Local sailor finishes longest race of his life

Rikki departs Jan. 21 from Miami for Jamaica during the 811-nautical mile Pineapple Cup. Adrian van der Wal, a Jamestown resident, crewed for the yacht as the mainsail trimmer.

Rikki departs Jan. 21 from Miami for Jamaica during the 811-nautical mile Pineapple Cup. Adrian van der Wal, a Jamestown resident, crewed for the yacht as the mainsail trimmer.

As his family was dealing with nearly freezing temperatures in Jamestown, Adrian van der Wal was sailing in shorts and a T-shirt from Miami to Montego Bay.

Van der Wal was a crewmember on Rikki during the Pineapple Cup, which departed Jan. 21 from Florida. Five days later, the crew disembarked from the yacht in Jamaica. Rikki, with the only amateur crew in the three-yacht race, finished in third place.

“We have more offshore races coming up so it was a fantastic practice opportunity,” van der Wal said.

Rikki, a custom Reichel/Pugh 42 owned by Bruce Chafee, was named after the song “Rikki Don’t Lose That Number” by Steely Dan. Van der Wal has been part of its crew since 2019.

The Pineapple Cup, at 811 nautical miles, was the longest race that all nine Rikki crewmembers had completed.

Van der Wal said only three boats competed in the Pineapple Cup because many boats decided to compete in the Caribbean 600 instead. For comparison, there were either 11 or 12 yachts in the previous three editions of the Pineapple Cup. Rikki nearly took part in the Caribbean 600, too, but logistics made them change their winter plans to the Pineapple Cup.

“The fact that the fleet dwindled down so much was heartbreaking,” he said. “We were so disappointed that only three boats competed in it. But we decided that we did so much preparation going into it that we were going to give our best. We learned a lot from it.”

Rikki, the smallest boat in the fleet, departed a day before the other two yachts. They ran into bad luck, however, when no wind was blowing during their headstart. The following day, the remaining two yachts departed in “a big breeze” out of the south.

“We were swept north by the Gulf Stream for a full day trying to get east in no wind,” van der Wal said. “That itself just killed our opportunity.”

In addition to losing their handicap due to the subpar wind conditions, Rikki was crewed almost entirely by amateurs, while the other two boats were crewed mostly by professionals.

Born to the sea

Van der Wal, 23, is the son of nautical photographer Onne van der Wal and his wife Tenley and grew up in Jamestown. He started sailing when he was eight, but he had been on boats since he was a baby. He took an especially keen interest in the hobby when he started sailing with a friend when he was 13.

“In certain conditions, when it would light up a little bit and go fast, I would just smile from ear to ear, and I thought it was the coolest thing ever,” he said.

After a few years of recreational sailing, van der Wal joined the sailing team at the Moses Brown School in Providence. In summers, he started to compete in larger races like the Buzzards Bay Regatta and enjoyed fleet racing. Van der Wal said what he likes about competitive sailing is different from what he likes about recreational sailing.

“Cruising is a very different thing, and I love that too,” he said. “I’ve always been a competitive person, so I think that competition aspect of out-playing your opponents is always something I’m drawn to.”

Throughout the years, van der Wal has participated in several crewed races. He started competing in longer distance races last winter when he was part of the crew of the boat Prospector in the Caribbean 600. He got involved with Rikki through a friend’s father, who connected him with Chafee. At first, van der Wal started in the pit before becoming the boat’s trimmer. In June, he and the Rikki crew did their first long race when they took part in the Newport Bermuda Race, where they came in fourth in their class.

Enjoying the ride

Before they set off for the Pineapple Cup, the Rikki crew had a few practice days in Miami. The course of the Pineapple Cup starts in Miami and cuts south through the Bahamas before turning west at the Windward Passage between Cuba and Haiti. The race then continues in a southwest direction before reaching Montego Bay on the northwest coast of Jamaica.

“It’s kind of this long arc where you start off going due east and you finish going almost due west in Jamaica,” van der Wal said. “It’s such a great route. It’s so much fun sailing through all these Bahamian islands. It’s beautiful blue water and flying fish and sea life.”

Most of the major long-distance yacht races like the Caribbean 600 and the Newport Bermuda Race are about 600 miles, but the Pineapple Cup is over 800 miles.

“It’s super interesting to have an 800-mile race,” he said. “That extra day and night is another aspect of getting into the groove of offshore sailing, and a little bit more towards the bigger stuff. The course is so cool. I love finishing somewhere that you didn’t start.”

Van der Wal said one of his favorite moments in the race came on the second-to-last night when they were coming around Cuba. The breeze had been building all day and they were in a depowered setup. They then tried a triple head sail setup that they hadn’t attempted before.

“It was awesome, the boat was just lit up,” he said. “We were doing almost 20 knots on this reach in the middle of the night for a couple hours.”

While Rikki had trouble with the wind at the start of the race, van der Wal had few qualms about the weather he experienced in the Caribbean.

“Not many races are as warm and pleasant as the Pineapple Cup,” he said. “We all appreciated that, except during the day when you’re trying to sleep down below and it’s like a sauna, but you win some you lose some. We could wear shorts and a T-shirt frequently at night which is almost unheard of in other races.”

The next race van der Wal and the Rikki crew will compete in is the Annapolis to Newport Race, which will start in June.