Breakout Session
Industry chatter on a topic that’s important to you
In this issue, we asked travel advisors this question: What is one of the craziest travel requests you’ve received from a client? Let’s take a look at what they had to say.
“We had a fiancé PROMISE his bride a stay in an overnight bungalow for their honeymoon and requested a quote for a three-night stay — stating that they couldn’t take more time off due to work. At this time, the only options were Bora Bora or Maldives or similar, so with flights they would have had a total of nine hours (one night) in destination, and the groom was still so interested that we even made a reservation to book it! Luckily, we convinced him how silly it was, despite the promise, and convinced them to do a much more memorable honeymoon in a closer location that they truly enjoyed.”
–Mitch Toren, chief vacation engineer at TripGuy.com
“One time, a client asked us to book a room with a balcony facing the full moon so they could ‘charge their crystals properly.’ They were really serious about planning their trip around the lunar calendar! I made the request, even though the resort couldn’t guarantee an exact room. When they checked in, they didn’t like their room number — it wasn’t ‘lucky’ enough — so they insisted on switching rooms. Somehow, we managed to find them a ‘lucky’ room with the perfect moonlit view. It was one of the more unique requests we’ve had, but hey, the client left happy!”
–Joslynne and Wade Light of Light Travels Inc.
“One of the wildest requests I’ve had? A client wanted to literally go back to her roots — by staying in a cave in Matera, Italy, where her family once lived. Yep, a cave! Luckily, some of Matera’s ancient ‘sassi’ have been transformed into stunning cave hotels with all the modern comforts. I planned a trip that let her sleep like generations before her … but with plush bedding and a wine list. It was a beautiful blend of old-world charm and modern luxury — proof that history can feel like a five-star experience!”
–Christi Malbasa, travel advisor at Magnolia & Palm Travel Company, a NEST affiliate
“A client called me, confused because she wasn’t allowed to check in to her hotel. Our client documents state that they need to provide a card for check-in and incidentals. She insisted the property wouldn’t accept her card. I spoke to the receptionist, who said the card had been declined. I asked the client to provide another, and she said that she had already offered her only card — a debit card with no money on it. She had only been told to bring a card, not a card that would be accepted. We have since clarified our client documents!”
–Shelly Ramirez, owner of Michelle's Destinations, a TRAVELSAVERS affiliate
“The craziest travel request I have had to date has been a request for a quad booking. Booking more than two people in the room does not always equate to a huge cost savings discount. It is ok when you have a group trip to just book two to a room and meet up in the common areas. I’m just happy that people are getting out and living! You’re on vacation; ensure that your resting environment is relaxing as well.”
–Chasity Strickland, owner/luxury travel curator of Get OUT and LIVE Travel Company
“My craziest and most stressful challenge was a couple who wanted an all-inclusive resort in Mexico that would accommodate a multitude of modifications to bedding, bath amenities and foods. The bedding must have a certain type of pillow and non-pillow top mattress. Their dietary restrictions were multiple: gluten free and allergies to tomatoes, carrots, mushrooms, peanuts, almonds, shrimp, oranges and grapes. Finding a resort that would actually follow through with modifications was worrisome for me, especially the foods. When they returned from their vacation, they had great things to say about the resort. You can imagine my relief!”
–LeAnne Rigsby, owner/travel advisor of Cricket Cruise & Travel, LLC, a NEST affiliate
“In 22 years, I’ve had at max two to three clients who lived in Hawaii looking to travel elsewhere. Around 2010, we had honeymooners contact us to book their very special honeymoon … to the Jersey Shore … during the heyday of the MTV series thinking that everyone there was like those on the show. As a person who spends summers at the Jersey Shore, I just couldn’t understand why anyone from Hawaii would ever want to come there. :) That said … we booked it!!”
–Mitch Toren, chief vacation engineer at TripGuy.com
“I had a young family with two under two who wanted to travel from Cincinnati to Bora Bora — talk about a hike! The first trip I ever booked was for a family of eight driving from Cincinnati to Utah. They explored several national parks, and I found unique, off-the-beaten-path homes that could accommodate them all. One client requested a Greek island with no traffic, so I literally found an island with no cars. I’ve even helped clients temporarily relocate to Europe. Accessibility and inclusivity are also big parts of what I do. I’ve planned LGBTQ honeymoons, trips for neurodivergent travelers, those with mobility challenges, dietary restrictions and more. For me, the unique requests normally begin once people arrive though. I once had a client get bitten by a shark — that was definitely a wild one to handle!”
–Rebecca Smiley, travel advisor at Smiley Travel (with KHM)
Originally appeared in the Spring 2025 issue of The Compass magazine
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