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

Part Two: Martinique to the Virgin Islands

by Don Street

If you�ve arrived in the Virgin Islands from the US East Coast, an unconventional but easier way to cruise Eastern Caribbean is to first head south directly from the Virgins or St. Maarten to Grenada, and then island-hop your way back up the chain. When you arrive back in the Virgins you will have sailed a loop of about 1,000 miles of mostly easy sailing.

See last month�s Compass at page 22 for general tips and sailing directions from Grenada to Martinique.

Martinique to Dominica
From Le Precheur to Scotts Head, Dominica, is 20 miles on a course of 355� magnetic, normally a good fast reach. If you draw seven feet or more, note the instructions in the booklet for Imray Iolaire chart A29 regarding the submerged rocks off Scotts Head.

As the late Tom Follett said, anchoring on the lee coast of Dominica is like throwing your anchor onto the balcony of the 86th story of the Empire State Building and hoping it will hold. I recommend continuing the 18 miles from Scotts Head to Prince Rupert Bay and the town of Portsmouth. This bay once had a bad reputation because of overly aggressive boat boys. However, the boat boys � now known as yacht service providers � realized that if they were nicer to visiting sailors, yachts would flock to Prince Rupert Bay. The Portsmouth Association of Yacht Services (PAYS) was born, and Prince Rupert Bay is now an excellent stop for yachts. Anchor in the northeast corner and check Chris Doyle�s Cruising Guide to the Leeward Islands, Southern Edition for information on the availability of the inland tours for which island is famous.

Dominica to the Saints and Guadeloupe
From the north end of Dominica to les Iles des Saintes, known as the Saints, is 17 miles on a course of 355�. This is almost always a windy passage as the tradewinds are compressed between the high mountains of Guadeloupe and Dominica. Access to the village of Bourg des Saintes from the south is between the islands of Terre de Bas and Terre de Haut. Anchoring is not allowed off the village; pick up a mooring buoy if available.

From the Saints to the southwest corner of Guadeloupe is eight miles on a course of 345� � guaranteed a fast reach thanks to the compressed tradewinds.
From the southwest corner of Guadeloupe to Deshaies at the north end is 28 miles; again hug the coast, watching for fish pots. A possible anchorage is at Goyave abeam of Pigeon Island, where you can find excellent diving.
Deshaies is a sheltered anchorage but when the groundswell is rolling in you may not be able to dinghy ashore. The groundswell regularly removes the dock.

Guadeloupe to Antigua
From Deshaies to English Harbour is 41 miles on a course of 015�. It is usually a nice close or beam reach. If the wind is north of east it can be really hard on starboard tack.
When you leave Deshaies you will probably have light air, so follow the coast around to the east and aim for the small islands of Ile � Kahounne and T�te Anglais until the wind fills in.
If it looks like a tough fight to get to English Harbour, head for Jolly Harbour on the west coast of Antigua, a course of 015� for 45 miles. Once in the Jolly Harbour, make another decision: do you continue north to Barbuda, or head south four miles and then east six miles to Falmouth or English Harbour? (See sailing directions in the booklet that accompanies Imray Iolaire chart A27.)

If the gods of wind have allowed you to end up in English Harbour and you plan to go on to Barbuda, you can head east to Nonsuch Bay, spend a day or so enjoying it, and then leave by Spithead Channel. Or you can head direct to Barbuda. A third option is to head west from English Harbour, round Cade�s Reef, enter either Jolly Harbour or Dickinson Bay to spend the night, and the following day carry on to Barbuda.

Antigua to Barbuda
From the east side of Antigua to the south coast of Barbuda is about 32 miles on a course of approximately 005�. From Dickinson Bay to Low Bay on the west coast of Barbuda is 30 miles on a course of 020�. In either case, once you clear Antigua it as a fast reach to Barbuda.
The best anchorage is behind Spanish Point, which is sheltered in all wind conditions. It is one of my favorite anchorages, as no more than about four boats can fit in. The anchorage off Low Bay is fine as long as the groundswell is not rolling in.
Unfortunately the Imray Iolaire chart has not been updated to show the effects of 2017�s Hurricane Irma and the changes ashore done by developers. Go to www.imray/ and click on A26 for updates.

Barbuda to St. Barth�s
From Barbuda to St. Barth�s the course is 300� for 58 miles. This is broad off, or, if the wind is south of east, dead downwind.
On the back of any old Imray Iolaire chart read the section �Rig for Down Wind� carefully. Be sure to rig a main boom preventer (a.k.a. foreguy) to prevent a potentially dangerous accidental gybe. I�ve worked it out so the main boom preventer can be rigged when sailing broad off without trimming the main and without anyone going forward.
Arriving in Gustavia try to organize a mooring stern to the quay, but read the warning in the booklet accompanying Imray Iolaire chart A24 regarding surges suddenly arriving in the harbor. Finding a spot to anchor is difficult; one solution is to anchor on the north side of the harbor in Anse du Corosol and use your dinghy for the one-mile run into town. Ashore, the old St. Barth�s populated by French fishermen has been replaced. It is amazing, going to St. Barth�s is the only way you can visit St. Tropez without flying to France.

St. Barth�s to St. Maarten
From St. Barth�s to St. Maarten is a short, broad off or dead downwind sail. Again, rig a main boom preventer. Check for current details on entering Simpson Lagoon through the opening bridge at Phillipsburg on the Dutch side of the island, and details on opening times for the causeway bridge in the lagoon.
If the opening bridge at Marigot is operational you may be able to exit Simpson Lagoon via the French side.
Enquire in St. Maarten about where you can clear into Anguilla.

St. Maarten to the BVI
From St. Maarten the course to Round Rock, British Virgin Islands, is 300� for 72 miles. On approaching the islands pass south of Round Rock rather than using the passage between Round Rock and Fallen Jerusalem: there is a seven-foot rock in the passage that is not marked. No one knows accurately where it is.
Anguilla to St. Croix
Instead of directly heading for the BVI, I recommend heading for St. Croix: 85 miles on a course of 075�. After spending a few days exploring spend a couple more pleasant days at Buck Island. Then take off on a course of 020� for 30 miles to Road Town, Tortola, BVI.
Explore the BVI then continue west to St. John and St. Thomas. You will have visited as many islands as you wished in the Eastern Caribbean chain with more time available in each and fewer clearances than if you had island-hopped both down and up � and with less windward work!
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 for piloting, rigging, hurricane and other information.


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