Which Below Deck Captain and Crew Member Are You?

(And What Cruise Line Fits You Best)

Let’s take a break from the serious stuff for a minute.

Because while cruise routes, global events, and travel logistics all matter… sometimes you just want to kick back, picture yourself on a ship somewhere warm, and have a little fun with it.

And if you’ve ever watched the show Below Deck, you know something pretty quickly: It’s not just the destination that shapes the experience, but it’s the people…their personalities, leadership styles, and the energy everyone brings onboard.

Which got me thinking that we should have a Below Deck personality quiz, matching you with the Captain and Crew Member position that best suites your travel personality. And what if we could then actually point you to the best cruise line for that personality? So we built a fun, two-part quiz to figure it out.

If you’ve ever wondered what kind of cruiser you really are, we actually took a deeper dive into that in our post on What’s Your Cruise Personality Type—but without the Below Deck twist on it.

How This Works

This is a quick, two-step personality check and it’s meant to be easy and fun.

• Quiz #1: Your Captain Style → how you lead and approach travel
• Quiz #2: Your Crew Role → how you actually experience the trip

As you go, jot down the letter (A, B, C, etc.) for each question.

Don’t overthink it, as your first instinct is usually the right one. At the end of each quiz, simply count up which letter you chose the most, and that’s your result.

Then we’ll take those two results and match you with the cruise line that fits your personality best.

Quiz #1: Which Below Deck Captain Are You?

Before you jump in, here’s a quick cheat sheet of the captains you might match with:

• Captain Lee Rosbach – Direct, disciplined, no-nonsense leadership
• Captain Sandy Yawn – Supportive mentor who develops her team
• Captain Glenn Shephard – Calm, adaptable, quietly confident
• Captain Jason Chambers – Hands-on, energetic, leads from the front

Now… go with your gut.

Quiz #1 – Questions

1. Your ideal vacation style is:

A. Structured with a plan for every day
B. A mix of adventure and growth
C. Go with the flow
D. Active and spontaneous

2. When something goes wrong, you:

A. Take charge immediately
B. Turn it into a learning moment
C. Stay calm and adapt
D. Jump in and fix it

3. Your leadership style is:

A. Direct
B. Supportive
C. Quiet confidence
D. Lead by example

4. Your travel group (or group of friends) would describe you as:

A. Tough but fair
B. Inspiring
C. Easygoing
D. Energetic

5. How do you handle stress?

A. Power through
B. Talk it out
C. Stay calm
D. Stay active

Quiz #1 Results

👉 Mostly A’s: Captain Lee
👉 Mostly B’s: Captain Sandy
👉 Mostly C’s: Captain Glenn
👉 Mostly D’s: Captain Jason

Quiz #2: Which Below Deck Crew Member Are You?

Now let’s talk about how you actually show up on vacation.

Here’s your crew breakdown:

• Chief Stew – Guest experience, organization, attention to detail
• Deckhand – Adventure, activity, hands-on energy
• Chef – Food-focused, passionate, a little intense (in a good way)
• Bosun – Leadership behind the scenes, keeps everything running
• Charter Guest Energy – Here for fun, stories, and unforgettable moments

Quiz #2 Questions

1. On a cruise, you’re most likely to be:

A. Making sure everyone’s having a great time
B. Exploring everything
C. Focused on food
D. Keeping things organized
E. Creating chaos (the fun kind)

2. Your vibe is:

A. Polished
B. Adventurous
C. Passionate
D. Responsible
E. Unpredictable

3. Your priority is:

A. Experience
B. Adventure
C. Dining
D. Organization
E. Fun

4. Your ideal cruise day looks like:

A. Planning something special for the group (dinner, celebration, etc.)
B. Getting off the ship and exploring the port
C. Trying multiple dining spots and maybe a drink package to match 🍷
D. Making sure everyone’s where they need to be (and on time)
E. Going wherever the day takes you… preferably with a drink in hand

5. Your friends would say your biggest “vacation trait” is:

A. You make everything feel a little more special
B. You’re always up for trying something new
C. You revolve your day around food (no judgment 😄)
D. You keep the group from falling apart
E. You’re the one they can’t quite predict—but it’s always fun

Quiz #2 Results

👉 Mostly A’s: Chief Stew
👉 Mostly B’s: Deckhand
👉 Mostly C’s: Chef
👉 Mostly D’s: Bosun
👉 Mostly E’s: Charter Guest Energy

So… Which Cruise Line Matches You? (10 Personality Matches)

Now we bring it all together.

