“…Boy, did I earn my commission that day!”

Travel advisors wear many hats, with planner and concierge among the more obvious. But crisis manager, educator and therapist can also be added to the list, especially when clients present unique challenges.

For instance: A client who hates the drapes in their hotel room; another who asks to bring a grill aboard a cruise for balcony cookouts; someone requesting a “short cruise” from Florida to Australia.

From the geographically challenged to the, er, less-traveled individuals out there, advisors have lived to tell some hilarious tales. Earlier this summer, Travel Weekly polled readers to ask them to tell us their craziest client requests. 

Kathleen Karsko, Mardi Gras Travel, Farmington, Minn.

In the ’80s, I had a client who needed to visit a monastery in Europe that was located on a steep hill. There wasn’t a regular road to the monastery, merely a small path. The monastery didn’t have a phone, and mail was sporadic.

The client asked me to arrange travel to the monastery. I always love a challenge, so I ended up calling a business in the nearest town, and they gave me a phone number for the person who spoke the best English. I explained the situation, and they said I needed to talk to a man who had donkeys and delivered goods to the monastery. I called back the next day and, through the translator, booked a donkey to take my client up to the monastery. I offered $50; later, I learned that $5 was the normal rate.

My client was so happy and later sent me a picture of the donkey and the man. I wish I still had it, but that was several moves ago. Anytime there was an odd request, my co-workers referred them to me since I could book a donkey.

Tammy Graham, Ithaca Sun Travel, Ithaca, N.Y.

After a client sat at my desk to purchase just an airline ticket, she asked if she could bring her dog. I said yes and proceeded to explain her options and prices. She said, “No, that’s not what I mean — I want to carry him on the plane.” “So, in a carrier…?” I asked. Again, no. She literally wanted to carry on her German shepherd so that she didn’t have to pay extra. She did add that she’d have him [sedated] first.

Dorothy Mowbray, Boscov’s Travel, Salisbury, Md.

I sent an older couple in their 90s on a cruise, and I was pretty sure it would be their last one. During the cruise, [the husband] died in the cabin, and his wife requested that he stay in the cooler until the cruise was over. That had been the last wish on his bucket list!

Marcie Karavakis, The Dream Experience Travel, Bonita Springs, Fla.

I was a new travel advisor and took any booking for practice. I booked air, and a client called me at 4 a.m. from the Vienna airport. She had a three-hour connection and thought she had enough time to take the train into town to have coffee with a guy she met on her stopover on the inbound [flight]! Of course, she missed her [connecting] flight. The airline wanted to charge her for a new ticket, and she said it was my fault. When I asked why in the world she left the airport with a three-hour connection, she said, “You didn’t tell me not to!” I somehow managed to persuade the airline to get her on a different flight for no charge. I think they did it because she was standing at the ticket counter yelling at me, and they felt sorry for me.

Angela Thompson, We Do Travel Right, Memphis

It all started on a Sunday when a client reached out, not only demanding to book a Disney Wish cruise leaving the following Friday — yes, less than five days out — but with perks. I’m always trying to go the extra mile, and I offered him some onboard credit if he committed and provided payment details that day so I could hustle to get the request in for his sailing. 

He didn’t respond until Wednesday — with the cruise sailing in less than 48 hours — and demanded to be on the sailing. I spent over two agonizing hours on the phone, pulling every string imaginable, finally managing to get him onto the ship’s manifest. But then the payment details weren’t forthcoming. Why? Because he didn’t have a dog-sitter. He scrambled for another two hours trying to find someone to watch his dog; all the while, the cruise couldn’t be put on hold. The balcony room I had miraculously secured was now gone.

When he finally got his dog-sitter situation squared away, he asked me to call back to see if the room was available. I told him I needed his payment information right then so I could try to secure it on the spot while I was on the phone. It took another two hours of calling and sweet-talking shoreside services to get him approved again for the manifest. The balcony was gone, but I managed to pull off another miracle: getting him a great deal on a Florida Resident Guarantee Ocean View window room. He accepted, made payment and was officially booked. 

We had a clear phone conversation where I explicitly told him that due to the extremely close proximity of his booking, he would not be able to prebook any dining or excursions until he got on the ship. He seemed to understand completely.

Fast forward to him getting onboard. My phone started blowing up with profanity-laced text messages. He was furious, claiming the cruise ship wasn’t going to feed him and that he was “firing” me for it. I calmly reminded him of our conversation, where I explained he had the late dining and had been wait-listed for earlier seating per his request. I even sent him a screenshot of his booking confirmation directly from the system. Nothing I said or did could satisfy him. He just continued with the insults and profanity. At that point, there was nothing to do but bless and release.

Sherrie Funk, Just Cruisin’ Plus, Brentwood, Tenn.

