This article originally appeared in the October 2009 issue
Many sailors think the best way to reach the Caribbean from the northeast U.S. is to head for Bermuda, spend a few days there, and then take an easy ride down to the islands. In my experience this is neither the quickest or safest route for boats under 55 feet. Many American insurance companies, and almost all Lloyds underwriters, now have hurricane season ending on 1 December. If that’s what your policy says, you should head south along the coast and wait in the lower Chesapeake until December. If your air draft allows you to get under the 64-foot bridge south of Norfolk, Virginia, think about continuing south via the ICW to Morehead City, North Carolina, and heading offshore from there.
Weather along the northeast coast gets progressively unstable as the year winds down and a mid-November forecast might be good for just 24 hours. Since you are in a gale area all the way to Bermuda, if you head south from around Newport, Rhode Island, your passage time on a 40-footer will be around four days. That means the chances of getting hit by at least one gale are very high. An approaching cold front with northwesterly winds of 20 knots or more will usually veer to the north and then into the northeast. In these conditions a boat caught in the middle of the Stream will experience very rough conditions even with 20 knot winds. Higher winds will create gear-damaging conditions and repairing things in Bermuda can be time consuming and expensive. That’s another reason you should head for the Chesapeake. The trip will train the skipper, crew and boat and if there are problems they can be corrected before you leave the states.
If you are heading offshore from Morehead City or Beaufort, North Carolina, wait for a northwesterly and leave on the top of the tide. A southeast course should put you in the Gulf Stream in eight hours and be across it in 24 hours. If all goes well the northwesterly will veer to the north and then northeast. These shifts won’t bother you, because you’ll already be across the Stream steering southeast for the Caribbean. If you’re lucky, the northeast breeze will hold you down into the northeast trades.
Mid-December is about the latest you should leave from Beaufort/Morehead. If you miss this window, continue south to St. Augustine, Florida. Don’t leave from Charleston, South Carolina, because it is further away from St. Thomas than Beaufort/Morehead City. More importantly, if you leave from Charleston, it will take you three or four days to get across the Stream.
Once you reach St. Augustine, wait until a norther is in the forecast and then leave 36 hours before it arrives. Head out across the Stream—it is very narrow and close to shore here—and when the norther arrives steer so you are sailing on either a beam or broad reach. You’ll be well on your way south, with a minimal amount of wear and tear.