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Anguilla at 40 to 50m is the bracket where the destination becomes a beach-landing market with St Martin as the hub. A 40 to 50m motor yacht Anguilla in 2026 peak Christmas and February weeks runs $200,000 to $310,000 per week plus 30 percent APA, takes 10 to 12 guests, and embarks Simpson Bay St Martin with day-anchor positions at Rendezvous Bay, Meads Bay, and Shoal Bay on the Anguilla side. The active 40 to 50m fleet on the Anguilla and St Martin triangle through the December to April Caribbean season is roughly 16 yachts, most splitting weeks between St Barths, Anguilla, and St Martin embarkation. Anguilla has no port-of-entry marina for the bracket; the embarkation and disembarkation work on the St Martin Dutch-side hub.
Why the bracket works Anguilla on a triangle pattern
Anguilla is an anchor-only destination at the bracket. The island runs 26km east to west on the north side of the Leeward Antilles, faces the Atlantic on the north shore and the Caribbean Sea on the south, and the south-shore beaches (Rendezvous Bay, Meads Bay, Maundays Bay, Shoal Bay West) form a 12nm string of day-anchor positions for the bracket. The north shore is open ocean and not workable for the bracket through most of the winter season.
Anguilla has no marina for the bracket and the cruising permit and immigration process runs through Road Bay (Sandy Ground). The standard week works Anguilla as part of a St Martin and St Barths triangle pattern with embarkation in Simpson Bay, two to three day-anchor positions on the Anguilla south shore, and the St Barths and Anguilla legs as bookends. Stand-alone Anguilla weeks are rare at the bracket and structurally do not justify the rate.
Weekly rate map for 2026 to 2027 season
Rates below are for peak weeks (Christmas through New Year, President's Day week) for the 2026 to 2027 season, before APA at 30 percent and gratuity at 12 to 15 percent. Anguilla cruising permit fees and the inter-island immigration costs run through the APA. The St Martin Dutch-side embarkation does not carry charter VAT at the rate the French Caribbean side does.
| LOA bracket | Motor yacht (low to high) | Sailing yacht and large catamaran (low to high) |
|---|---|---|
| 40 to 43m | $200K to $235K per week | $165K to $200K per week |
| 43 to 47m | $225K to $270K per week | $190K to $235K per week |
| 47 to 50m | $260K to $310K per week | $220K to $275K per week |
Off-peak Caribbean season (early December outside the Christmas window, mid-January through early February, March outside President's week, and early April) runs roughly 20 to 30 percent below the peak headlines. The strongest value window is the second and third weeks of January when the Atlantic swell drops and the Anguilla south-shore positions open up. For corridor context see the Caribbean bracket page, St Barths bracket page, and the 30 to 40m Anguilla bracket.
What is in the bracket in this bracket
Cabins. 5 to 6-cabin layouts dominate. The Anguilla triangle pattern is heavy on couples weeks at Christmas and friend-group weeks at President's, and the 5-cabin charter spec runs through the inventory.
Crew. 9 to 12 on motor yachts. The St Martin crew bench is the deepest in the Leeward Antilles for last-minute substitution and the chef bench at the bracket is workable through the season. Specify chef's prior Caribbean season at inquiry.
Tenders. A primary 9 to 10m fast tender plus a 6 to 7m beach-landing secondary is mandatory. The Anguilla south-shore beach landings at Rendezvous Bay, Meads Bay, and Maundays Bay all run on sand approaches and the secondary tender is the operational variable that decides whether the week works.
At-anchor stabilizers. Mandatory. Anguilla is a north-swell market through most of the winter and the south-shore anchor positions take a residual 1m to 1.5m swell when northeast tradewinds build above 22 knots. The at-anchor differential is the single largest comfort variable on the Anguilla south shore and the kit is non-negotiable at the bracket.
Helipad. Useful at the upper end of the bracket for the Anguilla to St Barths shuttle, but not required. The 8nm crossing to St Martin and the 30nm crossing to St Barths run on tender or on the yacht itself rather than helicopter for most weeks.
Trip shapes that fit the bracket
The St Martin and Anguilla triangle. Embark Simpson Bay St Martin, anchor day-one at Rendezvous Bay on the Anguilla south shore for a shore lunch at the resort, position to Meads Bay, day-shuttle to Shoal Bay West and Sandy Ground for the customs round, return to St Martin anchor at Anse Marcel or Grand Case for two nights, position to Tintamarre and Ile Pinel for a final day. Seven nights. The bracket fits the pattern and the destination grouping rewards the tender programme.
The Anguilla, St Martin, and St Barths triangle. Embark Simpson Bay, two nights Anguilla south shore, position to Gustavia for three nights at anchor off Shell Beach and Colombier, return via Tintamarre and Pinel, disembark Simpson Bay. Seven nights, the classic Leeward triangle. Best at the upper end of the bracket for the open-water St Barths crossings.
The Anguilla stationary five-night with St Barths bookend. Embark Simpson Bay, position immediately to St Barths for two nights, return to Anguilla for five nights stationary at Rendezvous Bay or Meads Bay with day-shuttles to Prickly Pear and Dog Island, return Simpson Bay. Seven nights. The bracket fits this and the stationary Anguilla section suits family weeks with shore lunches at the resort beach clubs.
For destination context see Charter Anguilla, Charter St Barths, and Best charter yachts Caribbean.
What the bracket does not do well in Anguilla
Stand-alone Anguilla weeks at the bracket. The Anguilla south shore is a day-anchor product but not a seven-night stationary one because the destination lacks the marina, the inner-harbour shore landings, and the topographical variety that the bracket's rate demands. Build Anguilla as a leg of the St Martin and St Barths triangle, not as the entire week.
North-shore Anguilla. The north shore of Anguilla faces the open Atlantic and the swell makes the north anchorages unworkable through most of the winter. The Shoal Bay east anchorage is a day-stop in flat conditions only.
Hurricane-season weeks. Anguilla took heavy hit from Hurricane Irma in 2017 and the rebuild cycle is complete but the hurricane-season risk pattern remains. Weeks priced into June to October at the bracket carry weather risk that the Mediterranean reposition does not.
What we would book
For two couples, seven days in late January, St Martin and Anguilla triangle with two nights stationary at Rendezvous Bay and lunches at Cap Juluca and the Belmond resort: a 43m motor yacht with 5 cabins and at-anchor stabilizers, embarkation Simpson Bay. Budget $220K plus APA, all-in roughly $295K. Booking lead time: 8 to 11 months for peak, 4 to 6 months off-peak.
For a family of 12, ten days at Christmas, Leeward triangle with St Barths bookend and a stationary five-night base at Meads Bay: a 47m motor yacht with 6 cabins, twin tenders, embarkation Simpson Bay. Budget $285K plus APA, all-in roughly $385K. Booking lead time: 12 to 15 months minimum.
For a friend group of 10, ten days in President's week, Anguilla and St Barths with two-night Tintamarre extension: a 45m motor yacht with 5 cabins, embarkation Simpson Bay. Budget $250K plus APA, all-in roughly $335K. Booking lead time: 10 to 13 months.
Build year, refit, condition
The Anguilla 40 to 50m fleet draws from the wider Leeward inventory based out of St Martin and St Barths, which means a mix of European builds repositioning from the Med and US-built tonnage on the Florida programme. A 2018 to 2024 build with current AV, full tender complement, at-anchor stabilizers, and a 2022 or later refit is the value zone. We would pass on units without documented post-Irma refit work if they were active in the region in 2017, on any unit whose tender programme does not include the 6m+ beach-landing secondary, and on any week where the Anguilla south-shore anchor positions are not confirmed in writing at contract.