St Maarten to Grenada · 14 nights · Simpson Bay, St Maarten to St George's, Grenada

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

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.

  • December - April
  • 15 Days / 14 Nights
  • Simpson Bay, St Maarten to St George's, Grenada
  • 15 days, 13 stops
  • Family & friends
1

St Barths

St Barths, northern Leewards · 16 nm · 1.5 h · Board, and straight across

Day 1, St Barths
  • Ninety minutes to St Barths
  • The quiet corner
  • Turtles under the boat
2

St Barths

St Barths, northern Leewards · 2 nm · 15 min · Gustavia and the beach clubs

Day 2, St Barths
  • Lunch at Nao or Shellona
  • Gustavia's boutiques
  • Bonito, then the night out

The idea of the week

The two weeks that make the Caribbean make sense. Start in St Maarten and run the whole chain south one way: St Barths for the glamour, St Kitts and Nevis for the green quiet, Barbuda for lunch at Nobu and Antigua for the dockyard, then the French islands and Dominica as the bridge, the Pitons, the Grenadines, and Grenada to finish. Fourteen nights, about 485 miles, and never the same anchorage twice.

Be honest with yourselves about the middle. Nights ten to twelve, from Dominica down to Bequia, are three days in a row with five or six hours at sea each: the mornings are on passage, the afternoons and evenings are the islands. Everything either side is a few hours. Superyacht charters start on any day of the week, so the route stands on its own. If you want the crowd and the DJs in St Barths, we line your dates up so those two nights fall on a Friday and Saturday. Legs are approximate, at a steady ten knots, and the captain adjusts them for the weather on the day.

  • Two weeks
  • Leewards and Windwards
  • Sailing
  • Seasoned charterers

What the week costs

The yacht's published weekly rate, plus an Advance Provisioning Allowance, customarily 30 to 40 percent, for fuel, food, drink and berths, plus local VAT where it applies. Every listing shows its rate.

How charter pricing works

Also on this coast

Everything we know about Caribbean: when to go, where the fleet is and the other weeks we have planned.

Open Caribbean

Woven into the week

What the crew arrange along the way

The parts of the week that need a phone call before you arrive: tables, guides, instructors and the toys on deck.

The beach picnic

The crew land a table, chairs, umbrellas and a kitchen on a beach with nobody else on it and cook lunch there. Anguilla is the best place in the Caribbean for one; the crew will find the others.

A themed day or night on board, at least one

The Caribbean is about the boat, so we plan at least one themed day or night. Tell us the idea before the charter and the crew have the costumes and decorations ready: pirate night is the classic.

Diving and snorkelling

Reefs off almost every anchorage, a dive instructor on most yachts, and gear for everyone. The Tobago Cays, Anegada's Horseshoe Reef and the Indians in the BVI are the ones people talk about afterwards.

The toys, every day

Seabobs, paddleboards, wakeboards, the slide if the yacht has one. In the Caribbean the water is the point, and the crew have them in by the time breakfast is cleared.

Nobu Barbuda

Lunch on Princess Diana Beach, booked with the charter.

Guests arriving late or leaving early

No problem. Most of the islands have a small airstrip and propeller planes run back to the gateway airport, so a mid-charter changeover is a short flight rather than the boat turning round.

  • St Barths, Anguilla, Nevis and Antigua all have strips
  • Virgin Gorda and Beef Island in the BVI
  • Bequia, Canouan and Union Island in the Grenadines
Helicopter day

A heli pick-up from the yacht for a day on another island, or the flight in from the gateway airport instead of the first cruise. We arrange it and the pilot meets you on the quay.

  • St Maarten to St Barths in twelve minutes
  • Antigua to Barbuda over the lagoon
  • St Thomas to anywhere in the Virgins

Yachts

Yachts available in Caribbean right now

Live from our charter list, in a different order every visit so you see the range. Every rate is the real weekly figure from the listing.

