The Leeward and Windward Islands in 14 nights: St Maarten to Grenada

Board in Simpson Bay and cross to St Barths in ninety minutes. The quiet north-west corner for the first night: no road, no building, turtles under the boat.

• Ninety minutes to St Barths
• The quiet corner
• Turtles under the boat

Into Gustavia for the day and the night. Lunch at Nao, Shellona or La Guérite, the boutiques, a swim at Shell Beach, dinner at Bonito and the DJ night if it falls on a weekend.

• Lunch at Nao or Shellona
• Gustavia's boutiques
• Bonito, then the night out

South-west with the wind behind, lunch on the move. The afternoon is the guided ATV tour up through the cane fields and rainforest with Mount Liamuiga above, then into Christophe Harbour's marina for the night and dinner at the Pavilion.

• Guided ATV tour
• Christophe Harbour marina
• Dinner at the Pavilion

Across the Narrows in under an hour. Pinney's Beach for the day, Sunshine's beach bar for a Killer Bee, and dinner at one of the old sugar plantation houses in the hills.

• Pinney's Beach
• A Killer Bee at Sunshine's
• Dinner at a plantation house

Five hours east across to Barbuda, the one leg against the wind, with a late lunch at Nobu on Princess Diana Beach as the reward. The frigate bird colony by tender in the late afternoon, and seventeen miles of pink sand with nobody on it.

• Lunch at Nobu Barbuda
• The frigate bird sanctuary
• Pink sand, nobody on it

Three hours south to English Harbour and the Georgian dockyard Nelson commanded. Alongside for the night, Shirley Heights for the sunset view over the harbour, and dinner at the Admiral's Inn or Catherine's Café.

• Nelson's Dockyard
• Shirley Heights at sunset
• A night alongside

Into the French islands. Stop at Pigeon Island, Cousteau's reserve, for the snorkelling on the way down the coast, then anchor off Deshaies, the fishing village with the botanical garden above it and the best rum shop on the route.

• Snorkel the Cousteau reserve at Pigeon Island
• Deshaies and its botanical garden
• French provisioning

Three hours to the little archipelago south of Guadeloupe. Bourg des Saintes is a French village with no cars, a fort above it and a bay the UNESCO list calls one of the most beautiful in the world. Pain de Sucre beach, a scooter round the island, dinner in the village.

• Bourg des Saintes
• Fort Napoléon for the view
• Pain de Sucre beach

Two hours to Prince Rupert Bay at Portsmouth. The Indian River by rowing boat under the bloodwood trees, a waterfall in the rainforest, and the chance of sperm whales offshore; Dominica has them all year. The adventurous stop of the trip.

• The Indian River by rowing boat
• Waterfalls in the rainforest
• Sperm whales offshore

The first of the three sea mornings. South along Dominica's coast and across to St Pierre, the town Mount Pelée buried in 1902, with the ruins still in the streets. The market, a rum distillery, and dinner at a table with French bread.

• St Pierre and the ruins of 1902
• A rum distillery
• French dinner

The second sea morning, down Martinique's leeward side and across the channel to Soufrière, where the Pitons rise straight out of the sea. Anchor beneath them, the sulphur springs and the drive-in volcano ashore, dinner with the biggest view of the trip.

• The Pitons from the water
• Sulphur springs
• A night under Petit Piton

The last sea morning, past St Vincent's volcano and into Admiralty Bay. From here everything is an hour or two. Bequia's waterfront path, the boat builders, Jack's on Princess Margaret Beach for the evening.

• Past St Vincent's volcano
• Admiralty Bay
• Sundowners at Jack's

An hour to Mustique for lunch and Basil's, then on to the Tobago Cays: five uninhabited islands behind a horseshoe reef, turtles under the boat, the clearest water of the trip. A lobster barbecue on the beach with the local boatmen at sunset.

• Lunch on Mustique
• Turtles at Baradal
• Lobster barbecue in the Cays

South past Union and Carriacou, with lunch at anchor off Sandy Island, a sandbar with a few palms, and on down Grenada's leeward side to St George's. The Carenage for the farewell dinner, nutmeg in everything.

• Sandy Island off Carriacou
• St George's and the Carenage
• Farewell dinner on the Spice Island

Alongside at Port Louis Marina. Twenty minutes to the airport, direct flights to London and the US.

• Port Louis Marina
• Twenty minutes to the airport