Cruise planning from someone who's actually sailed

Here's what nobody tells you: a disappointing cruise is almost never about the destination. It's the wrong ship — or the wrong cabin on the right ship. Let's make sure yours is neither.

What actually makes or breaks a cruise?

Itinerary is the fun part, and it's the part every booking site leads with. It's also the least likely thing to ruin your week. What ruins a cruise is a ship whose culture doesn't match yours. Or a cabin under the pool deck. Or a sailing date you booked without knowing what the weather does there in October.

1. The ship, not the line

Cruise lines are not monoliths. Two ships flying the same flag can feel like entirely different vacations. One is built around a waterpark and a buffet that seats four thousand. The other around adult-only sun decks and a restaurant you need to book. Royal Caribbean's newest hardware is a different proposition from its older, smaller ships. Virgin is adults-only and leans into it. Carnival's fleet spans a wide range.

I'll ask what a good day at sea looks like before I ask where you want to go. That answer narrows the fleet faster than a destination ever will.

2. The cabin category

The gap between the cheapest inside cabin and a mid-tier balcony is usually smaller than people expect, and the difference it makes to a seven-night sailing is not. It works the other way too: sometimes the smart money is the cheaper cabin, on an itinerary where you'll barely be in the room. I'll tell you when that's the case.

What I'm really watching for is location. Deck placement, what's directly above and below you, how far you are from the elevators, whether that "obstructed view" is a rope or an entire lifeboat. This is the part that's invisible on a booking site and obvious to anyone who has sailed the ship. Chad and I book our own cabins the same way I'd book yours — which is how I've changed my mind about more than one ship after sailing it.

3. When you sail

Alaska in May is a different trip from Alaska in August, and both are cheaper and quieter than Alaska in July. Caribbean hurricane season carries real risk and real savings, and whether that trade is worth it depends entirely on how much flexibility you have. Repositioning sailings are extraordinary value if you have the time and don't mind sea days.

What I book

• Ocean cruising — Caribbean, Alaska, Mexico, Mediterranean, transatlantic and repositioning sailings.
• River cruising — smaller ships, no sea days, and a different pace entirely. Worth considering if the idea of a four-thousand-passenger ship puts you off.
• Expedition — smaller vessels going where the big ones can't, with naturalists aboard rather than production shows.
• Family sailings — including Disney, where I hold graduate certification, and the lines with the kids' clubs worth using.
• Group and celebration sailings — milestone birthdays, family reunions, anniversary trips where you need several cabins near each other.

What do you get that you can't get yourself?

I book the same published fare you'd find online. What I add on top comes through Signature Travel Network. On many sailings that means onboard credit, prepaid gratuities, or a shore-excursion credit attached to your booking before you sail. It isn't available on every ship and every date — so you'll always know exactly what's on your booking, and what isn't.

I also watch your booking after it's made. Cruise fares move. If the price drops before final payment and the fare code allows it, I'll rebook you — which is which only happens if someone is looking.