All in a Day’s Work: Travel Agents Share Their Funniest Tales

Dealing with the public is always a challenge. From the clueless to the geographically challenged, the just plain demanding to the not quite legit – not to mention the ones just looking for love — travel agents have seen it all. We thought we’d ask some travel professionals to share the craziest requests they have ever gotten from customers, so we can all chuckle together. 

Where’s Waldo?
Foreigners are often appalled by Americans’ sense of geography, or lack of it, and travel agents are first-hand witnesses to just how right they are.

Brenda Pascoe an agent with Toronto’s Vision Travel Solutions, for example, had a client ask for an oceanview room at her Orlando hotel. But, Hawaii appears to be the most confusing destination. Stacy Sobo, an agent with Skye Travel Corp., Deerfield, N.H., and Kelly Sakryd, a strategic account manager with Royal Caribbean Cruise Lines, both had nervous flyers requesting Amtrak tickets to Hawaii; Angelica Berwick had one with the same request, thinking it would be less costly than flying.

When Rangerruss Travel Adventures agent Russell Black pointed out that train tickets to Oahu are impossible as there is water between Hawaii and the mainland, she said, “Okay, then I’ll take the bus.” Candie Steinman, an agent with Dream Vacations in Fort Myers, Fla., had a customer that insisted her friend had driven, and she was going to drive as well.

But Brenda O’Neale’s customer, who wanted to take a bus to Cancun, fared better. O’Neale, who is the owner of in Indianapolis, Ind., actually did the research for her — and discovered it actually is possible, though it takes about four days in each direction.

Equally challenging, it seems, is the idea of cruising from point A to point B. Leslie Richardson from Jetsetters Cruises in Houston, Tex., recalled a request for a three-day cruise “to Hawaii, from Miami.”

Angelica Berwick also recently was asked for a cruise from Oregon to Miami, five days or less. “I so wanted to tell him that’s a very popular cruise and all the tickets and sold out,” she said. “But I stayed professional.”

Amy Hobbins, Journeys Unlimited Travel, Green Bay, Wisc., recalled a client who wanted to cruise from Green Bay into Lake Michigan, down the St. Lawrence Seaway and to the Caribbean and back. After all, she had a whole week off.

Outside the U.S., things only get worse
Karolle Fleurke Screaton of Ottawa’s Savour the World Travel said she “had a honeymooner flip out at me over her flight to Sri Lanka. It was absolutely unacceptable to her that the flight spanned two days, and she insisted I do better. I calmly explained to her that as amazing as I am, I can’t change the international dateline for her.”

Lynda Westlake of Vision Travel Solutions in Port Hope, Ontario, recalls the Swedish tourists who walked into her office asking for a day trip “to see Indian Summer.” And when Lorraine Simpson launched a Facebook page called Covfefe after Trump made up the word, her phone was soon ringing with a request from someone wanting to book a trip there, “as it looked lovely.”

Linda Hanie Allen from Cruises by Linda in Harrison, Ark., recently had a request for a cruise in the Greek Isles, with two nights at each port, for a total of 12 nights.

Dedra Shahan, of Cowboy Way Travel, Stephenville, Texas, experienced a client that had a different sort of destination in mind. She so enjoyed her first cruise that she wanted to book another, this time to Las Vegas. “After I realized she was serious and possibly medicated, I explained that there were no ships doing that itinerary currently, and yes wouldn’t that be a fun sailing!”

That politeness, by the way, paid off. “Her mother-in-law became one of my best customers, who sailed over 25 times,” Shahan said.

Then there’s just the slightly clueless
Janella McKinney of McKinney’s Family Vacations in Gadsden, Ala., tells of a recent customer who asked if the oceanview cabins were under water. “I said ‘yep, just like being in a fish bowl.’”

Janine Corry, an agent with South Africa’s 24point7, had one who asked for a window seat for his flight to Mauritius as “he likes fresh air.”

Marnie Butler of Centre Holidays in Ontario had a client call from the airport a few days ago to report that his plane was delayed by two-and-a-half hours. “This was an evening flight, so by the time he was to arrive at his resort, it would not be until after midnight. So, he wanted me to reimburse him for the 2 hours and 30 minutes of missed vacation time. His reasoning was that he would now be arriving the next day.”

And who hasn’t had a customer just looking for love? Suzanne Haire, an agent with Travel Agent Suz in Indianapolis, Ind. recalls the destination wedding guest who asked for two rooms – and a guarantee that his wife and his girlfriend wouldn’t run into each other on the property. “I obviously advised that I could not and would not be part of this disaster waiting to happen,” she said.