Crew Compatibility 101: How to Pick the Right Boat or People
Because no one wants to feel trapped in paradise.
My perspective here is as crew, not at a boat captain looking for crew. But, most of these ¨rules¨ can go both ways.
Let’s be real — living on a boat with strangers can either feel like the most freeing experience of your life, or like you’ve signed up for a reality show with no off switch.
I’ve had both.
This is Captain Jack — my favorite of all! He’s the reason I left Canada in 2021. After about a month of getting to know each other long-distance, I flew from Toronto, Canada to San Diego, California to help prep his boat for the journey down the Mexican Baja Peninsula. I later boat-sat his boat solo at a marina in Chiapas, Mexico for three months and came out of it with some of the best friendships and memories I’ve ever made. Thank you, Jack!
His afterthoughts:
I, Jack Buckley, highly recommend Chantal to anyone needing a responsible and organized person to help or manage a vessel, household, or company's business. She has crewed for me on SV Magic Carpet (For Sale now, have a look!) and reorganized and watched over its care for months while I traveled away on business. I was always impressed with the improved condition of the boat upon my returns. She has a wide range of talents and is quite an intrepid and resourceful traveler. Having her as an organizer or manager will add value to your vessel, home, or company. I can always be contacted for additional verification.
- Jack Buckley
See this beauty of a boat here : SV Magic Carpet
New Boat, new captain, new stories; I’ve crewed over 1,300 nautical miles up the Pacific coast of Mexico, from south-west of Chiapas to Puerto Vallarta, in a situation that tested every part of me. This other captain? (I will mention any names) He had mild military PTSD, a small drinking issue that showed up here and there, and what I’d call little man syndrome with money. That said, he respected our personal boundaries. He wasn’t a bad person, but it definitely wasn’t smooth sailing the whole way.
And many more crewing gigs. But these ones stand out to me.
Here’s what I’ve learned about choosing the right boat or crew:
FREE Printable PDF: BOAT + CREW COMPATIBILITY CHECKLIST
1. Trust your gut.
If your body says no, listen. One time, I toured a boat and the guy literally stood in front of the hatch while I was inside. It made me feel trapped. I couldn’t get out fast enough. Instant no.
2. Early tension is a warning sign.
If you’re already arguing about little things before even leaving the dock, it’s not going to get easier at sea. I once backed out of a trip that was already planned, bags packed, because every conversation turned into a debate. I knew if I stayed, I’d be miserable.
3. Get organized.
When I’m looking for my next opportunity, I literally write out a list of about 15 options. Some come from Facebook groups, others from sites like:
- Find a Crew
- Crewbay
- Crewseekers
- Sailing Networks (like Boat-Sitting Crew Networking)
I write down where the boat is, where it's going, how many crew are on board, if there’s a cost or contribution, how much free time I’ll have, what’s expected of me, start and end dates, and whether it could be extended.
Then I take my time getting to know them. If the trip is two months away, I’ll make sure to call at least twice a week and send updates every couple of days. Nothing heavy — just small talk. “Hey, I updated my passport,” or “How’s the boat coming along?” We’ll hop on video calls, text back and forth, and build that trust before I ever step foot on the dock. It’s a simple but powerful way to feel like you already know the person, and it helps avoid walking into a totally unknown situation.
4. Check their references — for real.
I always call at least three people who actually know the person. I’m talking close friends, family, coworkers, or best of all, previous crew. I’ll take a voice message or video chat over text any day. It tells you so much more about who they are and how they operate on a boat.
5. Ask about romantic expectations.
This one’s huge — and often skipped. Most of the captains I’ve met have been single men. Some are respectful, some are lonely, some are both, and yes, some are looking for something more than just crew. Before saying yes, ask directly: are you looking for a relationship, or is this strictly platonic? etc. It might feel awkward, but not nearly as awkward as being stuck on a boat with someone who was hoping for more than you were offering.
Ask their past crew too — has anything ever felt off? Inappropriate? This isn’t about judging, it’s about staying safe.
6. Be clear about your boundaries.
Whatever matters to you — sleeping arrangements, alcohol on board, shared meals, personal space — talk about it. Early. The right boat will respect that.
Bottom line: your peace and safety come first.
There are so many beautiful, wild, unforgettable experiences waiting out there. But none of them are worth sacrificing your gut, your values, or your sense of safety. Say no when it doesn’t feel right. Say yes when it does.
The ocean’s big. You’ve got options.
Chanty on SV_Bullseye