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
The Peddler
Custom Line · 26m · 2019
8 guests | 4 cabins | 4 crew
$69k – 74k
SEA BLISS
Sunreef Yachts · 23m · 2024
8 guests | 4 cabins | 3 crew
€63k – 70k
BELLA
Feadship · 45m · 2008, refit 2014
12 guests | 6 cabins | 9 crew
€245k – 255k
SUNMOON
Fountaine Pajot · 20m · 2024
10 guests | 5 cabins | 3 crew
€42k – 65k
Just Enough
43m · 2012, refit 2024
11 guests | 5 cabins | 9 crew
$119k – 139k
YOLO
Sunreef Yachts · 22m · 2022
8 guests | 4 cabins | 4 crew
€59k – 70k
SHADES OF GREY
Sunreef Yachts · 24m · 2024
9 guests | 4 cabins | 5 crew
€70k – 80k
FRENCH WEST
Lagoon · 24m · 2020
8 guests | 4 cabins | 3 crew
$55k – 72k
ENCORE
Sunreef Yachts · 18m · 2026
8 guests | 4 cabins | 3 crew
$56k – 62k
ALFA G
Oceanco · 60m · 2004, refit 2024
12 guests | 7 cabins | 17 crew
€400k – 440k
GRAND ILLUSION
Palmer Johnson · 44m · 1994, refit 2017
10 guests | 5 cabins | 7 crew
$115k – 125k
Chakra
Devonport · 86m · 1998, refit 2025
24 guests | 19 cabins | 30 crew
€495k
MISS CHRISTINE
Trinity Yachts · 48m · 2006, refit 2024
11 guests | 5 cabins | 8 crew
$165k – 190k
ST DAVID
Benetti · 60m · 2008, refit 2025
12 guests | 6 cabins | 15 crew
€340k – 360k
SWEET CAROLINE II
Trinity Yachts · 50m · 2009, refit 2021
12 guests | 7 cabins | 11 crew
$199k – 230k
ALEXA OF LONDON
38m · 1992, refit 2025
9 guests | 4 cabins | 5 crew
€65k – 70k
REVERIE
Feadship · 50m · 2000, refit 2025
12 guests | 6 cabins | 12 crew
$255k – 295k
NO SURRENDER
Custom Line · 37m · 2022
11 guests | 5 cabins | 7 crew
$140k – 155k
SPIRIT OF THE C'S
Perini Navi · 64m · 2003, refit 2023
12 guests | 5 cabins | 13 crew
€210k – 230k
Q
Alloy Yachts · 52m · 2008, refit 2024
12 guests | 5 cabins | 9 crew
€255k
WONDERFUL
Gunboat · 22m · 2023
8 guests | 4 cabins | 3 crew
€55k – 69k
OCEAN CLUB
Trinity Yachts · 49m · 2009, refit 2025
12 guests | 5 cabins | 10 crew
$195k – 250k
YKNOT NOW
YYachts · 23m · 2020
6 guests | 3 cabins | 2 crew
€24k – 38k
Avanti
Privilege · 22m · 2005, refit 2025
8 guests | 4 cabins | 4 crew
$51k – 55k
CALYPSO
Feadship · 38m · 1978, refit 2025
11 guests | 5 cabins | 8 crew
$120k – 135k
PARSIFAL III
Perini Navi · 54m · 2005, refit 2024
12 guests | 5 cabins | 9 crew
€245k
HUNTRESS
Lurssen · 76m · 2009, refit 2024
12 guests | 6 cabins | 22 crew
$695k – 775k
HOUBARA
Sunreef Yachts · 24m · 2012, refit 2026
7 guests | 3 cabins | 3 crew
€34k – 45k
CROSSED SABRE
Burger · 44m · 2006, refit 2021
12 guests | 7 cabins | 11 crew
$175k – 195k
SLEEPOVER
Westport · 34m · 2008, refit 2021
8 guests | 4 cabins | 4 crew
$65k – 75k
Louder
Horizon · 27m · 2020, refit 2026
8 guests | 4 cabins | 4 crew
$85k – 95k
ARAOK
Fountaine Pajot · 18m · 2018, refit 2024
6 guests | 3 cabins | 3 crew
€25k – 29k
LUCKY LADY
Oceanco · 63m · 2002, refit 2025
10 guests | 5 cabins | 15 crew
€310k – 355k
WHISPER
Holland Jachtbouw · 35m · 2003, refit 2019
6 guests | 3 cabins | 5 crew
Price on request
QARA
Horizon · 25m · 2001, refit 2023
6 guests | 3 cabins | 3 crew
$37k – 42k
Lady Joy
Christensen · 48m · 2007, refit 2025
12 guests | 6 cabins | 11 crew
$199k – 225k
NORTHERN STAR
Hinckley · 23m · 1993, refit 2022
6 guests | 3 cabins | 3 crew
$52k – 60k
ELVIS MAGIC
Oyster Marine · 20m · 2003, refit 2025
6 guests | 3 cabins | 2 crew
$25k – 288k
ONYX
Nautor's Swan · 30m · 2005, refit 2021
6 guests | 3 cabins | 4 crew
Price on request
LOOMA
Fountaine Pajot · 20m · 2023
8 guests | 4 cabins | 3 crew
$48k – 65k
CHRISTINA O
Canadian Vickers · 99m · 1943, refit 2022
34 guests | 17 cabins | 40 crew
€700k – 740k
OKINAWA
Fountaine Pajot · 18m · 2024
10 guests | 5 cabins | 3 crew
$47k – 63k
LE PONANT
Société Française de Construction Navale (SFCN) · 84m · 1990, refit 2022
32 guests | 16 cabins | 34 crew
€540k
NEVER ENOUGH
Feadship · 43m · 1992, refit 2019
10 guests | 5 cabins | 7 crew
$110k – 127k
FRIENDSHIP
Oceanco · 53m · 2000, refit 2022
12 guests | 6 cabins | 12 crew
€245k – 265k
SOVEREIGN
Burger · 30m · 1966, refit 2020
8 guests | 4 cabins | 3 crew
$48k – 50k
REVE BLEU
Lagoon · 21m · 2023
8 guests | 4 cabins | 4 crew
$55k – 72k
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.