Hand has traveled to 15 islands in just the past few years, including Jamaica, Grand Cayman, Nassau, St. Martin. She takes particular interest in planning multigenerational vacations, like a recent trip for a family of 17 in Turks and Caicos. (The men went deep-sea fishing while the women spent a day at the spa.) Hand, an avid scuba diver who first fell in love with the Caribbean on her honeymoon two decades ago, is able to secure room upgrades, private sailing trips and yoga classes, spa credits, and other perks.
New favorite: The Malliouhana, an Auberge Resort, in Anguilla, reopened last November after a three-year renovation. Sitting on a hilltop with 360-degree water views, the 44-room resort now has an Auberge Spa, alfresco cliff-side dining, and a two-tiered infinity pool surrounded by private cabanas.
Specialties: The Caribbean, Destination weddings