Caribbean Down-Island Sailing Adventure Course

Embarking July 2. Detailed Down-Island Trip Plan.

Week 1 – Sunday July 2 – The British Virgin Islands to Guadeloupe, 300 miles

The down-island sailing adventure starts with a challenging, up-wind sail through St Martin, St Barths and Antigua finishing at the French island of Guadeloupe.

down-island sailing adventure tortola bvi st martin st barths guadeloupe

This first week of the down-island sailing adventure course is best suited to those who are after some high adventure. Those who can handle acceleration zones. Those who want to experience the broad gamut of conditions that are to be found in the Caribbean, mixed with quieter hours of trimming, reading, fishing. Then, once we make land, exploring the islands.

The trip starts in the West End of Tortola, British Virgin Islands, on a Sunday. We meet at the Fish N Lime Inn early in the morning and spend the day doing safety briefs and final preparations before departure. We clear HM Customs and set sail for St Martin.

Tortola to St Martin

This leg is usually directly upwind and takes around 24 hours to complete, depending on conditions. If sailing the entire way we will review such tools as Fastseas and Predictwind to determine the optimal route. Like any ocean sailing, we will time our departure for weather conditions rather than strictly sticking to clock. “Never sail to a deadline” is a sensible motto.

Once in St Martin we will check into the French side and enjoy some of the finest food in the Caribbean, in the quaint French village of Grand Case, located on the west side of the island. This is also a good opportunity to provision the boat. After wining and dining in great taste we will clear out of French St Martin and continue on our adventure.

St Martin to Antigua

This leg has us leaving St Martin and sailing upwind to the billionaires’ playground of St Barths. It is worth spending at least a day here as we enjoy the cafes and bars (including of course Le Select) of this formerly-Swedish, now French colony. The next leg, to Antigua, is usually the most challenging leg of the entire trip. We will time it for weather, then commit.

In Antigua we will dock at Lord Nelson’s old stomping ground, the impeccably-restored and beautifully protected English Harbour. This will be a shorter stop as we prepare for the final leg of the week, across the Guadeloupe Channel.

st barths sunset down-island sailing adventure

Gustavia, St Barths on Dusk

Antigua to Guadeloupe

We will prepare well before departing, as the Guadeloupe Channel can funnel the trade-winds to create acceleration zones just off the islands. This is a 60 mile journey we may do as an overnight passage. If we do, we will be sailing along the west coast of Guadeloupe in the early hours of the morning. We may stop for a croissant and cafe in Deshaies on the north western tip of the butterfly-shaped island, then sail on to Marina de Riviere Sens on the south western corner of Guadeloupe.
In Guadeloupe we will have a rest day. There is plenty to do on the island, or you can decide to just hang out in a cafe, enjoy a Lézarde and catch up on wifi. This is we turn south and the trip gets easier (with a big qualifier there saying *most* of the time. As always it is condition-dependent).
We encourage both weeks to be booked and so offer a 10% discount for doing so:

Week 2 – Sunday July 9 – Guadeloupe to Martinique, 110 miles

A week of land- and water-based adventure, sailing through Iles des Saintes, Dominica and on to Martinique.
down-island week 2 sailing adventure guadeloupe dominica martinique
This week involves huge diversity. We sail from the very French island of Guadeloupe to the even more French islets of the Saintes. We then spend time in Dominica, where much of Pirates of the Caribbean was filmed, and on to Martinique, arguably the coolest large island in the archipelago.

Guadeloupe to Îles des Saintes

A short sail to the gorgeous island of Terre de Haut. We stop there for lunch and if the conditions permit, the evening.
Called variously a Lilliputian Rio de Janeiro and Guadeloupe’s Gibraltar, these islands are first and foremost charming.
We can visit Fort Napoleon and, if conditions and desire agree, go scuba diving in one of the many dive sites of the area.

Îles des Saintes to Dominica

The sail south to Dominica is a five hour sail that may be anything from a beat to a beam reach, depending on how much south the trade winds have in them at the time.

In Dominica we arrive in Portsmouth for customs clearance. Once there we can explore the Indian River, where the witch-doctor scene for Pirates of the Caribbean was filmed. Thankfully the river itself retains its authentic, overgrown nature.

The second half of the Martinique leg involves our sailing to Roseau on the southern tip of the island. From there we can take a day to hike up to the Boiling Lake, an outstanding turquoise-coloured volcanic lake that literally boils with heat. For many this is a highlight of the trip.

down-island sailing adventure dominica

Walking up to Boiling Lake, an 8-hour Adventure

Dominica to Martinique

The sail from the bottom of Dominica to St Pierre, at the top of Martinique, usually takes around eight hours. Being oceanic, the conditions can show anything from bluebell sailing day on a beam reach to a choppy 45 knot acceleration zone. “Either beautiful or epic” as we like to say.

Once in St Pierre we check into Customs and explore the town. This town is the scene of the single largest volcanic eruption in the 20th century – anywhere in the world. Here in 1903 the entire mountain exploded, killing all but two of the 30,000 inhabitants of the town. For the rest of the century no volcanic explosion came close to the Pelee eruption. A local museum shows the devastation wrought by this event.

Sailing along the west side of the island, we stop in one or two coastal villages before arriving in the beautiful bays of Anse Noire and Anse Dufour on the southwestern quarter of the island. Our final destination is the natural hurricane hole of Le Marin on the southeastern corner of this magnificent island.

Book Week 2 Here

We encourage both weeks to be booked and so offer a 10% discount for doing so:

Book Two Week Adventure Here


This is a two week down-island passage through some fascinating, diverse islands. Bring your foul-weather gear, a camera and your sense of adventure. Entry to this sailing adventure course is by application only.

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