Caribbean · The Leeward Islands
The flat, calm island with the best beaches in the chain
Anguilla is sixteen miles of low coral island across the channel from St Maarten, with thirty-three beaches, water that stays flat in the trades, and food that outclasses islands ten times its size. It is the first or last night of most Leewards weeks and, for Ellie, the place for the beach picnic.
Where
Leeward Islands, 12 nm north of St Maarten
Fly to
St Maarten (SXM), then the yacht; an hour from boarding to anchor
Best months
December to April
Give it
One or two nights on a Leewards week
Known for
Rendezvous Bay, Shoal Bay, the beach picnic, Elvis’ at sunset
Water
Flat and calm on the south coast whatever the trades are doing
Ellie in Anguilla
My Anguilla, in pictures
The beach picnic, the sea pool off the back of the boat and sunset at Elvis' shack. My own photos from one of my favourite days of any Caribbean week.
Ellie Malouf · Ahoy Club
Why go
Anguilla, honestly
Anguilla is the opposite of St Barths and sits an hour from it. No hills, no harbour town, no scene. What it has is sand: Rendezvous Bay, Shoal Bay, Meads Bay and Maundays, long and empty, with water so calm the yacht barely moves at anchor. The island decided years ago to stay quiet, and the result is the best beach day in the Leewards.
The food is the surprise. For an island of fifteen thousand people, Anguilla has a run of serious restaurants, Blanchards and Veya among them, and a beach-shack culture that is the real draw: Elvis’ in Rendezvous Bay, the Dune Preserve, Sandy Island’s barbecue on a sandbar you can walk round in five minutes.
We use it as the first night out of St Maarten, when everyone wants to swim and sleep, or the last, when nobody wants to go home. On a St Barths week it is where the beach picnic happens: the crew land a table and a kitchen on the sand and cook lunch there.
Where we anchor
The anchorages, in the order we use them
- Road Bay, Sandy GroundAnchorage, clearanceThe island’s port and clearance point, a crescent of beach with the bars along it. Clear in here, then move.
- Rendezvous BayAnchorage, the picnicTwo miles of sand facing St Maarten, flat in the trades. The beach picnic, and Elvis’ for the sunset.
- Sandy IslandLunch anchorageA sandbar with palms and a barbecue shack a mile off Road Bay. Lunch, a swim, and back to the boat.
- Crocus Bay and Little BayAnchorage, snorkellingThe north coast cliffs and the snorkelling at Little Bay, reached by tender. A quiet night when the south coast is busy.
- Prickly Pear CaysDay stopTwo uninhabited cays six miles north with reef between them. A day for the toys and nobody else.
Ashore
Anguilla off the boat
Not a directory. If it is here, we have sat at the table or stood at the bar.
Eat
Serious tables for a small island. Book before you fly in season.
BlanchardsCaribbean fine dining steps from the sand on Meads Bay, and the shack next door for lunch.
VeyaA treehouse setting inland, fusion cooking, the dinner the island talks about.
EmberFire-grilled cooking with the sea in front of it. Relaxed and very good.
Drink and dance
Beach shacks, not clubs. The sunset is the event.
Elvis’ Beach BarRendezvous Bay. A piña colada, the locals, music from a speaker, hammocks and the sun going down behind the bay. Ellie’s favourite.
The Dune PreserveBankie Banx’s driftwood bar on the beach, live music, pure Caribbean.
Sunset Lounge, Four SeasonsThe polished version: cocktails over Meads Bay at golden hour.
Do
Beaches and water. There is not much else, which is the point.
Sandy Island barbecueTender to the sandbar for grilled crayfish under the palms.
Snorkel Little BayCliffs, calm water and fish, reached by tender from Crocus Bay.
- The beach picnicThe crew land a table, umbrellas and a kitchen on Rendezvous Bay and cook lunch there. The best place in the Caribbean for one.
Where it sits
Anguilla on the chart
Anguilla sits twelve miles north of St Maarten and twenty-three from St Barths, so it is the natural first or last night of a Leewards week and the calm counterweight to Gustavia. On a St Barths week it gets two nights.
