Leopards of the Seas – Bermuda Sloops in the Golden Age of Piracy

By Liam Taylor

It could be said that the great warships of the English Royal Navy in the latter half of the 17th and through to the 18th century might be characterized by the Lion. The Lion stands proudly as the figurehead on Albion’s warships throughout the period, its looming muscular power threatening to smash and tear its foe to pieces in righteous fury, and by main force. If this is so, then the Bermuda Sloop can equally be characterized as the Leopard; no less a predator – the consummate hunter reliant on incredible turns of speed and maneuverability to bring down its prey in a welter of gore. You cannot outfight the Lion…but you cannot outrun the Leopard!

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Bermuda Sloop on the left (Firelock Games model from the 2020 Raise The Black Kickstarter and reproduced by kind permission of Mike Tunez)

Wherever you turn in the pages of the histories of the Golden Age of Pirates and Piracy you will find references to Sloops and, more specifically, to “Bermuda Sloops” either in the role of predator or as prey. Indeed, in American waters (and most especially in the period from 1700 to 1730) Sloops appear as the most common vessel mentioned as the choice of Pirate ship – fast, maneuverable and excellent upwind sailors that usually gave their owners the ability to overhaul any prey that they were pursuing, or outrun any pirate hunter that might be a threat. If the Sloop then became a popular craft for “the Chase”, then the Bermuda Sloop was a particular type of Sloop that was considered to be the very best of the best.

Sloops and Small Single-Masted Vessels

The word Sloop in the 17th and early 18th century is not entirely straightforward to define. In reality in the 17thcentury the word “Sloop” (or “Shallop” as it was originally rendered) really meant little more than a small flush decked vessel varying in size from a few tons to 100 tons or slightly more. Sloops could be one, two or three masted, and (in an age of much experimentation) carried a bewildering variety of rigs and sail plans. Generally, and there really is no way of being too specific here, they were characterised by being fairly long and thin for their size, making them fast and handy sailers; but beyond that they could resemble almost any number of craft of different shapes and sizes, from little more than large boats through to and including a layout that was more akin to that of a small Frigate.

Gradually however, particularly in Colonial waters as we move into the 18th century, the word “Sloop” often became associated with a single masted rig, dominated by a large fore-and aft gaff rigged mainsail and headsails. The English in Jamaica began building Sloops of this form in the mid/late 17th century, and the “Jamaica Sloop” became one of the most common sights in the Caribbean Sea. As both licit and illicit trading became more and more important to the Jamaican colonists these small light vessels, manned with relatively small crews, became so prevalent that this local trade became known eponymously as “the Sloop Trade”.

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A typical standard Sloop rig of the later c17th or early c18th with a large fore & aft mainsail and headsail. Note the absence of a Topsail (model by Firelock Games and reproduced by kind permission of the Blood & Pigment Team).

Naturally, such a handy craft that could work its way against the prevailing wind either into or out of trouble, soon became a common vessel in the hands of Privateers and Pirates. The Bermuda Sloop was a further evolution and improvement of this single-masted small vessel, which would go on to refine the design to become, at least according to some, “the best small ship in the world”.


Development of the Bermuda Carrying Trade

It might seem odd that Bermuda, the home of this marvel of maritime engineering, had virtually no shipbuilding industry for almost the entire 17th Century. In its first seventy years of existence, from its foundation at the end of the first decade of the century, the Colony built no more than fifteen or so ocean going vessels – extraordinary considering its location athwart some of the most important trade routes in the world.

After its initial settlement, Bermuda was under the control of a Private Company based in London, the Somers Isles Company. The economic model that this Company pursued for the colony was essentially that of plantation; sugar, tobacco and citrus fruits. In support of this policy however, the Company also banned ship building on the island – except under very rarely issued license – ostensibly to protect the island and particularly its dwindling Cedar trees, which were needed to prevent or at least slow soil erosion (which would damage their important cash crops). The real reason for the ban was that the Company was then able to mandate the export of all goods from the island back to England on their own ships, ensuring the company held down the price of the commodities themselves, secured their duties as owed, and made a turn on the carriage. If that weren’t enough, the Company also then monopolized the supply of goods into the island, again on its own “magazine” ships, ensuring all imports were bought by the locals at a massive premium.

