Sailing in the Caribbean  

I spent many New Year's holidays sailing in the Caribbean. Each December, after I turned my grades in to the Registrar’s office of Chicago State U., and after a visit to Kansas City, I returned to Chicago, and Bob and I would fly to San Juan and thence to St. Thomas, to sail aboard a tall ship around the Virgin Islands..  This practice began in 1974 and continued until Bob and I broke up in 1981. Later I found a fellow sailor, Diane Goodson, to sail the Virgin Islands with.

St. Thomas

 I fell in love with St. Thomas that first visit in 1974.   I loved the balmy mornings, the sudden afternoon showers.   Before boarding, we stayed several days at the historic 1829 Hotel, while Bob introduced me to the island —to Megan’s Bay with its wonderful beach; to the Mafali Hotel, at the top, with one of the best views of St. Thomas Harbor; to the Windward Passage Hotel; to Bluebeard’s Castle; to the Charlotte Amalie Harbor with all its tall ships that each had a story, and to Sparky’s Waterfront Saloon, where we went in the evenings to listen to the crews off the ships, telling their stories.     Most of all we wanted to see the Maverick, a ship Bob had sailed on before and wanted me to experience.

The Maverick sailing in the Virgin Islands in 1974.

A Typical Sailing Week on the Maverick

We were signed up for a 7-night cruise on the Maverick, under Captain Jack Carstarphen and his wife Dee.   The Maverick was a 76-foot gaff-rigged, topsail ketch, “built on the lines of a Brixham trawler—it was built in Brixham, England, in 1935, by LTC, Claude Beddington, and christened as Cachelot.   The boat made two cruises before the war, which are recounted in Beddington's book, We Sailed from Brixham. Taken by the British navy for patrol duty during the war, the stocky ketch was strafed by a German Stuka in the English Channel and the colonel/captain was killed. ‘Captain Jack used to claim that when the ship was in danger, the colonel's ghost tapped his shoulder to warn him,’ Dee Carstarphen recalls. The big ketch was sold after the war, when she became Maverick, and brought, under an absentee owner, to Antigua in 1956.”   ( from an article on Dee Carstarphen. You can now find her books for sale on the website of her husband Stuart Hopkins. You can now find her at her husband's website for Dabbler Sails)


Dee and Jack Carstarphen on the Maverick in 1974

When Captain Jack bought the Maverick in 1960, he modified the interior, adding the eight pilot berths in the main salon. Working out of West End, Tortola, theMaverick carried 14 passengers (and 6 crew): 6 in three private cabins, and 8 in the main salon. People came for a week.   The original main and mizzen were wood but later he converted them to steel, selling the old wooden main mast to the America’s Cup winner America for a bow sprit. Captain Jack, who was British and had been in the Royal Navy, ran his ship with order and discipline.   No breaking out the booze before we were anchored (as was the practice with the Windjammer Cruises), and “the sun was over the yard arm,” usually around 4 p.m.

I loved the Maverick

We passengers helped the crew. The first mate showed us what to do.    He divided us into a starboard and a port watch, in 4-hour watches, to keep an eye out for pots, take the wheel, scrub the deck and the brightwork in the mornings, and stand by to raise or lower sails or come about.   We sailed every day, and anchored every evening in wonderful little harbors, bights, and bays, e.g. Cane Garden Bay.   We lined up to handle the halyards and learned how to “sweat” the last foot or so. Lunch was on deck, made by Fernando, the cook, from St. Lucia and looked like a pirate with his gold hoop earring.   A typical dinner was his shrimp creole.   His pumpkin soup was famous— Dee designed and put together the Maverick cookbook from all Fernando’s recipes.    

Captain Jack called his business Westindiaman Cruises. He and Dee had operated it for many years (more than 14, since the Maverick Club Newsletter, The Westindiaman, which I have, was No. 14).   Jack wanted his passengers to have fun, to escape from problems. He said “At the beginning of the week, when you’ve just arrived from the plane, you’re all tense, but as the week goes on, you gradually relax, until you’re completely relaxed, and then it’s time to get tense again and head back north.”  

