Three itineraries, two ways to sail them

Welcome aboard from 6 pm at Le Marin marina, the largest in the Lesser Antilles. Briefing, cabins, then lines off for a night passage on a broad reach. You run down the lee of Saint Lucia and Saint Vincent under the stars: the longest leg of the trip, and far and away the finest.

Early-morning arrival in Admiralty Bay. While the skipper clears customs, the day is yours: swimming, snorkelling, kayak, paddleboard. In the afternoon, ashore to Port Elizabeth — boatbuilders, model-ship workshops, rum at sunset. Optional island tour by taxi along the scenic coast road.

Under way at 5.30 am, breakfast at anchor in Britannia Bay, Mustique: discreet villas, empty beaches, Basil’s Bar with its feet in the water. Early afternoon, on to Mayreau, the smallest inhabited island in the Grenadines — 300 people, one village, and a stone church on the hilltop with the whole archipelago laid out below.

A slow morning on Mayreau. After lunch, a short hop to the Tobago Cays: five uninhabited islets inside a lagoon closed off by Horseshoe Reef. Arguably the finest anchorage in the Caribbean. Snorkelling on the reef, swimming with green turtles, trails through cactus and frangipani. Optional lobster barbecue on the beach.

Morning and lunch in the lagoon. Mid-afternoon, one last swim with the turtles, then a short sail across to Petit Saint Vincent, a discreet private-island resort ringed with turquoise water. Drinks ashore in the early evening if you fancy it.

A hop across to Morpion: a sandbar, a straw parasol, nothing else — the loveliest natural bathtub in the Grenadines. Around sundowner time, on to Chatham Bay, a wide wild bay on the lee side of Union. Turtles, snorkelling, paddleboarding, an empty beach and a couple of shacks serving dinner on the sand.

Away late morning, lunch at anchor off Palm Island. In the afternoon, a short sail to Clifton, the lively capital of the Grenadines: fruit market, kitesurfers across the lagoon, and the famous Happy Island bar, built on a heap of conch shells.

A big day on the water, close-reaching north. Lunch stop at Bequia, then on to Cumberland Bay in the lee of Saint Vincent: a tropical fjord walled in by volcanic cliffs, where you moor stern-to under the coconut palms.

Optional morning excursion inland: a creole village, the scenic Caribbean coast road, a swim at the foot of a waterfall. After lunch, across the Saint Lucia channel to the Pitons — two volcanic spires rising 770 m straight out of the sea. Anchor between Gros Piton and Petit Piton, right under the cliffs.

Optional morning ashore at Soufrière: botanical gardens, sulphur springs and the world’s only drive-in volcano. Lunch under way in the lee of the island, then back to Martinique and the anchorage at Sainte-Anne, off the village and its long beach.

Breakfast aboard and a last short sail into the Cul-de-Sac du Marin. Step ashore at 10 am.

Board at Bas-du-Fort marina, briefing, then away to Marie-Galante, the island of a hundred windmills. Anchor at Anse Canot, a long white-sand beach fringed with sea grapes. First night aboard at anchor.

Breakfast and a morning of watersports: paddleboard, kayak, snorkelling. Lunch aboard, then south to Dominica, arriving in the wide bay of Portsmouth at the north end of the island.

The crew handles customs and immigration. Dominica is the ‘Nature Island’: the greenest and wildest of the Antilles, with its primary rainforest, 365 rivers and volcanic hot springs. A free day aboard, or row up the Indian River through the swamp bloodwood.

A fine day’s sailing back north. Lunch at anchor off Pigeon Island, in the heart of the Cousteau Reserve — one of the world’s twenty finest dive sites, according to the Commandant himself.

A morning snorkelling in the reserve, with scuba available through the local dive centres. Lunch aboard, then across to the Saintes archipelago. Anchor or pick up a mooring off Le Bourg.

A full day in one of the most beautiful bays in the world. Le Bourg and its fishermen’s cottages, Fort Napoléon and its cactus garden, the view from Le Chameau. An afternoon of doing very little, snorkelling and watersports.

A short morning sail to Pain de Sucre, a basalt dome dropping straight into the water — the best snorkelling in the archipelago. Lunch aboard, then on to Îlet du Gosier and its little lighthouse. In the evening, the Gosier night market is well worth the trip ashore.

An early breakfast and one last short sail back to Bas-du-Fort marina. Disembarkation.

Welcome aboard in the late afternoon at Bas-du-Fort marina. Safety briefing, cabins and provisioning. First night at anchor off Îlet du Gosier, under the little lighthouse — the voyage starts on the very first evening.

An early start and a crossing of the Saintes channel, usually on a broad reach. Anchor off Le Bourg or at Pain de Sucre. Afternoon ashore: Fort Napoléon with its iguanas and succulent garden, or simply the lanes of Le Bourg and a tourment d’amour on the quay.

You work all the way up the leeward coast of Basse-Terre, sheltered by the mountains. Lunch stop and snorkelling at Pigeon Island, in the heart of the Cousteau Reserve. In the afternoon, on to Deshaies, whose deep bay and brightly painted village stand in as the set for the series ‘Death in Paradise’. Fresh provisioning and a proper rest: tomorrow you head north.

The big crossing of the trip, due north on a close reach in the trades. Away at first light, into English Harbour in the late afternoon. Clear in to Antigua, then anchor in the historic inlet beneath the fort.

A day ashore. Nelson’s Dockyard, the only working Georgian dockyard left in the world and a UNESCO World Heritage site. Then up to Shirley Heights for the view over both harbours — and, on Sunday evenings, the most famous steel band and barbecue in the Caribbean.

Sailing along the south coast, the most indented on the island: Carlisle Bay, Rendezvous Bay, Darkwood Beach. Round Johnson’s Point and head up to Deep Bay, where the wreck of the Andes lies in a few metres of water in the middle of the anchorage — mask and snorkel are all you need.

North to Barbuda, a flat and all but empty island — 1,500 people to 160 km². A careful approach between the reefs, then anchor off Low Bay, right on the beach. In the afternoon, take the dinghy into Codrington Lagoon to the largest frigatebird sanctuary in the Caribbean: several thousand birds.

A full day on one of the finest beaches in the world: seventeen kilometres of pink sand, tinted by crushed shell from the reef, and almost nobody on it. Snorkelling on the coral heads, the caves at Darby Sink and Two Foot Bay, lobster for lunch on the sand.

Back down to Antigua on a broad reach. Anchor at Jolly Harbour: clear out, provision, a shower ashore and a last drink facing an Antiguan sunset before the passage home.

The passage home, due south on a beam reach — the best point of sail of the whole trip. Clear in to Guadeloupe and back to the anchorage at Deshaies, with the very particular feeling of having returned from a real voyage. A free morning follows for the botanical garden or Grande Anse beach.

A morning at Deshaies — the botanical garden, laid out in Coluche’s former estate, is genuinely worth the walk. Then back down the leeward coast on flat water with the wind behind, with a lunch stop at Anse à la Barque, a small bay closed off between two lighthouses. Last night at anchor off Les Saintes.

Breakfast facing Pain de Sucre, a final swim, then back across the Saintes channel and up to Pointe-à-Pitre. Step ashore at Bas-du-Fort marina in the early afternoon.