A path between thorns: Sailing the windward route from the Bahamas to the Windward Isles

James and Jayne Pearce braved ‘the thorny path’ in the spring of 2023 with the help of Bruce Van Sant’s cruising guide The Gentleman’s Guide to Passages South – The Thornless Path

“You’ll never make it.” Our conversation with fellow cruisers about our plans suddenly ground to a halt. We were in Annapolis, on the east coast of the US, enjoying the city’s famous October boat show. We’d spent the last few months sailing from Boston to Maine, and were now in the Chesapeake shaking down Scout, our new Garcia Exploration 45. We were feeling pretty good about our progress so far.

At dinner one evening, we were chatting to some experienced fellow cruisers and the topic turned to our plans for the coming season. “Well,” we said, with bright-eyed enthusiasm as we imagined the island-hopping paradise ahead of us, “we’re heading south to Grenada.”

Their concerned response didn’t relate to an enjoyable few months in the Windward Islands, however, nor the beautiful Bahamas. Instead, with a glimmer of fear in their eyes, our friends were thinking of the section in between, the infamous ‘Thorny Path’.

First named as such by Christopher Columbus, this is a notorious sailing route that leads from the Bahamas, by way of the Turks and Caicos, Dominican Republic, Puerto Rico, the Virgin Islands and the Leeward Islands, to the Windward Islands. As you cross the Tropic of Cancer and hit the northern edge of the tradewind belt, inexorable 15-25 knot winds blow from the east, day in and day out. To reach the West Indies, you have at least 1,000 miles of sailing almost directly into them, together with the unpredictable currents and island effects that Columbus himself faced.

It’s a route that still proves a challenge to modern sailors. Hundreds of cruisers come down from Canada and the US to the Bahamas every winter, hoping to make the jump to the Caribbean in the spring, but you only have to look at the sprawling anchorages in George Town to realise that many soon get dissuaded or turn back, treating the Exumas as their terminus.

And the only alternative, the deceptively friendly-sounding ‘I-65’ route, is no easier. It involves staying north, heading out into the Atlantic for over 1,000 miles before turning south to the British Virgin Islands. Just six months into our full-time sailing lifestyle, we weren’t ready for such a large offshore passage, and the scare stories from that route sounded even worse. We were just going to have to tackle the thorns head on.

And so, as we wandered home on that balmy Maryland evening, we realised we needed to get serious. Scout is a high latitudes expedition boat and we bought her because we knew she’d always be a better boat than we are sailors. But we were going to need to plan ahead.

The path begins

We soon learned that the trick to the daunting Thorny Path was breaking it down into a manageable series of shorter sails. Some would be day-long, while others would be carefully timed overnight trips. Each would hinge on conditions; we were often going to need to wait for fronts to bring crucial northerly components to the prevailing winds.

By early February we’d made it down to George Town, and the conditions and timing to start the route were finally aligned. At the start of a week of forecasted light east-north-east winds, we departed the cays, into decidedly bluer waters, heading towards the more easterly outer islands of the Bahamas. Scout was finally on the path.

So far so good. We tacked and close-reached on a series of day sails to Long Island, Conception, Rum Cay, and the protective anchorage of Attwood Harbour on Crooked Island’s north-east coast.

But on our final hop to the most easterly Bahamian island of Mayaguana, the trades strengthened again. We willed ourselves into believing there was still a northerly component to the wind, but what started as a light, close-hauled sail ended with a bumpy four- hour motor into a headwind. Thorny indeed, and we learned that day the importance of patience.

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Mayaguana is where many cruisers linger to start their passages south, and after several days of solitary sailing we’d been keen to meet up with some of the dozen other yachts there to discuss passage plans. Our arrival coincided with a brooding mass of cumulus building to the east, and before Scout’s anchor was even secure, everyone else seemed to be lifting theirs in a seemingly synchronised evening exodus.The last of the boats passed us by as we settled in. Was it something we said?

Fortunately the squalls passed quickly, and while we considered catching up with the overnight caravan, lured by a safety in numbers mindset, the temptation of a hot roast chicken, a cold glass of chardonnay and an early start the following morning seemed much more appealing.

The next day’s sail was energetic and everything we’d expected of the route’s first bluewater offshore leg. One lesson we have learned from sailing Scout is that she thrives upwind; her sweet spot is at 42-45° apparent wind angle, coupled with decent wind and full sail.

