November marks that time of the year where New Englanders flock south to escape the impending frigid northern winters. Some fly, others drive and then there are those yachtsmen who brave the high seas and intercostal waterways to obtain winter warmth.

My solo migration sailing south for the winter began aboard Riverwind on November 1st with a thin sheet of ice covering the decks. Departing from Rowayton, CT at sunrise with the hell bent goal of reaching Cape May, NJ by sunset.

Once I hit the Atlantic, it was fairly smooth sailing down the east coast. Averaging 22 knots, 3 miles off-shore for about 8 hours a day, put me into Cape May, New Jersey for the 1st night, Virginia Beach for the 2nd, Beaufort, North Carolina for the 3rd and Conway, South Carolina for the 4th and final night before I reached my destination.


On a journey like this, utilizing every bit of sunlight is crucial, and besides, there really is nothing like an Atlantic sunrise while underway. I found myself not alone making the expedition down to warmer waters. Along with the annual migration of birds, humpback whales and bottlenose dolphins, migrating vessels were also heading down the east coast.


“We are seeing about 50-60 boats coming into and staying in Charleston for the winter. There are still quite a few transient customers that continue on to Florida or the Bahamas, but as the city’s popularity has grown, we are starting to see more and more people winterizing their boats here instead of heading further south” says Stephanie Collins, the Dock Office Manager at The Charleston City Marina.


The stretch from Virginia Beach to Beaufort included some Atlantic Ocean, but mostly an intracoastal duck-in at Pamlico Sound which was about 60 miles with an average of 9 to 12 feet of depth.  I attempted the open ocean from Beaufort to Conway, however, 9 foot swells and 30 knot winds, as well as the treacherous seas around Cape Fear, put me back through the intracoastal for the remainder of the excursion.


Four stops, 760 miles of open ocean and intracoastal waterways, and a six pack of Coronas later, I finally reached the Charleston SC port. Some treacherous moments, some passive, all awe inspiring.


In years to come, my wife and I plan to stay in Charleston for the winters at Luxury Simplified Retreats properties, such as Ivy Terrace. We  are also searching for an investment home for those long cold New England months that we can rent out for the times we are not in Charleston. For the time being, we will pop in and out to enjoy the boat with friends and family, even in the “dead of winter.”


Are you looking to sail south for the winter? Take a look at our portfolio of long- term luxurious homes that will serve as a perfect escape for the frigid months.