When Lake Michigan freezes over, Punta Mita is still in full boat-tour season. Nonstop flights from O'Hare reach Puerto Vallarta in under five hours, and a short drive takes you to La Cruz de Huanacaxtle, the marina for Punta Mita and the Riviera Nayarit. Rayando el Sol, our Tanna 47ft luxury catamaran, is chartered only for your group, up to 16 guests on day trips, so the whole deck, the trampolines and the shade are yours. Plan the day around what you came for: a cruise toward the Marietas Islands, snorkeling in warm, clear water, paddleboards, sea scooters and fishing rods, all included. Your private chef prepares a four-course gourmet menu, and the open bar pours craft cocktails, fine wine and mocktails. If you'd rather keep it short, the 3-hour sunset cruise for up to 12 guests is a perfect first night. Chicago's coldest months, December through March, also happen to be humpback whale season in Banderas Bay. Few trips feel this far from a Midwest winter for so little effort.