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The Cayman Islands at 40 to 50m is a port-of-call market, not a charter-base market. A 40 to 50m motor yacht calling Grand Cayman during the winter 2026 season (December through April) runs $165,000 to $245,000 per week plus 30 percent APA, takes 8 to 12 guests, and almost always books as the southern leg of a Bahamas to Cayman corridor charter rather than a standalone Cayman week. The active 40 to 50m fleet calling Cayman through any given winter is under 12 yachts, and most call for two to four days inside a longer western Caribbean rotation. There is no commercial 40 to 50m alongside marina on Grand Cayman; the bracket holds at anchor in the George Town roads or on the North Sound moorings.
Why the bracket reads Cayman as a port-of-call
Grand Cayman is 35km long, sits 290 nautical miles south of Havana and 200 nautical miles northwest of Jamaica, and the cruising ground at the bracket is small by the standards of the Caribbean. The west-shore roads off George Town and Seven Mile Beach hold the bracket on anchor in 12 to 25 metres of water on a sand bottom. The North Sound, the shallow lagoon north of George Town, runs at 1.5 to 3.5 metres of controlling depth across most of its area and is not workable for a 40 to 50m yacht inside the reef. The Stingray City sandbar inside the North Sound is the headline shore attraction at the bracket and runs on a 6 to 7m secondary tender, not the mothership.
Little Cayman and Cayman Brac sit 130km northeast and add a single overnight each on a paired run, but the standalone product on either is thin and the deep-water dive sites at Bloody Bay Wall on Little Cayman are the only structural reason the bracket runs the eastern islands. The seven-night Cayman-titled charter at the bracket does not justify the rate. The Bahamas, Cuba, or Jamaica corridor week with a two to three-day Cayman call does.
Weekly rate map for winter 2026
Rates below are high season (mid-December through mid-April) for winter 2025-26 and winter 2026-27, before APA at 30 percent and crew gratuity at 10 to 15 percent. The Cayman Islands runs a cruising permit regime through the Maritime Authority and the standard 40 to 50m commercial yacht clears at George Town on arrival. There is no charter VAT structure equivalent to the French Caribbean.
| LOA bracket | Motor yacht (low to high) | Sailing yacht and motor-sailor (low to high) |
|---|---|---|
| 40 to 43m | $165K to $195K per week | $140K to $170K per week |
| 43 to 47m | $190K to $220K per week | $165K to $195K per week |
| 47 to 50m | $215K to $245K per week | $185K to $220K per week |
Christmas and New Year weeks (21 December through 5 January) price at a 35 to 55 percent premium against the central January and February figure. Off-peak windows in mid-January and the second half of April drop the headline 20 to 25 percent. The bracket sees a smaller Christmas premium than the Bahamas or Mustique equivalent because the Cayman holiday demand at this size is driven by hotel guests calling the yacht as a day toy, not by stationary villa programmes.
What the bracket buys you in this bracket
Cabins. Five to six. The bracket on the western Caribbean rotation runs the 5-cabin Caribbean standard with a fraction of European-built 6-cabin convertibles.
Crew. Nine to thirteen. The Cayman crew bench is thin because no resident charter-crew labour pool of any depth operates from George Town. Crew rotate in via Miami or Nassau, and captain familiarity with the Cayman cruising permit and Maritime Authority clearance is the variable that decides whether the call runs cleanly. Confirm captain prior Cayman season at inquiry.
Tenders. A primary 9 to 11m fast tender plus a 6 to 7m secondary is mandatory. The Stingray City programme runs on the secondary because of the shallow sandbar approach, and the George Town tender dock at Royal Watler runs the secondary for shore landings during the cruise-ship windows when the inner harbour congests.
At-rest stabilizers. Required. The George Town west-shore anchorage takes north-shore swell wrap during late January and February northers and the at-rest spec is the difference between a workable and a non-workable charter night during a swell episode.
Helipad. Touch-and-go pad on the upper end. Owen Roberts International Airport sits 3 kilometres from the George Town anchorage and the road transfer is faster than the helicopter for most logistics. Helipad use on the corridor is structural rather than Cayman-specific.
The standard call shape
The Cayman call inside a 10 to 14 night western corridor runs as follows. Arrival from the Bahamas or western Cuba into the George Town anchor with overnight on the west-shore roads. Day two: North Sound tender programme to Stingray City and Rum Point with a late-afternoon return to the George Town anchor. Day three: Seven Mile Beach shore lunch at Tillies or Kaibo (tender access on the North Sound side, beach landing on the west side), with optional dive at Cheeseburger Reef or Eden Rock on the George Town side. Day four: morning departure for Little Cayman with overnight at Jackson Bay or the Bloody Bay Wall mooring, dive programme on day five. Day six: positioning leg to the next corridor stop, typically Jamaica's Montego Bay or Cuba's Maria la Gorda.
Standalone seven-night Cayman charters are uncommon at the bracket and structurally compress after day four. Cuba's reopening trajectory for US-flagged charter clients remains a constraint and we would not build the Cuba leg into a charter without confirming the current US Treasury OFAC posture in writing through the broker 60 days before embarkation.
Embarkation logistics
There is no 40 to 50m alongside marina on Grand Cayman. George Town harbour is a commercial cargo and cruise port and the yacht-alongside option is unworkable at the bracket. The standard arrangement is an anchored hold at the west-shore roads with crew clearance through the Port Authority dock and guest tendering to the Royal Watler terminal or directly to the Seven Mile Beach landings. Owen Roberts International Airport handles direct fixed-wing from Miami, Houston, and Toronto and has a general-aviation terminal that handles private aviation well. Crew rotation on the Cayman call runs via Miami in most cases.
What we said no to
Standalone seven-night Cayman charters at the bracket. The cruising ground is too compact and the bracket's all-in week rate does not justify the destination on its own. Build Cayman as a two to four-day call inside a longer Bahamas, Cuba, or Jamaica corridor.
Cruise-ship-day calls into George Town. When four or more cruise ships are in port, the Royal Watler tender congestion and the Seven Mile Beach shore-side density compress the day product. Confirm the cruise-ship arrival calendar against the planned call days at contract; the Cayman Cruise Authority publishes the schedule 12 months out and the broker should screen against it.
North-shore deep-draft yachts attempting the North Sound. The lagoon is unsuitable for the bracket and the only operational programme is tender-based from the outside anchor. Yachts above 3.2 metres draft also lose flexibility on the Little Cayman Bloody Bay moorings and the run should be pre-screened at the operating-draft level.
Hurricane-season weeks. The Cayman Islands hurricane exposure runs through August and September. Weeks priced into June to October at the bracket carry weather risk that the Mediterranean reposition does not.
Inventory
The live 40 to 50m Cayman corridor inventory updates weekly through the winter season.. For broker-side inquiry, see the brokers pillar and the Caribbean charter weekly rates report.