Preparing to Sail South


The fall migration from the East Coast to the Caribbean takes planning and preparation  (published August 2015)

Only you can decide whether this is the year to head offshore to the Caribbean for the winter rather than hauling, covering up with a tarp, and generally being landlocked ‘til spring. I’ve been fortunate enough to have done the spring and fall migration with boats from the Chesapeake, or other Atlantic ports, and Bermuda for most of the last 25 years, and have earned the cred to offer a few tips to make the trip safer and better. It’s a bucket list trip for many, thrilling, deeply satisfying and even life changing. However, without a stout boat and capable crew, both prepared for the weather, it can be somewhere between a nightmare and a death wish.

Although exceptions abound (Lin & Larry Pardey, in their 24 foot Seraffyn, for example) most seem to agree that 30 feet is about the minimum length of a voyaging sailboat, and will be more confident and comfortable in one somewhat larger than that. Defining a “blue water” boat is a trap I’ll try to avoid, but at minimum, it should be of sufficient stability and ruggedness to be able to weather gales, be weather-tight and have sails to meet a variety of wind conditions either underway or hove to. It should be shipshape with all systems and the rig checked and working well. The engine is critical and should have adequate spare parts to enable you to be self-sufficient for the most common problems like impellers or belts. Filters and fuel deserve particular attention. Boats that have lazed about the Chesapeake or other inland waters for years will often have gunk in the bottom of the fuel tank that in the first really rough weather (you’re guaranteed to get some somewhere along the way) will rise up in search of filters to clog. Time and money spent in getting fuel polished (a process in which all the fuel is pumped from your tank, filtered, and put back) is worth the investment unless the boat has been regularly and recently in rough weather using the engine.  An older reference for choosing and equipping the boat that still works well is Don Street’s The Ocean Sailing Yacht and a more modern one is The Voyager’s Handbook: The Essential Guide to Blue Water Cruising by Beth Leonard. And in a segue to the next section, if you choose to go with a rally, they will generally have good checklists for making sure the boat is ready.

After heavy weather wet one of the dry lockers
After heavy weather wet one of the dry lockers

Often, first time offshore cruisers are more comfortable joining one of the rallies. For the fall trip south, The ARC Carib 1500 is one of the larger and better known rallies and is set up for first time passagemakers.  For sailors with at least one long distance offshore run under their belts the Salty Dawg Rally is now the largest U.S rally in the Atlantic. Rallies have a number of advantages, beyond the social benefits of sharing anxieties and hopes with like-minded folks. They will help vet your boat and often engage weather routing services like those of Chris Parker’s Marine Weather Center, or Commanders’ Weather, to provide weather forecasting customized daily to your location. Initially, that will help you decide what day to leave, but both at departure and along the way will be giving suggested strategies for where to go next. Boats of differing sizes and speeds mean that even if you leave together, you’ll be soon spread over large swatches of ocean, out of visual contact. Rallies  generally have a daily “happy hour” on either VHF or SSB to check in with each other and the organizers to compare notes and positions, share weather observations, and if necessary, come to each others’ aid.

Selection of the crew is critical to the success of the voyage. Even if they’re all skilled sailors, they must be able go from being individuals sharing the same space to becoming a cooperative, collaborative, and congenial crew. If not, at best, most will come to wish they were someplace else, and at worst, be a danger to each other and the boat. I like to take a mix of experienced old dogs, and enthusiastic young bucks willing to learn, work hard, and miss some sleep when that’s called for.  I try to get one or two who enjoy and are good at cooking, and at least one who’s mechanically savvy. Having women aboard makes for more balance. A crew of six allows for a three watch system with two on watch—a safety factor, when weather goes sour, or maybe one is seasick. It can be and often is done with fewer, but the premium on experienced crew becomes more important and, frankly, it’s not as much fun.

Another factor affecting crew size is where you can put them. Ideally, each crew member will be in a dedicated fore and aft berth, with either bulkheads or lee cloths to ensure that whichever way the boat tacks and heels, no one rolls onto the cabin sole, and everyone remains snug and secure. The spacious double beds so comfortable for coastal cruising and nightly anchoring may need some modifying, and you may find that the boat that proudly advertises sleeping six or more has but four really usable sea berths. Hot bunking, when one person gets up for watch, her berth is taken by someone coming off watch, actually works pretty well once you’ve made the mental shift to limited privacy and personal space.

This trip generally starts in fleece and foulies, and ends in shorts. November weather north of the Gulf Stream is often cold and wet, and whether the crew bring their own, or the boat provides, everyone needs adequate warm clothing and foul weather gear. In addition, I require that each crewmember have a harness, knife, small flashlight, personal strobe and I recommend an inflatable PFD (often built into the harness) that is comfortable enough that it will actually be worn. Arriving with fewer people than you start with can be so embarrassing.

