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

SLIPSTREAM

SLIPSTREAM

CMN · 60m · 2009

12 guests | 6 cabins | 15 crew

€350k – 455k

BATELLO

BATELLO

Oceanco · 80m · 2007, refit 2025

12 guests | 9 cabins | 26 crew

€735k – 850k

AKULA

AKULA

Baglietto · 52m · 2024

10 guests | 5 cabins | 10 crew

US$325k – 350k

LAUREL

LAUREL

Delta Marine · 73m · 2006, refit 2014

12 guests | 7 cabins | 24 crew

€525k

SYCARA V

SYCARA V

Nobiskrug · 68m · 2010, refit 2024

12 guests | 7 cabins | 16 crew

US$650k

OCULUS

OCULUS

Numarine · 37m · 2024

12 guests | 6 cabins | 7 crew

US$180k – 210k

REMEMBER WHEN

REMEMBER WHEN

Christensen · 49m · 2011, refit 2024

12 guests | 6 cabins | 10 crew

US$230k – 260k

Katana

Katana

Westport · 26m · 2012

8 guests | 4 cabins | 3 crew

US$48k – 54k

CARPE DIEM

CARPE DIEM

Trinity Yachts · 58m · 2011, refit 2024

12 guests | 6 cabins | 11 crew

€294k – 375k

SEVEN SINS

SEVEN SINS

Sanlorenzo · 52m · 2017

10 guests | 5 cabins | 11 crew

US$300k – 315k

NORTH STAR

NORTH STAR

Sunrise Yachts · 63m · 2019, refit 2021

12 guests | 6 cabins | 16 crew

€430k

JOY

JOY

Feadship · 70m · 2016

12 guests | 7 cabins | 19 crew

€650k – 780k

NAILED IT

NAILED IT

Viking Yachts · 25m · 2017, refit 2026

8 guests | 4 cabins | 3 crew

US$55k

KOJU

KOJU

Benetti · 37m · 2022

10 guests | 5 cabins | 8 crew

US$160k – 175k

SYNTHESIS

SYNTHESIS

Amels · 74m · 2021, refit 2026

12 guests | 6 cabins | 19 crew

US$830k – 930k

ARTHURS WAY

ARTHURS WAY

Benetti · 44m · 2007, refit 2025

12 guests | 5 cabins | 9 crew

US$150k – 165k

JODI ANN

JODI ANN

Benetti · 43m · 2019, refit 2025

10 guests | 5 cabins | 9 crew

US$199k – 228k

ILLUSION

ILLUSION

Heesen · 65m · 2013, refit 2019

12 guests | 6 cabins | 15 crew

Price on request

CynderElla

CynderElla

Hargrave · 35m · 2022

10 guests | 5 cabins | 7 crew

US$125k – 145k

DIRT POOR

DIRT POOR

Trinity Yachts · 49m · 2007, refit 2026

12 guests | 5 cabins | 9 crew

US$195k – 225k

LES CINQ

LES CINQ

Feadship · 76m · 2025

12 guests | 6 cabins | 21 crew

€825k – 930k

HOLDIN' MY OWN

HOLDIN' MY OWN

Turquoise · 55m · 2011, refit 2026

12 guests | 6 cabins | 13 crew

€350k – 390k

SPIRIT

SPIRIT

Amels · 54m · 2011, refit 2025

12 guests | 6 cabins | 14 crew

€295k – 325k

LAURENTIA

LAURENTIA

Heesen · 55m · 2017

12 guests | 6 cabins | 13 crew

Price on request

NEFESH

NEFESH

Lagoon · 23m · 2022

6 guests | 3 cabins | 4 crew

€49k – 69k

VICTORIA DEL MAR

VICTORIA DEL MAR

Delta Marine · 50m · 2006, refit 2026

12 guests | 7 cabins | 11 crew

€245k – 270k

ATLAS

ATLAS

Lurssen · 74m · 2007, refit 2026

12 guests | 6 cabins | 19 crew

US$950k

MAVERICK

MAVERICK

Mangusta (Overmarine) · 50m · 2022

12 guests | 6 cabins | 11 crew

US$295k – 320k

ALTA

ALTA

Palmer Johnson · 44m · 2004, refit 2024

11 guests | 5 cabins | 9 crew

€185k – 220k

ODESSA

ODESSA

Christensen · 49m · 2009, refit 2025

12 guests | 6 cabins | 9 crew

US$250k – 275k

MUCHOS MAS

MUCHOS MAS

Crescent Yachts · 44m · 2016, refit 2025

11 guests | 5 cabins | 9 crew

US$198k – 238k

SIREN

SIREN

Nobiskrug · 74m · 2008, refit 2018

12 guests | 6 cabins | 18 crew

€500k – 580k

BATON ROUGE

BATON ROUGE

Icon · 63m · 2010, refit 2026

12 guests | 7 cabins | 18 crew

€455k – 500k

NORMA JEAN

NORMA JEAN

Palmer Johnson · 46m · 2009, refit 2024

10 guests | 5 cabins | 8 crew

US$160k – 180k

AS YOU WISH

AS YOU WISH

Westport · 50m · 2011, refit 2026

12 guests | 7 cabins | 11 crew

US$252k – 277k

SURINA

SURINA

Trident · 45m · 2000, refit 2022

10 guests | 5 cabins | 8 crew

US$148k – 168k

ADASTRA

ADASTRA

Moonen · 37m · 2025

10 guests | 5 cabins | 8 crew

US$168k – 182k

TITANIA

TITANIA

Lurssen · 73m · 2006, refit 2018

12 guests | 7 cabins | 21 crew

€660k – 760k

SEA CLASS

SEA CLASS

Christensen · 47m · 1997, refit 2024

12 guests | 6 cabins | 10 crew

US$190k – 230k

AVALON

AVALON

Delta Marine · 46m · 2009, refit 2024

12 guests | 5 cabins | 9 crew

US$185k – 230k

DEJA TOO

DEJA TOO

Amels · 52m · 2003, refit 2025

11 guests | 6 cabins | 13 crew

€259k – 280k

LA LA LAND

LA LA LAND

Sanlorenzo · 44m · 2023

12 guests | 5 cabins | 10 crew

€325k – 390k

BLU

BLU

Breaux Bay · 38m · 1979, refit 2025

8 guests | 4 cabins | 6 crew

US$95k – 115k

AWAY

AWAY

Sanlorenzo · 37m · 2009, refit 2023

10 guests | 5 cabins | 7 crew

US$120k – 145k

MOUSEA

MOUSEA

Sunseeker · 40m · 2016, refit 2026

10 guests | 5 cabins | 9 crew

€169k – 187k

HEMISPHERE

HEMISPHERE

Pendennis · 44m · 2011, refit 2023

12 guests | 5 cabins | 10 crew

US$260k – 280k

BARBARA

BARBARA

Oceanco · 89m · 2017

12 guests | 8 cabins | 27 crew

Price on request

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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