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Anguilla at 50 to 60m is an anchorage island, not a marina island, and the bracket visits Anguilla as part of a wider eastern-Caribbean itinerary embarking St Martin, St Barths, or Antigua. The 2026 weekly rate at the bracket runs $255,000 to $385,000 for motor and $205,000 to $310,000 for sailing, plus APA at 25 to 30 percent, Anguillan cruising permits at roughly $250 per vessel plus per-day per-guest fees, and gratuity at 10 to 15 percent. The bracket carries 10 to 12 guests in 6 cabins, with 14 to 17 crew. Embarkation almost always happens at St Martin's Simpson Bay or the Saba Rock outer berthing, with the Anguilla leg sitting at one to three nights inside a wider seven-to-ten-night week. Charter clients booking Anguilla as the primary destination should plan a Caribbean week with Anguilla as the structural pivot, not as the sole geography.
Why the bracket works as a port-of-call, not a base
Anguilla's coastline runs roughly 16 miles along the northern flank of the Anguilla Channel and the island has no commercial superyacht marina at any LOA. Road Bay (Sandy Ground) is the principal anchorage and customs entry, with 4 to 6 boats at the bracket comfortably accommodated on swing. Crocus Bay, Meads Bay, Maundays Bay, and Rendezvous Bay handle the bracket on day-anchor for lunch and beach service; overnight anchorage at the southern bays is workable in steady trades but not the default. Prickly Pear Cays (the two outer cays west of the main island) anchor at the bracket on the lee side for day operation.
The booking pattern at the bracket is the Caribbean week that visits Anguilla rather than the Anguilla-based week. A St Martin-based charter at the bracket runs Anguilla, Prickly Pear, St Barths, and the leeward Antigua approach inside a seven-to-ten-night program. The Anguilla-only week is a marketing construct, not an itinerary; the bracket exhausts the island's overnight anchorage variety in 36 to 48 hours and the trip rewards the multi-island geography.
The customs and immigration regime requires advance entry permit and per-vessel fees, with Road Bay as the only entry point for the bracket. The customs process is well-established for the yachting trade; the broker handles the paperwork at the booking stage.
Weekly rate map for 2026
The bracket rates below reference the full charter week for a Caribbean itinerary that includes Anguilla as a port-of-call. High season (mid-December 2026 to mid-April 2027), before APA at 25 to 30 percent and gratuity at 10 to 15 percent.
| LOA bracket | Motor yacht (low to high) | Sailing yacht and motor-sailor (low to high) |
|---|---|---|
| 50 to 53m | $255K to $295K per week | $205K to $245K per week |
| 53 to 57m | $290K to $340K per week | $235K to $275K per week |
| 57 to 60m | $325K to $385K per week | $265K to $310K per week |
Anguilla at the bracket carries a 5 to 8 percent premium on a like-for-like LOA against the BVI and a 10 to 15 percent discount against the St Barths NYE booking pattern. Christmas and New Year run a 35 to 55 percent premium and the St Barths cluster pulls the bracket east through the holiday window. For broader context see Caribbean charter weekly rates, the 40 to 50m Anguilla bracket, and the 50 to 60m St Barths bracket.
What the bracket includes in this bracket
Cabins. 6 cabins standard. The eastern Caribbean 50 to 60m pool is the Caribbean's deepest at the bracket because the St Barths NYE cluster repositions a heavy share of the Mediterranean fleet east through November.
Crew. 14 to 17. The crew bench for the eastern Caribbean is the strongest in the basin, with deep captain, engineering, and chef pools through the seasonal St Barths and St Martin rotation. Chef training in the European fine-dining vein is the bracket norm for the eastern Caribbean rotation.
Tenders. Primary 9 to 10m, secondary 7m. The Anguilla beach-club program runs the secondary tender hard for Maundays, Meads, and Shoal Bay landings; confirm the dual-tender capacity at inquiry.
At-anchor stabilizers. Required. The Anguilla Channel runs swell from the east through December and January and the at-anchor differential at Road Bay and the southern bays is a real charter-experience variable.
Helipad. Touch-and-go meaningful at the upper end of the bracket. St Martin's Princess Juliana airport is the primary embarkation airport and the helicopter shuttle to Anguilla runs the 8-minute flight to the Anguilla heliport.
Trip shapes that fit the bracket
The St Martin to Anguilla and St Barths seven-night. Embark Simpson Bay, two nights at Anguilla (Road Bay and Prickly Pear), three nights at St Barths (Gustavia, Colombier), one night St Martin lagoon, disembark Simpson Bay. Seven nights. The bracket fits the entire run and this is the eastern Caribbean's strongest week at the LOA.
The St Martin plus Anguilla plus Antigua ten-night. Embark Simpson Bay, work Anguilla and St Barths for four nights, reposition overnight south to Antigua, work English Harbour and Falmouth for three nights, return St Martin. Ten nights. The Antigua leg adds the Nelson's Dockyard evening anchorage.
The eastern Caribbean extended twelve-day. Embark Simpson Bay, work Anguilla and St Barths for four nights, run south through Antigua and Guadeloupe to St Lucia, disembark Rodney Bay one-way. Twelve nights. Best at the upper end of the bracket for the open-water passage south. For destination context see Charter Anguilla, Charter St Barths, and Charter Antigua.
What the bracket does not do well in Anguilla
Single-island weeks. Anguilla as the sole destination exhausts the bracket's geography in 36 to 48 hours. The bracket should plan Anguilla as a port-of-call inside a multi-island week.
Hurricane-window weeks. The eastern Caribbean fleet repositions north to New England or east to the Mediterranean for the August through October storm window. On-charter weeks in that range run on transient tonnage with structurally lighter slot certainty.
NYE inside St Barths-cluster slot windows. The St Barths NYE booking pull dominates the eastern Caribbean's 50 to 60m availability for the last week of December and the first week of January. Anguilla-leg bookings in those weeks compete with the Gustavia anchorage slot map.
What to book
For two couples, seven days in mid-February, St Martin to Anguilla and St Barths: a 53m motor yacht with 6 cabins, at-anchor stabilizers, twin tenders, embarkation Simpson Bay. Budget $300K plus APA, all-in roughly $395K. Booking lead time: 6 to 9 months.
For a family of 10, ten days in early March, eastern Caribbean with Anguilla and Antigua: a 56m motor yacht with 6 cabins, embarkation Simpson Bay, return Simpson Bay. Budget $345K plus APA, all-in roughly $465K. Booking lead time: 8 to 11 months.
For a friend group of 12, twelve days in late March, eastern Caribbean extended to St Lucia one-way: a 58m motor yacht with 6 cabins, embarkation Simpson Bay, disembark Rodney Bay. Budget $385K plus APA plus one-way premium, all-in roughly $530K. Booking lead time: 9 to 12 months.
Vintage and refit checks
The eastern Caribbean 50 to 60m pool is the basin's youngest, with a high share of 2018 to 2024 Italian and Dutch tonnage repositioned east through November. A 2023 or later refit with at-anchor stabilizers and confirmed twin-tender spec is the value zone. We would pass on legacy tonnage running original 2010-era AV through the eastern Caribbean rotation; the trade-wind humidity load is structurally hard on the kit and the dock-day reliability margin is thinner than the western Caribbean rotation.