BOOKING A TRIP can feel like Monty Hall’s old game show “Let’s Make a Deal”: You’re given options, each one promising a door to another world. But which door reveals the luxury car, not the proverbial goat?
In our new feature, Trip Quandary, three travel advisers take on a typical dilemma and do their best to calm decision-making jitters and suggest sound solutions. For the first challenge, we asked three trip planners with expertise in the Caribbean, Costa Rica and Belize to recommend a winter-break vacation for a multigenerational, Boston area-based family of 10, with $40,000 to spend on flights, food and comfortably plush digs for a five-day spree.
Read More: The Hardest Part of a Family Vacation? Deciding Where to Go