By Hank Schmitt

Salty Dawg rally There are a number of cruising rally options if you are planning to head south as the weather turns…not a bad option after last winter. All four of these rallies start the same weekend, as everyone wants to depart after November 1 and before the winter gales start. Only the NARC Rally (North American Rally to the Caribbean) departs from Newport, RI, with the other three departing from near the mouth of the Chesapeake Bay. The Caribbean 1500 and NARC Rally have been around for many years. The Salty Dawg Rally is a free rally that started three years ago, and has grown to be the largest.

These “Salty Pups” sailed with the “Big Dawgs” on the Salty Dawg Rally. ©

New this year is the Snowbird Rally, starting on the ICW (Intracoastal Waterway) and going “inside the ditch” all the way to Miami, FL. This event is being organized by Wally Moran, a contributing editor at SAIL Magazine.

NARC Rally

The 15th Annual NARC Rally departs from Newport on Saturday, November 1 or the best weather window after that date. The fleet will begin to gather at the Newport Yachting Center, with a special discount dockage rate for the week leading up to departure. The skippers meeting, weather briefing by Ken McKinley of Locus Weather, and opening party at Benjamin’s are all part of the pre-departure program in Newport. Boats will be ready for sea by Saturday, but most years the fleet has been delayed from one to five days waiting on weather. The NARC Rally stops in Bermuda and docks at the Bermuda Dinghy & Sports Club to wait for the next weather window for the second leg. Bermuda is God’s gift to sailors heading south in the fall, and it is a sin not to stop and have a Dark’n Stormy and Fish Fry. The government also waives the $35 per head tax for the fleet.

From Bermuda, the fleet sets sail for IGY Simpson Bay Marina in St. Maarten for the final party and reception, on November 18. All boats in the rally get two free days dockage at the IGY Simpson Bay Marina, plus 10% dockage discounts ranging from one week to the entire season, depending on your plans. If your final destination is the Virgin Islands or other Caribbean destination, you can stop in St. Maarten for the party, crew change, re-provisioning and repairs on the best island in the Caribbean for all three services. Or you can skip the party and go right to your winter destination.

Caribbean 1500

The longest running event, the Caribbean 1500, has its roots in a Newport departure, but was taken south to Hampton Roads, VA by founder Steve Black. The rally was sold three years ago to the World Cruising Club and has diminished in size since another rally, albeit a free one, set up shop departing from the same place and going to the same marina in the BVIs. After the initial clashing of logistics, the Caribbean 1500 has moved its departure point from Hampton up the river to Portsmouth, VA. This will be the Caribbean 1500’s second year departing from Ocean Marine Yacht Center.

Salty Dawg Rally

Organized by Bill and Linda Knowles of Bristol, RI, the Salty Dawg Rally still departs from the Bluewater Yachting Center in Hampton, VA, but now finishes at the Bitter End Resort in Virgin Gorda, BVI, conceding the finish in Nanny Cay BVI to the Caribbean 1500. Although the two fleets have the same departure dates this year, there is plenty of ocean for both fleets if they happen to depart on the same day. Last year, the Caribbean 1500 left a day early. The Salty Dawg fleet spread their departure over several days.

Snowbird Rally

The new rally this year is the Snowbird Rally, also departing from Hampton, VA November 1 but heading down the ICW with many stops along the way. Nights are short this time of year so boats running inside will take their time, mostly underway only during daylight hours. If you have never made this inside passage and have plenty of time, a shallow draft and less than 65-foot mast height, this may be a fun way to go. However, this option is not recommended if you are planning to go much further than the Bahamas this winter. If you’re going to the Caribbean, the further east you stay the better.

The NARC Rally has been helping organize the challenging passage from New England to the Caribbean since 2000. The rally is free to any seaworthy boat heading south, with an emphasis on larger and professional to semi-pro crewed boats along with a mixture of privately owned boats that have made the passage before. Participants get free weather routing, an offshore radio net and socials in Newport, Bermuda and St. Maarten, plus discount dockage, a Bermuda tax waiver, duty free fuel in Bermuda, and more. Owners needing crew receive free crew networking service through Offshore Passage Opportunities(OPO). We have been organizing the NARC Rally since its inception.

If this is your first time sailing south, I invite you to call me for advice on whether you should depart from Newport or heading further south to join one of the other rallies. OPO can also assist with hiring a skipper or finding experienced crew to help ensure a safe passage. If you do not have a boat and want to crew on OPO’s Swan for the 1,500 miles passage, for a fee, you can sail aboard a Swan.

The NARC Rally offers an open invitation to any boats in the other rallies that end up making a detour to Bermuda. Some boats may simply want to stop there to break up their passage south, while others might have to detour for fuel or repairs. Any boats wanting or needing to stop in Bermuda are welcome to meet up with the NARC fleet. Just head over to the Dinghy Club after you clear customs. You can still depart when you are ready and catch up to your rallies in the BVI from Bermuda. The classic route from the Chesapeake Bay to the Caribbean is to head east for three or four days (which brings you near Bermuda anyway), before heading south to catch the tradewinds and reach  down to the Caribbean. More recently as boats depart from the Chesapeake for a 7- to 10-day non-stop passage, they will carry a lot of extra fuel to motorsail most of the way to the Caribbean if necessary.

The Caribbean 1500 (visit for pricing) has a dedicated shore staff, very capably supervised by Andy & Mia Schell. There is a formal safety inspection and survival gear checklist as well as weather forecasts, socials and seminars. The Snowbird Rally charges $750. The Salty Dawg Rally is still free, but the organizers are asking for a $250 donation to get discounts in the BVI for the entire winter season. If you are planning on spending all, or most of your time in the BVI, this is a good deal. The Salty Dawg Rally is a much looser federation of boats that allows boats to depart from almost anywhere and go almost anywhere on the other end, while using Chris Parker as their common weather router. The Caribbean 1500 also offers a “Plan B” with a handful of boats departing with the fleet from Virginia, but making landfall in the Bahamas. The NARC Rally is still 100% free, with boats paying their own dockage and some socials.

OPO is also the crew network for the Salty Dawg Rally, and will also help any boat in the Caribbean 1500 find crew for their passage south. This service is free to all boat owners in the rallies. If you want to sign up for the NARC Rally, crew on a boat heading south or sign aboard a Swan, contact OPO at 800-4-PASSAGe (472-7724), email, or log onto