Drag to move. Double-click or ctrl-scroll to zoom.Zoom with the buttons, then drag to move.
When
When to be in Anguilla
- Jan
- Feb
- Mar
- Apr
- May
- Jun
- Jul
- Aug
- Sep
- Oct
- Nov
- Dec
- December to April: the season. Flat water on the south coast, warm, the restaurants open and full.
- New Year: busy by Anguilla standards, which means a few boats on each beach. A calm night after St Barths.
- Easter: Anguilla’s own boat racing, the national sport, if the dates line up.
- May to November: quiet and hot, with the hurricane season from July. Most restaurants close in September.
Itineraries
Itineraries that call at Anguilla
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.
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
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
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.
OpenYachts
Yachts in the Caribbean now
Every one of these can anchor off Rendezvous Bay tonight.
CORAL OCEAN
Lürssen · 73m · 1994, refit 2026
12 guests | 6 cabins | 28 crew
€650k – 790k
TANZANITE
Westship · 44m · 2004, refit 2023
10 guests | 5 cabins | 7 crew
$145k – 160k
ARKTOS
Lagoon · 24m · 2026
9 guests | 4 cabins | 4 crew
€70k – 96k
FRENCH WEST
Lagoon · 24m · 2020
8 guests | 4 cabins | 3 crew
$55k – 72k
WHISPER
Holland Jachtbouw · 35m · 2003, refit 2019
6 guests | 3 cabins | 5 crew
Price on request
CALYPSO
Feadship · 38m · 1978, refit 2025
11 guests | 5 cabins | 8 crew
$120k – 135k
REVE BLEU
Lagoon · 21m · 2023
8 guests | 4 cabins | 4 crew
€45k – 60k
BELLA
Feadship · 45m · 2008, refit 2014
12 guests | 6 cabins | 9 crew
€245k – 255k
NO SURRENDER
Custom Line · 37m · 2022
11 guests | 5 cabins | 7 crew
$140k – 155k
Louder
Horizon · 27m · 2020, refit 2026
8 guests | 4 cabins | 4 crew
$85k – 95k
VAGATOR
Fountaine Pajot · 20m · 2025
8 guests | 4 cabins | 3 crew
€38k – 57k
ARAOK
Fountaine Pajot · 18m · 2018, refit 2024
6 guests | 3 cabins | 3 crew
€25k – 29k
Just Enough
43m · 2012, refit 2024
11 guests | 5 cabins | 9 crew
$119k – 139k
MISS CHRISTINE
Trinity Yachts · 48m · 2006, refit 2024
11 guests | 5 cabins | 8 crew
$165k – 190k
BETH ANN
Westport · 34m · 2012, refit 2025
8 guests | 4 cabins | 5 crew
$65k – 75k
ALEXA OF LONDON
38m · 1992, refit 2025
9 guests | 4 cabins | 5 crew
€65k – 70k
SHADES OF GREY
Sunreef Yachts · 24m · 2024
9 guests | 4 cabins | 5 crew
€70k – 100k
HOUBARA
Sunreef Yachts · 24m · 2012, refit 2026
7 guests | 3 cabins | 3 crew
€34k – 45k
Avanti
Privilege · 22m · 2005, refit 2025
8 guests | 4 cabins | 4 crew
$51k – 55k
Aurelius 111
DUTCH YACHT BUILDERS · 34m · 2011, refit 2023
6 guests | 3 cabins | 3 crew
Price on request
MINE GAMES
Benetti · 50m · 2023
10 guests | 5 cabins | 10 crew
$330k – 350k
Lady Joy
Christensen · 48m · 2007, refit 2025
12 guests | 6 cabins | 11 crew
$199k – 225k
Chakra
Devonport · 86m · 1998, refit 2025
24 guests | 19 cabins | 30 crew
€495k
LOOMA
Fountaine Pajot · 20m · 2023
8 guests | 4 cabins | 3 crew
$34k – 65k
SIETE MARES
Lagoon · 24m · 2025
8 guests | 4 cabins | 4 crew
€65k – 69k
ENCORE
Sunreef Yachts · 18m · 2026
8 guests | 4 cabins | 3 crew
$56k – 62k
YOLO
