Feet in the sand, and the boat does the rest

The Caribbean is a yacht charter about the boat, the crew and the people you bring, not the shore. From December to March the fleet that spent summer in the Mediterranean sits between St Maarten and Grenada, and a week covers one of two island chains: the Leewards around St Barths, Anguilla, Antigua and the Virgin Islands, or the Windwards from St Lucia down through the Grenadines. It is rustic, local and almost never crowded; St Barths is the one exception, and the one everyone knows by name.

View itineraries

Season

December to April. The fleet arrives in late November and stays until the Med calls in May

New Year

St Barths. The biggest night of the season, so book early: ten-night minimums and peak rates

Fly into

St Maarten (SXM). Direct from New York, Miami, Paris and Amsterdam, twenty minutes to the boat

How long

A week for the Leewards or the Windwards. Two weeks to do both

Crowds

Quiet anchorages almost everywhere. St Barths over Christmas and New Year is the one busy spot

Who it suits

Nature lovers and anyone who wants to switch off, party-goers for St Barths. Friends, families, three generations

If you ask us Caribbean or Bahamas, the Caribbean answer is this. It is more rustic and very much the culture you expect going in: tiny islands with populations you can count, locals you get to know, zip lines and quad bikes ashore, and long days on the water. You will eat ashore a few times along the way, but it is not fancy and it is not a restaurant tour. St Barths is the fun, your Mediterranean fix, and outside it the week is nature, boat time and the friends you chose. It is honestly the best way we know to switch off.

That is also why the boat matters more here than anywhere. In the Mediterranean there are temptations ashore all day: the long lunch, the club, the shops. Here there are not, so the toys, the tenders, the crew and the water decide the week. If you have chartered in the Med a lot, this is the one to put on the near-future list.

Ellie on the Caribbean

How we do a Caribbean week

Ellie Malouf · Ahoy Club

The Caribbean is about life on the boat. You go ashore for a long lunch or a sunset drink, then you are back on the tender, because the water is the point and the next island is never more than a couple of hours away. That shapes everything we plan here.

What I always do · swipe

From the camera roll

“The Caribbean is raw, rustic and remote. Tiny islands, untouched nature and little beach shacks, with St Barths thrown in when you want a hit of Mediterranean energy.”

Ellie on the Caribbean

How we do a Caribbean week

These are the things we do every time, roughly in the order they happen, and the ones I would hand to a friend before their first week down there.

I have done every one of these myself, most of them more than once.

What I always do

01 / 05

Faena, Miami Beach
Dinner at Casa Tua
A night or two in Miami first
Flights into St Maarten are limited each day, so the schedule usually needs a stop somewhere, and we use it to land properly rather than arrive on the boat jet-lagged. A day at Faena on Miami Beach is always a treat, and you step onto the yacht already on holiday. We have also done Cuba on the way once, and if you want the week to start with a bit of culture before the beaches take over, that is the one.
Nao, St Barths
Shellona, Shell Beach
St Barths over a weekend
We plan St Barths across a Friday and a Saturday so the beach clubs and the nights out have some atmosphere, because midweek it can go quiet. Nao is my favourite beach club for a lunch that drifts into the afternoon, and Shellona on Shell Beach is the other table we always book. Two nights is plenty. Then you leave the scene behind and head back to the quiet islands, which is the whole point of the Caribbean.
The picnic, Anguilla
Elvis' shack, Rendezvous Bay
A beach picnic in Anguilla
Anguilla has some of the best beaches in the Caribbean for a picnic, and the crew set the table on the sand while you are still in the water. Stay for the afternoon, then go round to Rendezvous Bay for sunset drinks at Elvis' shack: a piña colada, locals, music, hammocks, and the sun going down behind the bay. It is my favourite evening of the week, every time.
Pirate night on board
At least one themed night on board
Because the Caribbean is about the boat rather than going ashore, we always plan at least one themed day or night, and I am usually the one hosting. I brainstorm ideas with the crew before the charter and they do the rest, costumes, decorations, the lot. Pirate night is the one we keep coming back to, and the grown-ups commit to it far harder than the kids.
ATVs, St Kitts
With our guide
A guided ATV tour round St Kitts
Half a day on ATVs with a guide, up into the green hills and back down to the coast. It is a completely different way to see an island than from the water, and after a few days of beaches everyone is glad of the change. Go in the morning before it gets hot, and be back on the boat for a swim by lunch.

From the camera roll

“The Caribbean is raw, rustic and remote. Tiny islands, untouched nature and little beach shacks, with St Barths thrown in when you want a hit of Mediterranean energy.”

