Cruises I Would Avoid - And Why

1 — Short Bermuda Cruises

Bermuda is one of Ilana's favorite itineraries — she's been nine times by cruise — but a four-day sailing to Bermuda is a different experience entirely.

What happened: A four-day Carnival cruise from New York left only a single short port day in Bermuda, with an all-aboard time of 3 PM. That ruled out the beach entirely and left only enough time to grab food and walk around briefly. Of the four days, roughly two and a half were spent at sea for only about eight hours in port.

The secondary issue: A four-day Carnival cruise also carries a noticeably different onboard atmosphere — more party-oriented, less relaxing — which compounded the disappointment.

The takeaway: Bermuda's appeal is the ability to dock overnight, use the ship as a hotel, and genuinely explore the island over multiple days. A short cruise eliminates exactly what makes Bermuda special.

2 — Bermuda Cruises in Winter, Early Spring, or Late Fall

Even on a properly-lengthed Bermuda itinerary, timing matters significantly.

The risk: When weather and seas are unfavorable, Bermuda cruises get rerouted — typically to Canada and New England. A recent example involved a Virgin Voyages five-day Bermuda sailing in April that ended up in St. John's, New Brunswick instead. Not a bad destination, but not what anyone booked.

Bermuda cruise season is generally late spring through early fall for this reason. Outside that window, rerouting is a real possibility.

3 — Three-Day Cruises

Ilana has done a few three-day sailings, but only one was fully by choice — a Celebrity Silhouette cruise to Key West and Nassau. Key West was genuinely enjoyable (rented a golf cart, had a great day), but the overall experience revealed something consistent about this cruise length.

The pattern: Three-day cruises attract a disproportionate number of bachelor/bachelorette parties and weekend party groups. The atmosphere shifts noticeably from a typical longer sailing on the same cruise line — and in Ilana's experience, even food quality, crew service, and overall product feel subtly different from what the brand delivers on longer itineraries.

Worth knowing: If you're choosing a cruise line partly for its reputation and experience, a three-day sailing may not be the best representation of what that line actually offers.

4 — European or Mediterranean Cruises in Winter

This one is personal, but Ilana considers it a firm rule for herself — she's declined brand invitations specifically because of winter Mediterranean timing.

The reasoning: For North American travelers, Europe and the Mediterranean still carry a bucket-list quality. Cold weather, heavy jackets, and the inability to sit outside at ports undercuts much of what makes those itineraries worth the travel. It doesn't need to be hot — but walkable, comfortable outdoor temperatures are part of the experience.

The nuance: For European travelers, a winter Mediterranean cruise may be perfectly fine given the proximity and lower-stakes nature of the trip. Context matters.

5 — Winter Cruises Departing from New York or New Jersey

A common consideration for travelers in the northeastern U.S. and eastern Canada who want to drive to embarkation — but the tradeoff is often underestimated.

What people don't anticipate:

• The first one to two days and last one to two days of the sailing can be genuinely cold, grey, or even snowy
• North Atlantic seas in winter are significantly rougher than Caribbean waters — Ilana has spoken to captains who describe this as one of their least favorite routes
• On longer itineraries (7–12 days) you do eventually reach the Caribbean warmth, but the opening and closing days can meaningfully affect the overall experience

6 — Alaska at the End of the Season

Alaska has a defined season, and the shoulder periods are not equal. The end of season carries specific drawbacks:

• Weather: Colder and rainier than peak season
• Seasonal workers: Alaska's tourism workforce is largely seasonal; toward the end of the season, workers head home, reducing staffing at shops, restaurants, and excursion operators
• Excursion availability and cancellations: Fewer options overall, and bucket-list experiences like helicopter and floatplane rides are more frequently canceled due to weather
• Port towns: Shops and restaurants may be closed; the energy in port is noticeably lower

The YouTube thumbnails showing cold, rainy, miserable Alaska cruises almost universally come from end-of-season sailings.

7 — Cruises Departing from Smaller, Less Popular Ports

Ports like Jacksonville, Baltimore, and Philadelphia serve a real purpose — especially for travelers who can drive to embarkation and avoid flights. But there's a tradeoff worth understanding.

The issue: Smaller, less trafficked ports typically don't receive the newest or most premium ships in a cruise line's fleet. Older ships are often assigned these routes. For experienced cruisers this may not matter much, but for first-time cruisers in particular, an older vessel at a secondary port may not represent the cruise line's current standard.

The advice: If you're choosing a departure port primarily because of price or convenience, be aware of which ship is assigned to that sailing before booking.

8 — Residential / World Cruises (as a Full-Time Living Situation)

Residential cruise living gets a lot of positive coverage, but Ilana's conclusion after watching many first-person accounts is consistent: the novelty wears off.

What she observed: Many people who commit to living on a cruise ship full-time report that after six months, then a year, then 18 months, the experience loses its appeal. The things that make cruising wonderful as a vacation — the novelty, the indulgence, the escape from routine — are harder to sustain as permanent life.

Her personal reasons for passing:

• Strong attachment to her dog (who can't come aboard)
• Values her home life and regular routine more than she expected
• Describes herself as "a bit of a homebody" despite genuinely loving cruise travel

The middle ground she's open to: A segment of a world cruise — a defined portion rather than the full commitment — has more appeal at this stage.

9 — Repositioning / Transatlantic Cruises (Position is softening)

Three years ago Ilana said she would never do one. She's reconsidering — but still has reservations.

The hesitation: Repositioning cruises often involve five to six consecutive sea days, with total itineraries of 12–16 days yielding only three to six port stops. The sea-to-port ratio feels too high for her preference — she wants land to look forward to.

What's changing her mind: Multiple friends now do two repositioning cruises per year and love them. They're actively trying to persuade Ilana and her husband to join them. She's genuinely more open to it than she used to be.

Still a no: The Queen Mary 2 transatlantic — purely ocean crossing with no ports — remains off her list. She needs some destination stops to stay engaged.