How to Plan Your Cruise

In September of last year, David and I took an impromptu cruise to Greece. We literally had less than two weeks to get everything together and go.

Now that it’s winter in many places, you might be considering a cruise to get away. But where do you begin? Maybe I can help you out.

When and where to cruise?

Know the peak dates.

Cruises, like most travel, follows seasons. For example, Alaska cruises are at their peak in June through August, when temperatures in Alaska are at their highest. (There are no Alaska cruises during US winter months, as you might imagine.)

Sailing the Caribbean and Hawaii are popular in winter (understandably– it’s cold elsewhere in the US). The Mediterranean is most popular from May to August and early September, when it’s warm and kids are on summer break from school.

If possible, go during shoulder season.

As I typically advise for travel, it’s best to go during “shoulder” season — that period right before or after peak, when demand lowers (along with prices!). That’s exactly how we booked our Greece cruise. It was around the beginning of September, just when prices were going down. We got a 12-day cruise for about $800 each, a great deal for Europe! The timing was perfect for us too; I was set to start a new position, so I figured I’d take my vacation in between jobs.

However, sometimes you can only go at specific times. This is totally okay, just be prepared to do a little research and pay in advance. For instance, if you really want to go to Mexico but the only time you have is spring break, you can do it. Just be ready for all the college kids to be doing the same thing, and make sure to pay for it when a deal pops up or you might find the prices a little higher than you’d like.

Which cruise line?

This can be easy or tough. In many cases, when purchasing something, people will choose the lowest price. It’s a little different when cruising. There are a few factors to consider, but it mostly…

Let your travel style decide.

Are you looking for a more easygoing, less formal type of cruise, with the option to still be dressy? Are you uncomfortable being locked down to a specific dinner time with the same group of people? Norwegian‘s freestyle cruising might be for you. The demographic tends to be a little younger, and dining is buffet-style for the most part except for several specialty restaurants you can try for a surcharge.

Is an elegant, old-world charm more your thing? Holland America specializes in classic ships, with well-appointed dining rooms and a more formal veneer. The demographic tends toward older generations — on our Greece cruise, David and I were probably among 5% of guests under 30.

Cruising shouldn’t mean lazing about, you say? Try Royal Caribbean then. All their ships have a rock wall on board, and they target a more active crowd. At least, that’s what they say — we’ve been looking for an opportunity to try them out!

And if you’re more high-class than any of these, well, cheers to you! Luxury lines, as they’re called, cater to a clientele with more expectations and more to spend. Nearly everything on board is free (yes, that includes alcohol) and the service is supposedly impeccable, but you do have to pay for it up front. Some of these lines are Silversea, Regent Seven Seas, and Azamara.

Got kids (that are coming with you)? This one’s a no-brainer, go for Disney. Unless you have a low tolerance for Disney, anyway.


Our last cruise was based on price, schedule and itinerary: I’ve been wanting to go to Greece forever, and I needed to go in early September. Holland America had a cruise at just the right time, for a reasonable price. So we booked it!

Now the hard part: packing! 🙂

Over the next month, I’ll be telling you all about the ports we visited and the amazing things we saw, did, and ate. Stay tuned! For a sneak preview, check out my Mid-travel Report.

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2 thoughts on “How to Plan Your Cruise

  1. Pingback: How to Prepare for Your Cruise | World and Time Enough

  2. Pingback: Life on a Cruise Ship | World and Time Enough

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