Sunreef Yachts · 22m · 2022
8 guests | 4 cabins | 4 crew
€59k – 70k
OKINAWA
Fountaine Pajot · 18m · 2024
10 guests | 5 cabins | 3 crew
$29k – 63k
LE PONANT
Société Française de Construction Navale (SFCN) · 84m · 1990, refit 2022
32 guests | 16 cabins | 34 crew
€540k
OCEAN CLUB
Trinity Yachts · 49m · 2009, refit 2025
12 guests | 5 cabins | 10 crew
$195k – 250k
QARA
Horizon · 25m · 2001, refit 2023
6 guests | 3 cabins | 3 crew
$37k – 42k
TOP FIVE II
Royal Hakvoort · 61m · 2021
12 guests | 7 cabins | 19 crew
$600k – 650k
SEA BLISS
Sunreef Yachts · 23m · 2024
8 guests | 4 cabins | 3 crew
€63k – 70k
ELVIS MAGIC
Oyster Marine · 20m · 2003, refit 2025
6 guests | 3 cabins | 2 crew
$25k – 26k
Southern Belle
Johnson · 27m · 2006
8 guests | 4 cabins | 4 crew
$54k – 59k
PERSEVERANCE 1
Baltic · 40m · 2021, refit 2025
8 guests | 4 cabins | 6 crew
€100k – 110k
RAY
Sunreef Yachts · 22m · 2025
8 guests | 4 cabins | 3 crew
€70k – 77k
IL MIO CANTO LIBERO
Nautor's Swan · 32m · 2014, refit 2026
8 guests | 4 cabins | 4 crew
€85k – 102k
NORTHERN STAR
Hinckley · 23m · 1993, refit 2022
6 guests | 3 cabins | 3 crew
$52k – 60k
CROSSED SABRE
Burger · 44m · 2006, refit 2021
12 guests | 7 cabins | 11 crew
$175k – 195k
The Peddler
Custom Line · 26m · 2019
8 guests | 4 cabins | 4 crew
$69k – 74k
GRAND ILLUSION
Palmer Johnson · 44m · 1994, refit 2017
10 guests | 5 cabins | 7 crew
$115k – 125k
NEVER ENOUGH
Feadship · 43m · 1992, refit 2019
10 guests | 5 cabins | 7 crew
$110k – 127k
YKNOT NOW
YYachts · 23m · 2020
6 guests | 3 cabins | 2 crew
€24k – 38k
VALINOR
Lagoon · 17m · 2023
8 guests | 4 cabins | 3 crew
€27k – 31k
SWEET CAROLINE II
Trinity Yachts · 50m · 2009, refit 2021
12 guests | 7 cabins | 11 crew
$19k – 230k
KASKAZI FOUR
Lagoon · 19m · 2016, refit 2025
8 guests | 4 cabins | 4 crew
€23k – 30k
UTOPIA IV
Rossinavi · 63m · 2018, refit 2022
12 guests | 6 cabins | 12 crew
$475k – 505k
48 yachts in rotation. The order changes with every visit so no boat is always last.
Questions we get asked
Anguilla, answered
Common questions
How do we get to Anguilla for a yacht charter?
Fly to St Maarten, which has direct flights from the US east coast and Europe. The yacht meets you in Simpson Bay and Anguilla is an hour away. Anguilla has its own small strip for propeller planes if anyone joins mid-charter.
What is the beach picnic?
The crew land a table, chairs, umbrellas and a kitchen on an empty beach and cook lunch there, with the yacht anchored in view. Rendezvous Bay and Sandy Island are the two places we do it in Anguilla, and Ellie rates it the best spot in the Caribbean for one.
Is Anguilla good for a first night?
The best in the Leewards. The water on the south coast stays flat whatever the trade wind is doing, so nobody is finding their sea legs, and Elvis’ at sunset is a gentle first evening.
Anguilla or St Barths?
Both, on the same week. Anguilla is the beaches and the quiet; St Barths is the town and the nights out. They are two and a half hours apart and most Leewards weeks give each a night or two.
Want Anguilla 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.