The model they were pursuing was not that unreasonable to their eyes – it had proved successful in Barbados, the Leeward islands and (after its conquest by England) Jamaica. But it fostered in the Bermudian planters, many of them now second or third generation, a desire for reform and control over their own destinies – an independence of spirit that would explode over the next few decades, and most importantly for our story, a hunger for ships of their own.

Clearly the Bermudians weren’t that happy with this situation from quite early on, but to make matters worse, by the 1660s it was also becoming obvious that the plantation economy was failing. After initial successes, the Bermudan soil was proving unable to sustain the crop yields necessary. Tobacco worms and other blights fell upon the crops, and the cost of Bermuda grown goods just became too high to be economically viable. By the 1670s, a few planters had secured permission to build their own ships from locally grown cedar and were able to ship some goods to and from the island to supplement their incomes. In 1684, the bankrupted Somers Isles Company was liquidated, and control passed to a Royal Governor, who rescinded the ban on shipbuilding in 1687. The tobacco fields were turned over to livestock or replanted with local Cedar trees. Bermuda had failed as a plantation – and if there was to be a future for the Colony, a new economic model was necessary; an economic model that looked to the sea as much as to the land.

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Sloops in New York harbour of varying sizes (from an engraving by William Burgis dated to 1717)

Fortunately, Bermuda sits in the Atlantic at a strategic point across the intersection of a number of vital trade routes; from the West Indies to the American colonies or back to England, and from the American colonies to the West Indies. Ships passing Bermuda could buy supplies, or sell parts of a cargo for breaking down and onward shipment to a host of smaller ports and markets. Free from the Somers Isle Company, Bermudians rapidly began to use their geographic position to become highly proficient in the “Carrying Trade”, freight forwarders if you like; from there they quickly found that they could become principles and merchants in their own right, dominating the small merchant cargo markets between the various colonies and their lesser ports.

The “Bermuda Sloop” was born from this explosion of Bermuda trade in the 1690s and early 1700s, and was the perfect tool for the job.

The ships that the Bermudians needed had to be small, but capable of handling a reasonable cargo for their size; they needed to be capable of sailing both inshore and over deep water to cross the open Atlantic, able to access smaller ports and estuaries, and then make it back again home (and across Bermuda’s notorious rocks and reefs); they needed to be good upwind to access different markets through the different seasons even when the prevailing winds were against them; and they had to be fast – both since the commodities they carried were often perishable, and since the seas they plied were already haunted by hostile privateers and pirates. The single-masted, fore and aft rigged Sloop was the obvious platform that answered these requirements– and the Bermudians began to build their own improved version of the Sloop in huge numbers.

The Bermuda Sloop

Bearing in mind that up to 1687 and the rescinding of the ban on shipbuilding the Bermudians had only built about fifteen ocean going ships in some seven decades, the explosion of shipbuilding on the island was remarkable. By 1700, Bermuda boasted a merchant fleet including “four ships of about 100 tons, six brigantines from about 40 to 70 tons, and sixty sloops of 30 to 40 tons” (Edward Randolph, Surveyor of the British Colonies). In addition, there were three to four hundred smaller boats and lighters for coastal work, acting as tenders, local transports and fishermen – many of which may also have been rigged as Sloops. Every year, more and more Bermuda Sloops were being laid down, and planters would start building a new Sloop as soon as one launched – since they became so popular as a design that they could be sold on after a year or two in almost any port, just as soon as the next one became available. By the second decade of the eighteenth century, Bermuda Sloops (whether Bermuda owned or not) were to be found everywhere from the Caribbean to Newfoundland and beyond.

By roughly the end of Queen Anne’s War the Bermuda Sloop had reached its mature form, but what was it that made these ships so successful and so popular? What improvements were made to the Sloops that gave them such an advantage – and why did they become so prevalent amongst the real Pirates of the Caribbean and North American Atlantic Seaboard?

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A Bermuda Sloop without a topsail, and with her sails being taken in (Pierre Ozanne)

As with many smaller ships of the later 17th and early 18th centuries, there are few detailed descriptions or pictures that can be definitively identified as “Bermuda Sloops”. Nonetheless, we can piece a good picture together from the various accounts and drawings that do exist, and in particular from a draft of the 1740s published slightly later in the 1760s by Frederick Chapman (reproduced below).