A reply from someone who has been, usually the same day.

The chart

See how the islands fit together

Two chains and the Virgin Islands, with the Greater Antilles further west. Pick a trip to light up the chain it uses and the order we would run it, tap an island for the one line that matters about it, and zoom out to see how far Cuba really is.

Build a trip

Or one chain at a time

Drag to move. Double-click or ctrl-scroll to zoom.Zoom with the buttons, then drag to move.

Positions are to scale; shapes are schematic. Zoom out for Puerto Rico, Hispaniola, Jamaica and Cuba.

Itineraries

Six weeks we start from

Tried and tested: three weeks, two ten-nighters and one fourteen, every leg marked in miles and hours. Every one is a starting point we reshape around your group, your yacht and your dates. No two weeks are the same.

Most popular10 nights

The Leeward Islands in ten nights

Antigua7 stopsSt Maarten

Antigua to St Maarten, downwind the whole way: lunch at Nobu on Barbuda, Nevis and St Kitts, a weekend in St Barths and Anguilla's beaches to finish.

Open

7 nights

A week in St Barths and Anguilla

St Maarten5 stopsSt Maarten

Three nights in St Barths over the weekend, Anguilla's beach picnic either side, and an uninhabited island in between. Six hours of cruising all week.

Open

7 nights

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

7 nights

A week in the Virgin Islands

St John7 stopsSt Thomas

From St Thomas: St John's park, the Caves at Norman Island, the Baths, Anegada's lobster and the Soggy Dollar. The first charter we recommend to most families.

Open

10 nights

St Barths then the Virgin Islands

St Barths8 stopsSt John

A weekend in St Barths and Anguilla's beach picnic, an overnight passage downwind, then a week in the Virgins. St Maarten to St Thomas.

Open

14 nights

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.

Open

Where we actually go

Two chains, one week each

Nobody says Leeward or Windward out loud; they say St Barths, the BVI, Antigua. But the islands sit in two chains, and a week covers one of them. Two weeks joins them. There is no right order within a chain: avoid going back and forth, so run a loop, or go all the way up and come slowly down.

A week, the northern chain

The Leeward Islands

Where most Caribbean weeks happen. Fly into St Maarten and the islands are a few hours apart: Anguilla just north, St Barths just east, St Kitts and Nevis and Antigua to the south. The Virgin Islands sit a day's run west and are a week of their own.

St Barths The hot spot. Gustavia's harbour, the beaches, and the one week of the year with real competition for berths. Busy over New Year, back to normal by February, lively again for the sailing in March. Party group? Check which DJs are playing and when, and shape the week so you are in Gustavia for those nights or the weekend, when it is busiest.
St Maarten The door, not the destination. Fly in, board in Simpson Bay, and be at anchor off another island by evening. Mid-charter changeovers route back here on the small island planes.
Anguilla Flat, calm and across the channel from St Maarten, with the best beaches of the chain and the food to match them. The first or last stop on many weeks.
Antigua English Harbour and Nelson's Dockyard, a beach for every day of the year, and direct flights from London, which is why our ten-night Leewards route starts here. The Classics and Sailing Week fill April.
Barbuda An hour north of Antigua: seventeen miles of pink sand, the frigate bird colony, almost nobody, and lunch at Nobu on Princess Diana Beach.
The Virgin Islands, British and US Line-of-sight islands and a calm channel: the first charter we recommend to most families, and a full week on their own. Add them to a Leewards week only on ten to fourteen days, or make them the trip and touch one or two Leeward islands at the end.BVI →USVI →
St Kitts and Nevis Green, quiet, with a plantation-house dinner or two and Nevis Peak over the anchorage. Often a night between St Barths and Antigua.

A week, the southern chain

The Windward Islands

Greener, wilder, and better sailing. Less spoken about, touched just as often. Fly into St Lucia or Grenada and run the chain one way, with the Grenadines in the middle.

St Vincent and the Grenadines Bequia, Mustique and the Tobago Cays: the best anchorages in the chain and the reason to come this far south.
St Lucia The Pitons from the water, and the usual northern start or finish of a Windwards week.
Grenada The southern end: spice markets, a sheltered marina to end in, and Carriacou on the way.
Dominica The nature island. Rainforest, hot rivers and whales offshore. A stop for the adventurous, not the beach crowd.
Martinique French, with the food and the markets to prove it. A provisioning stop as much as a destination.
The chain in one week How we would run it, island by island: St Lucia to Grenada in seven nights, with the legs in miles and hours.

