Getting ready to sail to Antigua

“Clear Caribbean waters, pink and white sandy beaches, a hot tropical climate, refreshing breezes, and friendly people draw tourists to the island of Antigua. Located in the Eastern Caribbean roughly 17 degrees north of the equator and ringed with coral reefs, Antigua is the largest of the English-speaking Leeward Islands. Known as the “gateway to the Caribbean,” Antigua was a strategic port in the 18th century. English Harbour on the southern tip of the island was once an important naval base and is now a flourishing boating center.” 

This is what catches my attention as I think about the winter coming. The Farmers Almanac is predicting a bone chilling cold and long winter for 2023. I am working on the solution to this…. take the boat down to Antigua. Last year, I had a great experience sailing down to Bahamas with the Salty Dawg Sailing group. They tracked my progress along with 30 or 40 other boats so that I arrived safely. Negotiating with COVID was not easy but, I was able to spend the month of April exploring the Exumas, and other great deserted islands in the Bahamas and it was an amazing experience, before sailing the boat back to Toronto in May, 2022. This year there are over 100 boat sailing down to Antigua with the Salty Dawgs and my plan is to join them. There are zoom calls two or three times a week with other sailors to discuss various aspects regarding weather, safety, necessary equipment, and areas to explore once we’re down there. As with any worthwhile venture, there are obstacles along the way that must be overcome

The first obstacle I faced was trying to find at least two people that were crazy enough to sail to Antigua with me. My wife, Ileana is a Fairweather sailor and finding herself hundreds of miles from the nearest shore at the tail end of hurricane season is not her idea of a good time. Some might even say she is a sensible person. After much searching, I was able to find two sailors. Paul has done several transatlantic crossings and has delivered sailboats to places such as Panama. Neil has been sailing on Lake Ontario for over 30 years and is a very experienced sailor.

The next obstacle I faced was insurance. It turns out, sailboats are a losing insurance venture, and there are fewer and fewer companies willing to give insurance to sailboats especially those sailing offshore. The reason for this is that many boats are lost or damaged in hurricanes. Hurricane season is not officially over until the end of November, so my November 1 departure might be seen as a little dodgy….The company that currently insures my boat was able to give me a Level 3 rider which allows me to keep the boat in the Caribbean for the winter with certain conditions. However, on reading the policy, I am not allowed to be further than 200 miles from any shore. With the Salty Dawg rally to Antigua, there will be times when I will be 500 or 600 miles away from shore. When I spoke to my insurance broker about this, he says this is “cast in stone” and there is no way I can get insurance for this trip to Antigua in the open ocean. If I deviate further than 200 miles from any shore, I would have to “self insure”. When I explained there are over 100 boats going to Antigua with the Salty Dawgs, and that salty dawgs insist that they must adequate insurance to be part of the group, he told me that the only way they can go down is if they “self insure”.

Neil, Paul and I had some discussion among ourselves as to how to manage this insurance issue. The plan of “self insurance” we all agreed was crazy especially given my colorful past history. We discussed sailing to the Bahamas to stay within the 200 mile limit, and then waiting for a good weather window to go to the Caribbean, but traditionally, this is a very difficult passage against the prevailing easterly trade winds and the currents. I spoke with our weather router, Chris Parker, who said the best way to get to the Caribbean after leaving Hampton Virginia is to get as far east as possible before you get to the tradewinds and this will make the passage easy. This would take us about 600 miles from shore before we head south. Neil was able to connect me with a broker in the United States who was able to find insurance through or a British company called Concept, and with $2500 rider, would insure the return passage from Hampton to Antigua allowing us to be more than the 200 mile limit from shore.

The next piece of the puzzle was how to get the boat down to Hampton for the beginning of the Salty Dawg Rally for November 1st. One option is to take the boat to Oswega at the other end of Lake Ontario, go through the locks of the Erie Canal and on to the Hudson River to New York, as I did last year when I brought the boat back to Toronto. Unfortunately the canal is closed for the season on October 12. To get the boat through the canal with this tight timeline would mean that the boat would be in New York City in the worst month of the hurricane season. The hurricane season this year is slow to arrive and undoubtedly, we have not seen the worst of it yet. Another option is to put it on a truck and have the boat shipped down for the end of October to Annapolis. It is then an 18 hour sail from Annapolis to Hampton where we can wait for a weather window to leave for Antigua with the rest of the Salty Dawgs. Andrews trucking is booked to pick the boat up in October 18 to ship the boat to Bert Jabin’s yard in Annapolis. I am hoping that Steve from MYachts is able to put the boat back together again like he did last year so that we can leave on October 27 for Hampton. When it comes to sailing and planning for such travels, things never goes exactly as planned. I’m just not sure yet what part of the plan is going to fall off the rails but I shall be ready for when it happens with alternative plans. I see this level of uncertainty as adding to the adventure and excitement.

I recently did a safety at sea course and checked out my inflatable life preserver. There were many features I did not know. For example, if I am tethered to the boat with my safety harness and happen to fall overboard, there’s a real possibility that I would be dragged through the water and drown. This safety harness is equipped with HRS (harness release system) that I did not know about. All I need to do is pull a small lever at the bottom of the harness and it releases the tether so that I am not dragged under the water and prevents me from drowning. The downside of this approach is that I would now be bobbing around in the huge ocean as my boat speeds further and further away from me…….. It would seem that this system, although brilliant, is delaying the inevitable…. but there is a solution that I am working on. I already have a PLB (personal locator beacon) attached to the life preserver. This sends a signal anywhere in the world via satellite that I am in distress and every country has agreed to respond when this is activated in an emergency. However, it may take up to 24 hours to reach me. It is now possible to put in a personal AIS (automatic identification system) which will allow me to transmit a signal to my friends on my boat who can come back and pick me up. It will identify my exact location on the chartplotter. I also carry a VHF radio with my GPS position that I can radio to any rescuers.

I’ve also had some work done on the boat. Last year, my autohelm broke. It turns out, that likely the auto helm was not as strong for the tremendous strains and pressures in the open ocean as it could have been. It’s possible, that when the boat was designed, it was for the charter market. The tremendous stresses on the autopilot system as seen in the open ocean would not be expected in the calm waters off Croatia. I put in an autohelm system that is twice as strong as the old one and have been using it. It seems to be working amazing.

Other things I’m working on is getting a second forestay so I could put up a very large jib for light weather conditions, looking for the leak in my freshwater system, getting the bow thruster repaired, and getting a booster put on my generator so I can run the air conditioner while at anchor. I feel blessed to have a new boat! I can only imagine what can go wrong on a boat that is 10 or 15 years old!

I have an image of a hammock on the beach that is waiting for me in the Caribbean. This image recurs in my dreams. All of the planning and all of the obstacles to overcome to get there make the goal of lying in the shade of the palm trees while the warm fragrant wind caress my soul worthwhile. The only worry that I expect will cross my mind is where is the best spot for Ileana and I to watch the sunset that evening…………