Dud Destinations: Overcoming a Negative First Impression

Not every destination makes a stellar first impression. Misunderstandings happen, plans fall through, expectations are dashed. And nowhere in recent memory did I find that truer than in Cabo San Lucas.

I had high hopes before I arrived in this happening resort town on the Mexican Riviera. As a celebrity magazine addict, I knew that Cabo was considered the perfect spot for A-listers to blow off steam: Justin Timberlake plays golf there, George Clooney celebrates birthdays, the Kardashians do what Kardashians do. Jennifer Aniston comes so often that she might as well be on the tourist brochure.

But I forgot that they don’t go where I went, which, unfortunately, was straight to Medano Beach. I knew from the moment I arrived at a popular beachfront restaurant there that I had chosen … poorly.

I ordered a margarita, singular. Little did I know this was an impossible request in Cabo. A waiter arrived bearing two aquarium-sized glasses. “No, no, just one,” I told him nicely.

“No, lady. Two is better!” he replied. We went back and forth over my request for a while, until he finally took the unsolicited beverage away. (At that point, I was so irritated by his persistent upselling that I almost needed the second drink.)

That wasn’t the end to the Medano madness. Within a few hours, I was hassled by timeshare salesmen, encouraged to smile by water taxi drivers and offered illegal drugs. I saw more ugly tattoos than on an episode of “Jersey Shore,” and it wasn’t even spring break. The last straw came when I slipped on one of Cabo’s steeper streets, landing firmly on my rear.

“I hate Cabo,” I texted to my husband.

Luckily, I had time for a do-over; subsequent days there exposed me to the city’s first-class adventure opportunities, including kayaking and snorkeling with Baja Outback, parasailing with Cabo Expeditions and a camel safari with Cabo Adventures (yes, camels! It’s become the company’s number one excursion). I even found some great places to go on Medano to escape the nuttiness free-for-all, including Nikki Beach (for those who like Miami style) and Tabasco Beach (for those who like feet-in-the-sand style). I have a list of things to do if and when I come back, including visits to San Jose del Cabo and Todos Santos and a deep-water fishing excursion.

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But the experience made me think about the best ways to handle a new destination if it isn’t exactly what you expected:

Switch gears: The best thing I could have done after the margarita skirmish was hightail it out of Medano on a water taxi to the Marina, a less pushy part of the city. If you’re in a neighborhood that’s rubbing you the wrong way, try another one — stat.

Blow off steam: Zip-lining wasn’t what you expected? Don’t stomp back to the hotel angrily. If time allows, walk around, do some shopping or enjoy a snack at an establishment that looks more your speed. Being able to calm down and look at the situation with some distance will usually turn it into an amusing memory rather than a trip-wrecking horror.

Conduct a post-mortem, part I: That night, make the effort to talk to a few fellow travelers, either at your hotel or a local bar. What have they done that you haven’t? Swapping stories means you can unearth valuable intel that may allow you to make out better the next day.

Conduct a post-mortem, part II: Once you’re home, go online and see if others have had your experience. Did they have the same issues you did, or did you just happen to catch that attraction or neighborhood on a bad day? Keep in mind that factors like weather, local strikes and staff turnover can vary the experience significantly.

Maybe it’s you. We all have bad days. Maybe you’re not feeling well, or maybe your travel companions are working your last nerve. If you set out for the day with a monster chip on your shoulder, don’t be surprised if the slightest thing knocks it off — and really, who’s to blame for that but yourself?

Tell us! How have you salvaged a poor experience in a new destination?

— written by Chris Gray Faust