The general layout of the Sloops was as a small flush deck vessel. Flush deck just means a single continuous deck above a hold area, although larger ones may have mounted small platforms in the hold toward bow and stern to accommodate the small crew and assist in stowage. At the stern the larger Sloops would have a quarterdeck/poop over a small cabin at deck level, or alternatively some Sloops’ decks would have been stepped down to form the cabin beneath the quarterdeck for the Master and any passengers. This cabin may have had small windows or lights on each quarter but were often only illuminated by scuttles in the deck above or the bulkhead forward. The Rudder head ran up through the deck level to allow steering by a long tiller, although a few might possibly have used a wheel in later years. Generally our Bermuda Sloops were in the 30-60 ton BM range, and around 40 to 60 feet long on the deck; but larger ones were also built – Chapman’s example being closer to 120 tons BM and 65 feet.

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Chapman’s Bermuda Sloop. The waterline is the straight line marked in blue and clearly shows the increased draft toward the stern – referred to as ‘Drag”in the text.

Most Bermuda Sloops were pierced for guns, usually light 3-4 pounders with anything from 4-12 being carried (averaging 6-8 probably); nonetheless, many would have sailed unarmed or carrying just a few swivel guns for close defence.

The most obvious and distinguishing feature of the Sloop is its rig. In Bermuda Sloops the mast was often raked back more steeply than was the case in other Sloops, giving quite a distinctive appearance, and increasing speed and performance upwind. All Sloops had a large gaff rigged mainsail (the spar at the top of the sail), and by the time the Bermuda Sloop was being perfected, had added a boom (spar at the foot of the sail) that allowed it to increase significantly the size of the sail and improve its handling. Over time both the gaff and boom increased in length, again allowing for a larger more powerful sail to be carried, and this increase in sail area was a feature of the Bermuda Sloops.

Headsails were of the triangular fore and aft variety and usually two or three in number; the Bermuda Sloops tended to have a noticeably longer or extended bowsprit, usually adding a jib boom which again allowed for larger or extra sails to be carried forward.

Finally, as far as rig is concerned, the Bermuda Sloops tend to be depicted with a square Topsail Yard and Topsail, its foot secured to a “cross-jack yard” sitting immediately above the gaff. Early Sloops tended not to have this feature, but on Bermuda Sloops it seems quite common. Early variants of Topmast and Topsail may have been jury rigged, mast and yard being hoisted aloft for use in the right conditions, but by the 18th century they appear to be more of a fixture, further distinguishing the Bermuda Sloop’s profile. Adding the topsail again allowed for an extra turn of speed through the water, especially when sailing downwind, but was probably struck when sailing close-hauled.

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Rig of an 18th century Bermuda Sloop as suggested by Howard Chapelle. Note the topsail, extended jib boom and large sail plan. Although there is the outline of an additional square main course here, it is unusual to see this in other depictions of Bermuda Sloops actually under way from the period, and if carried was probably only set when the gaff rigged mainsail was not in use.

As distinctive as the rig was for the Bermuda Sloops – with their signature rake, long bowsprit and topsail – the hull itself was also extensively modified and improved by the Bermudians. Bermuda Sloops were built from Bermuda Cedar wood, a unique variety of Cedar which proved excellent for shipbuilding. Bermuda Cedar is hard and durable, but at the same time comparatively light. This combination of durability and light weight gave Bermuda Sloops great longevity, two or three times that of other common woods used at the time; and it made them strong and rigid for the size of their timbers, most excellent traits for a ship that wants to go fast and point to wind well.

The shape of the hulls were also modified from their Jamaican cousins. The great historian of American colonial shipbuilding Howard I Chappelle gives the following description of a typical hull form;

“The Bermuda sloop was wide and deep; the entrance was short, convex, and full; the run line long and fine. She had moderate drag to the keel, much rake to the stern post, and a well-rounded rabbet. The sheer was marked with a high-crowned roof over a stern cabin, The midsection was formed with a straight sharply- rising floor, high well-rounded bilge, and upright or slightly flaring topside. The midsection form eased the sweep of the buttock-bow lines, reducing the average cambers sharply over what a flat-floored midsection with the same relative length and depth of hull would require. This sloop hull had good flow lines for her proportions, being without sudden change in overall form or excessive fullness anywhere under water. She would sail well on the wind as far as the cut and material of her sail would permit.”

