned a similar lesson early on: if a trip came with a really low price and a “tour of the resort” you’d just booked yourself a timeshare presentation.

  • That sounds rough! I always fully look into any vacation I’m planning especially if it sounds too good to be true in which case it normally is. I’m glad you learned a lesson though because while it may have been a royal pain I’m sure you’ll never make those mistakes again. Hopefully you’ve had some awesome vacations since then though :)

  • Ann

    Went on one of those cheap Bahamas trips back in 1990, , I did have the foresight to call AAA to make sure the hotel existed, and it did.. they just didn’t know anything about it, Well we cruised there, cabbed it to hotel in a run down minivan with other people…ick, hotel did exist, was ok, but as we went out, in the lobby of our hotel, found other people that paid more than we did for a hotel that DID NOT exist! They lost their money and there were at least 40 people very mad!

  • Amy Stuwart

    I like to look at review sites that have comments regarding the hotels, I find that is very helpful when vetting a vacation location.

  • Fran Gangluff

    Vacation packages nowadays are more expensive but i always look for vacation packages with discount offers online.

  • Tonya

    There are so many vacation packages online but be careful because some of them are scams. I’ve learned from first hand experience!

  • [...] Penzo spills on the worst vacation he’s ever had.  Yes, rain spilled on him, and he’s sharing the [...]

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