Further out

The Greater Antilles: Cuba, Jamaica, the Dominican Republic, Puerto Rico

Further out and far less travelled. No charter fleet is based here for the season, so bringing a yacht in usually carries relocation fees. That makes these islands the territory of owners on an extended cruise, the second leg of a long charter, or a seasoned charterer who has done the chains and wants somewhere new. Zoom out on the chart above to see where they sit.

Cuba Dominican Republic

When to go

Best Good, quieter We'd go elsewhere

November: the fleet is arriving from the Mediterranean. Some boats take charters, many are still crossing. Good value if the dates line up.
December: the season proper, building to New Year in St Barths, the most competitive week in yachting. Book that one by June.
January to March: our months. Trade winds, warm water, and far fewer boats than the Med ever has. Deals appear as the season goes on. March brings the sailing back to St Barths.
April: the season winding down and the boats preparing to cross east. Antigua's Classics and Sailing Week are the last hurrah.
May to October: closed. The boats are in the Mediterranean and the Bahamas is the nearer option, though summer there has its own winds.

Getting there

St Maarten (SXM) is the door: direct from the US east coast and Europe, and the boat is waiting in Simpson Bay to cruise straight out. Most islands have a small strip for propeller planes, which is how we handle guest changeovers mid-charter: a group swap or an early leaver flies back to St Maarten rather than the boat turning round.

How we'd plan it

What we tell people before they book

New Year is the one busy week
St Barths at New Year is the hot spot of the whole yachting year. Most boats hold a ten to fourteen-night minimum at peak rates, and the good ones are booked by June. Ask early, and have a second week in mind.
The rest of the season has deals
Outside New Year the Caribbean is nowhere near as busy as the Mediterranean. Rates drop to low season and there are often deals, especially later on. St Barths heats up again for the sailing in March.
Party groups: plan around St Barths
If the group is here for the nights out, look at the DJ dates in St Barths before anything else and shape the itinerary around them, or line the week up so you are in Gustavia over the weekend, when it is busiest. The quiet islands fill the days either side.
Fly to St Maarten
It is the main gateway from the US and Europe, and the boat cruises straight out from there. Mid-charter changeovers use the small island strips and propeller planes back to St Maarten; nobody goes far.
One chain per week
A week covers the Leewards or the Windwards comfortably; the Virgin Islands are a week of their own. There is no right order: avoid back and forth, so loop, or go all the way up and come slowly down. Two weeks joins the chains without rushing.
Summer is closed
The Caribbean charter season runs December to March. Some boats accept November and April, but many are still crossing to or from the Mediterranean. In summer the fleet is gone.
The Greater Antilles are for the long trip
Cuba, Jamaica, the Dominican Republic and Puerto Rico are further out and less travelled, and with no fleet based there a charter usually carries relocation fees. They suit owners on an extended cruise, the second leg of a long charter, or a seasoned charterer looking for somewhere new.

New Year is the one busy week

St Barths at New Year is the hot spot of the whole yachting year. Most boats hold a ten to fourteen-night minimum at peak rates, and the good ones are booked by June. Ask early, and have a second week in mind.

The rest of the season has deals

Outside New Year the Caribbean is nowhere near as busy as the Mediterranean. Rates drop to low season and there are often deals, especially later on. St Barths heats up again for the sailing in March.

Party groups: plan around St Barths

If the group is here for the nights out, look at the DJ dates in St Barths before anything else and shape the itinerary around them, or line the week up so you are in Gustavia over the weekend, when it is busiest. The quiet islands fill the days either side.

Fly to St Maarten

It is the main gateway from the US and Europe, and the boat cruises straight out from there. Mid-charter changeovers use the small island strips and propeller planes back to St Maarten; nobody goes far.

One chain per week

A week covers the Leewards or the Windwards comfortably; the Virgin Islands are a week of their own. There is no right order: avoid back and forth, so loop, or go all the way up and come slowly down. Two weeks joins the chains without rushing.

Summer is closed

The Caribbean charter season runs December to March. Some boats accept November and April, but many are still crossing to or from the Mediterranean. In summer the fleet is gone.

The Greater Antilles are for the long trip

Cuba, Jamaica, the Dominican Republic and Puerto Rico are further out and less travelled, and with no fleet based there a charter usually carries relocation fees. They suit owners on an extended cruise, the second leg of a long charter, or a seasoned charterer looking for somewhere new.

Yachts

On the water in the Caribbean now

Live from our charter list, in a different order every visit. Most of them crossed from the Mediterranean in November and cross back in April.

