Last updated: 09:00 AM ET, Tue October 18 2016

Cruising 101: Picking Your Ocean Cruise Itinerary

Cruise Line & Cruise Ship Disney Cruise Line Jason Leppert October 18, 2016

Cruising 101: Picking Your Ocean Cruise Itinerary

In our Cruising 101 series, you’ve selected an ocean cruise line and cruise ship, as well as a destination, but which exact itinerary will you embark on? The Caribbean alone offers a cornucopia of choices, so let's dive right in and take a look at the options.


Expanding upon the Caribbean example, there are Western, Eastern and Southern (also known as deep) Caribbean routes to choose from and each are different with occasional overlapping ports of call. An Eastern one visits islands exclusively, but a Western one can take you to the Yucatan Peninsula mainland of Mexico. Meanwhile, Southern Caribbean itineraries can include the likes of Aruba. Elsewhere in the world, other large destinations are divided into separate regions as well.

READ MORE: Cruising 101: Choosing an Ocean Cruise Line


The exact region and itinerary you choose is largely determined by where it is you want to sail from. If you prefer to homeport from Floridian embarkation cities of Ft. Lauderdale or Miami, for instance, your choices, at least for a weeklong cruise, are going to be limited to more northerly routes. If, however, you’re willing to fly to San Juan, Puerto Rico, a roundtrip Southern itinerary is not out of the question. 


Itineraries are roundtrip or one-way, and each has its benefits. Roundtrips are more convenient, especially from and to local homeports, but one-way cruises may see a more interesting selection of ports along the way. In Alaska, leaving from Vancouver with a return to the Canadian city will take you to places like Juneau, Ketchikan and Skagway, but a northbound version may end in and also feature Seward or others and vice versa.


The duration of your cruise will also dictate an itinerary, the shortest of which are usually three days. These usually leave from a homeport like Los Angeles, California to head for places such as the Mexican Riviera with a singular stop at Ensenada, whereas longer ones may include Catalina Island as well as combinations of Cabo San Lucas, Puerto Vallarta and Mazatlan, Mexico. Of course, those longer than a week will provide even more options.

READ MORE: Cruising 101: Deciding on an Ocean Cruise Destination


If you have the time, some cruise ships alternate itineraries week after week, so you could stay onboard, say, Disney Cruise Line’s Disney Fantasy for two weeks and see both the Western and Eastern Caribbean. Or you could embark on Holland America Line from San Diego and visit the Mexican Riviera and the Hawaiian islands on a 21-day total sailing.


If Europe is more your speed, you’ll almost always have to leave to and from a foreign port unless it’s a repositioning cruise. These are the ones that transition ships between seasonal destinations like Alaska to the Caribbean or the Caribbean to Europe. So, a departure from New York, for example, could take you across the Atlantic Ocean to the Baltic or Mediterranean. Another fringe benefit of repositionings are canal transits, particularly the Panama Canal (pictured above) between the Caribbean Sea and Pacific Ocean, which provide fascinating looks at engineering marvels.