Offshore Odyssey - questions to ask before stepping on

Does sailing into the sunset sound dreamy? Then tell me why there are so many nightmare stories of people going offshore, only to come back and say, they’re never sailing with that captain or crew again?

Nothing is guaranteed, but here are some interview questions to ask an owner or captain prior to a trip to give yourself the best chance of having the time of your life and not the time you almost died.

Before any trip, ask yourself what you hope to gain out of a trip? A high sea adventure? A cruise to an exotic destination you’ve never been to before? Are you qualified for the journey? Or perhaps you’re trying to gain sea time for your captain’s license.

There’s a matrix for skill set, type of journey, length of trip, size of boat, equipment, menu planning, financial budget, sail plan and personality fit. Generally, the more skills you bring to the table, the more attractive you are to the overall program. For example, when I was a new sailor, I was more or less a warm body and spent my time cooking, cleaning and doing night watch under supervision; in other words, I was crew but not really sailing. At that point, I didn’t know what was safe or not, but knew that a clean boat and a fun captain who wasn’t creepy, were my main requirements. Little did I know there’s so much more to sailing than that.

As I got better at sailing, meaning I had done day sails, some overnight cruises and some classes, I could cook and clean but also knew how to provision, menu plan, organize the pantry and gear storage and knew some sailing. I met captains through findacrew and Latitude 38 and got to sail down the West Coast on the Baja Haha and around the Sea of Cortez and also up and down the coast of California.

There’s always so much to learn so one of my main criteria before stepping on a boat is trying to find out how much am I going to learn. Some things are trial by fire but hopefully, there’s rapport with the owner/captain to learn more about navigation, engines, electrical systems and plumbing. Many of these things you’re learning on the job as things break, but you definitely want to learn from someone who has rebuilt things rather than someone who tinkers and bandaids everything together on a tight budget.

Here are the types of things I usually try to find out:

Type of Boat, year built, rigging, engine, sources of power.
Knowing these will tell you if it’s been recently fixed up or is it on it’s way out? Depending on how they answer it, it will also tell you where their priorities are. Safety is important to me so ideally, the boat is well maintained, this means, they’re proud to tell you about all the work that’s been done on it, rather than a list of all the things that need to be fixed.

Journey - how long is the trip and where are you going? How much fuel do you have and what type of sails and alternate sources of power do you have? And what’s the policy on motor sailing. I prefer not to go slower than 5kts but some captains don’t want to burn fuel or they don’t have enough fuel capacity.

Emergency equipment: life raft, EPIRB, AIS, Starlink, Radar, Garmin, other tracking devices, PFD, tethers, etc. You don’t want to run into an emergency and not be able to call for help, even if you’re in the middle of the ocean, you want assurance that someone knows you’re there or if need be, someone can come and fetch you.

Crew, watches and menu planning. I like to know how a captain thinks about sleep and eating. Some captains are hardcore and don’t mind longer solo watches and grab a meal if you’re hungry. I prefer to be well rested and well nourished. Some captains also won’t go on long passages if you’re vegetarian or vegan so you need to specify that. Some captains don’t want to ‘cook’ underway so you should find out - this could mean, propane, inverter or no inverter for microwave (it depends on their resources), toaster, coffee maker, etc. I have traveled with boat owners who have two freezers and two fridges and all the gadgetry and I’ve also traveled on boats with no fridge at all. When I raced to Hawaii, our dinner was hot boiling water into an MRE bag (Meal, Ready-to-Eat). Ask about the alcohol policy. I prefer a dry-boat or at minimum, a boat who won’t drink underway, especially at night. If it’s the doldrums, fine, have a cold beer. But don’t get drunk. Others do drink and I just tend to stay away if they’re a party boat. They usually want to split the food cost and want to include alcohol. But I usually prefer the drink tab as separate.

Therefore, find out who the crew is, how many there are and if possible, their sailing experience and personality type. I’ve sailed with plenty of awesome sailor with horrible personalities and others who were inexperienced sailor but awesome character traits. Some crew are going to want to go hiking, biking, kayaking, snorkeling or drinking. Others want to tuck into a book and not talk to you at all and maybe you’re ok with that. Find out what kinds of toys are on board. Dinghy? Do you know how to operate an outboard motor?

Lastly, finances. Find out if you’re contributing and for what? Food, alcohol, travel? Generally, crew does not contribute towards boat expenses unless it’s a charter. It’s a grey area so find out. If you’re well-skilled, you could instead be paid, especially if it’s a delivery. If so, find out the day rate (whether you’re paying or they’re paying you). And if you’re traveling to a foreign country, make sure you have your letters for the immigration control and exiting/entering.

Good luck on your next journey! No question is a dumb question. Transparency is key!