Some of the key points here are worth examining. Bermuda Sloops are regularly noted as being “wider” in the beam and “deeper” than other Sloops, and the floor of the hull is noted as “sharply rising”.   The underwater lines of the Bermuda sloop can be imagined then as being very smooth, reducing resistance and allowing her to cut through the water; the shape of hull toward the keel was more of a V (from the “sharply rising floor”) than the common U shape, which would have increased her draft slightly, but also given her speed and reduced heel (much like the keel on a modern racing yacht). The “moderate drag” to her keel also became a feature of Bermuda built vessels, “drag” being an increase in the amount of water a ship draws as you move toward the stern, enhancing her ability to point upwind.

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Bermuda Sloop mid 18th century (artist unknown)

One interesting by-product (or perhaps intended consequence) of this unusual hull form was that Bermuda Sloops were often underestimated for tonnage by the authorities. Burthen Tons were calculated by a formula based on length multiplied by breadth (LxBx1/2B divided by 94), but with extra depth to the hold than usual the Bermuda Sloop was under-rated by between 5% and 10%. Since Customs Tolls were paid in most ports based on a ship’s Burthen Tons, the Bermudians gained an advantage in paying less for their actual tonnage. Less tolls, less cost, more profit. Alternatively, if a diligent customs official were paying careful attention to the ship’s “lading” (cargo carried), the clever Bermudian skipper might find he had a few “extra” tons of unfilled cargo space on board that the official would not notice, and he might fill that space with goods that were perhaps more in the way of untaxed contraband…

Rapidly the Bermudians became major players in the Colonial carrying trade, assisted by their very uniquely designed and highly cost effective small Sloops. Both they and their vessels became completely integrated into, and a very visible part of, life in the Caribbean and North American world of the 1690s and early 18th century. Thanks to their draft and rig, they could sail almost anywhere reliably, and their speed could get them to market fast and (if necessary) keep them out of trouble.

The Bermuda Sloop was a hull form built to fly; light, sharp but surprisingly spacious and able to carry a good cargo. Great for inshore work, they were equally at home on the open ocean (some larger ones even sailing as far as the Indian Ocean). Their rig complemented the modified hull form perfectly, and (although pirates and privateers sailed with larger crews) they actually needed only a very small crew to handle the simple suite of large sails – 5 to 10 men being common in a merchant.

Smugglers, Privateers and Pirates

Although the Bermuda Sloops were designed initially for the Carrying Trade, it did not take long for their excellent qualities to become recognised by other, perhaps more dubious members of the sea-going fraternity. Speed, ease of handling, a stable platform, the ability to sail tight to the wind and close inshore soon meant that Privateers were taking Bermuda Sloops to cruise for prey, and Smugglers were using them to run the gauntlet in and out of their secluded inlets and ports of call.

The Bermudians themselves took quickly to Privateering and to “interloping” (smuggling in the eyes of many), and several famous names became associated with Bermuda merchants and planters who seemed to walk a somewhat equivocal legal line on occasion. Interlopers were essentially traders who broke the monopolies of the various mercantile operations such as the East India Company by sailing into “their” waters (usually on the West Coast of Africa or into the Indian Ocean) in search of cargoes with which they could undercut the market back in the Americas. Bermudians, including perhaps the Governor, appear to have participated keenly in sponsoring such activity; Thomas Tew for example (the famous Pirate who was the first of the North American rovers to sail to the Red Sea in search of prizes) appears to have operated out of Bermuda as an interloper/smuggler earlier in his career before making his name as a Privateer and then Pirate. His Sloop (the Amity), was almost certainly of Bermuda design, and he sailed it from America all the way to India to plunder the Pilgrim Fleets of the Mughal Emperor not once but twice. Similarly, and at about the same time, there are suggestions that Henry Avery himself may have worked for the Bermudan Royal Governor in bringing slaves back to the Americas possibly without proper authority; this opens the interesting possibility that Avery and Tew might have actually met on Bermuda some years before their supposedly fortuitous encounter in the Red Sea at the same time and in the same place as several other pirates – again to hunt for Indian shipping.

