In April, Eric and Charlotte Kaufman, two weeks into a monthlong sailing trip from Mexico to New Zealand, sent a distress call to the U.S. Coast Guard. Their 1-year-old daughter, Lyra, was sick and unresponsive to antibiotics, their boat was running low on fuel and taking on water, and they were 900 miles from the nearest coastline with Lyra and their other daughter, 3-year-old Cora, on board. Three National Guard aircraft and a Navy frigate rescued the family and returned them to safety in San Diego, at a cost to taxpayers of $663,000. The incident sparked outrage among many parents who wanted to know: What were they thinking?

The trend of extreme family vacations leaves me asking that same question. More and more, I see clients who have the means to go anywhere foregoing traditional travel destinations for places that are obscure, unexplored and even forbidden. They tell me that they’re seeking rare and authentic experiences for their family. Charlotte Kaufman, the mother from the boat incident, offered a similar justification. “How many people will ever experience the feeling of being surrounded by waves and wind for weeks and weeks?” she wrote on her blog. “It is…completely worth it.” Would she have felt the same if they didn’t get rescued?

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Recently, in a span of three weeks, three clients came to me with travel requests. One wanted to take his children biking through the rice paddies of Vietnam. Another wanted to explore the mountains of Afghanistan with his family to see firsthand the locale of the war on terror. And the third was looking to backpack through the hills of Colombia with his wife to learn more about the Revolutionary Armed Forces of Colombia (FARC). In all three cases, we advised the families not to go—a recommendation they accepted, but not happily.

Now, I realize that my barometer for risk is stricter than most. I err much more on the side of caution than the majority of people, and especially more than the adventure-lovers. But I try to examine every client request through an objective lens and answer one simple question: Does the risk outweigh the reward?

With my client who wanted to bike through the Vietnamese rice paddies, I had to explain that nearly 15 percent of the country—and particularly the rice paddies—is contaminated by as many as 30,000 unexploded landmines left over from the Vietnam War. I had to remind my client who wanted to take his family to Afghanistan that the State Department warns against all travel to the country. Even areas of the country considered fairly safe can fall victim to attacks: In January, suicide bombers stormed a restaurant in Kabul, killing 21 people, including three Americans. And for my clients looking to go to Colombia, I pointed out that FARC is a group of guerilla rebels who are actively fighting—and who wouldn’t look kindly on adventure-seeking Americans poking around their strongholds.

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There are also trips where the risks are less obvious but just as threatening. Wealthy people often want to visit incredibly remote locations; they want to visit places where their friends have yet to go. That’s fine—but it’s the responsibility of a security consultant to determine if the location has a U.S. embassy presence, and if not, the degree of difficulty involved in your safe removal. If I can’t get you out safely in a crisis, I’m not going to give the trip my stamp of approval.

Despite my scariest warnings, some clients insist on moving forward with their plans. So I tell them, “Go—go and enjoy your vacation. And when I have to get you out of there, I won’t hesitate to send you the invoice.”