Every cruise port hands you the same call: cruise excursion or on your own (or stay on the ship) — and you get exactly one day to be right. After seven sailings (and one wasted beach day I’ll own up to below), we now run every port through four questions before leaving the cabin. Here’s the framework, with the real ports where each question earned its keep.

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Cruise excursion or on your own? The short version

Book the ship when a port has a signature experience or real time-risk; go solo only after ninety seconds of homework and a word with the shore team; and remember that staying aboard a half-empty ship is a legitimate — sometimes superior — answer.

Question 1: Is there ONE great thing here I can’t do anywhere else?

If yes, book it through the ship and build the day around it. That question is how we ended up sliding down waterfalls in the Dominican Republic, exploring caves near Cozumel, and walking the sea floor in a dive helmet off Aruba. When a port has a signature experience, the excursion isn’t the expensive option — missing it is. (Corollary from our De Palm Island day: one great thing per port. It will take the whole day. Let it.)

Question 2: What happens if I’m late?

The rule that settles cruise excursion or on your own more than any other: a ship-booked excursion runs late, the ship waits; a private booking runs late, that’s your problem in a foreign country. The further an activity takes you from the pier, the more the ship excursion earns its price. Our Bonaire catamaran was ship-booked — so when a sea turtle crashed the snorkel stop, nobody watched the clock.

Question 3: Have I done the 90-second homework? (The beach day we lost)

Solo days are wonderful in the right port — we’ve had easy, lovely do-it-yourself days in flat, walkable, friendly places like Oranjestad (Aruba) and Kralendijk (Bonaire), steps from the gangway. But once, we skipped a paid beach excursion because a public beach sat within walking distance of the ship. It was knee-deep in seaweed and lined with trash. Not swimmable. Beach day gone.

So solo is now earned, never assumed: check recent visitor photos (not the tourism board’s), and ask the ship’s shore team one direct question — “is this a wander port, or a stay-close-to-the-pier port?” They know. It’s their job to know.

Question 4: Would staying on the ship beat this port?

Nobody asks this out loud, so I will: on port days the ship half-empties. Quiet pool, no chair hunting, no lines — the whole ship exhales. If a port doesn’t excite you, staying aboard isn’t surrender; it’s choosing the least crowded resort in the Caribbean, one you already paid for. In fact, some of our most restful days had a port sitting right outside the window.

The rule under the rules

Cruise excursion or on your own — whatever you pick, pick it on purpose, the night before, together. The worst port days aren’t the wrong choices; they’re the unchosen ones. Sixty seconds with these four questions and you’ll never stand at a gangway wondering.

Put the framework to work: Caribbean cruise tips over 55 · The 12-item cruise packing list

Your turn: what’s your best “stayed on the ship” day — or the port where going solo paid off? Comments below; I read every one.