St. Lucia We normally wouldn't advise heading down to the Caribbean for the winter, but getting there in early January can save a lot of time and money. St. Lucia is more of a couple's resort than a family place, especially on the island's exclusive south end. If you don't have kids in tow, it may be worth considering a three-night, $55-a-night stay at the Alize Resort Inn and Guest House with a free welcome glass of spiced rum. The Bay Gardens Inn, meanwhile, offers $88 rooms through late March. Yes, there's still the small matter of flying down there, but prices of rooms and flights really start to take off in late February and early March.