There’s no such thing as a bad cruise, right? Well, after more than 50 cruises, I can honestly say there are some I would happily skip in the future, and a few I’d never book again under any circumstances.
This isn’t just based on my own travels over the past few years. For about 20 years, I worked as a travel adviser specialising in cruises, so I’ve seen patterns in what clients loved and what left them disappointed. These are the cruises I personally avoid, and the reasons why you might want to think twice before booking them too.
1. A Short Bermuda Cruise
Bermuda is honestly one of my favourite cruise destinations. We’ve sailed there nine times, and I think it’s one of the most underrated itineraries out there because most ships dock overnight, so the ship basically becomes your hotel while you explore the island.
So when I spotted a 4-day Carnival cruise from New York with one day in Bermuda, I thought it sounded perfect. A quick getaway with a bit of pink sand thrown in. What could go wrong?
Here’s what we didn’t think through. On a 4-day cruise, the time in Bermuda is incredibly short. We had to be back on the ship by 3pm, which meant no trip to our usual favourite beach. We grabbed a meal, walked around for a bit, and that was it. Out of 4 days, we only had around 8 hours actually on the island. The rest was sea days.
By the time we got home, we just didn’t feel fulfilled. If you’re considering a Bermuda cruise, I really recommend looking at the longer sailings where you get 2 to 3 days in Bermuda to actually explore. There’s so much to see, from Horseshoe Bay Beach to the Royal Naval Dockyard, and you simply can’t fit it in on a short sailing.
2. A Bermuda Cruise in Winter or Early Spring
Speaking of Bermuda, here’s another one to avoid. Booking a Bermuda cruise during winter, early spring, or late autumn can mean your itinerary doesn’t actually take you to Bermuda at all.
Bermuda cruises tend to get rerouted when the weather and seas aren’t cooperating. And when that happens, the ship usually heads to Canada and New England instead. Recently, a couple were on a 5-day Virgin Voyages cruise to Bermuda in April. Instead of pink sand beaches, they ended up in Saint John, New Brunswick.
Now, New Brunswick is a beautiful place, but it’s not where you want to be in April when you packed for the beach. If you’re set on Bermuda, stick to the warmer months when the climate is reliable and ships are far less likely to detour.
3. A 3-Day Cruise
This one might surprise you, because I’ve actually done a few 3-day cruises. The most recent was on Celebrity Silhouette about a year ago, which we genuinely enjoyed. The itinerary was great, with stops in Key West and Nassau, and we had a brilliant day renting a golf cart in Key West.
Here’s the thing though. It didn’t really feel like a Celebrity cruise. Compared to the Edge-class ships or even Celebrity Summit, the atmosphere on a 3-day cruise was completely different. Lots of bachelorette parties, bachelor parties, and weekend partygoers.
That isn’t necessarily bad, but the food, the service, and the overall vibe felt almost like a different product to a typical longer Celebrity sailing. If you’re hoping for the full premium experience, a longer cruise is usually a better bet. Short weekend cruises tend to attract a party crowd, and that can really shape your experience whether you want it to or not.
4. A Mediterranean Cruise in Winter
This one is personal, and I’ll admit I’ve turned down brand opportunities to do exactly this. A Mediterranean or European cruise during winter just isn’t for me.
There are cruise lines, including MSC, that do sail the Mediterranean through the cooler months, and if you’re European with the Med on your doorstep, this might suit you perfectly. But from a North American perspective, traveling to Europe still feels like a bucket list moment for me.
I want warmer weather. Not necessarily hot, but warm enough to sit outside, walk the historic sites without a winter jacket, and enjoy long evenings at a café. If you’re planning a Mediterranean cruise, my honest advice is to know what kind of weather you actually enjoy. The shoulder seasons of late spring and early autumn can be lovely, but packing for a winter Med cruise is a very different exercise.
5. A Winter Cruise from New York or New Jersey
Living in Montreal, I see this one come up a lot. Cruisers in the eastern US and northeastern Canada often look for cruises they can drive to so they can skip the cost and hassle of flying. That’s how a 7 to 12 day winter cruise from New York or New Jersey to the Caribbean can look really tempting.
