The first step to taking a cruise is, well, booking one! And this by itself can be wildly overwhelming since there are so many options. The first thing is to challenge yourself to answer these questions:

The Big Three

• What is your preferred itinerary? For first-timers, I recommend a Caribbean sailing, as they’re generally more affordable with shorter sailings, and the options are abundant. I recommend using an aggregator like Cruise Direct to assist with your search because it will allow you to see all options and filter down.
• What is your preferred length of sailing? If you’ve never cruised, I recommend a shorter sailing of 3-5 nights. Because as much as I personally love cruising, I acknowledge that it’s not for everyone. And nothing would be worse than figuring out you hate cruising then being stuck on a cruise for a week or longer. Anything less than 3 nights, however, isn’t giving it a fair shot.
• What’s your preferred departure port? Once you have determined your itinerary and sailing length, you can start to narrow it down a bit. The next step is to decide where you want to sail. Port Miami, Port Everglades, and Port Canaveral are the big boys for Caribbean offerings. Depending on where you live, some ports may be more accessible than others.

Narrowing it Down

• What are your available sailing dates? Now that you’ve answered the first big three questions, you’re really cooking. From there, you can narrow your search based on your dates. Using an aggregator like Cruise Direct is a fantastic option to see all of your options and continue refining from there. As for “when’s the best time to cruise”, I believe there’s no bad time to cruise. I hate the advice of “avoid hurricane season” because that spans nearly half the year. And sailing in the off-season can yield significant savings.
• What’s your budget? Now that Cruise Direct has populated a list of options based on your itinerary, length of sailing, and potential departure ports, you can eliminate options outside your price range. MSC and Carnival are often the most affordable, and Disney is the most expensive.
• What’s your vibe? Once you’ve eliminated options not in your price range, you should decide your preferred vibe. Carnival and Royal Caribbean are excellent choices if you want fun and family-friendly. Holland, Princess, and Norwegian are good bets for a quieter, older crowd. If you want the “Disney experience,” obviously go with Disney. MSC is usually the cheapest option, and it provides more of a chill, European vibe.

Fine-Tuning Your Pick

• Where do you want to go? The first thing you determined if your preferred itinerary, but now is the time to fine-tune because, for example, “Carribean” is vast and can include dozens of port options. At this stage, you want to start looking at specific ports of call for your potential itineraries. To get the most bang for your buck, prioritize those that have more ports of call (this means stops at ports) versus sea days (meaning days you are on the ship and do not get off or on). In my opinion, there are no “bad” ports, but some are generally considered more desirable than others. Check out my posts on ports to explore the options and learn more about each.
• What class of ship do you prefer? My first few sailings, it never crossed my mind to think about this, as I mistakenly thought all cruise ships were pretty much the same. In fact, there can be a vast difference in experience based on the class of ship. With Carnival, for example, the cheapest fares are usually with their “Fantasy Class” (i.e., smaller, older ships) versus their “Excel Class” (i.e., newer, bigger, fancier ships like Jubilee, Mardi Gras, and Celebration). As you refine your search, consider the ship itself as part of your decision-making process.