Caribbean · The southern chain
The southern chain: greener, wilder, better sailing
Dominica, Martinique, St Lucia, St Vincent and the Grenadines, and Grenada: the Windward Islands run four hundred miles south from the French islands to the top of South America. Taller, greener and less visited than the Leewards, with the best sailing water in the Caribbean. A week covers St Lucia to Grenada.
Where
The southern half of the Lesser Antilles, Dominica to Grenada
Fly to
St Lucia (UVF) or Grenada (GND), both with direct London flights
Best months
December to April
Give it
A week, St Lucia to Grenada one way
Known for
The Pitons, the Grenadines, the Tobago Cays, Grenada’s spice
Wind
Steadier trades than the Leewards; every leg is a reach
Why go
The Windward Islands, honestly
The Windwards are the Caribbean the Leewards used to be. Volcanic islands tall enough to make their own weather, rainforest to the summits, towns that still turn out for the ferry, and anchorages where the only other light is a fishing boat. The sailing is the best in the region: steady trades on the beam, islands an hour or two apart, and the Grenadines in the middle like a string of beads.
The chain runs from Dominica in the north, the nature island with its rivers and whales, through French Martinique to St Lucia and the Pitons, then St Vincent and its thirty Grenadines, and Grenada at the bottom with its spice markets and the prettiest harbour town in the Caribbean. Barbados sits a hundred miles east on its own and is a flight connection more than a stop.
A week covers St Lucia to Grenada one way, which is the route we run. Dominica and Martinique are the bridge from the Leewards on the fourteen-night run down both chains, not part of the week.
Where we anchor
The anchorages, in the order we use them
- St Lucia, SoufrièreAnchorage, the startUnder the Pitons. The biggest view in the Caribbean for the first night.
- Bequia, Admiralty BayAnchorageThe gateway to the Grenadines and its friendliest harbour.
- The Tobago CaysAnchorageTurtles behind the reef, five uninhabited islands, the best water in the chain.
- Grenada, St George’sMarina, the finishPort Louis Marina in the prettiest harbour town in the Caribbean. Twenty minutes to the airport.
Ashore
The Windward Islands off the boat
Not a directory. If it is here, we have sat at the table or stood at the bar.
Eat
Beach shacks, plantation tables and one famous bar.
- Dasheene, St LuciaDinner between the Pitons at Ladera, the view the island is known for.
- The lobster barbecue, Tobago CaysGrilled on the beach by the local boatmen at sunset.
- Grenada’s CarenageDinner on the harbour in St George’s, nutmeg in everything.
Drink and dance
Rum punch at sunset. The jump-ups are the nights.
- Basil’s Bar, MustiqueOn stilts over the water, Wednesday night.
- The Frangipani, BequiaThursday steel band on the waterfront.
- Carriacou’s Paradise BeachThe Off the Hook bar and a rum punch before Grenada.
Do
Sail, snorkel, hike a volcano.
- The PitonsFrom the water at dawn, then the sulphur springs and the drive-in volcano ashore.
- Turtles at BaradalThe Tobago Cays sanctuary, waist deep.
- Dominica’s Indian RiverBy rowing boat under the bloodwood trees, on the fourteen-night route.
Where it sits
The Windward Islands on the chart
The Windwards are the southern of the two chains, a day south of Antigua across the French islands. A week covers St Lucia to Grenada; two weeks joins them to the Leewards.
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When
When to be in The Windward Islands
- Jan
- Feb
- Mar
- Apr
- May
- Jun
- Jul
- Aug
- Sep
- Oct
- Nov
- Dec
- December to April: the season. Steadier trades than the Leewards, and the best sailing weeks in the Caribbean.
- Late January: the Mustique Blues Festival. Easter: the Bequia Regatta.
- May: St Lucia Jazz, and the quietest good weather of the year.
- June to November: hot and wet, hurricane season from July. Grenada sits south of most storms, which is why the fleet winters there.