Sailing plan for the Maverick's week-long cruise
(Map by Dee Carstarphen)

On a typical sail, Maverick headed out of Charlotte Amalie on St. Thomas and sailed upwind (the Easterly trade winds blow from the east) into the British Virgins, going through customs in Cruz Bay, St. John’s.   We raised   the sails—the main, mizzen, main topsail,   jib, jib staysail and flying jib.   We were on “pot watch,” making sure we didn’t run over any fisherman’s pots, when we   saw the Flying Cloud, a three- masted schooner, closing in on us as we were nearing Tortola.

The Flying Cloud at anchor.

Our alert captain signaled us to fall off and come about and bear north toward Jost Van Dyke, our first anchorage in Great Harbor.   Since it was December 31, we were heading for the New Year’s party at Foxy’s, a shed on the beach of Jost Van Dyke.   Heading ashore in the Maverick’s lifeboat/tender we had a vision. A boatload of beautiful young girls went floating by singing in the night, as if they were sirens of water nymphs.    We met the famous Foxy, danced in the sand, drank rum with a bit of coke, scratched at the “no-see-ums” that were biting our ankles. We were relaxing and getting into the Island rhythms.

Jost Van Dyke

The next morning we climbed up the mountain on Jost, (the highest in the Virgin Islands), looked at the ruined sugar mill, then sailed off for Marina Cay on Tortola. Near Beef Island, while Bob was at the wheel and we were flying along, we heard a loud boom.   I thought we had struck a reef, although there wasn’t any concussion.   “Broken bob stay,” the first mate shouted.   We turned on the motor and took down the headsails, so that the great strain on the bowsprit wouldn’t break it, now that the bobstay was broken.    We headed for Marina Cay, where we anchored overnight while the bobstay was being repaired.    Next day we sailed to Virgin Gorda.  

Virgin Gorda

I was learning the local lore.   Columbus had discovered these islands, and called them after St. Ursula and her thousand virgin companion.   The Virgin Gorda he named because it looked so very fat.   Our first stop on Virgin Gorda was the Bitter End , the peninsula jutting out at the far eastern end of the islands. In the sailing days of yesteryear, the last nub of land that galleons and schooners passed on the long journey back to the Old World was the North Sound of the British Virgin Islands - known as the "bitter end". Today, this remote peninsula of Virgin Gorda holds one of the busiest resorts in the Caribbean - "one which remains true to the nautical tradition of wind, water, and sails” -- the Bitter End Yacht Club which was only a small marina then.   Since then, I read that it  has slowly grown to become “a huge self-contained complex which caters to visiting and vacationing yachtsmen, boaters . .”

Virgin Gorda

Our next anchorage was everyone’s favorite -- the Baths at Virgin Gorda.   We went ashore and waded amongst and climbed upon the gigantic boulders that were piled on each other to form caves.   Later we played in the pools inside the caves.   As Virgin Gorda was at the "bitter end" of the Virgins sailing eastward, we were now sailing back home, westward, downwind through Drake’s Passage, the inside passage through the Virgins.   Our next stop was Salt Island, one of the “Little Sisters.” (Norman Island --the original “Treasure Island”--, Peter, Salt, Cooper, Dead Chest, Pelican and Ginger Islands.)   Salt Island is the site of the wreck of the Rhone, where the movie The Deep with Jacqueline Bisset was filmed. ( Read about it at   We snorkled on the RMS Rhone as well as on other spots around these islands.  

Our next stop was the bight at   Norman Island where we took the dinghy into the cave that is supposed to be where the treasure was hidden in “Treasure Island”, based on Norman Island.  

Anchoring at Norman Island to see the Treasure Island cave

Our last island stop was St. John’s, where we first anchored in Leinster Bay to visit the Annaberg Sugar Plantation.   As we were walking along the shore , heading for the Annaberg Sugar Mill ( St. John’s had been a huge sugar producer back in the 19 th Century),   Jack bent over a piece of driftwood and suddenly held up a doubloon that he had just “found.”   I believed him.   I always fell for tricks like that.  

