Ask a Cruiser: Your Most Common Questions, Answered

October 9th, 2025 by team

(Part I)

by B.J. Porter (Contributing Editor)

If you’ve been reading this blog for a while, you may have noted that I spent many years (about nine) living on a sailboat and traveling around in the world. I say “traveling around in the world” because our goal was never a circumnavigation, but to see as much as we could and go where it interested us. We got about halfway around.

I meet lots of boat-curious folks. Once they pick up on that cruising background, they have questions. It’s enjoyable to talk about, and I don’t mind answering. But most of the questions are similar and fall into a few categories, so I’ve had a lot of time to figure out some answers.

This month and next, I’ve put together the most common questions I get and my answers to them. Other cruisers have different answers; this is solely from our experience. But hopefully, you’ll enjoy learning a little about our experience with cruising. And maybe they’ll inspire you.

The Dangerous Stuff

These are almost always the first questions asked, and the most common. So many people assume it’s a lifestyle fraught with high adventure and risk, with many dangers ranging from weather and storms to pirates and catastrophic boat failures and sinking in the middle of the ocean. While the risks are real, it’s not so exactly fraught with danger.

Did you ever run into any big storms?

If you mean things like hurricanes and cyclones while we were offshore? Not really. Most cruisers move based on global seasonal weather patterns. So you have a pretty good idea of when and where it’s hurricane and cyclone season, and you just don’t go there at high risk times.

Instead, you plan long term, and make sure you’re near a safe place or somewhere where the risk is minimal. That may be Grenada or Trinidad in Atlantic hurricane season, or New Zealand turning cyclone season in the South Pacific. And your insurance company also has rather strong opinions about covering your boat during storm seasons, and may force your hand.

That doesn’t mean we never hit bad weather. We caught our fair share of storms and squalls offshore, and some decent winds. And we rode out Hurricane Sandy at anchor in Deltaville VA, and had the remnants of a tropical cyclone catch up with us in New Zealand. But we hit no long and exhausting stretches of dangerous weather.

Were you worried about pirates?

My wife and I lived in New York City for years. One thing the city teaches is situational awareness. There are places you don’t go at certain times, or places to avoid, if you don’t want to be a victim of crime. The same situational awareness applies to cruising.

It’s no secret that some areas of the world are dangerous, and piracy is really nothing more than crime on the water. The only time anyone ever boarded my boat intending to commit a crime before we went cruising, in the U.S. on our mooring at our yacht club. Some kids tried to steal our dinghy to take on a joyride, and we were sleeping on board before an early morning departure for vacation.

Just like avoiding hurricanes, you check on resources that track crime in coastal areas and stay alert. The one time we felt truly uncomfortable in an anchorage, we left the next day.

What was the most dangerous thing that ever happened?

Probably the time our backstay broke en route to St. Martin from Virgin Gorda. It was early in the morning, just before sunrise, about five miles from shore. We were trying to hit a tight window of good weather to make the trip to meet family on the other end. When the backstay parted, we secured the rig with our checkstays and a spare halyard. Then we turned around and went to Tortola to get it repaired and got back on the water in time to still catch the window.

Far more often, we had annoying things happen. Like losing our autopilot 300 miles into a 3,000 mile passage and finding out the backup didn’t work either. That seemed awful at the time, but it turned out OK. Or having the generator leak water hundreds of miles from shore so we couldn’t use it, then finding water leaking from the oil cooler on the engine when we ran it too. Shout out to JB Weld for patching that one so we could charge our batteries. But it wasn’t dangerous, per se. Just…irritating.

Were you ever scared?

Not really, though we had a few things to deal with. One thing we learned early is that our boat was tough – much tougher than we were. Having a solid boat that we knew well, and being prepared for many eventualities with a plan to address them really helped with that. But nothing that we encountered ever left me frightened enough to doubt we’d make it back to shore.

One reason we stabilized the rig so quickly when the backstay failed was that we’d talked through what we’d do with a rigging failure after we experienced a similar failure on a different boat. We had a plan, so we reacted quickly instead of being scared.

The Trip

We’ve been to some exotic locations, and more than a few places most people haven’t heard of. The journey and where we traveled and what we saw are a big part of people’s questions.

What’s your favorite place you visited?

This is one of the hardest questions, and I refuse to answer with a single favorite. We so so many cool places and cool things I can’t pick one. The problem is that two places may be equally incredible, but for completely different reasons. Or for the same reason in different ways. I can pick the top four, and even that is at best overly broad and vague and leaves out many places we loved.

Those top four would be:

  • New Caledonia, an amazing French island surrounded by the 3rd largest barrier reef in the world. It’s a double reef, and the lagoon gets visits from whales and deep ocean fish, and the snorkeling is stunning. Also, there are killer French bakeries and restaurants with a delightful blend of the South Pacific with a French flair.
  • French Polynesia, specifically the Tuamotu Atolls, but you could drop me anywhere in French Polynesia and I could stay indefinitely. Gorgeous scenery, beautiful weather, and so much to see. And French food…
  • The Galapagos, with wildlife that isn’t particularly afraid of you, animals you won’t find anywhere else, and otherworldly geographic features from the volcanic activity.
  • New Zealand, with its amazing beauty,with a different marvel around every corner. We spent almost three years there in total, and never ran out of things to see and do.
Bay of Islands, New Zealand

Of course, there were many more unique, cool and amazing places we visited. The eco-tourism in Dominica, the cultural experiences in Trinidad, and even the view under dark, cloudless sky hundreds of miles offshore all those and more could easily make the list.

What was the coolest thing you ever saw?

This is kind of similar to the “favorite place” question, because there are too many answers. I can’t possibly pick just one thing. There are always highlights from the places I mention as favorites, but so many others.

A few things I might throw out include:

  • The view from the first volcano we climbed.
  • Whales…humpback whales breaching in tandem. Or breaching right near the boat. Sperm whales chilling on the surface. A curious family of Orcas where the baby swam right under our stern to check us out.
  • Water so clear you can see the anchor throw up clouds of sand on the bottom in fifty feet of water.
  • So much sea life under the water when snorkeling.
  • Hanging off the swim ladder with a snorkel and mask in the Tuamotus, watching sharks swimming around the boat.
  • Dugongs.
  • The Panama Canal.
  • And so many, many other things.

Did you ever see any (insert thing here)?

That depends on the question, but it’s usually whales, dolphins, sharks, or other marine life, and the answer is almost always “yes.”

Ask Me Anything

This is just part one; next month I’ll get more into the sailing (“How far did you get from land? What was your longest trip offshore”) and the lifestyle (“What did you do about food? Did you homeschool the kids?”).

But in the meantime, please add more questions in the comments, and I will do my best to address them next month.

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