Itineraries
Itineraries that call at The Windward Islands
Full plans, day by day, with the boat each one runs on. Send one to the people coming with you; we reshape it around your yacht and dates.
A week in the Grenadines
St Lucia7 stopsGrenada
The Windward Islands, St Lucia to Grenada one way: the Pitons, Bequia, Mustique, the Tobago Cays and the Spice Island. Greener, wilder and far less spoken about.
Open
The Leeward and Windward Islands in 14 nights
St Barths13 stopsGrenada
St Maarten to Grenada, all the way down: St Barths, Nevis and St Kitts, Barbuda and Antigua, the French islands, Dominica, the Pitons and the Grenadines.
OpenYachts
Yachts in the Caribbean now
The sailing yachts in the fleet earn their keep here.
CORAL OCEAN
Lürssen · 73m · 1994, refit 2026
12 guests | 6 cabins | 28 crew
€650k – 790k
MUCHOS MAS
Crescent Yachts · 44m · 2016, refit 2025
11 guests | 5 cabins | 9 crew
US$198k – 238k
Sheergold
Amels · 42m · 1987, refit 2025
10 guests | 4 cabins | 8 crew
€135k – 139k
NEFESH
Lagoon · 23m · 2022
6 guests | 3 cabins | 4 crew
€49k – 69k
SPIRIT
Amels · 54m · 2011, refit 2025
12 guests | 6 cabins | 14 crew
€295k – 325k
LAURENTIA
Heesen · 55m · 2017
12 guests | 6 cabins | 13 crew
Price on request
HOLDIN' MY OWN
Turquoise · 55m · 2011, refit 2026
12 guests | 6 cabins | 13 crew
€350k – 390k
MAXIMUS
Vitters · 59m · 2023
8 guests | 4 cabins | 10 crew
Price on request
OCULUS
Numarine · 37m · 2024
12 guests | 6 cabins | 7 crew
US$180k – 210k
LA LA LAND
Sanlorenzo · 44m · 2023
12 guests | 5 cabins | 10 crew
€325k – 390k
MOUSEA
Sunseeker · 40m · 2016, refit 2026
10 guests | 5 cabins | 9 crew
€169k – 187k
REMEMBER WHEN
Christensen · 49m · 2011, refit 2024
12 guests | 6 cabins | 10 crew
US$230k – 260k
BIRUBI
Benetti · 50m · 2022
10 guests | 5 cabins | 10 crew
€308k – 360k
JOY
Feadship · 70m · 2016
12 guests | 7 cabins | 19 crew
€650k – 780k
ILLUSION
Heesen · 65m · 2013, refit 2019
12 guests | 6 cabins | 15 crew
Price on request
SLIPSTREAM
CMN · 60m · 2009
12 guests | 6 cabins | 15 crew
€350k – 455k
CARPE DIEM
Trinity Yachts · 58m · 2011, refit 2024
12 guests | 6 cabins | 11 crew
€294k – 375k
ALVIA
Feadship · 76m · 2024
12 guests | 7 cabins | 21 crew
US$875k – 900k
SURINA
Trident · 45m · 2000, refit 2022
10 guests | 5 cabins | 8 crew
US$148k – 168k
DEJA TOO
Amels · 52m · 2003, refit 2025
11 guests | 6 cabins | 13 crew
€259k – 280k
KOJU
Benetti · 37m · 2022
10 guests | 5 cabins | 8 crew
US$160k – 175k
NORTH STAR
Sunrise Yachts · 63m · 2019, refit 2021
12 guests | 6 cabins | 16 crew
€430k
AS YOU WISH
Westport · 50m · 2011, refit 2026
12 guests | 7 cabins | 11 crew
US$252k – 277k
JODI ANN
Benetti · 43m · 2019, refit 2025
10 guests | 5 cabins | 9 crew
US$199k – 228k
DIRT POOR
Trinity Yachts · 49m · 2007, refit 2026
12 guests | 5 cabins | 9 crew
US$195k – 225k
ODESSA
Christensen · 49m · 2009, refit 2025
12 guests | 6 cabins | 9 crew
US$250k – 275k
DOKINHA
Mangusta (Overmarine) · 50m · 2025
12 guests | 6 cabins | 11 crew
US$300k – 350k
TITANIA