Checking the status, the author on the foredeck
Checking the status, the author on the foredeck

Ah, there’s the rub. Most are going for the winter, or longer, so will leave in the fall. With good reason few want to plan that trip for hurricane season. On the other hand, the later you leave, the more frequent and severe the cold fronts and their associated lows become. For most, that means leaving the northeast as soon after the first of November as a good weather window appears. Whether you have a weather routing service, or do your own routing using some of the excellent free web based services like, securing the best advice and information you can as you commit to a departure day will pay dividends. The right decision, and a bit of luck, may give you southwest winds to reach out and across the Gulf Stream, picking up the manageable north and northeast winds of the front that follows those southwest winds to get down to about 29 degrees north by 65 degrees west (sometimes called Highway 65 in the south going crowd) where you can pick up the easterly trades for the rest of the trip. I’m not sure I’ve ever had it happen exactly like that, and most years, you’re compromising and trying to pick the best window and route from less than ideal choices, with incomplete information. Those initial southwest winds may be from somewhere else, depending on the weather systems moving through, and the trades can be disturbed by those systems too. Once you’re underway, if you’re not getting custom weather routing, the NOAA high seas forecasts via SSB will become an essential daily ritual.

At that time of year, cold fronts, commonly called northers, are becoming a weekly occurrence, often associated with lows that come roaring up the lower east coast to about Cape Hatteras before breaking from the coast on an accelerating track to Europe. If they’re weak, you can sometimes pick one side or the other of the low to move you along your course, but in general, it’s best to avoid them if you can. Sometimes they move more slowly, or stall, and become severe tropical storm systems, making ducking into a port of refuge like Beaufort for a few days an attractive option. For just about all pleasure boats, the trip will take longer than can be accurately predicted by a weather forecast, and no matter how good things look on departure day, they’ll have changed three more times by the time you tie up at the other end.

Before you leave, be sure to have plotted the locations of the Gulf Stream, warm core (counterclockwise) and cold core (clockwise) eddies—circular gyres of water spinning off the Gulf Stream, on either side. As with the lows, knowing which side of an eddy to be on can add or subtract half a day or more from the trip as you place yourself in either favorable or adverse currents.

Although the days before departure are sure to be busy, with last minute shopping runs, repairs and upgrades to systems, adding to spares, and the logistics of getting everyone there, it’s best to leave with a good night’s sleep for all the crew if you can. Not always possible, but worth the time and effort.

If any crew are untested, or know that the first days at sea will find them seasick, they should start taking any preventive medicine the night before departure, to ensure that it will be thoroughly into their system when needed.

They say an army travels on its stomach, which is no less true for the little navy you’ll be sailing with. Try to keep meals simple, but nourishing and tasty. While I generally schedule each watch to prepare a meal, when possible I’ll schedule the folks with the most skill and interest in cooking for dinner. In nasty weather, soups and prepared stews are warming and welcoming. In the middle of the night, those on watch will find snacks and some warm drinks like tea or hot chocolate bracing. And in prepping for an offshore trip, plan meals for a trip 50 percent longer than you anticipate. That last 50 percent can be canned goods, dehydrated foods, and other things that will not spoil and be good for the next long offshore passage. Some trips just take longer and running out of food can’t be an option.

Mahi mahi, with crew Claude Bilodeau and the author
Mahi mahi, with crew Claude Bilodeau and the author

As the days become more routine, with the generally better weather of the trade winds, some diversion and the prospect of fresh fish for the table can come from trolling a lure, or maybe the flying fish you found on the deck one morning. (They not uncommonly go flying at night, only to knock themselves senseless when they hit the cabin in the dark.) Likely catch could be mahi mahi or wahoo, both excellent eating fish. A proper fishing rod and reel are good for this, but a hand reel with some stout monofilament and a bit of bungee cord to absorb the initial strike also works pretty well.

The support teams for your crew, family and friends at home, love to know what progress is being made along the way and that all is well. If you have regular contact via SSB or Sat phone, well and good. Devices like Spot can also achieve that pretty effectively and economically.

Helmsman Fred Lipp, happy with the progress we are making
Helmsman Fred Lipp, happy with the progress we are making

So is this all you need to know to point your boat 1,500 or more nautical miles to the south? Of course not. If you attend to these, it will be a good start, and if you complete that first offshore run successfully, it could be the start of the rest of your life.

Jack Morton has cruised with his wife, skippered tall ships & research vessels, and for many years taught offshore voyaging for the Maryland School of Sailing, on voyages to and from Bermuda and the Caribbean.  When not busy on teaching cruises, he does deliveries, and paddles his kayak in Florida, where he lives with his family. He can be reached at