The Caribbean is one of the finest and most popular charter destinations in the world. The Caribbean Sea is bounded by the northern coast of South America, the east coast of Central America, the large islands of Cuba, Haiti, the Dominican Republic and Puerto Rico, and a beautiful ring of islands to the east known as the Windward and Leeward islands.
The Caribbean offers a huge variety of charter destinations, all offering a relaxed winter getaway. The best time of year for yacht chartering in the Caribbean is from November to April.
Chartering in the Caribbean evokes images of gentle breezes, palm trees, white sandy beaches and amazing marine life. Short 'hops' from one to the next of the more than 7000 islands in this area make it ideal for chartering. Due to the easy navigation and regular breezes, the Virgin Islands—divided between the U.S. Virgin Islands and the British Virgin Islands—feature the largest bareboat charter fleets in the world. The French islands of Guadeloupe and Martinique, plus the French portion of St. Martin/Sint Maarten, host fleets nearly as large. And islands such as St. Barths bring in the jet set from all over the world.
Chartering in the Caribbean evokes images of gentle breezes, palm trees, white sandy beaches and amazing marine life. Short 'hops' from one to the next of the more than 7000 islands in this area make it ideal for chartering. Due to the easy navigation and regular breezes, the Virgin Islands—divided between the U.S. Virgin Islands and the British Virgin Islands—feature the largest bareboat charter fleets in the world.
Antigua is a great place to begin a charter because the island itself offers quite a bit to see and do. The hub of yachting activity is in the southeast, where Falmouth Harbour, English Harbour, and Nelson’s Dockyard are within easy walking distance of one another. All three locations have marinas where charter yachts are based and where guests can find historic museums, local shops, dance clubs, gourmet restaurants, and crew bars. Walking through Nelson’s Dockyard is like walking through history, with centuries-old buildings like the Admiral’s Inn, which was once home to Royal Navy legend Horatio Nelson himself. This part of Antigua is also home to Shirley Heights, which offers exceptional views of the surrounding sea as well as a steel-drum-and-rum-punch dance party every Sunday night at sundown.
While not part of the Caribbean geographically, the Bahamas provide the same laid-back island charter experience. 132 companies offering charters in the Bahamas, and many of the islands are within a couple hundred miles of the Florida coast, so it’s an easy destination to get to by air from the US.
Barbados has a beach for every day of the year, abundant bays, and dramatic sandstone cliffs. Thanks to the mild, subtropical weather, Barbados abounds with an astonishing assortment of plant life.
Guadeloupe is actually two islands connected by a drawbridge. A large international airport and several bareboat fleets make it an excellent place to start your charter adventure.
Martinique mixes haut cuisine and the latest fashions with one of the largest bareboat charter fleets in the Caribbean. Fort-de-France, the island’s capital, is located on one of the safest, most beautiful bays in the region.
Puerto Rico has several marinas within walking distance of Old San Juan. Several international fishing tournaments are held here each year, and a large fleet of local sportfishing yachts is available for charter.
Saint Lucia is a great charter destination for nature enthusiasts and also has a well-protected harbor. The gem-like Marigot Bay, located on the west coast, is a natural hurricane hole where the British fleet hid from the French back in the 18th century. Today, it is home to a modern megayacht marina.
St. Barths offers a different type of experience—one that combines a fun Caribbean scene with the fineries of civilization. Most charter yachts make Gustavia Harbour their home base for two or three days, using it as a nighttime anchorage within easy cruising distance of various beaches and sailing stretches around the island. This is where kite surfing, paddle boarding, and all the latest water sports are on display. Charter yacht guests often swim and snorkel right from their own swim platforms, using the yacht’s tenders and other toys for water skiing, wake boarding, and the like.
On Sint Maarten, itineraries can include an array of different experiences. The island is divided in half—Sint Maarten is the Dutch side, while St. Martin is the French side—and the cultures on either side blend Caribbean history with the European nation of choice. Many of the megayacht marinas are on the Dutch side, while most of the gourmet restaurants are on the French side (along with the nude beaches).
Read more about Northern Caribbean Yacht Charter
One of the reasons why chartering in the Caribbean is so popular is the weather, especially in winter, when sailors from northern climes delight in the balmy breezes and warm temperatures. The (mostly) reliable trade winds blow between 15 and 25 knots from the northeast, and a steady temperature in the low to mid 80s provide great sailing and comfortable nights.