On our last night we dropped anchor for the night in Caneel Bay.   As usual, the crew put in the swim ladder, and we dove over the side with our snorkel gear on.    Snorkeling under the boat that afternoon in the blue-green water, I saw a giant sea turtle.   That night we had our farewell party.   Jack gave everybody a badge as the best at something.   I was the best dancer!  


The years spent on the deck out in the sun were taking a toll on Jack’s fair skin, so he was seeking to sell the boat and business that year.   That was Jack’s last season.  He must have had a premonition.    He sold the Maverick, and we later heard that he had died of melanoma in 1975, after an illness of only 4 months.    I am grateful that I had the chance to sail with him once—on his last year.  

The next year we sailed on Maverick again with the new skipper, but he was nothing like Jack.   He complained about the expenses, about having to get a new mast, etc.   With him the boat wasn’t an escape but a big problem.   We didn’t sail on it again.

Maverick was wrecked when Hurricane Alan struck Charlotte Amalie in the fall of 1996. Dee remarried a sail maker and now lives in North Carolina where she is an artist and writer.

The Tiki

In 1976 Bob and I looked around for another tall ship for our New Year’s sail.   One that sounded good was the schooner Tiki, which the ad claimed was the original schooner that had been in the TV series Adventures in Paradise.   (I looked this up and found that the original Tiki had been renamed Sea-Spray and was chartering in the South Pacific.)   We all believed that we were on the original Tiki, which made its present condition all the sadder.   It was big--100+ ft (135 with the bow sprit), but it was dilapidated.   The wood was rotting.   Someone went through the deck the first night.   The electrical system did not work.   We had no lights, and we had to take buckets of water below whenever we wanted to flush the head.    The 3-man crew (6-man was the usual) consisted of   Julian, the first mate, John, the second mate, who wore the same pair of dirty shorts the entire week, and his not too clean girlfriend, Mimi, our cook.   It was the captain’s first time in these waters.   He did not know the reefs or passages.   Fortunately Julian was local and steered us through all the hidden reefs.   The owner was in New York and had not (so the captain claimed) sent any money to provision the ship, so we had to forage for food.   Julian got us a lamb off the island he was from.   Other days we brought back conch from diving, and these became conch fritters under Mimi’s inexpert hands.   (A number of us wondered if our severe indigestion that night could have come from this meal.)  

The passengers on this cruise had come from all over the country, including a number of students from a college in Schenecdoty, New York, who had come to learn to sail a tall ship and were getting college credit for the cruise.   The first day they spent labeling all the halyards and sheets.   Their three leaders did not join us in our complaints about the ship; they did not want the students to get into a complaining mood, so they kept them busy learning about ships and the sea.   There was a marine biologist among them, who dissected everything we brought aboard, including a conch, which she spread out on the deck and labeled.   Bob and I and a few others were lucky these students were aboard, for we joined in their lessons and ignored the complainers, notably a couple from New York City who had read the ad for the Tiki in New York Magazine, and were furious that it was far from an adventure in Paradise.   It was an adventure, all right, only not the one they had expected.   They showed up what that was when they wore different expensive yachting clothes every day.   They finally gave up and got off at Virgin Gorda, and stayed at the Bitter End, which was well-named as far as they were concerned.

The Tiki at the Bitter End

The Harvey Gammage

            We also sailed on the Harvey Gammage, several times, since it was run more like the Maverick, had a full crew, was clean, orderly, provisioned, and the heads worked.     


The Harvey Gammage at anchor 

The Roseway

 By the time Bob and I split up, I owned my own sailboat, Rum Tum Tugger, a Cape Cod Cat , which I sailed on Lake Michigan out of Jackson Park Harbor in Chicago in the summers, but I continued to sail in the Caribbean out of St. Thomas in the winter.   Diane Goodson had a Cape Dory in the same harbor with me in Chicago and we became sailing buddies. In 1991 she and I sailed on the Roseway, with Capt. George Sloane. It was her first time in the Islands and she fell in love with them. She cherished the memory of that sail, her last in the islands. She died of breast cancer a couple of years later.  

The Roseway--Diane taking down the jib.

Capt. George Sloane was really a good skipper.   He was on The Roseway for a number of years before it was sold to a sailing school and hauled out for a complete redo in Camden, Maine, where I saw it anchored in 2002.