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Cruising the Island Chain:
South to North is the Winning Strategy!

Part One: Grenada to Martinique

by Don Street

Boats coming from the US East Coast to the Eastern Caribbean in the fall nearly all intend to cruise the Eastern Caribbean island chain for the winter. For many, the goal is to island-hop down to Grenada and then island-hop back up again, before heading back to the US or onward to Europe in May.
A typical route involves a landfall in St. Thomas or Tortola, and then fighting your way across the Anegada Passage and on eastward to Antigua, all to windward against the ever-present and sometimes very strong easterly trades and a westward-flowing current. From the Virgin Islands to Antigua the straight-line distance is 240 miles, but tacking to windward on a cruising boat your actual sailing distance could be as much as 500 miles. Only after reaching Antigua can you head south and enjoy the majority of the rest of the trip to Grenada with eased sheets. It’s 300 miles from Antigua south through the islands to Grenada, then 500 miles back up through the islands to St. Thomas. The total sailing distance will be about 1,300 miles with up to 500 miles of it really hard work.

An unconventional but easier way to cruise Eastern Caribbean is to first head south directly from the Virgins or St. Maarten to Grenada. In the information that follows, all courses are magnetic and distances are approximate. (Editor’s note: These litigious times compel us to say, “This article is not to be used for navigation.” The prudent mariner will use all available resources, including up-to-date information on Covid protocols related to border crossings [see page 24], and his or her own skill, in passage planning.)
From St. Thomas straight to Grenada the course is about 170° for 415 miles; from St. Maarten the course is 180° for 410 miles. From Grenada you can cruise north through the entire chain with little or no beating to windward.

The passage to Grenada from the Virgin Islands or St. Maarten is usually easy sailing on a close or beam reach. Then going north almost all passages will be close or beam reaching. Toward the end of the trip — Antigua to the Virgins — you will be sailing broad off.
When you arrive back in the Virgins you will have sailed a loop of about 1,000 miles of mostly easy sailing versus 1,300 miles with over a third of it hard work.
When sailing or motor-sailing up the lee sides of the islands stick right up on the beach. Norie and Wilson’s 1867 Sailing Directions for the West Indies advised that when passing the lee of the high islands, stay “within two pistol shots distance of shore or seven leagues off.” Inshore you may find wind and you will always find smooth water and excellent scenery.

There are a few inter-island channels in the Windward Islands where, going northward, if you are unlucky and the wind is north of east, you may be hard on the wind on starboard tack to stay on the rhumb line. Guadeloupe to Antigua can also be to windward. But if you check the time of the Meridian Passage of the Moon (see page 35 in this issue of Compass) and cross the inter-island channels with a weather-going or neutral current it will take much of the pain away. If you do not lay the course, wait until you have passed the south end of the island and are in smooth water where the wind has eased off before going on port tack.
As you will be on starboard tack most of the time heading north, and as roller-reefing headsails set best if they are rolled counterclockwise on starboard tack, I advise doing some re-rigging to your roller-reefing headsails (and in-mast roller reefing main if fitted). See details in my article “Crossing Inter-Island Channels with Minimal Pain” on page 18 of the January 2021 issue of Compass at

Grenada to Carriacou
If the wind is east or south of east, you can sail up Grenada’s windward coast. See sailing directions in the booklet accompanying Imray Iolaire chart B34.
If leaving from one of the bays on Grenada’s south coast, it’s a downwind sail to Point Saline. Once you have rounded Point Saline, come hard on the wind and short tack along the coast, avoiding the shoal off Quarantine Point, until you can turn north and sail right up to the lee coast.
Hug the shore about 100 yards off, sailing, or motor-sailing. You will have smooth water and a very scenic trip to the island’s northwest point, Tanga Langa. Here a decision must be made. The course is 055° for 15 miles to Tyrell Bay, Carriacou. It can be hard on the wind so, unless you can lay 065° or 070°, tack eastwards along the north coast of Grenada, out of the sea and westerly flowing current, until near Sauteurs. Then stand north for Carriacou.

Or, if the groundswell is not running, you can anchor behind the breakwater at Sauteurs. Anchor bow and stern or use a Bahamian moor to minimize your swinging room. Explore ashore. The village has been largely bypassed by tourists. Check the Meridian Passage of the Moon, published monthly in Compass, and time your departure for two hours after moonrise or two hours after moonset. This will give you either a weather-going current or a neutral current, which will increase your chances of laying Carriacou with a fast, eased-sheets passage. The course is 040° for seven miles until north of Kick ’em Jenny, and then 055° for seven miles to Tyrell Bay.
Remember the Rule of 12. In the first hour of a rising or falling tide the tide rises or falls one twelfth of its total rise, the second hour two twelfths, the third hour three twelfths, the fourth hour three twelfths, the fifth hour two twelfths, and the six hour one twelfth. Thus, the strongest tides and currents will be during the third and fourth hour after moonrise or moonset.

The Grenadines
Zigzag your way through the Grenadines and enjoy the various anchorages. Use Imray Iolaire charts B31, 311 and 30 and study the booklets accompanying them for piloting directions to all Grenadines anchorages, including some not mentioned in Doyle’s guide.

The one sometimes hard leg, if the wind is in the north, is from the northwestern end of Canouan to West Cay, Bequia, 22 miles on a course of 027°. Again, do some figuring of the current as previously described. Try to depart the north end of Canouan two hours after moonrise, or moonset so that you have a weather-going or neutral current.

