Caribbean Windward and Leeward Islands 2023-24
December 2023 - April 2024

About the Windward and Leeward Islands

We have an absolutely wonderful itinerary available to you in the warm and sunny Caribbean. Beats the cold and gloomy European winter hands down. The Grenadines including Tobago Cays is our favorite cruising ground, but we do love St Lucia, Martinique, Dominica and Guadeloupe as well. There are some rough edges to the Caribbean, yes, but when you know the people, you have nothing at all to worry about.
We keep Fort-de-France, Martinique as our base camp because it is the most convenient place to fly to from Europe. From there we can explore both the Windward and the Leeward islands. The way it works is that we have two options: we either go south exploring Martinique, St Lucia and St Vincent (including The Grenadines), or we go north exploring Martinique, Dominica and Guadeloupe (including Iles des Saintes and Maria Galante). Your choice! We can do the provisioning for you in advance, if you want to, to save time for the actual cruising. Below are some examples that can easily be tweaked according to your preferences.

Example agenda heading south

  • You arrive to the yacht in Fort-de-France Tuesday evening.
  • On Wednesday we head south to St Lucia – Soufriere and the Pitons
  • Thursday: Leaving St Lucia, going south into the Grenadines, first stop Admirality Bay in Bequia.
  • Friday: Exploring Mustique. Dinner at the legendary Basil’s Bar.
  • Saturday: Sailing to Tobago Cays, maybe the most beautiful place in the Caribbean. Dinner on board.
  • Sunday: We stay another day at Tobago Cays, snorkeling and watching the Sea Turtles. Grilled Lobster on the beach, organized by the locals.
  • Monday: Going down to Clifton, Union Island, beautiful island with the unmissable Happy Island Bar out on the reef. Dinner in town.
  • Tuesday: Going around to Chatham Bay, the most popular bay on Union and “The Sunset Cove”, where you get a glimpse of the green flash every other evening.
  • Wednesday: North to Mayreau to Saline Bay, Troissant Bay or Salt Whistle Bay. Dinner ashore.
  • Thursday: Back to Admirality Bay in Bequia with some more time to explore the best place in the Grenadines.
  • Friday: North to St Vincent, spending the night in Cumberland Bay, Chateaubelair or Wallilabou (Pirates of the Caribbean).
  • Saturday: Leaving St Vincent for St Lucia, arriving in the famous Rodney Bay.
  • Sunday: Back to Martinique and Fort-de-France

Example agenda heading north

  • You arrive to the yacht in Fort-de-France Tuesday evening.
  • On Wednesday we head north to St Pierre.
  • Thursday: Leaving Martinique, going to Roseau, the capital of Dominica
  • Friday: Exploring the waterfalls and nature of Dominica
  • Saturday: Going north to Portsmouth, the second largest town in Dominica. Several possible excursions, e.g. boat trip up the Indian River to Calypsos Lair (Pirates of the Caribbean)
  • Sunday: Visiting Maria Galante, an island belonging to Guadeloupe
  • Monday: Going up to Point-a-Pitre, the largest and most picturesque town on Guadeloupe.
  • Tuesday: Visiting Isles des Saintes, another group of islands belonging to Guadeloupe
  • Wednesday: Back south to Portsmouth/Roseau
  • Thursday: Back to Martinique, to e.g. Le Carbet or Case-Pilote
  • Friday: Going south to anchor in some beautiful cove, e.g. Grand Anse or Anse Chaudiere
  • Saturday: Into FdF Bay to Anse Noir, Anse Dufour, Anse Mitan or Les Trois Ilets
  • Sunday: Back to Fort-de-France

We recommend a 12 day cruise of the Windward Islands, but you are free to book any length of time. We keep Fort-de-France, Martinique as our main base, because it, easy to fly there from Europe, but we can also pick you up on Grenada, St Vincent or St Lucia.

Pricing for Caribbean Windward and Leeward Islands 2023-24

200€/day/cabin (cabin sleeps two)

Pricing listed as per cabin (max 2/cabin).


  • Boat and crew (skipper&hostess)
  • Cleaning and cooking
  • Bedding and towels
  • Snorkeling gear
  • Yacht insurance
  • Safety equipment
  • Unforgettable days

Not included:

  • Travel to/from boat
  • Personal insurance
  • Possible Covid related testing and fees
  • Meals and shopping ashore

Fees and expenses (NB these will be split between the guests and paid on board at the end of the cruise):

  • Immigration and cruising fees
  • All provisioning (including food for the crew)
  • Marina/mooring fees (marina fees applicable to Rodney Bay, otherwise mostly at anchor or mooring)
  • Park/visiting fees (applicable to Soufriere/Pitons, Tobago Cays and Mustique)
  • Fuel