Twenty questions across the five waypoints of The Passage. Not a test — a way to find out what you already know, and what's worth asking about before you're standing on the dock.
There's no pass or fail here. Answer honestly and each waypoint will point you to what's worth reading next — nothing more.
Why you actually want this.
Have you named the actual use case — family weekends, entertaining clients, solo Bahamas runs — or are you still shopping the idea of "having a yacht"?
If this is a step up from your current boat, have you priced the delta in ownership cost — crew, dockage, insurance, haul-out — not just the difference in purchase price?
Does anyone else in the decision actually want this at the frequency you're imagining, or is that untested?
Are you upgrading because the boat you have stopped fitting your life — or because you've stopped being honest about how often you use it?
Who's actually representing you.
If this broker relationship is new, have you re-confirmed how they're compensated — or are you assuming it works the way it did with your last one?
Would this broker still point you at this boat if there were zero commission in it for them?
Have you talked to someone who bought through this broker recently — not a testimonial, an actual reference you can call?
Are you leaning on instincts from your last purchase in a market that's shifted — flatter, more consolidated, less inventory-starved than 2021–22?
What you're really buying.
Have you compared this listing's asking price to actual closed sales in this size and class — not just other askings?
Do you know what "motivated seller," "priced to sell," or "bring offers" signal on this boat, in this market — or are you reading them the way you would have three years ago?
How long has this listing sat, and why? A stale listing and a fresh one carry very different negotiating room.
Have you sized a realistic survey allowance for a boat this age and class, before you're negotiating one under pressure?
What the inspection does and doesn't prove.
If this boat is a different class than your last one — crewed vs. owner-operated, or a real step up in size — are you assuming survey dealbreakers work the same way? They don't: a minor line item on a smaller owner-operator can be a six-figure issue on a crewed yacht.
Have you asked to see maintenance records and who performed major service — not just been told the boat is "well maintained"?
Who's choosing the surveyor, and do they work regularly with the listing broker?
Are you prepared for the survey to surface real issues — and do you know that's the start of a second negotiation, not a reason to walk?
What happens after you say yes.
Do you know what happens to your deposit if the deal falls through after survey — who holds it, under what terms — on this deal specifically?
Have you budgeted for closing costs beyond the purchase price — documentation, registration, possible sales tax, delivery?
Do you know what "acceptance of vessel" commits you to on this transaction, and what walk-away rights remain up to that point?
Have you lined up insurance and, if needed, crew or management before closing — or are you assuming your current setup just carries over?
Taking this to a broker meeting? — no email needed either way.
Unrelated to this page — just the newsletter. The Rutter arrives roughly twice a month, when there's something worth sending.