Read time: about 2.5 minutes. Published 2026-03-01

In an ideal world, there are no hiccups, glitches, or unexpected gusts of wind to blow you off course. But if you fly the coop often enough, eventually you’ll hit a patch of turbulence. It’s just the "law of averages," and the best we can do is be prepared so a little hitch doesn’t turn into a total nose-dive.

Luckily, I’ve got two big ways to keep your wings level.

1. Don’t Fly Solo – Use a Travel Agent

The most obvious advice? Let us handle the navigation. If your flight is cancelled or you're stuck at a hotel with a "No Vacancy" sign staring you in the face, you have a choice: Spend four hours on hold with three different companies explaining your life story, or make one call to your agent. We can’t always work miracles, but we know the shortcuts to get things sorted while you focus on taking care of yourself.

2. Get the Nest Egg (Travel Insurance)

Insurance is like a parachute—you hope you never need it, but you're sure glad it's there when you're in the air. Here are a few real-life stories from our "flock" that prove the point:

• The Puerto Rico Cautionary Tale: A friend of ours ran into medical issues mid-flight and spent their entire "vacation" in a hospital bed. Because of their medical condition, they couldn't fly home and actually had to book a cruise ship back to the mainland. The Lesson: Since they did not have travel insurance, they were on the hook for everything – the medical bills, the missed hotel in Old San Juan, and the entire cost of the cruise back home. It was a massive financial hit on top of a medical emergency.
• The Mexico "Oops": One of our founders (who shall remain nameless to protect his pride) made the classic mistake of drinking the water in Mexico. He got sick and had to see the ship's doctor. Because the crew had to be extra careful about outbreaks, he was quarantined to his cabin for the last day as a precaution to ensure it wasn't a communicable illness. The Lesson: Not only did the travel insurance policy cover the expensive onboard medical bill, but it actually reimbursed him for that missed day of the cruise. Most people don't realize insurance can pay you back for the "lost time" you're stuck in your room!
• The Seattle Stall: Friends heading to Alaska had to cancel their entire cruise on day one due to an emergency, after they had already flown into Seattle. The Lesson: Between the cruise, the shore excursions, and the extra hotel nights for her partner, they would have been out thousands. Their policy covered the whole bird’s nest.

Bottom Line: These things happen. Hopefully, they never happen to you! But the peace of mind is worth every penny. Don’t wing it – protect your investment so the only thing you have to worry about is which tropical drink to order next.