Caribbean Cruise Itineraries

In the language of yachting, the southern Caribbean is called the Windward Islands and the northern Caribbean is described as the Leeward Islands. Both are popular charter destinations, but the Leewards tend to have more boats available.

The Leewards comprise about 120 miles’ worth of individual islands from Anguilla in the north to Dominica in the south. The Leewards are not as big a bareboating destination as the Virgin Islands to their north, but they are the home of St. Maarten, a hub for power-driven megayachts, and of Antigua, a home base for many fully crewed sailing yachts.

If you want to charter a fully or partially crewed yacht during the winter months, the Leewards usually offer you the most choices.

In fact, each December there are industry-only charter yacht shows held on St. Maarten and Antigua. Charter brokers tour dozens upon dozens of yachts to see what kind of shape they’re in, which crew members have come and gone, and other details that they can later use to help you book the right boat for your needs.

Because many yachts attend these boat shows and then stay in their slips at the marinas after the boat shows end, St. Maarten and Antigua are often recommended as beginning and/or ending points for charter vacations.

What might a Caribbean cruise itinerary look like during a week onboard a charter yacht? It will vary from yacht to yacht—depending on what you, your charter broker, and your yacht captain decide you want to do given the local weather and your personal desires.

With that in mind, though, here’s one option for which islands you might cruise to visit on each day of a weeklong Caribbean vacation. Don’t be surprised if you see the names of islands you’ve never heard of before; most charter yachts are small enough to get into places that the bigger cruise ships have to pass by.

Day One: Antigua and Barbuda. 
Day Two: Barbuda to Nevis
Day Three: Nevis to St. Kitts
Day Four: St. Kitts to St. Barts
Day Five: St. Barts to Ile Fourche
Day Six: Ile Fourche to Tintamarre
Day Seven: Tintamarre to Anguilla
Day Eight: Anguilla to St. Maarten.

For a look at additional Caribbean cruise itineraries (including round-trip options), along with charter yacht itineraries in other parts of the world, you can read Have the Whole Boat: The Insider’s Guide to Private Yacht Charter Vacations, from which this information is adapted.