One of my travel dreams is coming true! My husband and I are going on a Southern Caribbean cruise. That’s right; we are trading increasingly cold New England for sugar sand beaches and snorkeling.

For me, part of the joy I will get out of the vacation will be seeing all my research come to fruition. As this is a first cruise for both of us, I did an immense amount of research to try to figure out the ideal cruise for us. There’s just so much to consider! Prices, destinations, cruise lines, times of years, etc. Thinking about a cruise for yourself? I’ve done my best to outline factors that will help you determine which cruise is right for you.

Bear in mind that these factors are not in any particular order. It’s up to you to determine which is most important and then go from there.


Once you decide you’re going on a cruise, the inevitable question that others will ask is: Where are you going? As the cruise industry is rapidly expanding, you can go almost anywhere on a ship. You can go to standard places like the Caribbean or Mediterranean, more unconventional destinations like Asia or Africa, take a river cruise through Europe, or even go nowhere (just spend a few days floating out at sea).

Where you go is all about personal preference. Want an experience steeped in fine art and cuisine? Try a cruise that stops in Italy and Greece. Have a desire to get in touch with your inner beach bum? Make sure to find a cruise that stops at as many beaches as possible.  As you search, just keep in mind that parenthesis matter. What do I mean? Well, at first glance, you may think your cruise makes port in Rome. Your head immediately fills with visions of the Coliseum, Pantheon, and Trevi Fountain. However, you’ll soon see that Rome is in parenthesis and you’re actually stopping at Civitavecchia, a town roughly 50 miles away from Rome. Sure, it’s only an hour away, but it means you’ll probably need to take a shore excursion to get into the city or do some advanced planning to get there on your own. Do your research. Make sure you’re stopping where you think you’re stopping.

You may also want to think about how many different stops you want to make. Some cruises will stop at a different port each night while others will dock in one spot and stay for several nights.


Wherever you end up going, you need to consider that each region has a high season and a low season. Prices are at a low for the Western Caribbean in September, but that’s partly because you’re going to be there smack dab in the middle of hurricane season.  There are pluses and minuses to each region’s high or low season. In general just know that high season is more crowded and expensive while low season tends to have iffier weather but great bargains. Here’s a quick summary:


  • High Season: June-August. Temperatures are warm and you’re more likely to see wildlife, but the demand is higher so crowds are bigger.
  • Low Season: May & September. The possibility of snow (read: higher chance of a cancelled excursion) means fewer people and lower prices.


  • High Season: June-August. A wide selection of ships and departure ports, plus families get to take advantage of summer vacation. As a result, the ships are more crowded.
  • Low Season: April/May & September/October. The weather is mild and wonderful… unless there’s a hurricane.


  • High Season: June-August, the winter holidays, February-April. Convenient times since school is out of session and you have the chance to escape winter. The result is crowded ships and lots of families and children. However, there’s a high price to pay when trading snow for sunshine.
  • Low Season: April/May & September-January (excluding holidays). Great weather and smaller crowds, but it’s also hurricane season. Most ships will simply go to a different port to avoid bad weather, so if you have your heart set on a given port, you may be disappointed. Also, bad weather may make it challenging to get to your point of departure.


  • High Season: May-August. European and American families alike use summer vacation as an enriching experience for themselves. However, the temperatures are high and the crowds are big. Beware: Some parts of Europe are in high season all year round.
  • Low Season: March/April, September-November. Milder weather, fewer kids, great bargains. However, not all cruise lines have a low season.

(to be continued in Part 2 and Part 3