CORAL OCEAN

CORAL OCEAN

Lürssen · 73m · 1994, refit 2026

12 guests | 6 cabins | 28 crew

€650k – 790k

CROSSED SABRE

CROSSED SABRE

Burger · 44m · 2006, refit 2021

12 guests | 7 cabins | 11 crew

US$175k – 195k

FRENCH WEST

FRENCH WEST

Lagoon · 24m · 2020

8 guests | 4 cabins | 3 crew

US$55k – 72k

ELVIS MAGIC

ELVIS MAGIC

Oyster Marine · 20m · 2003, refit 2025

6 guests | 3 cabins | 2 crew

US$175k – 288k

NO SHORTCUTS

NO SHORTCUTS

Westport · 34m · 2006, refit 2022

8 guests | 4 cabins | 6 crew

US$65k – 75k

REVE BLEU

REVE BLEU

Lagoon · 21m · 2023

8 guests | 4 cabins | 4 crew

US$55k – 72k

MISS CHRISTINE

MISS CHRISTINE

Trinity Yachts · 48m · 2006, refit 2024

11 guests | 5 cabins | 8 crew

US$165k – 190k

SCOTT FREE

SCOTT FREE

Abeking & Rasmussen · 60m · 2009, refit 2022

12 guests | 6 cabins | 16 crew

€420k – 450k

SEA AXIS

SEA AXIS

Heesen · 38m · 1988, refit 2026

12 guests | 5 cabins | 7 crew

US$105k – 135k

BLACKSHEEP

BLACKSHEEP

Palmer Johnson · 38m · 2009, refit 2023

8 guests | 4 cabins | 6 crew

US$85k – 95k

QARA

QARA

Horizon · 25m · 2001, refit 2023

6 guests | 3 cabins | 3 crew

US$37k – 42k

HUNTRESS

HUNTRESS

Lurssen · 76m · 2009, refit 2024

12 guests | 6 cabins | 22 crew

US$695k – 775k

PAPER MOON

PAPER MOON

Benetti · 44m · 2026

10 guests | 6 cabins | 9 crew

US$240k – 260k

HOUBARA

HOUBARA

Sunreef Yachts · 24m · 2012, refit 2026

7 guests | 3 cabins | 3 crew

€34k – 45k

BELLA

BELLA

Feadship · 45m · 2008, refit 2014

12 guests | 6 cabins | 9 crew

€245k – 255k

NAMASTE

NAMASTE

Benetti · 37m · 2013, refit 2023

10 guests | 5 cabins | 7 crew

US$105k – 135k

LOOMA

LOOMA

Fountaine Pajot · 20m · 2023

8 guests | 4 cabins | 3 crew

US$48k – 65k

SHADES OF GREY

SHADES OF GREY

Sunreef Yachts · 24m · 2024

9 guests | 4 cabins | 5 crew

€70k – 80k

KEFI

KEFI

Christensen · 46m · 2005, refit 2026

12 guests | 6 cabins | 9 crew

US$175k – 195k

PARSIFAL III

PARSIFAL III

Perini Navi · 54m · 2005, refit 2024

12 guests | 5 cabins | 9 crew

€245k

NORTHERN STAR

NORTHERN STAR

Hinckley · 23m · 1993, refit 2022

6 guests | 3 cabins | 3 crew

US$52k – 60k

SOVEREIGN

SOVEREIGN

Burger · 30m · 1966, refit 2020

8 guests | 4 cabins | 3 crew

US$48k – 50k

Q

Q

Alloy Yachts · 52m · 2008, refit 2024

12 guests | 5 cabins | 9 crew

€255k

Chakra

Chakra

Devonport · 86m · 1998, refit 2025

24 guests | 19 cabins | 30 crew

€495k

NO SURRENDER

NO SURRENDER

Custom Line · 37m · 2022

11 guests | 5 cabins | 7 crew

US$140k – 155k

REVERIE

REVERIE

Feadship · 50m · 2000, refit 2025

12 guests | 6 cabins | 12 crew

US$255k – 295k

NEVER ENOUGH

NEVER ENOUGH

Feadship · 43m · 1992, refit 2019

10 guests | 5 cabins | 7 crew

US$110k – 127k

SEASCAPE V

SEASCAPE V

Benetti · 44m · 2005, refit 2024

10 guests | 5 cabins | 9 crew

US$153k – 180k

CHRISTINA O

CHRISTINA O

Canadian Vickers · 99m · 1943, refit 2022

34 guests | 17 cabins | 40 crew

€700k – 740k

LE PONANT

LE PONANT

Société Française de Construction Navale (SFCN) · 84m · 1990, refit 2022

32 guests | 16 cabins | 34 crew

€540k

ST DAVID

ST DAVID

Benetti · 60m · 2008, refit 2025

12 guests | 6 cabins | 15 crew

€340k – 360k

FRIENDSHIP

FRIENDSHIP

Oceanco · 53m · 2000, refit 2022

12 guests | 6 cabins | 12 crew

€245k – 265k

The Peddler

The Peddler

Custom Line · 26m · 2019

8 guests | 4 cabins | 4 crew

US$69k – 74k

BEACHFRONT

BEACHFRONT

Hargrave · 33m · 2006, refit 2022

10 guests | 5 cabins | 5 crew

US$65k – 90k

UNBRIDLED

UNBRIDLED

Crescent · 35m · 1995, refit 2024

8 guests | 4 cabins | 5 crew

US$65k – 75k

SPIRIT OF THE C'S

SPIRIT OF THE C'S

Perini Navi · 64m · 2003, refit 2023

12 guests | 5 cabins | 13 crew

€210k – 230k

Louder

Louder

Horizon · 27m · 2020, refit 2026

8 guests | 4 cabins | 4 crew

US$85k – 95k

YKNOT NOW

YKNOT NOW

YYachts · 23m · 2020

6 guests | 3 cabins | 2 crew

€24k – 34k

ARAOK

ARAOK

Fountaine Pajot · 18m · 2018, refit 2024

6 guests | 3 cabins | 3 crew

€25k – 29k

Lady Joy

Lady Joy

Christensen · 48m · 2007, refit 2025

12 guests | 6 cabins | 11 crew

US$199k – 225k

YOLO

YOLO

Sunreef Yachts · 22m · 2022

8 guests | 4 cabins | 4 crew

€59k – 70k

NO BAD IDEAS

NO BAD IDEAS

Trinity Yachts · 49m · 2000, refit 2024

12 guests | 6 cabins | 9 crew

US$225k – 250k

ESCAPE

ESCAPE

Hatteras · 35m · 1995, refit 2023

9 guests | 4 cabins | 5 crew

US$55k – 65k

LUCKY LADY

LUCKY LADY

Oceanco · 63m · 2002, refit 2025

10 guests | 5 cabins | 15 crew

€310k – 355k

WHISPER

WHISPER

Holland Jachtbouw · 35m · 2003, refit 2019

6 guests | 3 cabins | 5 crew

Price on request

Just Enough

Just Enough

43m · 2012, refit 2024

11 guests | 5 cabins | 9 crew

US$119k – 139k

SOUTH

SOUTH

Heesen · 55m · 2012

12 guests | 6 cabins | 13 crew

US$320k – 350k

Avanti

Avanti

Privilege · 22m · 2005, refit 2025

8 guests | 4 cabins | 4 crew

US$51k – 55k

48 yachts in rotation. The order changes with every visit so no boat is always last.

Back to Caribbean

The other weeks we have planned on this coast, and when to go.

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