Lurssen · 73m · 2006, refit 2018
12 guests | 7 cabins | 21 crew
€660k – 760k
MAVERICK
Mangusta (Overmarine) · 50m · 2022
12 guests | 6 cabins | 11 crew
US$295k – 320k
NORMA JEAN
Palmer Johnson · 46m · 2009, refit 2024
10 guests | 5 cabins | 8 crew
US$160k – 180k
NYMPHEAS
Turquoise · 79m · 2025
12 guests | 7 cabins | 21 crew
€950k – 995k
Katana
Westport · 26m · 2012
8 guests | 4 cabins | 3 crew
US$48k – 54k
SEA CLASS
Christensen · 47m · 1997, refit 2024
12 guests | 6 cabins | 10 crew
US$190k – 230k
LES CINQ
Feadship · 76m · 2025
12 guests | 6 cabins | 21 crew
€825k – 930k
SYCARA V
Nobiskrug · 68m · 2010, refit 2024
12 guests | 7 cabins | 16 crew
US$650k
SCINTILLA MARIS
Damen Yachting · 46m · 2023
10 guests | 5 cabins | 8 crew
Price on request
BARBARA
Oceanco · 89m · 2017
12 guests | 8 cabins | 27 crew
Price on request
LAUREL
Delta Marine · 73m · 2006, refit 2014
12 guests | 7 cabins | 24 crew
€525k
VICTORIA DEL MAR
Delta Marine · 50m · 2006, refit 2026
12 guests | 7 cabins | 11 crew
€245k – 270k
GIOIA
Codecasa · 43m · 2024
10 guests | 5 cabins | 9 crew
€235k – 285k
AKULA
Baglietto · 52m · 2024
10 guests | 5 cabins | 10 crew
US$325k – 350k
BACA
Royal Denship · 43m · 2009, refit 2019
10 guests | 5 cabins | 9 crew
€185k – 195k
SIREN
Nobiskrug · 74m · 2008, refit 2018
12 guests | 6 cabins | 18 crew
€500k – 580k
ASANI
Benetti · 50m · 2024
10 guests | 5 cabins | 12 crew
€308k – 343k
SYNTHESIS
Amels · 74m · 2021, refit 2026
12 guests | 6 cabins | 19 crew
US$830k – 930k
SANTOSHA
Heesen · 57m · 2024
12 guests | 6 cabins | 13 crew
US$400k – 483k
ALTA
Palmer Johnson · 44m · 2004, refit 2024
11 guests | 5 cabins | 9 crew
€185k – 220k
BATON ROUGE
Icon · 63m · 2010, refit 2026
12 guests | 7 cabins | 18 crew
€455k – 500k
48 yachts in rotation. The order changes with every visit so no boat is always last.
Questions we get asked
The Windward Islands, answered
Common questions
Which are the Windward Islands?
Dominica, Martinique, St Lucia, St Vincent and the Grenadines, and Grenada, running south from the French islands to the top of South America. Barbados sits out to the east on its own. The Leewards are the northern chain, from the Virgin Islands to Antigua.
How long does the Windward chain take?
A week covers St Lucia to Grenada one way with four or five nights in the Grenadines, which is the route we run. Adding Dominica and Martinique makes it part of the fourteen-night run down both chains.
Windwards or Leewards for a first Caribbean charter?
The Leewards, usually: shorter legs and St Barths. The Windwards are for people who want the sailing, the reef and the rustic islands, often on their second Caribbean trip.
Where do we fly into for the Windward Islands?
St Lucia to start and Grenada to finish, both with direct flights from London and connections through Miami and Barbados.
Want The Windward Islands in your week?
Tell us the dates and who is coming. We will say which nights to give it, which berth to hold, and whether the week you want is still open.