Your Captain style shapes how you approach travel.
Your Crew role shapes how you experience it.

And when those two click, that’s when you find the cruise line that just fits.

1. Captain Lee + Bosun

👉 Princess Cruises or Holland America Line

You’re the “let’s do this right” traveler.

You like structure, reliability, and knowing things are handled. These cruise lines deliver a smooth, polished experience where everything just works. No chaos and no surprises.

Why it fits: You don’t want to manage your vacation, instead, you want it to run like a well-oiled machine.

2. Captain Lee + Chef

👉 Oceania Cruises

You’ve got standards and food is at the top of the list.

You care about quality, detail, and experiences that feel refined. Oceania is known for its incredible cuisine and more intimate, upscale feel. If you’ve ever found yourself debating between luxury and mainstream cruising, this is exactly that sweet spot we talked about in our Luxury vs Premium Cruise Lines breakdown.

Why it fits: Your cruise revolves around great food, and here, it shows.

3. Captain Sandy + Chief Stew

👉 Celebrity Cruises

You’re all about creating an elevated experience for yourself and everyone around you.

Celebrity hits that perfect balance: beautiful ships, strong service, and a polished (but still relaxed) vibe.

Why it fits: You tend to notice the details, and Celebrity delivers them.

4. Captain Sandy + Deckhand

👉 Royal Caribbean International

You like variety and you’re great at making the most of it.

Royal Caribbean gives you options: adventure, entertainment, relaxation… all in one place.

Why it fits: You want a little bit of everything, and you know how to use it.

5. Captain Glenn + Bosun

👉 Princess Cruises

You’re relaxed but you still appreciate when things are organized.

You don’t need hype or chaos. You just want a cruise that flows smoothly, with time to unwind and enjoy the journey.

Why it fits: Calm, easygoing travel with just enough structure to keep things effortless.

6. Captain Glenn + Deckhand

👉 Norwegian Cruise Line

You want freedom. Explore when you want. Eat when you want. Do what you want.

Norwegian’s freestyle approach gives you exactly that.

Why it fits: Your ideal cruise has no rigid schedule—just options.

7. Captain Glenn + Charter Guest Energy

👉 Carnival Cruise Line

You’re here for fun. Plain and simple.

You don’t need perfection, instead you need energy, laughs, and a good atmosphere.

Why it fits: You’re not overthinking this… and Carnival isn’t either.

8. Captain Jason + Charter Guest Energy

👉 Virgin Voyages

You bring the energy and you want a cruise that matches it.

Virgin Voyages is modern, social, and experience-driven. Great food, no kids, and a totally different vibe from traditional cruising. And if food is even part of your personality mix, it’s worth checking out our full breakdown of the dining experience in Virgin Voyages Culinary Delight—because it’s a big part of what makes this line stand out.

Why it fits: You want your cruise to feel like an experience—not just a trip.

9. Captain Jason + Chief Stew

👉 Virgin Voyages or Celebrity Cruises

You love great experiences but you also want them done well.

You’re social, but selective. You want fun, but not chaos.

Why it fits: You get the best of both worlds—energy + elevated experience.

10. The “Balanced Cruiser” (Mixed Results)

👉 Royal Caribbean International or Celebrity Cruises

If your answers were all over the place… that’s actually a good thing. It means you’re flexible. You can enjoy different types of cruises depending on the mood, the itinerary, or who you’re traveling with.

Why it fits: You’re not locked into one style—and these cruise lines give you options.

And if you didn’t land perfectly in one category? That probably just means you’ve got more than one cruise personality—and honestly, that’s where things get interesting.

Your Turn

Alright… now I’m curious.

What did you get?

• Your Captain
• Your Crew Role
• And your Cruise Line match

Drop your results in the comments as I’d love to see how these line up… and whether your travel group is actually a perfect fit… or heading toward their own version of Below Deck 😄

And assuming you’ve cruised before, does this feel spot on, or did it totally surprise you?