Best of the Best, bigger than ever

The Best of the Best Regatta draws wooden Bahamian racing sloops from the many far-flung islands of the Bahamas. The 2024 regatta, the largest ever with more than 85 entries, was sailed December 5-8 off Montagu Beach in Nassau, The Bahamas.

Article and Photos by Jan Pehrson

It’s Regatta Time again in Nassau. Hundreds of sailors are coming to town. For two days from dawn to dusk, Bahamian wooden racing sloops arrive in the harbor as deck cargo on inter island barges. They are loaded onto trailers, hauled to the launching crane, and dropped in the water.

This regatta is growing so much that the organizers are talking about relocating it to another beach and harbor with more room for land-side as well as water-side activities. On the land, there is so much entertainment that many regatta goers don’t realize that sailboat racing is going on – they are there to party! On the water, inter island rivalries lead to fierce competition.

There are four racing classes – Class-A (28 feet long), Class-B (21 feet long), Class-C (17 feet long) and Class-E (12 feet long).

The most spectacular boats are the A-Class. In windy conditions, they sometimes have as many as 18 crew. The number, like the mast height and boom length, is unlimited. With long overhanging booms and masts of unlimited height, sails are huge and billowing and easily overpower the hulls. Sails are balanced by movable human ballast hiking out on “pry boards” held to the deck by large staples, and lead ballast in the bilges. The pry crew – hopefully! — keep the sloops from capsizing.

“What makes the Best of the Best Regatta so special?” I asked Dari Turnquist from the Bahamian Government’s Regatta Desk.

“I think it is the number of sailors who come from all over the Bahamas,” he replied. “There are 22 regattas throughout the Bahamas, but some regattas are restricted and can’t accommodate the larger sloops due to the time of the year and the harbors they are sailing in. We have all the sailors coming together into one big regatta where every class is featured.

“We are trying to put the sailing back into the regattas and put the emphasis on sailing. We don’t want people to think that regattas are only about having a good time, these guys are out there actually competing. They want to be respected. We want to highlight the sailors; they are the stars of our national sport.”

“Why all the growth in sloop sailing?” I asked the organizer Clyde Rolle.

“There are many new boats, especially in the E and C classes,” observed Rolle. “Sailing is going to the next level, and I am so proud to have been a part of it for the past 61 years. E-Class was designed for the juniors and then we made it an open class and since we opened it, sloop sailing has grown by leaps and bounds. I don’t know what we are going to do, we are going to have to put a stop to it. Everybody wants to own an E-Class, it is so affordable.”

E-Class is more of a one design. In the other classes, mast and boom dimensions are unlimited. As boat builder Mark Knowles points out, the masts, which on a 28-foot-long A-Class boat can be much more than 60 feet high, are self-limiting: “If I build them too tall, they take themselves down.”

E-Class boats are easier to manage than the other classes, as the 12-foot-long boats have a limitation on mast height (20 feet) and boom length (12 feet). Teacher Sheldon Gibson designed and built the first E-Class boats in 2010 for children, and about ten years later the class was opened to seniors as well as juniors. Now that this is an open class, the juniors are beating the seniors. The introduction of the E-Class brought youth into sloop sailing and encouraged boat building on various islands.

Race Organizer Dwayne Higgins points out that “with the E-Class, you can experiment with boat building as you don’t lose a lot if you make a mistake, so they are a good way to learn to sail as well as learn the art of boat building. There are multiple boats under construction right now.”

Nassau is the capital and largest city of the Bahamas, but boats are here from the Out Islands of the Bahamas. There are approximately 700 Out Islands, about 30 inhabited. The Out Islands are also referred to as the Family Islands.

Sailing families from the Family Islands are all over the water at the Best of the Best.

Nothing brings people from the Family Islands together like a regatta. For sloop sailors, regattas are about sailing with your cousins against the families from other Bahamian islands and coming together after the racing for some good times. And teaching your children and grandchildren to sail.

At the Best of the Best just about everybody is family. A few – just a few – of the families are:

The Knowles family from Long Island
Known as “Tripple Crown” because he won the A-Class, B-Class, and C-Class at this year’s Best of the Best, Stefan Knowles is the winningest sloop sailor in recent years. He sails, with family on board, in wooden Bahamian sloops built by his brother, master boatbuilder Mark Knowles.

Mark has built more than 30 beautiful and fast boats, harvesting the wood himself and using no plans other than his artist’s eye. Stefan is often in crowd pleasing, dramatic photo finishes sailing against his brother David Knowles.

Brother Ian Knowles serves as bowman for one or the other brother. This is the most trusted crew position on the Bahamian sloops, as the helmsman cannot see through the huge mainsail and must rely on his bowman to avoid collisions. The current generation of the Knowles family can track their lineage back six or seven generations of Bahamian boat builders.

The Leslie “Buzzy” Rolle family from Exuma
Buzzy is multi-talented. He builds boats that he skippers himself and is invited as guest skipper on other boats who bring a master helmsman on board in hopes of winning trophies at the prize giving. Sailing with his wife “Boss Lady” Kayla, their sons Chris and Vano, and other family, Buzzy’s sailing photos decorate the walls of the fish fry that he and Kayla own.

The Jeff Gale Family and Friends from Abaco
Most of the sailors on the two Abaco sloops, B-Class Lonesome Dove and C-Class It Ain’t Right, are not related family but close friends from Hope Town, Abaco, who have sailed together for 20 years. Skipper Jeff Gale’s family represents three generations of sloop sailors.