Luckily, that was exactly what we got. Despite the big sea state we had the winds out of the east at around 20 knots and our angle to Providenciales in the Turks and Caicos was perfect. We rattled along at over seven knots.

The islands of the Turks and Caicos sit around the incredible blue waters of the Caicos Bank – which, after a few days in Providenciales, we needed to cross to the south-east. It is only about 40 miles to South Caicos, but given the distinct shallowness of the bank and the numerous uncharted coral heads, we opted to motor. Though we were dead into the wind, the shallow waters made for a comfortable crossing before we anchored next to Cockburn Harbour with its desolate, deserted salt pans and curious donkeys.

The 110-mile sail to the Dominican Republic would be the route’s first overnight passage for us. There are several destinations worth considering, including Puerto Plata, Luperon, or even further east to Samana if the winds allow. But our sights were set on the former, partly because of the lure of a marina and the chance to rinse months of salt off Scout’s decks.

After a few days in South Caicos’ swimming pool-like waters, we spotted a weather window, but it would be brief, so we had to time it carefully. Not long after we’d indulged in a final morning snorkel, the wind turned abruptly north and we quickly raised anchor and set ourselves on a sweet south-easterly course.

Racing out from the banks we decided to put out a fishing line and almost immediately we got lucky. After weeks of little success, the haul kept us motivated through our evening watches. As the night passed, a subtle scent of petrichor grew and hinted at our destination. The pre-dawn light confirmed our sensory suspicions and the sleeping giant of the mountainous Dominican Republic emerged on the horizon.

Dominican surprises

After the sandy slips of land we’d been sailing around in the Bahamas, the vastness of Hispaniola was quite a sight. The effect that this mass of land has is significant. During the day, winds are accelerated around the high rocky coastline in unpredictable ways, while at night and in the early morning there’s a ‘night lee’, a cushion of calm caused by the land breezes blanketing the prevailing trades. Many guides to sailing the Thorny Path recommend using this phenomenon to its best advantage, making overnight hops along the coast in the katabatic bubble and arriving at your next destination before the trades start to dominate again.

As we approached Puerto Plata we were rudely introduced to this. Sailing into wind, and a few miles north off the coast, the clock struck 0900 and the night lee lifted. Scout abruptly swung 90° to the west. Noted!

Culturally, as well as geographically, the Dominican Republic was a shock. We had to scrape together our rudimentary Spanish vocabulary to get by in the bustling coastal towns. The sights, the sounds and the smells were all different to what we were used to.

With rough seas forecast for the week after our arrival, we took the opportunity to drive inland to the mountain town of Jarabacoa and historic city of Santiago de los Caballeros, and these trips gave us a glimpse of the interior of this wonderful country.

But it was soon time to push on. We needed to reach Samana, on the north-eastern side of the island, before the more challenging jump to Puerto Rico.

The Navy likes to keep track of boats’ movements along the coast, and so we registered our intent and set off, first to the small town of Río San Juan, a pretty place that specialises in officially sanctioned artistic graffiti, then the anchorage at Puerto Del Vella, and finally into the protection of Samana Bay and the excellent Marina Puerto Bahía.

The dilemma for each of these hops was choosing between day and night sails. At night the wind and waves are calmer, but day sails bring one distinct advantage: there’s a shelf that comes several miles offshore and it’s shallow enough for the local fishing community to lay seemingly endless pots and barely visible nets. The night lee stretches about five miles offshore, but there are fish traps as far as four miles out, so it’s a narrow path to thread in the dark.

With her twin rudders, Scout isn’t a fan of floating objects and fishing lines – and neither are we. So we opted for early morning motorsails, opting to bash upwind in daylight rather than risk becoming incapacitated in a maze of nets in the dark. With mostly lighter winds that week, our strategy paid off.

The Mona Passage

Six months on from the ‘You won’t make it’ prediction, we were in Samana, and about to tackle the biggest challenge of all: the notorious Mona Passage.

Stories abound of rigging damaged from sudden storms, treacherous shoals, and the unpredictable equatorial current. So we wanted conditions to be just right: ideally a large front passing to the north of us, strong enough to provide its own protective veil from the trades for the 24 hours we needed.

With nothing coming for a while we sailed across the bay to the outstanding Los Haitises National Park, where a dramatic limestone karst coastline of conical hills, cliffs and mangrove-hidden caves come down to the waterline.

But it wasn’t long before we spotted a suitable front, and that was our big opportunity. One well-regarded cruising guide recommends hugging the coast at night, and crossing the Mona Passage north of Hourglass Shoals during the day.

