Three Ways South

Veteran cruisers debate three fall routes from the US East Coast to the islands.

- DAVID H. LYMAN

An autumn passage from the US East Coast to the Caribbean is one of sailing’s great adventures. Every fall, hundreds of sailing yachts make this voyage— alone, with a buddy boat, or in a rally. ¶ No matter which route you choose, it’s approximately 1,500 miles, taking eight days to two weeks of sailing time in the Atlantic, over the Gulf Stream, and through the Bermuda Triangle. There’s a high probability you’ll be hit with a 30-plus-knot cold front and a couple of squalls before you pick up the trade winds for a few of days of delightful beam-reach sailing into the islands. ¶ Here’s a look at three ways you can head south.

OPTION ONE: FROM NEWPORT, SOUTH

Being from Maine, I used to sail down to Newport, Rhode Island, for the boat show in September, and then leave for Bermuda when the forecast was favorable. At that time of year, the weather windows are usually wide open. I’d keep an eye on the tropical weather and, if no storms were brewing, I’d leave, knowing I’d get to Bermuda in five days, before a hurricane could form and beat me there.

More recently, I’ve taken to joining Hank Schmitt and other delivery captains on the North American Rally to the Caribbean, which departs from Newport in late October. Schmitt has been organizing the NARC Rally for the past 24 years and is planning on turning over the tiller to the Salty Dawg Sailing Association in 2024.