Most “cruise mistakes” articles are written from a checklist. This one is written from receipts. Across five sailings — a transatlantic crossing, the Mediterranean, the Greek Islands twice, and the Mexican Riviera — we’ve made every mistake on this list personally, and some of them cost us real money, real time, or a very long queue on a Greek island.
Here they are, in roughly the order they can hit you: booking, packing, embarkation, and port days. Each one comes with what it cost us and the simple fix.
Booking Mistakes
1. We booked our return flights late — and paid for it via Helsinki
On our Mediterranean cruise, we booked the outbound flights and waited on the returns, hoping prices would drop. They went up instead — and the only affordable option by then routed us home through Helsinki, adding an overnight airport stay to the end of the trip. A cruise has fixed dates; there is nothing to wait for. Book both directions the day you book the cruise.
2. We booked the expensive ship excursion when the port didn’t need one
In Puerto Vallarta we paid $100 per person for a ship-organised resort excursion — a pool an hour’s drive away, when the ship had better pools on board. It was also on discount, which in hindsight might have been the first clue. The description promised singing birds and bikes to explore the grounds; what greeted us was one parrot in a cage and electric bikes that didn’t work. It remains our most regretted cruise purchase.
That’s not to say ship excursions are never worth it — some genuinely are exciting and well run. The fix isn’t “never book ship excursions” — it’s matching the tool to the port: ship excursions for genuinely complex logistics, local guides or independent walking everywhere else. In Puerto Rico, a local guide cost $80 and gave us the best port day of the crossing.
3. We assumed every cruise line works the same way
After several MSC sailings, we knew the rhythm — walk into the main restaurant, get seated, done. Then we tried Princess, and discovered the rules had quietly changed: restaurant tables need to be reserved through the app, ideally before you even leave home, not decided each evening on the ship. We hadn’t done it, and found ourselves scrambling for a table on the first night. Every line runs dining differently — check the reservation system for your specific ship before you sail, not after you’re standing in the doorway.
Packing Mistakes
4. Two swimsuits on a 17-day warm-weather crossing
Between the pools, the water park, and the sun deck, a swimsuit never dried fast enough for the next day — and with only two, one of us was always waiting on wet fabric. Three or four is the right number for anything over a week in warm weather.
5. No book for ten sea days
A 17-day transatlantic crossing includes long stretches of open ocean, and we deliberately skipped the Wi-Fi package — being properly offline for that long turned out to be one of the best parts of the trip. What we hadn’t planned for was the flip side: no book either. Lying by the pool on a sea day with nothing to read gets old fast, and we ended up buying one in Tenerife at tourist-shop prices. If your itinerary has sea days, pack something to read — you’ll use it more than half the things in your suitcase.
6. Dressing for the weather, forgetting the air conditioning
Warm-climate cruise, thin summer dress, evening theatre show — and genuine cold. Ship interiors run aggressively air-conditioned regardless of the climate outside; on some ships the cabins do too, even at night. One light layer — a cardigan or thin jacket — belongs in every cruise suitcase, tropical itinerary or not.
Embarkation Day Mistakes
7. Arriving in the middle of the check-in window
On Discovery Princess, there was no option to book a specific hour — every passenger simply had the same 11 AM–2 PM window, and everyone showed up at once. We joined the queue right as it peaked, about an hour of standing. In Barcelona, with the app paperwork done in advance and MSC’s staggered time slots, boarding took twenty minutes.
If your line doesn’t offer a specific slot, consider arriving later in the window instead of right at the start — by then, most passengers are already aboard, which means a shorter queue and, as a bonus, a quieter buffet once you’re on the ship too.
Port Day Mistakes
8. Santorini on our own — the three-hour queue
The one port where independence actively worked against us. The walking path was closed, every tender passenger funnelled into the funicular queue, and the wait back down took three hours — long enough that we were relieved to find the ship still there. Crew told us afterwards it’s completely normal for Santorini.