The trade winds originate off the coast of Africa, and have been known to carry dust from the Sahara desert all the way across the southern North Atlantic to the Caribbean Islands. They have a huge impact on the Caribbean Islands from Hispaniola all the way down to the ABC’s (Aruba, Bonaire, and Curacao), and their influence affects different parts of the Caribbean in different ways. Because they are further south, the Windward Islands (Dominica, Grenada, Martinique, and St. Vincent and The Grenadines) see milder temperatures during winter than the Leeward Islands (Antigua and Barbuda, Anguilla, the British Virgin Islands and U.S. Virgin Islands, Guadeloupe, Montserrat, Nevis, Saba, Sint Maarten/St. Martin, St. Kitts and Nevis). The Windwards also have a more reliable breeze.
With their more northerly location, the Leeward Islands are more influenced by fronts drifting down from the mainland U.S., and can be slightly cooler and less windy, especially in the winter months. Because the trades are so reliable other effects can be noted as well. On mountainous islands the warm air is shunted up into cooler air, which produces rain. On islands such as Dominica, Nevis, and St. Lucia rain forests can be found, especially on their windward sides.
One drawback to chartering in winter can be the sheer number of fellow charterers who have all decided the same thing; that two weeks in the BVI in January is far better than two weeks in Chicago. Prices are higher, reservations are more difficult to get, and popular destinations are overcrowded.
Is there another time of year when the Caribbean is less crowded, less expensive, but still delightful? The simple answer is yes, and that time is in the summer, though you need to plan carefully so you don’t end up hunkered down in a hotel room watching palm trees get blown down and praying the power stays on as a hurricane roars overhead.
The two main worries of off-season in the Caribbean are hurricanes and the rainy season. Hurricane season runs from June 1 to November 30, with the most active period running from mid August through the end of October. From May to July and October through December, the odds are definitely with you.
The hurricane probability table shown at left reveals the odds for individual islands. The best odds for a major hurricane strike in any given year in the Caribbean belongs to Antigua, which has a 6.7-percent chance. The lowest is Bonaire, with a 0.6-percent chance. Puerto Rico rings in at 4.2-percent, with the USVI scoring a 5.9-percent. In contrast, Miami scores an impressive 11.1-percent, and Cape Hatteras checks in with a 5.3-percent. See the rest of the list of hurricane probabilities for the continental USA.
Another way to virtually assure that hurricanes won’t mess with your charter, even at the height of the season, is to head “down island,” to islands such as Aruba, Curacao, Trinidad and Tobago, Grenada and Barbados. Those lucky few who live on boats in the Caribbean year round often head to those islands in hurricane season for that very reason.
The rainiest months of the year are May to June and September to October, but again, location is everything. The ocean temperature is cooler in the southern parts of the Caribbean due to upwelling (in which cold water rises to the surface as the wind pushes the warmer water south and west) and this helps prevent cloud formation, which means less rain and less likelihood of hurricane activity. The Caribbean islands which most benefit from this are Aruba, Bonaire, and Curacao.
A common misconception is the summer temperatures, which one would imagine would be much hotter than those in winter. But thankfully that’s not the case, and that, again, is due to those oh-so-helpful trade winds. The average temperature in Antigua in January is 83 degrees, but in August it’s only 88. The chance of seeing 100-degree temperatures is far more likely in the mainland U.S. than it is in the Caribbean, where such temperatures are mostly unheard of.
I’ve successfully delivered boats across the Caribbean Basin from Florida to Panama in August, from Tortola to New England in September, and from Sint Maarten to Panama in June, all safely and without worries, thanks to good forecasting and a firm grasp of the odds.
For more information about the Caribbean, or to find a yacht to charter, visit the YachtWorldCharters.com Caribbean page.
Tortola - Peter Island - Virgin Gorda - Jost Van Dyke - Norman Island
Sail from Road Town or Nanny Cay south across Sir Frances Drake Channel to Peter Island, a good overnight anchorage.
Depart early for the Baths, the site of an unusual rock formation at the southwestern end of Virgin Gorda.
Enjoy a few hours of snorkeling and exploring. Since the moorings and anchorage at The Baths are subject to an uncomfortable groundswell, enjoy a short sail across the channel to Marina Cay for the night.
A longer sail will take you up to the northeastern end of Virgin Gorda into the well-protected Gorda Sound. Enjoy the hospitality at The Bitter End, which is wonderfully welcoming to cruisers with four restaurants and a handful of bars.
Another long sail west along the north side of Tortola will take you to Jost Van Dyke, an area where you could easily spend a day or two exploring places like Sandy Cay.
