10 Guests
North Sound
Rum Point
Spotts Bay
Barcadere Marina
Bloody Bay, Little Cayman
Wade with the stingrays at Stingray City
Dive Bloody Bay Wall off Little Cayman
Snorkel the wreck of the USS Kittiwake
Walk the Mastic Trail rainforest
Tour Pedro St. James, the Birthplace of Democracy
Camana Bay
Pedro St. James
Hell, West Bay
Cayman Brac
Little Cayman
December through April brings the driest, calmest conditions, with steady trade winds and the clearest water of the year for diving. May through November is wetter and warmer and falls within the official Atlantic hurricane season, though direct hits are relatively rare given the islands’ position south of the main hurricane belt, making shoulder months a reasonable trade-off for lighter marina traffic.
Owen Roberts International Airport (GCM), a few minutes from George Town on Grand Cayman, is the main gateway, with direct flights from the US East Coast, Canada and the UK. Little Cayman and Cayman Brac each have their own small airfields, Edward Bodden Airfield (LYB) and Charles Kirkconnell International (CYB), reached by a short inter-island hop for guests continuing on to the quieter sister islands.
North Sound, on Grand Cayman’s northern side, is the sheltered base for most Stingray City trips and has room for a large fleet at anchor. Rum Point and Spotts Bay offer quieter, more local alternatives on the same island, while Bloody Bay on Little Cayman, beneath one of the Caribbean’s best regarded walls, rewards the extra distance for divers willing to make the crossing.
Four or five days cover Grand Cayman comfortably: Stingray City, Seven Mile Beach, a wreck dive on the Kittiwake and an evening in Camana Bay. A week or more allows a crossing to Little Cayman and Cayman Brac, roughly forty miles northeast, where the diving is quieter and the pace slower, though the crossing depends on settled weather since the passage runs through open water.
Pirates Week, the Cayman Islands’ national festival, runs across all three islands each year, opening in Cayman Brac in late October before moving to Grand Cayman and finishing in Little Cayman in November, with a landing ceremony, a parade through George Town and fireworks. Now approaching its fiftieth year, it began as a low season tourism initiative and has grown into the territory’s biggest cultural event, so marina space around those dates needs booking well ahead.
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