Our tip now: before your cruise, check a site like Cruisemapper for how many ships are docking in Santorini that day — it tells you exactly how crowded the cable car queue is likely to be. One or two ships, independence works fine. Several ships, and it’s the single port on a Greek itinerary where we now say: book the ship excursion and skip the chaos.
9. Not pre-booking the Acropolis time slot
A pre-cruise day in Athens, an afternoon walk up to the Acropolis — and the discovery that entry now runs on timed slots booked in advance. The next available times were evening-only, and we had to let it go. In summer, same-day entry to headline attractions is increasingly a gamble anywhere in Europe. If a specific sight anchors your port day, book the slot before you fly.
10. Cutting the return to the ship too close
From Bari we took the trip to Alberobello — an hour each way, absolutely worth it — but the train back ran long and we reached the port thirty minutes before departure. Thirty minutes feels fine until you remember the ship does not wait for independent travellers. Our rule since: for any out-of-town port excursion, plan to be back a full hour early, and treat local transport timetables as optimistic fiction — the extra hour costs you nothing but a coffee at the port, and it saves you the stress of watching the clock instead of enjoying the trip.
Quick Reference: 10 Mistakes and the One-Line Fix
| Mistake | What it cost us | The fix |
|---|---|---|
| Late return flights | Detour via Helsinki + airport night | Book both directions with the cruise |
| Wrong ship excursion | $100 pp for a pool we had on board | Match excursion type to the port |
| Assumed all lines are the same | Scrambling for a table, first night on Princess | Check the reservation system before you sail |
| Two swimsuits | Always waiting on wet fabric | Pack 3–4 for warm sailings |
| No book | Tourist-shop prices in Tenerife | Pack reading for sea days |
| No warm layer | Cold evenings in the theatre | One cardigan, every suitcase |
| 1-hour check-in queue in LA | 1-hour check-in queue in LA | Arrive later in the window, not right at the start |
| Santorini independently | 3-hour funicular queue | Book the ship excursion — just there |
| No Acropolis slot | Missed the visit entirely | Pre-book timed attractions |
| Tight return to ship | 30-minute margin in Bari | Be back a full hour early |
FAQ: Cruise Mistakes
What is the biggest mistake first-time cruisers make?
Budgeting only the fare. Drinks, Wi-Fi, gratuities where applicable, and excursions add a realistic €25–50 per person per day, and first-timers who don’t plan for it get an unpleasant final statement. The fare is the start of the cost, not the total.
Should you book cruise excursions through the ship or independently?
Independently for straightforward, walkable ports — most Mediterranean stops need no tour at all. Through the ship only where logistics are genuinely hard, like Santorini’s tender-and-funicular system. Our worst purchase was a $100 ship excursion in an easy port; our best port day was an $80 local guide.
What happens if you’re late back to the cruise ship?
Unless you’re on a ship-organised excursion, the ship leaves on schedule and reaching the next port is your problem and expense. Build a full hour of buffer into any independent port day, and more if local trains or buses are involved.
Do you need to book attractions in advance for cruise port days?
Increasingly, yes — major sights like the Acropolis now run on timed entry slots that sell out same-day in summer. If one attraction is the point of your port stop, book the slot before your trip and plan the day around it.
What do people always forget to pack for a cruise?
A light layer for the air conditioning, enough swimwear to rotate while one dries, and something to read for sea days. None of them take luggage space, and all three are annoying and expensive to fix on board or in port.
Mistakes Are the Best Souvenirs
None of these ten ruined a cruise — but every one of them cost something a five-minute decision would have saved. The pattern behind most of them is the same: a cruise runs on a fixed schedule, and anything you leave to chance — flights, time slots, return journeys — gets decided for you, usually expensively.
Book everything with dates the day you book the cruise, pack for the ship as well as the destination, arrive early to everything, and give Santorini the respect it demands. The rest, honestly, you’re allowed to figure out the way we did.