Take some time to re-provision and check in with reality at West End (Sopher’s Hole) Tortola, where the WiFi is available for a fee and covers most of the anchorage.
A trip over to Norman Island will introduce you to the lure of that floating bacchanalia known as Willie T’s, a floating bar and restaurant located conveniently in the mooring field.
Photo courtesy Bitter End Yacht Club
St. Thomas - St. John - Tortola - Virgin Gorda - Cooper Island - Salt Island - Norman Island
Depart Compass Point Marina, St Thomas, cruise to Leinster Bay, on the north side of St John. Snorkel at Water Lemon Cay. Overnight anchorage.
Soper's Hole, West End, Tortola. Clear customs and visit the shops and restaurants. Spend the afternoon snorkelling and exploring Sandy Cay. Overnight at Little Harbour, Jost Van Dyke or Cane Garden Bay, Tortola.
Cruise up to Monkey Point at Guana Island for spectacular snorkelling. Overnight at Trellis Bay or Marina Cay.
Snorkel the Dogs and overnight at Virgin Gorda.
Enjoy the magnificent boulders at the Baths and continue on to overnight at beautiful Cooper Island.
Explore the Wreck of the Rhone at Salt Island before heading to Norman Island to overnight at the Bight. Snorkel the Caves for a breathtaking view of colourful Caribbean fish.
Cruise to St John. While anchored at Caneel Bay, head into Cruz Bay to clear customs and visit the village. Overnight at Hawksnest Bay before returning to St Thomas the next day.
Read Chris Caswell's story on a Virgin Islands powerboat bareboat charter.
The best way to explore St. Vincent and the Grenadines is by traveling one-way. The archipelago is like a string of pearls come undone and scattered in a line. Winds are often from northeast to southeast at 10 to 25 knots, with sailing more challenging in the winter months compared to summer. During hurricane season, the Grenadines are usually one of the safest locations in the Caribbean, which means the cruising can be terrific here all year round.
A smart starting waypoint is Kingstown, in the south of St. Vincent, because it is both close to an international airport and well-positioned for raising anchor and heading south to the rest of the Grenadines. Kingstown itself is a busy urban area that offers plenty of provisions and supplies at the start of a cruise. With a one-way itinerary, a one week charter can start in Kingstown, meander through the Grenadines, and end in Grenada, where there is also an international airport.
Bequia is the first stop along this north-to-south route, and a lovely stop at that. The island is far less populated than St. Vincent, and the waterfront area is also more welcoming for cruisers. Boutiques and cafés line the beachfront at the main harbor, which also includes a concrete walking path with gorgeous views of all the boats at anchor.
The next of the larger islands is Mustique, which, on approach, appears to offer far less civilization than Bequia. Don’t be fooled; the development on Mustique is simply more exclusive and spread out. The waterfront area at the main harbor includes only a couple of boutiques, eateries, and a small fresh-fruit stand, but the island itself is filled with villas and mansions that lure the rich and famous. A small airstrip offering local flights is inland for private planes. Also just inland, within walking distance of the harbor if you don’t mind an uphill hike, is a cocktail bar called The Firefly that offers the absolute best views of the boats at anchor.
Continuing south from Mustique, you can stop to play on the beaches at Petit Mustique and Sevan Island, or make way a bit farther for Canouan. It is home to two major resorts with luxury golf courses, along with an airstrip for local flights. The Moorings has its Grenadines base at Canouan if you are interested in bareboating.
South of Canouan is perhaps the prettiest part of the Grenadines: The Tobago Cays. Its five uninhabited islands are part of a national park and wildlife preserve that includes beautiful reefs for snorkeling and scuba diving, clean waters for swimming, and even a few bays that are frequented by large sea turtles. Day charters do visit here from nearby island hotels, but if you anchor for a day or two, you can quietly enjoy all that the area offers during the morning and early-evening hours. At sunset, barbecues take place on Petit Bateau. The butter-coated lobster is fantastic when enjoyed at picnic tables on the beach overlooking the harbor filled with boats.
The next major stop to the south is Union Island, which offers a local airport as well as some waterfront eateries and restaurants. Union Island is less affluent than Bequia or Mustique, so expect a more authentic day-to-day Caribbean ambience.
Should your travel schedule allow, you can cruise beyond Union Island to Palm Island or Petit St. Vincent, both of which offer lovely beaches for relaxing. Just beyond them, over the Grenadines border, is Grenada. It boasts a megayacht marina along with an international airport for flights to the United States, Europe, and beyond.