
It was an early alarm. My wife likes it loud, and loud it was. The clanging clanged my nerves. I was suddenly wide awake and, looking out my bedroom window, I noticed that a soft snow was falling. Icicles had formed on each window pane and the pre-dawn view was bleak. Gray on gray with gray trim. None of it mattered. This was the alarm that we had been looking forward to since Christmas when we told our four teenage boys that we were taking them to the Caribbean for a week’s sailing. It was going to be a new tradition for our family. In the future, the Christmas gifts would be traveling to someplace special, and a week in Antigua on a Moorings charter yacht would be special by any measure.
The road to the airport was not too bad. Snowplows had been out early, and they had salted and sanded things allowing us to make our plane with plenty of time to spare. The boys, who were usually dragging and barely coherent at that time of day, were bright-eyed and wide awake. My wife, Sally, shot me a look that said, “If only it was always like this.” After a lengthy de-icing we finally took off into a pale morning sky: Antigua bound. This was our first trip away since Sally and I had tied the knot last summer and formally blended our family into a unit that we lovingly refer to as “The Tribe.” Sally has twin 14-year-olds. I added a 14-year old of my own and a soon-to-be-done-with-school 17-year-old. Definitely a lot of mouths to feed, but, as soon as the airplane passed through the cirrus, I felt that we deserved and had earned a week in the warmth. February in New England can be brutal.

After a few stops to change planes, it was dark when we finally touched down at V. C. Bird International Airport. The last time I had flown out of Antigua the airport was pretty much a one-room shack, but that was a while ago. The new airport is modern and welcoming, and less than 20 minutes after touching down, we were out front hailing a taxi. The Caribbean air hung warm and moist, laden with the scent of tropical flowers. I am not sure the boys noticed the scent, but Sally and I sure did, and it was like a balm. What the boys did notice, somewhat to their alarm, was that the cab driver was negotiating the narrow streets on the “wrong” side of the road. A history of British influence meant that the cars drive on the left unlike in the United States, but it didn’t really matter. The road was narrow and the driver stayed mostly in the middle, dodging the occasional chicken or goat that had wandered off into the street. He dropped us off at the historic Nelson’s Dockyard, the very heart of sailing in the Caribbean, and we dragged our bags across a cobbled pathway looking for our boat. The entire harbor was lit up from the spreader lights of more than a dozen superyachts in addition to hundreds of smaller sailboats out on anchor. I was wondering where I would find our boat when from behind I heard someone say, “Are you Mr. Hancock?” She had a gentle Caribbean lilt and hearing her words suddenly washed away years of mess and stress from living in a fast-paced world. We had arrived, and our host, the lovely Lovena Bailey, showed us to our yacht. “We upgraded you to a larger catamaran,” she announced. “I hope that’s OK with you.”

It’s rare, if ever, that we have seen our boys speechless, but the beautiful Leopard catamaran that was to be our home for the next week rendered them mute. With bugged-out eyes and impish smiles they clambered aboard in total shock. The boat was expansive enough that each kid would get a bedroom of their own. Furthermore, each got his own private shower. I had to educate them that a bedroom on a boat is called a cabin and the shower is called a head, but that would come later, along with knot-tying lessons. Sally and I enjoyed their excitement and knew that we had made the right decision to travel instead of purchasing those new iPhones. I noticed that The Moorings had kindly stocked a bottle of Antigua rum and some mixers. With a cold one in hand, Sally and I climbed up to the steering station to take in the view.
There are few, if any, more iconic sailing harbors in the world than English Harbor. It’s located on the south side of the island and is completely protected. The entrance bends and turns, and the harbor is surrounded by high peaks making it a perfect hurricane refuge. This salient point was not lost on the British who, during the 18th century, had their navy establish its base of operations for the area there. The harbor served as a base for the British in a time that is referred to as the Great Age of Sail. Indeed, Admiral Lord Nelson aboard the HMS Victory took up station, and the base of operations became known as Nelson’s Dockyard. The dockyard quickly expanded, but was gradually abandoned in the 19th century and closed in 1889. Today Nelson’s Dockyard has been completely restored and is the only Georgian dockyard in the world. I am not sure if it was the rum or just a sense of well being, but when Sally and I climbed into our comfortable bunk in our cozy cabin all seemed right with the world.

