Check the schedules for available sail or race dates, and make a reservation online or by phone up to six days in advance of your planned voyage. The season opens around mid-April, but very large parties should contact the company by phone about early booking.
Show up early for your scheduled cruise. Annapolis traffic can be heavy, so leave extra time to get to the dock and find parking. The boats board 10 minutes before cruise time.
Suit up for a sail. Wear soft-soled deck shoes and a windbreaker -- breezes on the water can be chilly. Take a hat, sunblock and sunglasses, even in spring or fall. And put any child under 35 pounds in an approved life vest. The boat and the Coast Guard require that you supply your own, and you will not be allowed on board with a lightweight sailor who isn't wearing her own vest. The vessel has life vests aboard for all passengers who weigh more than 35 pounds.
Stay on deck while under way to enjoy the sail and the picturesque coastline. There is room below deck if you need to take a break or use the head. But seasickness is minimized in the open air on deck, and raising and lowering the sails, adjusting the trim and helming the boat are part of the cruise. Photographs are better topside as well.
Leave alcoholic beverages, smokes and pets home. The nonsmoking boats serve light snacks. Some cruises are booked with catered food, and there is a cash bar for soft drinks and alcoholic beverages. Bring an individually wrapped food item for yourself if you follow a special diet.
Be prepared to cruise rain or shine. Unless there is a tropical storm headed toward Annapolis, cruises won't be canceled until right before departure time. Check in if you are concerned. Some rain and even distant thunderstorms are not a big concern on such a large boat, but the captain reserves the right to call off a cruise if the weather is questionable.
Sign on for the Wednesday night race if you are a competitive sailor. Both Woodwinds match race against each other, beginning just after the start of the Annapolis Yacht Club weekly races. The boats are Class-A light schooners when racing competitively, but they are flat-out rivals when racing against each other. Expect to work the sails and shift your weight from port to starboard, as the helmsman orders, to make the boat go fast.
