Pineapple House

The Nicholson Sisters

Of English Harbor, Antigua

The draft of a story that will appear in the February 2022 edition of Caribbean Compass magazine

My sailing buddy, Larry, and I pulled into English Harbor two years ago and anchored off Pigeon Beach. We had just completed the offshore voyage, 1700 miles, from Maine to Antigua, hungry to get ashore. I had an assignment to cover the Antigua Charter Yacht Show for Caribbean Compass starting a few weeks and needed a base ashore and Larry, who knows the island and everyone here, knew just the place.

“Pineapple House!” He shouted as we launched the dinghy. “Wait ’til you meet Libby Nicholson. She’s from the family that started the charter industry in the Caribbean.” Larry and his 54-foot sloop, The Dove, is one of the charter boats Nicholson Yacht Charters represents, and has for over 30 years. Larry’s been in the charter business longer than most.

We jumped in the RIB and sped into the dinghy dock at The Seabreeze Cafe next to the Yacht Club. Five minutes later we were climbing the stone steps to Pineapple House.

“This is were all the yacht crews hangout.” Larry told me. “When not on charter or racing.

The wooden brown door swung open and there I saw a West Indian cottage colony, 10 individual cottages and the “great house” spread out over the hillside that overlooks English and Falmouth Harbours, the Antigua Yacht Club and its docks full of mega-yachts below.

“Great view,” I told Larry. Then Libby hove in sight, flying down the cascading stone stairs to embrace the two of us, with a hug that would have broken the backs of lesser men. Libby is, after 60 years of living on and off this island, is still one of the major characters in English Harbor society. She’s an energetic woman of in-determinant age with a ready smile, and an artist’s flare. An accomplished silversmith and interior designer, Libby makes her own statement, with silver bracelets dangling from both wrist, colorful fabrics, draped over her statuesque form, flowing as she moves.

“Let me warn you,” Larry whispered. “This may be a B&B, but the second B is not for breakfast, it’s for booze.”

We were just in time for Libby’s early evening soirée. She went on mixing up a few gallons of rum punch chatting away, full of questions of our delivery. Most evenings, Libby holds court on the veranda of the Great House. “Its a tradition my grandfather, the Commander, started over 60 years ago.” Libby told us, pouring ample amounts of the local Cavalier rum into the mix. “Guests, locals, yacht captains and crews, even a stray journalist, gather here to swap stories, tell lies and share observations of life in the tropics.” The seating area was soon packed, people reclining on colorful cushions, standing in open doorways, siting on the porch railing, or on someone’s lap.

It’s here you hear about a narrow escape from the calibinaire in an Italian port, a particular captain who had to marry the daughter of his yachts’ owner, the lavish lifestyle of charter guests, races and romances won and lost. It’s here yacht crews come to get off the boat, take a shower, and sleep in a real bed.

I’d walked into a writers paradise, full of characters and stories. The all-female crew from Maiden, of “The Whitbread Round the World Race” fame, had just arrived in Antigua and all eight ladies moved into Pineapple House. Bedraggled from a 10,000 mile voyage across the Pacific via the Panama Cannel, Pineapple House was the first shower and horizontal bed they’d seen in months.

“It’s not all yacht crews,” Libby adds. “We have honeymooners, travelers, couples, families looking for an affordable vacation.” A Dutch soccer player rented the enter place for ten days that fall, and brought in his and his wife’s families for a two week reunion. “There were twenty people here.”

Pineapple House and this cottage colony has materialized out of Libby’s artistic dreams. Nine cotages are scattered over the hillside above English Harbor in a style she calls "West Indian cottage chic." Just down the hill is South Point, a $500 a night hotel, with a swimming pool, a beach, and resturant. But it could be a hotel anywhere. Pineapple House is definitely Antiguan West Indian.

Libby was born and raise on Antigua, in English Harbor. Nelson’s Dockyard provided a playground for Libby and her two sisters Dana and Shelby. Their parents Rodney and Julie ran the vthriving yacht charter business Nicholason & Son Yacht Charters out of the old Powder Magazine. After sailing to ther Med, still in her early 20s, Libby went to New York to run the charter operation of Sparkmen and Stevens, the yacht design firm. Soon after arriving, in walked a hansone Canadian yacht captain. She married him and and had a grown son, Russel, nd a daughter, Christie, both living in BC.

Twenty years ago (2000) Libby returned to the island to take up a simpler life. Simpler life? I question that, as I watch her juggle a staff, guests, workmen, laundry, a thriving hotel business, with additional rental properties in Maine and BC, and an active social schedule.

“I wanted to get black to my roots,” she admits. On a hillside over looking English Harbor and the yacht club’s docks, she had a few of the “local boys” build her a cottage.

“Nothing fancy, mind you. Just a simple West Indian cottage.” There are no doors, no windows, just shutters to keep out the rain. There is no swimming pool, no fancy finished walls, just open rafters, studs, boards and bare wood floors. Air conditioning?

“We’re high enough to catch The Trade Winds,” Libby boasts.

“How did all this get started?” I asked Libby, seated in her “apartment” overlooking the yacht basin.

“Well, someone offered to rent my cottage when I was away, so I build another,” Libby explains. “Than another and another. There are now eight cottages scattered over the hillside, with names such as Frangipanny, Hisbiscass, and Rum Jungle. The “Crews’ Cottage” is one large open bedroom, with half-a-dozen queen and twin beds scattered around. “Its co-ed,” Libby explians. “Yacht crews are used to communal sleeping arrangements,” Libby throws off with a laugh.

The rustic cottages over the hillside, many just a single room, others with a modest kitchen, provide Libby with blank canvases on which to practice her art of color and texture. She uses fabrics to replace doors, shutters replace windows. Books, pottery and things Libby has collected occupy shelves adding a splashes of color. Fresh flowers besides the sinks in the moldest bathrooms give the place a lived in, homelike atmosphere. Libby loves pillows. They are scatters around, providing comfort and striking colors, all set against white-wash walls and ceilings.

I could move in. I’d spend the season, writing stories of a Caribbean Island life that’s fast disappearing. (In fact, I think I will.P) Libby and her sister Shelby are holding on to this romantic life of boats, adventure and the people who still seek of adventure and are eager to write their stories.

To take a look at the accommodations CLICK here.