My expectations for this family vacation had at first been rather grand. I have been lucky enough to sail around the world a number of times, and each time was a life-changing experience. I thought that a humble circumnavigation of Antigua would provide a similar experience for my family, but by breakfast the next morning I knew that they were already changed. For a start, Sally’s boys had only ever experienced the frigid waters of New England. Now they were making the most of the warm turquoise water in English Harbor and were off snorkeling looking for treasure. Life would never be the same again.
The Moorings staff stopped by and suggested a briefing to go over possible anchorages and must-see beaches. Their advice was excellent, and I heeded their warning that the windward side of the island would see a big increase in wind later in the week. “It might be a little bumpy,” Bobby said, flashing his brilliant white smile, “if you know what I mean.” I knew what he meant and decided that we would head for the leeward side to stay out of most of the wind. No need for any baptism by fire for The Tribe. Bobby also gave us a thorough walk-through on the yacht showing us how everything worked, and I, for one, was amazed by how simple and, if I may use the word, foolproof they had made things. Even if you have very little knowledge of sailboats it would be hard to mess things up. Bobby then left, but not before suggesting that the best way to get to the grocery store was to take the dinghy. “They have their own dock,” he said.
We provisioned at a well-stocked grocery store that was a short dinghy ride away. At first we were shocked to see the prices of everything until we realized that their prices were in EC dollars, not U.S. With an exchange rate of $2.70 EC to one U.S. the prices suddenly seemed much more reasonable. Our yacht had a freezer, so we bought some frozen goods as well as fresh fruit and fish. I couldn’t wait to introduce the kids to Ting, a drink found throughout the Caribbean. It’s a carbonated beverage flavored with Jamaican grapefruit juice and is both sweet and tart. It was an instant hit, perhaps too much so, as we saw the dinghy filled with green bottles and consumed by the dozen. They weren’t expensive, but they weren’t cheap either. Sally shot me a look that said, “We are on vacation, let it be.”
Before leaving the dock I briefed my crew on duties and responsibilities. Tom, the eldest, would be in charge of anchoring. He would be ably assisted by Seth, who was light, agile and perfect for just about any job handed to him. Eli would be captain of the dinghy and would be responsible for making sure that it was securely on its davits after each use. Kyle, well let’s just say that he was excused from most duties. His modus operandi finds him usually with ear buds in and music floating in his head. Kyle marches to the beat of a different drum, but the smile on his face nearly the entire time we were in Antigua meant that the music was playing beautifully and all was well in his world.
We nosed our way out of English Harbor completely blown away by the size and number of the superyachts docked stern-to. We noticed that one particular yacht had its own lap pool. My preference was more toward the smaller boats at anchor, young carefree sailors enjoying time in the sun without a care to raise their blood pressure. I wondered how much Mr. Superyacht owner actually got to sail his yacht and how much time he spent dealing with the stress of whatever job paid for it. The bare-chested blond who waved to us as we motored by had my vote for how to live a good life. Raising the sails was easy. We set the main in the lee of Shirley Heights, a high headland at the entrance to the harbor which provided a perfect lee. The lazyjacks and an electric winch made it a cinch, and unrolling the headsail was no more onerous. I bore off and felt the warm tropical breeze at my back. We were officially on our way, and I had a lovely anchorage picked out for the evening. Bobby had told us that there was good snorkeling there, and the boys were excited.
I am not going to give you a travelogue, nor am I going to bore you with what we ate for breakfast each morning. Our goal was simply to let the experience wash over us and enjoy each other’s company. We also tried to have each meal in a different location, if possible. The Leopard cat was set up with so much forethought that dropping and raising the hook required hardly any effort, and finding a perfect spot to pull over and fire up the grill was just as easy. It also did not take long before we started to find our children again. It seems that once they became teenagers they had become strangers. Always in their rooms, plugged in and not much interested in their parents. Now on the boat, which by the way we had renamed The Tribe, their individual personalities started to return. There was so much laughter and family bonding that Sally and I had to pinch ourselves. The sun drenched us each day, and the boys started to turn brown: except Eli, who turned a bright pink and then began to peel. He would turn 15 the week we were in the Caribbean, and I asked a friend who had lived in Antigua to recommend something special to do on that day. “Take them swimming with the stingrays,” she suggested, and that’s what we did. We returned to English Harbor, mostly because it was easier to get a taxi from there, but partly because I knew that I would not relax knowing that the boat was out there swinging on the hook no matter how much I trusted the ground tackle.

I was worried that swimming with stingrays would be a tacky tourist operation, but it was not. It was awesome, and while the stars of the show were the stingrays who loved to eat squid out of our hands, the other part of that experience was the people. The people of Antigua are among the loveliest in the world. They have a beautiful soft lilt when they speak, and it’s soothing to listen to. The crew that worked the stingray park were funny and very much focused on everyone having a good experience. They were led by a local man who introduced himself, but then told us to forget his name and to just call him Scooby-Doo. How perfect and how typical. In fact, if I have any single takeaway from Antigua it’s not the fact that they have 365 beaches, one for each day of the year. It’s not the tropical sun and constant trade winds rustling the palms. It’s the people. Everyone seems happy and they are generous with their time and spirit. They live in a juxtaposition between simple island life and a sailing community that routinely has a billion dollars worth of yachts tied to their docks. If there is envy or malice they don’t show it. Instead, they enjoy each day as a gift and we can all learn from that.

Before leaving the island we had to perform a ritual that I had been doing since first visiting Antigua 40 years earlier: the Sunday night party at Shirley Heights. The high headland offers a spectacular view over English Harbor and beyond that, Falmouth harbor. It’s also a perfect place to see the sunset, and we watched it go down slowly sputtering and sizzling as it sank below the horizon. The smell of jerk chicken and burgers mingled with the tropical cadence of the steel drum band and later with an excellent reggae band. It was heady stuff and a night that will long be remembered by four sun-saturated teenage boys.
Reentry was a bitch, as you might imagine. We docked the boat at The Moorings and bade goodbye to the staff who had become our friends. Kyle bemoaned, “I am going to miss taking the dinghy to get to the grocery store.” Three plane rides and a lot of airport food later, we were suddenly back in the cold chill of New England and the traffic and jams of suburban life. For now, we still have our children as they were in Antigua, although they are starting to drift back into their rooms and are slowly increasing screen time, but they will forever have the memory of a week aboard “The Tribe” in the warm waters of the Caribbean Sea. That’s a Christmas gift that keeps on giving.
Brian Hancock and his family chartered with The Moorings. A principal of Great Circle Sails, Hancock is a lapsed ocean racing sailor and a frequent contributor to SAIL.
February 2020