A number of years ago, we had a female client who was taking her son and mother on an Alaska cruise-tour. This was when Canada had started requiring passports from U.S. citizens. She also needed a notarized letter from the child’s father giving her permission to take him out of the country. She provided the passport information for all three of them along with the letter, but it was signed by her, not the father. We explained that it was required that the father sign the document, and after a number of probing questions, she eventually said the child had been conceived by artificial insemination. She had to get the documents showing this was the case and that her name was the only one on his birth certificate.

Alan Rosen, Sand & C Travel, Parkland, Fla.

A client once called asking for a short cruise from South Florida to Australia. They didn’t want to fly. I just explained there is no such thing, and tried not to laugh.

Gwen Bourgeois, Dickinson Travel, Dickinson, Texas

Two sisters were in our office, sitting in front of my desk, booking a trip to Anchorage. One sister says to the other, “Oh, my toenail is hurting; please cut my toenails for me.” She puts her leg on her sister’s and she proceeds to cut her toenails. I was finishing up their booking, so thankfully I could look at my screen as I continued typing. One sister made the comment, “Gwen will tell everyone that some crazy sisters cut toenails in her office.” I have been in the travel business since 1978 and always worked in a storefront. I can honestly say this is the craziest thing I have ever had happen.

Sharon Schmiedel, Expedia Cruises, Staten Island, N.Y.

I had clients who asked if they could bring a small BBQ grill so they could cook on their cruise ship balcony. They also wanted to bring along raw chicken cutlets. I told them no, that would be a fire hazard and you can’t bring perishable food onboard. I let them know of the many food venues on the ship and that they could bring nonperishable snacks onboard.

Stephanie Phillips, Globe Travel, Philadelphia area

I had a client going to Kathmandu. I booked charming and reasonably priced accommodations that he rejected in favor of a Holiday Inn Express so he could get his points — he preferred low-end American hotels to those with local character. And the client is always right.

Mindi Phillips, Beloved Getaways, Brandon, Miss.

My craziest request was from a bride getting married at Sandals Royal Bahamian. She wanted a long, beautiful aisle to walk down that was filled with people. She asked if the resort could ask all its guests to fill the seats or if there was a company we could rent people from as seat fillers.

Sharon Hatcher, executive travel planner, Northeast Ohio

In my travel career spanning over 36 years, it was during my 23 years at AAA as a leisure travel professional that I received my strangest request. It was from a client in Hawaii who called me from his hotel room to tell me he hated the drapes and wanted me to change them immediately. At this time, we all had two phones on our desks (this was before the days of cellphones). I placed him on hold and used my other phone to call the hotel.

The agent that answered offered to show him some other room options. He agreed. They looked at different rooms with different decor — nothing suited this gentleman. 

After lengthy rants on the quality of the drapes in this hotel, the staff offered to remove the drapes completely. The client pondered this and finally agreed. His room for the week did not have drapes, curtains or anything hanging in front of the sliding doors out to the balcony.

I remember thinking to my very young self, “This is all this person has to worry about? He’s going to stay in his room and stare at the drapery. Why isn’t he outside?” To this day, I do not understand the conundrum. It honestly still baffles me.

Charlie Funk, CSF Travel Consulting, Brentwood, Tenn.

A number of years ago, it was my practice to go to work early so I could catch up on stuff before the rest of our staff came in. It was shortly after 7 a.m. on a Thursday when the phone rang. Barely had the words “Thank you for calling Just Cruisin’ Plus, this is Charlie, how may I help you?” escaped my mouth when a voice obviously in tremendous distress blurted out, “Thank God you’re there. I was petrified that I wouldn’t reach anyone this early. I leave to go on my trip this Saturday and just realized my passport has expired. What am I going to do?”

I am certain everyone reading this has had such a moment when your stomach muscles are clenched hard as a rock as you try to seem calm and not panic as you frantically ask and input the person’s name and phone number.

All the while she is beating herself up, explaining that she was a middle school teacher who got wrapped up in final exams, getting tests graded and distributed, closing out the school year and on and on. Just as her record displayed, checking the second page with booking details told the story.

Me: Ma’am, your trip indeed starts the day after tomorrow …

Her: I know, I know, and my passport has expired!

Me: Ma’am, your vacation is a land tour of Hawaii …

Her, talking over me: And my passport has expired.

Me, barely able to get in a word edgewise: Hawaii is a state, just like Kentucky.

 Dead silence. 

Then, a mumbled query from her, more like an abject statement: Hawaii is a state.

Me: Yes, ma’am.

There was a fraction of a second of dead air and a click as she terminated the call. One can only hope she didn’t teach geography.

Lisa Wright, Hola Weddings, Playa del Carmen, Mexico

We received a client lead for a destination wedding some time ago, requesting resort information, quotes, etc. Full-on planning mode — until we found out that the bride was planning her dream wedding but didn’t actually have a partner yet for the wedding. That’s when we unfortunately had to explain that we aren’t able to help with imaginary weddings.