7 Cruise Booking Mistakes That Cost Us Thousands (We're Not Proud of These)
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Real talk — we've made some expensive mistakes on cruise ships. Between the two of us, we've sailed over 60 times, and y'all, some of those early trips had us looking at each other like, "Why didn't anybody tell us this?"
That's exactly why we're being transparent today. These are 7 cruise booking mistakes we made — some more than once — that cost us real money. We're talking hundreds, if not thousands of dollars, we could've kept in our pockets if we'd just known better.
We're sharing these because we want you to cruise smarter, not just more. Whether you're a first-timer or you've got a few sailings under your belt, at least one of these is probably going to hit different.
Okay so listen — let's get into it.
Mistake #1
We Skipped Travel Insurance (And Then We Needed It)
This is the one that still stings. On an early cruise, we missed our same-day flight for a family Thanksgiving cruise. Flights for 5 people, two cruise cabins, drink packages, excursions, and more. No travel insurance. Non-refundable reservation. We lost over $4,200 that trip — not from cruising, but from not going.
Travel insurance is not optional. Especially if you're booking premium sailings, suites, or group trips. Medical evacuation alone from international waters can run $50,000–$100,000 without coverage. That's not a scare tactic — that's the actual number.
What we do now: We book through a third-party insurer (not the cruise line's policy — those are often weaker). We look for "cancel for any reason" coverage on high-ticket trips. Non-negotiable for us.
Mistake #2
We Booked the Wrong Cabin Without Doing the Research
We booked an interior cabin on a 7-night sailing to save $300. What we didn't account for: waking up not from an alarm but from the sound of the anchor being let go at every port or the sounds of crew members in the wee hours of the night. We did not check the location of WHERE our cabin was.
We didn’t know that checking the location of where the cabin is was a thing until we were stuck with it.
The reverse happens too — people upgrade to a balcony on a short, port-heavy sailing where they're off the ship 10 hours a day and never use the balcony once.
What we do now: Match the cabin to the itinerary AND your travel personality. Long at-sea days? Get that balcony. Port-intensive trip? Interior can work. Always read the deck plan and check if your cabin is near the elevators, Lido deck, or crew areas.
Mistake #3
We Pre-Paid for the Drink Package Without Doing the Math
This one embarrasses us a little because Addy is a former professional chef who has spent 15+ years in hospitality. We should have known better. We bought the premium beverage package on a cruise, excited about "unlimited" drinks — and then drank maybe $30 worth per day when we needed $65/day to break even.
Y'all. We spent over $900 on a drink package and saved zero dollars. In fact, we lost money.
The break-even math is everything. Every drink package has a per-person, per-day cost. Add up what you actually drink in a day — coffee, juice, alcoholic beverages, specialty drinks, bottled water — and be honest with yourself.
What we do now: We calculate the break-even before every sailing. On Virgin Voyages, the Bar Tab works great for us because of how we drink. On some other lines, we go pay-as-you-go. It depends entirely on your habits.
Mistake #4
We Waited Too Long to Book and Lost the Cabins We Actually Wanted
Ask us how we know: you can wait too long. We missed a great price on a Junior Suite on a Celebrity sailing because we spent two weeks "thinking about it." The cabin category sold out. We either upgraded to a suite (didn't fit the budget) or downgraded to an interior. Neither felt right.
The best cabins — midship balconies, family staterooms, certain suite categories — go fast. Especially on popular itineraries, holiday sailings, and ships people are excited about.
Early booking also tends to mean better pricing. Cruise lines reward people who commit early. Final payment deadlines are usually 90–120 days out, but the price you lock in is often the best price available.
What we do now: We book as early as possible for the sailings we actually care about. We watch for price drops and re-fare when they happen (yes, cruise lines will often honor lower prices if you ask before final payment). And we don't wait if we find a cabin we love.
Mistake #5
We Didn't Read the Fine Print on What Was Actually Included
Cruise fares are advertised like they include everything. They don't. We showed up to a specialty restaurant on our first Celebrity sailing thinking dinner was covered. It was $65 per person extra — not in our plan, not in our budget, and not great when you're already at the table.
On top of that: automatic gratuities (often $18–$25 per person per day), Wi-Fi, specialty coffee, branded sodas, certain excursions, and port fees that somehow weren't in the original quote. All of these add up to hundreds more per person on a 7-night sailing.
What we do now: We read the actual inclusions list — not the marketing language, the actual what's-in-the-fare breakdown. We budget for gratuities and one or two specialties as a standard line item. No surprises allowed.
Mistake #6
We Booked All Our Shore Excursions Through the Cruise Line
This is the one most people know about but still do anyway because it feels safer. We get it. The cruise line excursions come with a guarantee — if the tour runs long, the ship waits for you. That's a real benefit.
But we paid 30–40% more than we needed to on excursions we could have booked independently for less. Over multiple sailings, that's easily $500–$1,000 in unnecessary spending.
And here's the thing — the independent operators often give you a smaller group, a better guide, and a more flexible experience. We've had some of the best port days of our lives on non-cruise-line excursions.
What we do now: We use cruise line excursions strategically — for remote ports where timing is tight or there's real risk if we miss the ship. For popular ports with reliable independent options, we book outside. Viator, GetYourGuide, and port-specific Facebook groups are our go-to resources.
Mistake #7
We Chose a Cruise Line That Wasn't Actually for Us
This is the most expensive mistake on this list because it doesn't just cost money — it costs a whole vacation.
Early on, we booked a line that everyone around us was raving about. The marketing was good. The price was competitive. But the vibe? Not us. The demographic skewed slightly older. The entertainment wasn't our speed. The food was fine — but "fine" on vacation is disappointing when you're Addy, who has higher standards than most people will ever have for cruise ship food.
We finished the trip. We didn't hate it. But we talked the whole way home about what we could have done differently if we'd just researched cruise line culture before booking.
What we do now: Every cruise line has a personality. We study that personality before we book — not just the brochure, but what actual passengers say, what the onboard energy is like, whether we'll feel at home. It matters more than price.
The Bottom Line
None of these mistakes are unique to us — we've heard every single one of them from viewers in our comment section too. That's how we know this is stuff that trips people up.
The good news: all of them are 100% avoidable once you know what to look for. And now you do.
Cruise smarter, not just more — that's the whole mission.
Ready to cruise smarter? Addy is a Certified Leisure Travel Specialist and Virgin Voyages Top 100 First Mate. She can help you find the right ship, the right cabin, and the right price — before you make any of the mistakes above.
If you're also thinking about a group cruise experience, Sistahood@Sea 2027 is our women-focused group cruise for 2027 aboard Celebrity Beyond — July 11–17, 2027, sailing to CocoCay, Grand Turk, and Puerto Plata.
Watch the full video: "7 Cruise Booking Mistakes That Cost Us Thousands" — on our YouTube channel @addyandterry