Every yacht in the Caribbean

CORAL OCEAN

Lürssen · 73m · 1994, refit 2026

12 guests | 6 cabins | 28 crew

€650k – 790k

Chakra

Devonport · 86m · 1998, refit 2025

24 guests | 19 cabins | 30 crew

€495k

RAY

Sunreef Yachts · 22m · 2025

8 guests | 4 cabins | 3 crew

€70k – 77k

REVE BLEU

Lagoon · 21m · 2023

8 guests | 4 cabins | 4 crew

€45k – 60k

Vivi

Sunreef Yachts · 18m · 2024

8 guests | 3 crew

$53k – 58k

KASKAZI FOUR

Lagoon · 19m · 2016, refit 2025

8 guests | 4 cabins | 4 crew

€23k – 30k

VALINOR

Lagoon · 17m · 2023

8 guests | 4 cabins | 3 crew

€27k – 31k

ENTRE 4

Sunreef Yachts · 24m · 2024

8 guests | 4 cabins | 4 crew

$100k – 125k

NORTHERN STAR

Hinckley · 23m · 1993, refit 2022

6 guests | 3 cabins | 3 crew

$52k – 60k

SIETE MARES

Lagoon · 24m · 2025

8 guests | 4 cabins | 4 crew

€65k – 69k

QARA

Horizon · 25m · 2001, refit 2023

6 guests | 3 cabins | 3 crew

$37k – 42k

MISS CHRISTINE

Trinity Yachts · 48m · 2006, refit 2024

11 guests | 5 cabins | 8 crew

$165k – 190k

VAGATOR

Fountaine Pajot · 20m · 2025

8 guests | 4 cabins | 3 crew

€38k – 57k

REVA NUI

Lagoon · 24m · 2025

8 guests | 4 cabins | 4 crew

€60k – 83k

BELLA

Feadship · 45m · 2008, refit 2014

12 guests | 6 cabins | 9 crew

€245k – 255k

MINE GAMES

Benetti · 50m · 2023

10 guests | 5 cabins | 10 crew

$330k – 350k

ALEXA OF LONDON

38m · 1992, refit 2025

9 guests | 4 cabins | 5 crew

€65k – 70k

SHADES OF GREY

Sunreef · 24m · 2024

9 guests | 4 cabins | 5 crew

€70k – 80k

Lady Joy

Christensen · 48m · 2007, refit 2025

12 guests | 6 cabins | 11 crew

$199k – 225k

FRENCH WEST

Lagoon · 24m · 2020

8 guests | 4 cabins | 3 crew

$55k – 72k

Just Enough

43m · 2012, refit 2024

11 guests | 5 cabins | 9 crew

$119k – 139k

The Peddler

Custom Line · 26m · 2019

8 guests | 4 cabins | 4 crew

$69k – 74k

ENCORE

Sunreef Yachts · 18m · 2026

8 guests | 4 cabins | 3 crew

$56k – 62k

HOUBARA

Sunreef Yachts · 24m · 2012, refit 2026

7 guests | 3 cabins | 3 crew

€34k – 45k

LE PONANT

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

32 guests | 16 cabins | 34 crew

€540k

SHADES OF GREY

Sunreef Yachts · 24m · 2024

9 guests | 4 cabins | 5 crew

€70k – 100k

OKINAWA

Fountaine Pajot · 18m · 2024

10 guests | 5 cabins | 3 crew

$29k – 63k

WHISPER

Holland Jachtbouw · 35m · 2003, refit 2019

6 guests | 3 cabins | 5 crew

Price on request

LOOMA

Fountaine Pajot · 20m · 2023

8 guests | 4 cabins | 3 crew

$34k – 65k

Southern Belle

Johnson · 27m · 2006

8 guests | 4 cabins | 4 crew

$54k – 59k

ARKTOS

Lagoon · 24m · 2026

9 guests | 4 cabins | 4 crew

€70k – 96k

GRAND ILLUSION

Palmer Johnson · 44m · 1994, refit 2017

10 guests | 5 cabins | 7 crew

$115k – 125k

XENIA 74

Alliaura Marine Group · 23m · 2012

8 guests | 4 cabins | 4 crew

$37k

Ascension

Lagoon · 19m · 2018, refit 2023

8 guests | 4 cabins | 3 crew

$38k – 44k

SEA BLISS

Sunreef Yachts · 23m · 2024

8 guests | 4 cabins | 3 crew

€63k – 70k

IL MIO CANTO LIBERO

Nautor's Swan · 32m · 2014, refit 2026

8 guests | 4 cabins | 4 crew

€85k – 102k

YOLO

Sunreef Yachts · 22m · 2022

8 guests | 4 cabins | 4 crew

€59k – 70k

SWEET CAROLINE II

Trinity Yachts · 50m · 2009, refit 2021

12 guests | 7 cabins | 11 crew

$19k – 230k

UTOPIA IV

Rossinavi · 63m · 2018, refit 2022

12 guests | 6 cabins | 12 crew

$475k – 505k

Aurelius 111

DUTCH YACHT BUILDERS · 34m · 2011, refit 2023

6 guests | 3 cabins | 3 crew

Price on request

TOP FIVE II

Royal Hakvoort · 61m · 2021

12 guests | 7 cabins | 19 crew

$600k – 650k

CROSSED SABRE

Burger · 44m · 2006, refit 2021

12 guests | 7 cabins | 11 crew

$175k – 195k

NEVER ENOUGH

Feadship · 43m · 1992, refit 2019

10 guests | 5 cabins | 7 crew

$110k – 127k

CALYPSO

Feadship · 38m · 1978, refit 2025

11 guests | 5 cabins | 8 crew

$120k – 135k

OCEAN CLUB

Trinity Yachts · 49m · 2009, refit 2025

12 guests | 5 cabins | 10 crew