From Admiralty Bay, Bequia, to the south coast of St. Vincent is an interesting passage that few boats do correctly. The channel between Bequia and St. Vincent has such a strong westerly current driven by the tradewinds that the weather-going tidal current minimizes but seldom overcomes it.
When the tidal current is running westwards it can suck you off to leeward like a vacuum cleaner. With a strong spring weather-going tide, the first mile out of out of Admiralty Bay can be the roughest in the entire Eastern Caribbean.

The course from Admiralty Bay to the south coast of St. Vincent, where you’ll find Young Island Cut and Blue Lagoon, is a distance of seven miles on a course of 045°.
Unless you can sail 070° or 075° do not try to go across the channel as soon as you leave Admiralty Bay, as you will not lay your anchorage. You’ll then have to tack up to the south coast of St. Vincent, which is a good way to go backwards. Instead, short tack up the northwest coast of Bequia until you are far enough east to lay your anchorage allowing for a 20-degree westerly set.

Continuing north along the lee coast of St. Vincent, stay 100 yards offshore, sailing or motor-sailing and enjoying the scenery and smooth water. Stop at Cumberland Bay, which has developed a good reputation for catering to the cruising yachtsman and makes a good jumping-off point for the leg to St. Lucia.

St. Vincent to St. Lucia
Before leaving Cumberland Bay to head to St. Lucia, again check the Meridian Passage of the Moon and try to cross the channel with the weather-going or neutral current. Wind against the current will make the first few miles of the passage rather lumpy but at least you will not be sucked off to the west. Hug the St. Vincent coast and follow it around the corner to the east until the sea builds up to a point that it is time to crack off and head north on a course of 030° for 20 miles.
 If you’re not laying the Pitons not to worry, as most of the time once Vieux Fort comes abeam the wind swings a bit to the south and the seas become smoother, allowing you to head up and get back to the rhumb line.
 If you are still too far to leeward, continue north until you are behind St. Lucia where the wind has eased off or died and the sea has flattened out. Then tack back east. You can find a mooring buoy and go ashore to clear in at Soufriere, or carry on to Rodney Bay.
North from Soufriere to Rodney Bay hug the coast but avoid the unmarked rock of Grand Caille Point just north of Soufriere, which through the years has nailed a number of boats.

St. Lucia to Martinique
When planning to sail from Rodney Bay or Pigeon Island to Martinique, decide whether to sail straight to Cap Salomon and then up the lee coast, or to Ste. Anne. At Ste. Anne there is a choice between sailing up Martinique’s lee coast or windward coast.

From Pigeon Island to Cap Salomon the course is north for 20 miles. This is my favorite inter-island passage as it is guaranteed to be a very fast beam or broad reach.
To Ste. Anne the course is 025° for 21 miles. This is likely to be a tight reach or, if the wind is north of east, hard on it. Again, plan to time your passage to benefit from a weather-going tidal current. If you are not quite laying Ste. Anne, do not tack to until you are sheltered by the south end of Martinique.
Once you have enjoyed Ste. Anne, loaded up with French wine, cheese and other wonderful things, and visited Marin by dinghy, it’s time to decide whether to head west to Cap Salomon and onward to Fort de France and the lee coast as described below, or cruise the wonderful east coast of Martinique, which I consider the best cruising in the entire Eastern Caribbean now that Venezuela is unsafe for yachts.

Do not believe those who say that it’s “too dangerous” to cruise the east coast of Martinique. I did eight cruises there in the engineless yawl Iolaire. The first time was in 1963 with my late wife, Marilyn, and our two-year-old daughter.
To prepare to cruise this area, be sure to have Imray Iolaire chart A301, and read the booklet that accompanies Imray Iolaire chart B30 carefully. See also my Cruising Guide to the Eastern Caribbean: Martinique to Trinidad (available from Amazon). When in Marin buy the excellent local French guide Martinique, côtes et mouillages, produced by local yachtsman Jerome Nouel, who has spent 40 years cruising Martinique. Even if you do not speak French you will still be able to gather enough information from the guide to make purchasing it well worthwhile. Check the weather forecast — clear, settled conditions are best for eye-balling your way through the many reefs. Allow a week or better ten days to explore the wonderful east coast with its uncrowded anchorages.

From La Caravelle, the easternmost point of Martinique, to Scotts Head in Dominica will be a glorious broad reach for 32 miles on a course of 325°.
Alternately, from Ste. Anne head ten miles west, dead downwind to Diamond Rock and Pointe du Diamant. If you do not have a spinnaker pole or whisker pole, rig a main boom preventer and wing your headsail out on the other side. Sheet it outside the lifelines through a block as far aft as possible and thence to a winch. Dead downwind a genoa will fill beautifully even without a pole.

Once Pointe du Diamant has been passed you have numerous anchorages available. Avoid Grand or Petite Anse d’Arlet from Friday afternoon until late Sunday afternoon, as both will be inundated with local weekending boats.

For anchorages in Fort-de-France Bay, see the booklet that comes with Imray Iolaire chart B30, pages 4 and 5.
From Fort-de-France to Le Precheur at the north end of Martinique is 15 miles of sailing or motor-sailing right up on the beach. At Le Precheur is a small shelf where the local fishing boats are anchored. If the groundswell is not running an anchorage could be found. The village has been bypassed by tourists but has a superb restaurant on the beach.
If you prefer, anchor a few miles south at St. Pierre and explore the history of the town, which was decimated by a volcanic eruption in 1902 and has recovered.
Next month: Part Two, Dominica to the Virgins.

Don Street is the author of The Ocean Sailing Yacht, Street’s Transatlantic Crossing Guide, Cruising Guide to the Lesser Antilles and more. He compiled the Imray Iolaire Caribbean charts and wrote the booklet that accompanies the charts. Visit his website at www.street-iolaire for piloting, rigging, hurricane and other information.


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