A caller was running late for a flight out of San Francisco and asked me to call the cockpit to let the pilot know he was on his way and was driving a white Toyota.
Anon. 

I was explaining the time/date difference to a caller who was going to be flying over the International Date Line. When I mentioned the term, he asked if he could have a window seat so he could see the International Date Line when his plane flew over it.
Anon. 

I am situated in the middle of Canada (Winnipeg, Manitoba) obviously quite a trek to get to any ocean. I had a customer walk in and wanted to take a cruise from Winnipeg to San Francisco. At first I thought he meant fly to San Fran and take an Alaskan cruise or something, but as I started to do the leg work he specified to me that he indeed wanted to cruise from Winnipeg to San Francisco. I let him down gently.
Angeline, Winnipeg

A woman called and asked what documentation she required in order to fly from Canada to the US with her squirrel. She then quickly added “And not just any kind of squirrel…a water-skiing squirrel”. Oddly, I saw this woman and her squirrel on a US talk show later that month. And yes, the squirrel can water-ski.
Anon.

A caller’s flight was delayed on the tarmac. She noticed another flight was preparing for takeoff, so she called our center to see if we could get her on that flight.
Anon.

A caller told us he was at the front desk of a upscale hotel in London and they wanted to charge him the cost of an extra room and the cost of a mattress. Apparently, he had wet the bed in the middle of the night and made up some excuse to change rooms. His first question was what was my company going to do about it.
Anon. 

I took a call one day with an inquiry about an Alaskan Cruise.  I asked if they wanted a roundtrip Inside Passage cruise or a one-way that ends in Alaska.  He said he wanted the one-way and then asked if he could board the ship in Halifax.
Tracy. Fredericton, New Brunswick

A woman whose flight was delayed, was furious that she had to wait an hour because there were “a whole lot of other  planes just sitting out there –use one of them”.Anon

I worked at the front desk of a hotel in Mississauga, Ontario.  A family of 5 stayed with us for 3 nights.  They used the pool for the first night and upon the check-out, the woman complained that our pool made her swimsuit color fade out and made her and her boys’ skin fade too. They looked fine to us.
Anon

2 about cruising:
Client booked their cruise with me and asked the day before they where to depart the following “Do I need to bring my own toilet paper?”

Client asked, “do they have microwaves in the staterooms for my midnight snack” I responded “They do have 23hrs and 59mins of free room service”.  OK then.
David. New Westminster, BC

A man wanted to take a train to London England from Toronto as he was afraid to fly and afraid of the water.
Lenie. Richmond Hill. Ontario

A man wanted to take his dog on a flight and I told him it was not possible as only seeing-eye dogs were allowed.  He immediately said his dog was a seeing-eye dog. I said he was not blind.  He insisted he was.  (It was very strange). I suggested he go over to the other counter (pointing) and tell them, perhaps they could help.  He walked over to the place I had pointed out, without the dog, and without hitting or bumping into anything – also no cane.  The dog didn’t travel.
Anon.

A woman came to the check-in desk.  She said she had a baby travelling with her who would need a boarding pass. The agent refused to check her in without actually seeing the baby.  When finally produced, “baby” was sixteen years old.  Mother and baby travelled after Mother paid for “baby”.
Anon.