$195k – 250k

ELVIS MAGIC

Oyster Marine · 20m · 2003, refit 2025

6 guests | 3 cabins | 2 crew

$25k – 26k

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

Questions we get asked

The Caribbean, answered

Common questions

When is the best time for a Caribbean yacht charter?

December to March. New Year in St Barths is the peak, with ten to fourteen-night minimums and peak rates; January to March is quieter with deals later in the season, and St Barths picks up again for the sailing in March. November and April are possible on some boats, but many are crossing to or from the Mediterranean. The season is closed over summer.

Caribbean or Bahamas: how do we choose?

The Caribbean is more rustic and cultural: tiny islands, locals you get to know, activities ashore, and St Barths as the one glamorous fix. The Bahamas is the clearest water we know, beach picnics every day and a little more built up in places. Both are about the boat, the crew and the water rather than restaurants, and both are far less crowded than the Mediterranean. Tell us the group and we will tell you which.

Where do you fly into for a Caribbean charter?

St Maarten. It has direct flights from the US east coast and Europe, and it sits in the middle of the Leewards: the yacht meets you in Simpson Bay and Anguilla, St Barths, St Kitts and Nevis and Antigua are all a few hours away. For the Windwards, fly to St Lucia or Grenada. Guests arriving late or leaving early are no problem. Most of the islands have a small airstrip, and propeller planes run back to St Maarten, so a mid-charter changeover is a short flight rather than the boat turning round.

Which Caribbean islands can we see in a week?

One chain. The Leewards from St Maarten: St Barths, Anguilla, Antigua and Barbuda, St Kitts and Nevis, or the Virgin Islands as a week of their own. Or the Windwards: St Lucia, the Grenadines with Bequia, Mustique and the Tobago Cays, and Grenada. Two weeks joins the chains.

Is the Caribbean crowded in high season?

Rarely. Outside St Barths at New Year you are often at an island with a handful of boats in sight, or none. It is one of the biggest differences from the Mediterranean, and one of the reasons people who have chartered a lot in the Med come here next.

Can we charter in Cuba, Jamaica or the Dominican Republic?

Yes, and we do. They are further out and less travelled, and because no fleet is based there a charter usually carries relocation fees to bring the yacht in and out. That makes them best for owners on an extended cruise, the second leg of a long charter, or a seasoned charterer who has done the chains and wants somewhere new. For a first week or two, the Leewards, the Windwards or the Bahamas are the better call.

Want this shaped around you?

Tell us the dates and who is coming. We pick the chain, the islands and the boat for that group, and tell you straight whether New Year is realistic.

How we do a Caribbean week

How we do a Caribbean week

A night or two in Miami first

St Barths over a weekend

A beach picnic in Anguilla

At least one themed night on board

A guided ATV tour round St Kitts

See how the islands fit together

Six weeks we start from

The Leeward Islands in ten nights

A week in St Barths and Anguilla

A week in the Grenadines

A week in the Virgin Islands

St Barths then the Virgin Islands

The Leeward and Windward Islands in 14 nights

Two chains, one week each

The Leeward Islands

The Windward Islands

The Greater Antilles: Cuba, Jamaica, the Dominican Republic, Puerto Rico

What we tell people before they book

New Year is the one busy week

The rest of the season has deals

Party groups: plan around St Barths

Fly to St Maarten

One chain per week

Summer is closed

The Greater Antilles are for the long trip

On the water in the Caribbean now

The Caribbean, answered

Common questions

Want this shaped around you?