Caribbean Itineraries

Clients often ask us about itineraries in the Caribbean. The area itself extends 2,000 miles from the Bahamas to Trinidad. Here is the best way to think about this group of islands:  similarly to the GREEK ISLANDS they are best addressed by dividing them into GROUPS.

The Virgin Islands Group.  This group comprises the British Virgin Islands (BVI), the US Virgin Islands (USVI) and the so called Spanish Virgin Islands.  The most popular islands in the BVI sub-group are Tortola, Virgin Gorda, Anegada, Jost van Dyke and other smaller islands like Peter, Norman, Cooper, salt and others. The BVI is a sailor’s paradise and very nice to cruise in all kinds of weather, all year round. You can always find a neat little bay or cove or anchorage where you can have a great vacation no matter where the wind is coming from.  See the CYBA itinerary at .

The US Virgin Islands sub-group comprises St. Thomas, St. Croix and our favorite, St. John which has amazing beaches and bays and great anchorages. 2/3 of St. John is a national park and is administered by the National Park Service of the United States.  Both the BVI islands and the USVI islands of St. John and St. Thomas can be visited in a one week trip.  They are never boring, always welcoming and almost always safe. St. Croix is too far away to include it in a typical charter itinerary; the crossing from St Thomas to St. Croix can also be quite choppy.

The Spanish Virgin Islands are best accessed from Fajardo, or Marina del Rey, Puerto Rico but can also be reached from St. Thomas. This sub-group is Spanish speaking and includes Vieques, Culebra, Icacos, and Luis Pena.  

The BVI and USVI which together constitute one of the most popular cruising destinations in the world are excellent for a one week vacation on a motor yacht or sailing vessel.  Plan to fly into St. Thomas which has a major international airport (STT).

It’s a full day’s sail or a sometimes choppy overnight trip from the BVI to St. Martin especially if you are travelling east into the wind. The reverse is easier but either way you lose two charter days.

The Leeward Islands. To visit and develop an itinerary in the Leeward’s, it’s always best to fly into St. Martin (Sint Maarten) that has a major international airport. Typical itineraries in the Leeward’s include St. Martin (where both French and Dutch are spoken), Anguilla, St. Bart and St. Kitts – Nevis.  See the CYBA itinerary as follows . Antigua, Barbuda and Montserrat are a little out of the way for a one week sailing vacation but can be reached easily on a motor yacht. The Leeward’s can be choppy in winter because of the large swells that can come in from the Atlantic. The Leeward’s are best in late spring, summer and autumn.

The Leeward Islands stretch further South to Guadeloupe, Marie Galante, Dominica and Martinique.  Guadeloupe and Martinique are French speaking ( as “Departments” they are actually an integral part of France), Dominica is English speaking and very agricultural.

The Windward Islands.  This group of islands starts in St. Lucia (which has an excellent international airport) and runs all the way down to Grenada (also with a good airport). The prevailing wind is from the NE so it’s always better to organize your charter on a one-way basis starting from St. Lucia and ending in Grenada. The Windward’s include the Islands of St. Vincent, Bequia, Mustique, Canouan, Mayreau, Union and Carriacou ending in Grenada.  See the CYBA itinerary for the Grenadines at .  This itinerary actually shows a start in St. Vincent, however, we always advise our clients to start in St. Lucia where there is an excellent airport, so you need to add a day or so to this itinerary for a sailing yacht.

The Grenadines are great cruising grounds that are better, again, in late spring, summer and autumn when they are less exposed to the Atlantic swells while crossing between islands as you progress southwards.  Having said this, the area is famous for its autochthonous culture, great food and unique marine wildlife.  Do not attempt to include Barbados in this group, it is too far away.

Puerto Rico and the Dominican Republic.  Highly populated and not recommended for charters due to rough seas and relative lack of nice coves and beaches to hang out. Both these locations are great for self-contained resort vacations but not for chartering. Exception: the Eastern end of Puerto Rico from where you can visit the Spanish Virgin Islands of Vieques, Culebra, etc. as previously mentioned.

Cuba.  Is great for bareboating on its Southern Coast and there are several European Bareboat companies that have bases in Cayo Largo, Cienfuegos and Trinidad. US visitors have visa restrictions.  There are few professional crewed yachts in operation in this area although we have knowledge of yachts traveling down from the Bahamas Out Islands very successfully. Conditions are very primitive but the locals are delightful, friendly and will go out of their way to help foreigners.

Belize. Is primarily a diving paradise and there are several crewed yachts and bareboat companies available that specialize in SCUBA.  The waters and the country of Belize are pretty safe but do not attempt to use Belize as a jumping-off point for other Central American countries since the area S of Belize is dangerous and rife with drug-runners and pirates.

The Bahamas. This marvelous group of flat coral islands is not in the Caribbean proper since it is not actually in the tropics and is quite cold in winter.  Nevertheless it is an excellent cruising ground in late spring, summer and autumn.  The Bahamas is a huge expanse of water with over 700 islands.  There are specific self-contained areas that are good for cruising, The Abacos, the Exumas and the Out-Islands. Each has its charm but because of the huge distances involved, do not try to do more than one group at a time. Choose the area you’d like to explore and go for it. There is a CYBA itinerary here at  . This itinerary starts and ends in Nassau and includes parts of the Exumas and parts of the Out-Islands. It is a very nice motor yacht itinerary.  Do not attempt to explore the Abacos or the Sea of Abaco  in a motor yacht, it’s too shallow.  It is NOT possible to cross from the mainland to the Bahamas for a week’s vacation: too far and too much sailing time.  In 10 or 12 days and in good weather you can successfully get to the Berry Islands and back to Miami, this is a nice vacation.

In summary, the Caribbean is composed of many islands, island groups, cultures and languages. Do not over-extend yourself or you’ll spend too much time sailing and not enough time exploring and having fun. 

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