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Threading the Needle: A Sailor's Journey Through the Thorny Path

Written by Salty Dawg Sailing Association | 1/5/26 5:00 AM
Our team at Dockwa is stoked to be collaborating with the Salty Dawgs Sailing Association (SDSA), bringing real cruiser stories to life in The Running Fix Newsletter! 

If there’s one thing long-distance cruisers understand, it’s that not all miles are created equal. Some are earned inch by inch, against the wind, the current, and the clock, through patience, persistence, and a healthy respect for weather windows. In this story, the crew of SV Temagami takes on the Thorny Path, a notoriously challenging southbound route that demands flexibility, humility, and a willingness to let the plan change.

It’s a reminder that cruising isn’t just about getting south, it’s about how you get there, who you rely on along the way, and the lessons the harder passages tend to teach best.

The Thorny Path: A Sailor's Guide

By: William, Hugh and Stewart Giles – SV Temagami

After completing the Caribbean Rally to Marsh Harbour, SV Temagami, our refitted 2002 Grand Soleil 46.3, we explored the Bahamas for several weeks before picking a weather window to head on through the thorny path. 

The Thorny stretches from the Bahamas to the Eastern Caribbean. This 1,200-mile journey is notoriously difficult because it requires heading southeast, directly against prevailing easterly trade winds and opposing currents.

Understanding the Thorny Path

Unlike the offshore route, which involves a long blue-water passage towards Bermuda before turning south to Antigua or St Martin, the Thorny Path relies on coastal hopping from the Bahamas to Turks and Caicos, Hispaniola, the Mona Passage, Puerto Rico and the Virgin Islands.

Before venturing out, we did our prerequisite research including reading the go to book on this passage by Bruce Van Sant’s Gentleman's Guide to Passages South, which emphasizes "leisure sailing" and patience and taking advantage of the night lees, weather windows and cold fronts from the north. Putting this advice to practice was a different story. As our good friend and fellow Salty Dawg Marv Magee said “man plans and the weather gods laugh.”

We waited in Georgetown for a calm weather window following a cold front and we set off predawn with the expectation that we would have favorable conditions for at least 36 hours. Our planned course was past Long Island and Crocked island and straight on to Luperon, Dominican Republic. 

When the Plan Changes

Well, Temagami’s flat hull and the head on waves made for some serious slamming and we reduced speed to make the passage smoother. After a couple hours we decided to alter course and change our route. We considered tucking into Flying Fish Marina but decided not to because it was too shallow. Instead, we charted a more forgiving course to Mathew Town, Inagua, a little known port that turned out to be a pleasant surprise. The port was basic and at only 18 dollars a night, a great place to wait for the next window and to enjoy the majestic cargo sailing boats from Haiti.

Haitian cargo boat

A Window to proceed to Dominican Republic did not present itself but there was an opportunity to stage in Turks and Caicos Blue Haven Marina and then head south from there. To accomplish this, we staged-in Man of War Bay at the north end of Inagua, next to the Morton Salt operation. We departed at 0300 to enjoy the offshore breeze and better waves.

Once again we slowed to prevent slamming. As Chris Parker might say, “the conditions were spicy”. We did not arrive in Turks and Caicos until well after dark’.  Providenciales Island was a true resort destination, only a stop we made to afford a better approach for Dominican Republic. Fortunately, our next window was long enough to go all the way to Samana instead of the shorter hop to Luperon.

Because each of these passages was intentionally in low wind or up wind we were required to motor a majority of the time. This was less than ideal but better than beating up wind while racing against the constraints of a cooperative weather window.

A Fouled Prop and a Clean Escape

Crossing from TCI to DR presented an additional challenge. While passing through some sargassum we snagged a gym bag in our propeller, and the engine made an horrendous noise. We shut it down before is stalled. In the middle of the open sea between Grand Turks and Caicos, we were adrift. Luckily, Hugh and Stewart had scuba equipment on board.  Hugh was able to cut the tangled gym bag from the prop and in about an hour, we resumed our passage.

We crossed from Blue Haven Marina to Samana in about 37 hours. Samana and the DR was a highlight.


The route in the Boating App

The Mona and Beyond

The next leg of our journey was through the Mona Passage which is said to be the most challenging of the thorny path. It has current against wind and waves which create a treacherous seascape. To tackle this we, once again, picked a calm wind window and we planned a route that would avoid an area in the Mona passage known as “the bow tie”. We cleared out of customs in Samana and were underway by 1300h. We encountered several hours on the graveyard shift where the seas were unsettled and we slowdown to prevent slamming on the sharp waves. About 21hours after setting off, we made landfall in Puerto Real, Puerto Rico and cleared in using the CBP Roam app.

Puerto Real was a quiet little town with not much to do so we pushed on the next morning to La Parguera where we took in the glowing plankton at Bahai Fosforescente and spent the night in a secluded anchorage.

At dawn we set out for Salinas and a four-night layover to explore and to wait for an appropriate window to press on. The waves were slow to settle in the thorny path and we had to push on as soon as the head wind tapered and manage waves over six feet until they gradually settled as well.  With seas and wind finally in our favour, we pressed all the way from Salinas to Culebra Island the eastern most island attributed to Puerto Rico.  After just one night behind a protective shoal, we pressed on the St Thomas US where we waited for four days for the next good opportunity to cross to Jost Van Dyke BVI.  

Charlotte Amalie is a great place to provision, visit Home Depot and to enjoy some great restaurants. It is set up to receive cruise ships and the jewelry and tea shirt shops line the waterfront.  It is a busy destination.


Charlotte Amalie Harbour

The cross to the BVI and where we plan to meet family for the holidays was quick and although we did not select a “window”, Jost Van Dyke is North and that provided us an opportunity to sail.

 

 
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