A-List Travel Advisor Louisa Gehring

Gehring is just as skilled at planning dreamy honeymoon getaways and multigenerational trips as she is at organizing monthlong solo adventures that span numerous islands. Lately, she’s been recommending newly refurbished classic hotels, like Belmond Cap Juluca in Anguilla and Eden Rock–St. Barths. One of the biggest trends she’s observed is the rise of lesser-known islands like Dominica and the St. Vincent and the Grenadines—which she attributes to concerns of overtourism. “Easy flights from the U.S. has led to rampant development and the emergence of ‘hotel strips’ with no local culture,” she says. “My clients are willing to work a bit harder to get to special destinations that aren’t overwhelmed by the masses.” Thanks to Genring’s deep familiarity with the Caribbean’s geography and the flight routes connecting various islands, she’s able to pull together itineraries that allow for seamless transfer between destinations. She recently planned a three-week vacation for a couple that included stays on 8 different Caribbean islands, including Barbados, Antigua, and St. Martin.