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Old 11-03-2002
John Kretschmer John Kretschmer is offline
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The Annual Tropical Bash;
Thoughts on Sailing to the Caribbean


The month-long period between October 20 and November 20 is the favored window for embarking on a trip to the Caribbean from the East Coast.

Sailors all along the east coast are starting to stir. It's that time of year. Hurricane season is waning, it's getting dark too early and visions of sunnier climes are waxing. If you're headed south it's time to get moving, because cold fronts are becoming much too frequent. Many sailors have been planning for this moment for years, preparing their boats and themselves for an escape to the tropics. Is this the year that you make the plunge and push off for the islands?

The only thing separating your boat from a long winter on the hard or at the dock and a mooring in the British Virgin Islands is 1,000 - 1,500 miles of Atlantic Ocean. That's all. Do the math. If you average 150 miles a day, you're ten days or less away from paradise. Even if you plod along at 120 miles a day, a mere 5 knots, you're about 12 days away from admiring your boat's sweet sheer line from the perspective of a beachfront tiki bar. Anyone can endure twelve days at sea, right? Okay, I know, I am beginning to sound like a yacht broker. Sorry, let's step back from the sizzle and take a look at the steak — what is really involved with sailing from the US east coast to the Caribbean.

Bill Stone, author of the classic but now out of print, A Cruising Guide to the Caribbean, issues this warning in the book's introduction. “It is not a simple matter to select the right route at the right time for a small boat passage to the Caribbean in the often unpredictable North Atlantic. Those who embark casually with dreams of sailing off into the sunrise are due for a rude awakening unless they have diligently studied their pilot charts and alternative routes.” Although many cruisers have traded their pilot charts for sophisticated weather routing services, Stone's message still rings true. The passage south and east to the islands is never easy. More often than not it is a bash, and we're not talking about a party with steel bands and rum punch, we're talking about slugging it out against the prevailing winds and currents day after day.

Most delivery skippers know this route only too well. It's our version of a waterfront office. For every delivery back from the islands, there are five available heading toward them. I have sailed between the east coast, be it New England, New York, the Chesapeake Bay, Moorhead City or Ft. Lauderdale, and the Caribbean Islands dozens of times. Although I am usually wary of espousing axioms in Neptune's domain, geography and weather dictate some obvious routing decisions.


Windward sailing dominates in most routes to the Caribbean, especially those starting from Charleston, SC and points south.

From anywhere along the coast, the best time to depart is between October 20 and November 20. This is usually a benign period between the end of hurricane season and the onset of winter storms. The key word being usually. If you sail the direct offshore route, wait for a favorable weather window and make sure there aren't any late season tropical low-pressure systems brewing. Generally speaking, the further north your departure point, the less windward sailing is required. The east coast bends east as you make your way north, making the route to the islands more southerly. Also, a New England departure makes Bermuda a viable and logical waypoint, breaking the route into two shorter legs.

Fortunately winds from the southern quadrant are not all than common in the fall. If you time your departure with passing of a cold front you can usually ride a west, or northwest, wind offshore. The easterlies usually kick in just south of the 30th parallel (again note the key word usually). Coastal geography can be misleading. Newport, RI is approximately 400 miles east of the Virgin Islands, while Charleston, SC is more than 800. If you shove off from Newport, by the time you pick up the prevailing easterlies you should be able to reach or close reach down to the islands. Of course, the further north your departure point the greater the likelihood for encountering bitter cold weather and an ugly nor'easter. However, by departing from Charleston or points further south, the odds of beating your way to the islands are much greater.

Steve Black, the founder of the popular West Marine Caribbean 1500 Cruising Rally, has chosen the mouth of the Chesapeake Bay as the ideal departure point for a passage to the Caribbean. I tend to agree with him. This route usually avoids biting north winds that can strike New England in the late fall and gives you a day to find your sea legs before the dreaded encounter with the Gulf Stream. Although the start of the rally is north of Cape Hatteras, prevailing westerly winds near the coast often help you get well offshore, diminishing the impact of the unpredictable weather that haunts this infamous headland. With a bit of luck, you can get your easting in early and have a fast point of sail once the easterlies are encountered.

Black doesn't downplay the serious nature of the passage. “Every year we have some excitement.” he said, “Preparation is the key.  You and your boat have to be ready for extreme weather.” This is the 12th running of the rally and more than 600 boats have participated. This year's event departed November 3 with fifty-one boats, ranging in size from 38' to 62', crossing the starting line.

"Offshore sailing requires a certain verve, certainly not arrogance or hubris for nobody spots false pride faster than old Neptune..."

Circumnavigator and author Jimmy Cornell makes two important points in his best selling book, World Cruising Routes, when discussing the best route from the US east coast to the Caribbean. “The route has a lot of alternatives, which depend on the type of boat and experience of the crew.” Although the purpose of this article is to examine routes, not boats, Cornell's advice should not be ignored. Any boat and crew planning this offshore passage must be able to take a pounding day after day and endure severe weather. If you have your doubts about either or simply dread the prospect of a long sea passage, there is another way, the so-called ‘thorny path.'

Despite the fact that it is almost always a windward slog, more boats depart from South Florida and make their way to the Caribbean by island hopping through the Bahamas and Greater Antilles than from any place else. If you have time and patience, this route is an attractive alternative. The undisputed guru of this passage is Bruce Van Sant, author of the intriguing guidebook, The Gentlemen's Guide to Passages South and a true believer that there is indeed, a ‘thorn less' path through the islands. He has legions of followers who treat his book like the bible.

I used to live next to Bruce and his lovely wife Rosa, on the canals of Ft. Lauderdale. Our boats were docked next to each other and although our politics and voyaging philosophy were dramatically opposed we became good friends. Bruce believes that by carefully waiting for the right weather pattern and riding frontal passages from one island to the next, it is possible to sail from Florida to the Caribbean without beating your brains out. He is a brilliant guy and has made this passage countless times. His wonderfully opinionated book is something of a marvel as it delves into detailed local weather phenomena, well-positioned anchorages and specific strategies for seizing the moment to advance further toward you ultimate destination.

I was busy during this time delivering a new Hylas' from Ft. Lauderdale to St. Thomas, a 1,000-mile uphill passage that I routinely completed in 7 days or less. For awhile, I made this passage once a month. I drove Bruce crazy. I would say goodbye and then a week or so later I was back. Over a gin and tonic in the cockpit he would shake his head and ask, “how can you stand all than windward sailing?” My standard reply was, “Hey, its my job,” but there was more to it than that. Like Bruce, I had developed my own path of least resistance to the islands but it required a different mindset.

Offshore sailing requires a certain verve, certainly not arrogance or hubris for nobody spots false pride faster than old Neptune, but you need confidence, you have to enjoy being at sea and accept the good and bad. Bruce would cringe when I explained that windward sailing was simply part of the equation for me, and in some ways, once you adapted to the motion, an efficient method of passage making, especially in modern boats that are not really well suited for off-the-wind work. His usual reply was that I was simply too young to understand.

My well-worn route to the Caribbean was to work east of the island of Eluethra and then draw the rhumb line to St. Thomas. If I couldn't lay the track, and usually I couldn't, I steered the best course possible, usually in six-hour tacks. Although I tried to avoid getting too far south or west, I wasn't obsessed with getting east early. During the course of a week's passage I invariably found a lift, and more often than not had a nice close reach to the finish line. As soon as I e-mail this article off to the editors at Sailnet, I am heading to Trinidad, by airplane, to deliver a boat back to Ft. Lauderdale. I must confess, I am relishing the prospect of an off-the-wind passage through the islands. Just don't tell Bruce.