“My parents were both sailors and I learned to sail from them at a very young age,” shared Gale. “My father was crew on the Rough Waters which was an A-Class sloop out of Man O War Cay, Abaco in the 1970s. They let me on when I was 11 and I was part of the Rough Waters and then Abaco Rage crew in the 1980s. I have been sailing sloops ever since. My son Joey is also an accomplished sailor and we often sail together. He has crewed for me in previous Best of the Best regattas and has skippered It Ain’t Right in other regattas.”

The Lee Armbrister Family of Friends, homeport Duncan Town, Ragged Island
At 81-years-old, Lee Armbrister just loves to sail and has spent his life on the water. At the Best of the Best, he drove the B-Class sloop Ants Nest II to a second-place finish. Earlier this year, Lee won the A-Class National Championship on Ed Sky. Supported by steady backup helm and crew such as James Wallace and daughter Janaee, who flies in from Atlanta for regattas, Lee continues to demonstrate, in each new regatta, that he remains one of the top sloop sailors in the Bahamas.

The Emmett Munroe Family, homeport Duncan Town, Ragged Island
The Bahamian sloop sailing community lost a sailing legend this year with the passing in November of Captain Emmett Munroe. Captain Munroe and family sailed the Original Courageous, built by Edgar Moxey in 1977 in Nassau. New Courageous followed in 1997, built by Mack Knowles in Mangrove Bush, Long Island.

My introduction to Captain Munroe began like this: “Welcome to my sloop. Let me introduce you to my crew, my sons and grandsons. I learned to sail at Ragged Island on weekends. Two or three of us young boys would sail on a boat together and watch the older guys. I came out of school at 15 and went to sea with my father. He was in the sloop trade between Cuba and Haiti. We had only a compass and used dead reckoning. I have always worked on the water. I was a captain on the trade boats—barges and tugs—and mail boats.”

The Knowles Family from Exuma
At the Summer Olympics in Tokyo 1964, Durward Knowles and Cecil Cooke became the first athletes representing The Bahamas to win an Olympic gold medal, competing in sailing in the Star Class. At the 2024 Best of the Best, Sir Durward’s great grandnephews, Joss and Emit Knowles, placed 1st and 3rd in the E-Class, representing the Exuma Sailing Club. Joss is also the Junior National Champion.

The Exuma Sailing Club was started to teach young Bahamians to sail and develop them into international sailors as well as Bahamian sloop sailors. Learning to sail from a young age from their dad, Exuma Sailing Club lead coach Dallas Knowles, and their mom, coach Tamara Knowles, both Joss and Emit have continued the family tradition of collecting sailing medals. Youth sailors from the Exuma Sailing Club swept the E-Class at the Best of the Best, finishing 1-2-3.

The Effort Kemp Family from Blackpoint
At 83-years-old, Effort Kemp is the oldest of the sloop skippers, drives the B-Class sloop H20, surrounded by his brother and sons and nephew and grandsons. Says his son Kelly Kemp, “I would say he is the most winningest skipper there is, he being around from ancient times, and sailing on the legendary Tida Wave and winning many regattas. Now he is sailing on my boat, H20. We are from Blackpoint.”

The Smith / Robinson Family from Blackpoint
Just as families have a family lineage, boats have a lineage too. The A-Class Sloop Red Stripe competed in and won sloop regattas for years, skippered by Captain Lundy Robinson, one of the most renowned and revered skippers in the Bahamas. When Captain Robinson passed in 2021, Red Stripe missed a few regattas.

Now she’s renamed Silent Partner and owned by Chuckie Smith from Blackpoint, Captain Robinson’s homeport. Chuckie is on the mainsheet, and Robinson family and Smith family cousins from Blackpoint round out the crew. Chuckie brought in guest helmsman Buzzy Rolle from Exuma for this regatta. Red Stripe / Silent Partner is back!

The Cartwright family from Long Island
Colin Cartwright, Sr. and his two sons, Colin and Colin, sail sloops from all classes at the Best of the Best. Sometimes as crew, sometimes as owner/skipper. To avoid confusion, the boys are called CJ and Cristo, leaving their dad to be called Colin.

The family have sailing in their genes. Says Colin, “My grandfather was Rupert Knowles the boatbuilder back in the 1950s and 1960s. He built all the boats like the famous sloops Tida Wave and Lady Muriel. After he passed, his sons kept building. Now the grandsons are getting into it. I’ve been sailing for more than 40 years now, and my sons have been sailing with me since they were babies. Cristo and C.J. sail all day long now, in all four races.

In the past, sloop skippers ranged in age from 80-plus-year-olds to teenagers. Now with the E-Class growth, the sailors are getting even younger, and the fleet is getting larger. As Colin Cartwright says, “Will sloop sailing be dying out any time soon? No, it will keep going until judgement day comes!”

Race Results:

Class-A: (1) Running Tide, Stefan Knowles, Long Island (2) New Legend, David Knowles, Long Island (3) Rufff Justice, Joshua Knowles, Long Island
Class-B: (1) Susan Chase V, Stefan Knowles, Long Island (2) Ants Nest II, Lee Armbrister, Duncan Town, Ragged Island (3) Ole Boy, Roger Fox, Salt Pond, Long Island
Class-C: (1) Sassie Sue, Stefan Knowles, Long Island, (2) Whitty K, Cochise Burrows, Long Island (3) Bull Reg, Leslie “Buzzy” Rolle, Exuma
Class-E: (1) Lady Kayla, Joss Knowles, Exuma (2) One Bahamas, Tanaj Manos, Exuma (3) Mako, Emit Knowles, Exuma

Jan Pehrson is a sailing photojournalist who spends summers in San Francisco, California and winters in St. Pete Beach, Florida. As a racing and cruising sailor and Coast Guard licensed skipper, Jan’s familiarity with sailing and the sailing community lends an in-depth element to her prolific array of photographs and articles. Contact her at www.janpehrson.com