During the 1690s several Privateers operated out of Bermuda, and this continued and expanded through into the 18th Century and Queen Anne’s war. Amongst the most famous of these Privateers in the early 1700s was Henry Jennings, who later moved to Jamaica and then Nassau. From a well-to-do Bermuda family, Jennings was a leading Captain in the famous Flying Gang that operated form New Providence, and became one of the main protagonists in the switch from legitimate Privateering to outright piracy. The Bermuda Sloop had found a new role as a lethal hunter amongst the new wave of raiders and pirates that burst onto the stage in the wake of the Treaty of Utrecht that ended Queen Anne’s War.

David Cordingly in his book “Under the Black Flag” notes that between 1710 and 1730 over half of the attacks by Pirates in American and Caribbean waters were made by “Sloops”. Almost every major Pirate of this period, and most especially those who based themselves out of the “Pirate Republic” at Nassau, is noted as sailing a Sloop for part or even the majority of their careers; Jennings, Vane, Hornigold, Bellamy, Rackham, and of course the infamous Blackbeard himself, all sailed Sloops. Whilst it is impossible to be certain what kind of Sloops many of these were, the overwhelming likelihood, due both to their ubiquity and their utility, is that the majority were the Bermuda Sloops described here.

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Bermuda Sloop on the right (Firelock Games model from the 2020 Raise The Black Kickstarter and reproduced by kind permission of Mike Tunez)

The Bermuda Sloop was perfect for these rovers; the vital speed which the Bermuda Sloop could unleash allowed a hunter to swiftly overhaul potential prey, and use their extreme agility to outmaneuver their victim if they tried to turn and fight by ducking out of the arc of a broadside and closing on the stern or quarter to board. Alternatively, as the authorities began to take measures to hunt down the Pirates, the Bermudan could use that same speed to escape, often heading upwind where a larger square rigged vessel could not hope to compete in a chase.

The Bermuda Sloop could make lengthy voyages across the open seas between the Caribbean and the North American coast (or farther afield) fairly swiftly, allowing the Pirate to disappear and move to new hunting grounds if necessary. But their handiness and shallow draft meant they were equally at home in the bays, keys and shallows that lined the thousands of miles of coastline throughout the New World. Being so low in the water (Bermuda Sloops had a fairly low freeboard) also meant they could hide; with sails lowered a Sloop could lie in the troughs of the waves waiting for their prey to unwittingly close, only spotting the danger when the hunter raised their sails for the final dash and assault; or they could lie close into shore obscured by reefs and cays, avoiding the authorities while being able to pounce on any potential prize.

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Blackbeard and his Sloop the Adventure (Firelock Games model from the 2020 Raise The Black Kickstarter and reproduced by kind permission of Mike Tunez)

As a fighting platform the Bermuda Sloop also enjoyed several advantages over other small craft and Sloops. Their slightly greater breadth and depth made them heel less under a full press of sail, resulting in a more stable platform for using the great guns. Speed and maneuverability enabled them to dictate the course of any fight, by allowing them to close or extend the range as the situation demanded. Whilst small and able to be sailed by a mere handful of sailors, the Sloop could still carry a fairly large complement of men, 40-50 not being unusual (even more for relatively short cruises) – which was more than enough to overwhelm the small crew of a hapless merchant.

Of course there were some disadvantages to the design. The Bermuda Sloop was not suited to a prolonged exchange of broadsides due to her lightness of build, and a single mast made her vulnerable to being disabled. Although they were able to sail long distances (even as far as India) a larger square rigged ship would have made for a far more comfortable voyage; in truth, Bermuda Sloops were really at their best when operating close to a nearby base like Nassau or Port Royal. Overall however, these disadvantages were outweighed (particularly in close or inshore waters) by the Sloop’s significant advantages in design and performance. Pirates would often sail with a number of Sloops in a small squadron, spreading the risk of being dismasted or holed, and increasing the intimidation that their victims would feel by seeing themselves so obviously outnumbered.

The very popularity of the Sloop amongst the merchants of the Americas also made the Bermuda Sloop a great choice for the aspiring Pirate; they were so ubiquitous that it was often impossible to tell what a Sloop was up to when first spotted; a harmless coastal trader or tobacco merchant going about their business, a fisherman perhaps, or maybe a smuggler quietly trying to avoid the authorities; or perhaps a Pirate slowly stalking toward you ready to make a final dash – but when the attack came, it would be at the ferocious acceleration and speed of the Leopard.

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