But with 12 hours of light southerly winds forecast followed by 12 of lull – and given our aversion to fish traps – we decided on the opposite. We’d tackle the Passage itself in the dark.

A fluking humpback whale seemed to wave us farewell as we traversed the Dominican Republic coast in perfect 10-12 knot conditions. As evening fell the forecasted change arrived and the light winds dropped to a mere whisper. Perfect.

We furled sails and motored east. Nature had even more resplendent plans as the light from an incredible full moon radiated down on Scout, casting an ethereal glow over the tranquil waters around us. This would be our completely unexpected memory of the Mona Passage: in complete contrast to its notoriety, it emanated an overwhelming sense of peace.

Puerto Rico to the Virgin Islands

Once dawn rose, a video call to Puerto Rico Customs and Border Control made for a painless clearing-in process – having British and American citizenship has its perks.

Sailing east along the south coast of the island would normally involve a week of tacking, but again the weather gods were smiling on us and the remnants of the front we’d ridden miraculously gifted us moderate westerly winds. A few days of rare spinnaker sailing took us to Isla Caja de Muertos and some sweet reaching to Salinas (much-needed re-provisioning opportunities), and Patillas. We stopped in at Palmas del Mar and sprawling Puerto del Rey marinas to meet up with family, and take a weekend break in the vibrant capital city of San Juan.

Pushing east again, the island of Vieques (famous for its bioluminescence), Isla Palominos, and the charming island of Culebra involved a healthy series of tacks into the trades, but each was a short and bearable hop.

Our final destination in Puerto Rico was the uninhabited island of Culebrita, where Scout floated once more in crystal-clear waters. We snorkelled to find an impressive quantity of aquatic life such as green turtles, parrotfish and spotted eagle rays.

It was April and we were on the final leg of the Thorny Path, and time to work our way through the Virgin Islands. With the trades in full daily onslaught, our luck with helpful wind conditions had run out. But now we had navigational options on our side.

We chose our next stop of St Croix, predominantly because it was more south than east of Culebra (a very comfortable upwind sail) and were rewarded with a fascinating destination in its own right.

Unlike most of the Caribbean islands, which have a Spanish, French or English past, the US Virgin Islands have a Danish colonial history, and we spent a week exploring unusual forts, plantations and even a local vodka distillery around friendly Christiansted.

Our giant tack back north, towards the US island of St John, was a spectacular 30-mile long beam reach. But sailors’ pride often comes before a fall and our luck with fishing pots was about run out. We saw a lone lobster pot marker just ahead of us as we approached the island, but it was too late.

As we turned to avoid it, the line beneath it got tangled in our rudder and our glorious 7 knots dropped to a miserable 2 knots as we dragged 300m of line (and probably a surprised lobster) behind us.

It was a beautiful day and the sea was warm, so after a quick heave-to, James jumped in and untangled things before we were on our way again.

After a few days soaking up the sophistication of Cruz Bay, it was time to head east one final time, with our sights on the northern end of the chain of islands that would take us south to Grenada.

It would be a 36-hour upwind sail and our strategy was to use the British Virgin Islands as a protected way to make progress eastwards. It felt strange not stopping and enjoying the beautiful cruising grounds, but the Sir Francis Drake Channel was perfect for a day of tacking upwind in calmer waters.

As we passed between Necker Island and Punta Gorda before a glorious sunset, the wind shifted north slightly as forecasted and we shot out of the BVIs at a perfect angle. A pleasant night’s sail later, morning brought sight of the Dutch islands of Saba and Sint Eustatius, and then our destination, the twin islands of St Kitts and Nevis.

Farewell Thorny Path

We were finally east of 63°W. As we pulled in to anchor by the pretty town of Basseterre, accompanied by dolphins and the distant sound of soca music, we couldn’t help but smile. Our Thorny Path trials and tribulations had come to an end, and we’d proven that we could indeed make it.

This is a route with a reputation for a good reason, but if you have time and flexibility it can be broken down into many smaller, manageable sections. Early in the calendar year fronts passing over the US can disrupt the trades locally, sometimes significantly, and those are the chances to take.

Stretched between the much more popular and well-known Bahamian and Eastern Caribbean cruising grounds, the lesser-travelled coastlines we explored each held their own surprises and delights.

The recollection of the days bashing upwind would soon fade, but the spectacular places we saw along the way will stay with us forever.

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