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Sailing The Caribbean, Which Caribbean Itinerary Is Best For You?

Updated: Nov 12, 2022

Heading to the Caribbean can mean different things to different people.

You could be sailing on a megaship, exploring the jungles, or lounging at the beach bar - but either way, you are experiencing the Caribbean they way YOU want to experience it.

One of the most popular ways to visit the Caribbean is through cruising, and choosing the right cruise line is a task in itself - but for us, it's primarily about the destinations itself. That's why choosing the right Caribbean itinerary for you is our crucial first step to planning the perfect cruise vacation.

Sailing the Western Caribbean

Sailing the Western Caribbean is basically Cruising 101 for most people. It has a good balance of port days and sea days, typically departs easily from a Florida or even central coastal port (think Maryland or South Carolina but they are rare departures), and more often then not price better for first timers just testing the waters with cruising. Itineraries almost always include a port in Mexico, a port in Jamaica, and a port in the Bahamas, which is usually the cruise lines private island. I'll admit - when I can't get my hands on a Southern Caribbean sailing, Western is where I turn. This is mainly because I look for things like ziplining, ATV's, hiking and other adventurous land activities for my excursions. I also have visited these islands so many times that I am comfortable going off the beaten path and doing the more cultural adventures without the help of the cruise line. So while the Western Caribbean is perfect for both the Adventurous Traveler and the Cruising First Timer - we suggest you talk it all over with a specialist to ensure you are getting a good balance of newbie and adventurous experiences in a safe and manageable way.

Mexico Quintana Roo Yucatan Mayan Ruins

Sailing the Eastern Caribbean

Sailing the Eastern Caribbean is perfect for both the entry level cruiser and the experienced cruiser, if you are looking for something that provides primarily water based excursion options. Typically when you sail the Eastern Caribbean you are heading to islands like St Thomas, St Kitts, The Virgin Islands and almost always at least one Bahamas stop. These islands are most well known for water lovers and beach goers - which is really the only reason this itinerary comes in third place for me. This is the perfect itinerary for someone who loves fishing, boat tours, snorkeling, or just relaxing on a pristine beach. A major upside in my book is that these islands also typically are well known for architecture and food connoisseurs. First time sailors, as well as those looking for more water then land adventures, are the perfect fit for the Eastern Caribbean.

St Kitts

Sailing the Southern Caribbean

Sailing the Southern Caribbean can sometimes require a longer itinerary, and sometimes require going out of a non continental port such as San Juan. So we usually suggest this for the experienced cruiser. That being said though, there is almost always a 'something for everyone' vibe on these itineraries. Southern itineraries typically include Aruba, Bonaire and Curacao (The ABC Islands), St Lucia, Barbados and Grenada. They also often can be combined with some of the Western and Eastern Islands to make for a much longer extended vacation. But regardless of the island options, the Southern Caribbean has a few things to their advantage. My personal favorite is that they tend to have more immersive cultural offerings then some of the other islands. But this isn't due to the lack of interesting cultures, it's mainly due to the fact that the other ports are so heavily cruised that they have often become a bit more commercialized then those in the southern islands. You also have a really good balance of water and land adventure options as well as some more laid back beach options. That alone makes the Southern Caribbean perfect for the Immersive Traveler and those families that simply can't agree on what to do!

St Lucia, Pitons


No matter what you pick in the Caribbean, you're sure to have a major dose of sun, relaxation, excitement and joy. But it's important to know, just how vastly different these itineraries truly can be. Even once you nail down western vs eastern vs southern - taking into consideration the different ports on each island, the different access and hours of each cruise line, and the multiple partnerships with excursion companies can sometimes be overwhelming, even for the most experienced cruisers. That's why we always suggest you book a consult with one of our specialists and make sure we have you sailing in the right direction!

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