The catch? The first day or two and the last day or two are cold. Sometimes there’s snow on departure day. Yes, you’ll eventually reach the Caribbean and get some warm weather, especially on longer sailings. But the seas can also be much rougher in winter on this route.
I’ve actually spoken to ship captains who’ve told me this is one of their least favourite routes to sail. If you’re set on a winter cruise from a Northeast port, just go in knowing what you’re getting into.
6. An Alaska Cruise at the End of the Season
Like every cruise destination, Alaska has its peak and shoulder seasons. The end of the season comes with some real downsides that often get glossed over.
Here’s what tends to happen toward the very end of the Alaska cruise season:
- The weather is colder and noticeably rainier
- Seasonal workers start heading home, which means fewer staff at attractions
- Excursion options shrink, and weather-related cancellations increase
- Bucket list experiences like helicopter and floatplane rides get cancelled more often
Cruisers who’ve sailed late in the season often mention that some restaurants and shops have already closed, and the overall energy in port towns feels a little flat. Honestly, when you see those YouTube thumbnails about cold, rainy, miserable Alaska cruises, that’s almost always when they sailed.
If you’re heading north for the first time, the best months to cruise Alaska are typically June, July and early August. Avoiding common Alaska cruise mistakes starts with picking the right time of year, and there are plenty of Alaska cruise tips worth knowing before you book.
7. Cruising From Smaller, Less Popular Ports
At the risk of upsetting some cruisers, here’s another one I’d avoid. I’m talking about ports like Jacksonville, Baltimore, and Philadelphia.
There’s nothing wrong with these cities, and if you live nearby, the convenience can be brilliant. The issue is that smaller, less popular ports usually don’t get the newer, more premium ships. So when a price catches your eye and you book without checking the ship, you might end up on something older that doesn’t represent the cruise line at its best.
If it’s your first cruise, this can make a real difference to your impression of the brand. Always research the specific ship before booking, not just the price and the port.
8. A Residential Cruise
I love cruising, but living on a cruise ship full time? Not for me.
There are people who absolutely love this lifestyle and share it online, and that’s wonderful. What I noticed watching their stories over time, though, is that the novelty often wears off. After 6 months, then a year, then a year and a half, many of them seem to feel the shift.
A world cruise sounds incredible, and I can absolutely see myself doing one (or a segment of one) at some stage. Making a cruise ship my actual residence is a different conversation. I love my dog, I’d miss my parents, and I’d genuinely miss the rhythm of home life.
As much as I love cruise life and having someone else handle housekeeping and meal planning, I’m a bit of a homebody. The freedom of a vacation lies partly in coming home from it.
9. A Repositioning or Transatlantic Cruise
This last one comes with a confession. About 3 years ago, I made a video saying I’d never do a repositioning or transatlantic cruise. I’m coming around on it.
My original concern still stands. On a typical 12 to 16 day repositioning sailing, you might only have 3 to 6 ports, with 5 or 6 sea days in a row at one stretch. The port-to-sea-day ratio felt too tilted toward sea days for my preference. I like having land to look forward to.
But I’ve spoken to so many cruisers who absolutely love repositioning sailings, including friends who now do two a year and are trying to convince us to come along. A member of our Facebook group recently shared that the slower pace, the gradual time changes, and the chance to spend extended time on a great ship is exactly why they keep going back. Many people in our cruise community say it’s the best value cruising they’ve ever found, often comparable in price to a 7-day Caribbean sailing.
I’m curious whether a back-to-back cruise that includes a repositioning might be the sweet spot for me. If you’ve done one, I’d love to hear what you thought and which ship you’d recommend.
Final Thoughts
Some of these cruises won’t suit me, but they may be perfect for you. That’s the beauty of cruising. There’s so much variety, and what feels like a dream sailing to one person can feel like a disappointment to someone else.
The bigger lesson is to know what you want from a cruise vacation, then research the ship, the season, and the itinerary carefully. A bargain price isn’t a bargain if you end up on the wrong cruise for you, and there are plenty of warning signs to watch for before you book. Pair that with a few cruises that are worth avoiding for other reasons, and you’ll be in a good position to book one you’ll genuinely love.
Now I’d love to hear from you. Which cruise would you avoid, and is there one on this list you’d actually defend? Let me know in the comments.