Somewhere around the first gray week of November, a lot of us start picturing warm sand and turquoise water. The trick is that the best winter beach trips are usually booked before the cold sets in, not after.
The holidays go first
Christmas, New Year's and Presidents' Day weeks are the busiest and most expensive times of the year in the Caribbean and Mexico. The most popular resorts and room types for those dates often fill up by early fall. If your trip has to land on a school break, the sooner you book, the more choices you'll have.
January is the sweet spot
The first few weeks after New Year's are one of the best values of the winter. The holiday crowds are gone, prices drop, and the weather in most beach destinations is at its best: warm, dry and sunny. If your schedule is flexible, mid-January through early February is hard to beat.
Spring break books up early, too
March and early April fill up fast with families and college crowds. If you're traveling with kids on a fixed break, aim to book by the end of the year. If you're not tied to the school calendar, consider avoiding those weeks entirely for a quieter, less expensive trip.
Booking early doesn't mean locking in
Many resort and package bookings only need a deposit up front, with the balance due closer to travel. And if prices drop or a better promotion comes along, an advisor can often apply it to your existing booking. Booking early mostly means you get first pick.
Don't forget the flights
Winter flights from colder cities to the beach fill up quickly, especially nonstops on Saturdays. Getting flights locked in alongside the hotel keeps the whole trip from being held hostage by airfare later on.
If a winter escape is on your mind, tell me your dates (or how flexible you are), who's going and what kind of beach trip you're picturing, and I'll pull together a few options while the good ones are still available.