A DISGRUNTLED Mother Nature can be a photographer's worst nightmare. But when harsh winds and choppy seas off Grand Cayman Island forced a Swimsuit shoot indoors, photographer Walter Iooss Jr. couldn't have asked for a more ideal backup than Calico Jack's. A rickety old beach bar planted a few short steps from the water on the north end of Public Beach, Calico Jack's has an unabashed affinity for the Swimsuit Issue. Scores of photos from past issues paper the establishment's walls, and patrons down tropical drinks out of mugs emblazoned with wallet-sized images of the models. "I saw some of my best stuff in there," says Iooss, a veteran of 20 Swimsuit shoots. "I should have asked for royalties."
Calico Jack's may have been the most SI-friendly location on the island, but the favorite among the traveling party was the replica pirate ship that was anchored some 100 yards offshore in George Town Harbor. Onboard, rookie model Melissa Haro struck her best "shiver me timbers" pose alongside a group of buccaneers (or, more precisely, privateers—these mercenaries were flown in from Seattle) in town for the island's renowned Pirate Week, a 10-day festival that attracts thousands of tourists every year. Each day fireworks explode to the sound track of pulsating Caribbean rhythms, and on the event's final Saturday natives as well as visitors line the streets for the "pirate invasion," when the swashbucklers make a "surprise" landing at George Town. The invasion culminates with a mock trial in which the pirates are found guilty of pillaging and plundering. Their sentence: banishment from the island for one year.
The festivities (and pretty much everything else) are a short taxi ride from the Westin Casuarina. Located on Seven Mile Beach, the Westin possesses the usual amenities valued by the high-end traveler (spacious rooms, plush beds and private balconies), but it also offers a distinct bonus: approximately 800 feet of private, white-sand beach, where guests can rent wave runners or search the ocean floor with the aid of a snorkel. You never know where you might find gold.