Jay Caunter’s sailboat anchored near Georgetown in the Bahamas. Photo courtesy

Local man sells everything, sails to Caribbean

By William Crooks

Local Journalism Initiative

Editor’s note: The following is the sequel to an article printed Nov 17, 2023. The Record caught up with Jay Caunter over the internet April 30 while he was anchored near Saint Martin in the northeast Caribbean.

Townshipper Jay Caunter sold his belongings and sailed down to the Caribbean, determined to fulfill his dreams. He is currently in the Caribbean, with his next major goal to be south of Grenada by June. He is staying connected with friends via phone and internet while prioritizing safety.

Caunter lived in Toronto for about 25 years before returning to North Hatley in 2011 to care for his father. After his father passed away, with no remaining family ties, he felt free to chase his aspirations. He sold everything, acquired a larger boat, a 1979 Sabre 34, in Sarnia, Ontario, and embarked on his journey.

“Rainstorms today,” Caunter said April 30 over the internet to The Record, “it’s been crazy.” It had been raining for three days. “Since I’ve been on the boat, I rarely know what day it is, let alone the time,” he added.

He said he has a “buddy boat” with him, and is waiting for him to put on a new sail. He has been in Saint Martin for about a month, which was not a part of his plans. Caunter is making some minor repairs to his boat before continuing on. “There’s always something to do,” he said.

He was in Luperon, Dominican Republic, for two weeks. He made quite a few repairs there, too, with inexpensive parts readily available. He also ordered a new sail while he was in the Bahamas, which he picked up at a friend’s place in the Virgin Islands.

The new sail is “really nice,” his old one was ripping all the time. His old main sail came with the boat originally; it was around 50 years old. Every time he would fold it up and put it away it would tear, and it used to tear in strong winds. He ran out of patching material about a month ago.

“The boat itself has been wonderful,” he went on, “nothing serious has gone wrong.” However, his new electronics have been “giving him grief.” His autopilot is right at the limit for what it can handle given the size of boat he has. It cost him a lot of money to fix, but he trusts the worker at the marina he visited knew what he was doing.

A friend of his came to join him in Miami for his crossing to the Bahamas. “It was the crossing from hell,” he said. Instead of the wind being 15 knots, it was 30 knots, and the waves were 15 feet tall. Caunter used his motor; sailing was too dangerous.

Waves like that need to be taken at a bit of an angle, but he more or less took them straight on. The trip took 11 hours. They left Miami at 4 a.m., so the first few hours were in the pitch black.

Caunter’s friend had never been on the ocean before. “When you can’t see the waves, you don’t realize how big they are,” he said, “it wasn’t really fun.” I was his first big excursion out into the ocean. When they reached Freeport, Caunter’s friend left and flew back to Vermont.

Caunter then continued on to Nassau, which was a “beautiful sail, lazy, not much wind.” In Nassau, he spent two weeks getting over Covid. He isolated himself on his boat while he was sick. “I had no energy, I could nap all day if I had to,” he said, “it took me 10, 12 days to feel human again.” Some of his fellow sailors visited, but did not get on his boat.

After getting over Covid, another friend from Vermont joined him on his sail to Georgetown. He ran into weather troubles again, and had to wait a few days for the wind to die down before making the trip. Once in Georgetown he had to wait three weeks to continue on, “waiting for a weather window to leave.”

“The hardest part is waiting,” he admitted. This year has been “extremely bad” for anybody sailing east. The wind is always coming from the east and it blows hard and kicks up big waves. He has to look carefully at the three days on either side of a potential weather window, because forecasts are not always spot on.

The weather was too bad for him to make a planned stop at Crooked Island, still in the Bahamas. He then made his way to Luperon and stayed a few weeks. One of his most “terrifying moments” happened in Luperon when approaching the “extremely dangerous” harbour at night.

He tried three times and was about to give up and just sail out a few miles, point into the wind, and wait until morning, but a local fisherman ended up leading him in. Caunter did not trust his electronics in the situation and could hear the waves crashing on shore nearby. Three markers were not working and you have to travel within 50 feet of nearby cliffs.

He eventually made his way to Saint Martin where he docked and prepared for the next leg of his voyage. He plans on being south of Grenada by June to ride out hurricane season there.

“What are you plans after that?” this reporter asked. “My plans after that are written in sand at low tide,” Caunter said.