Made-To-Order Weekend: Use Your Hands

First lesson at the basic “Become a Sailor in One Weekend” course at the Annapolis Sailing School: Regardless of the height of the waves, “heave to” doesn’t mean what it sounds like. Nor does anything else, really. Rope isn’t rope, it’s “line” — but it can also be a sheet, a halyard, an outhaul or a downhaul. No worries; cheerful, patient instructors and the right ratio of blackboard time to boat time will leave you comfortable enough rigging, trimming and steering to establish a lifelong obsession with gliding across the briny blue (7001 Bembe Beach Road, 800-638-9192; annapolissailing.com; $375).

Digs: Old salts get mighty uneasy when they can’t feel the spray on their faces, so it’s a helpful thing that some rooms at the Marriott Annapolis Waterfront offer bay views or private balconies right on the water (80 Compromise Street, 888-773-0786; annapolismarriott.com; $319 a night).

Eat: The night before you start earning your captain’s bars, feel like a captain of industry at Harry Browne’s, a Deco–style power room at the Maryland State House that serves classic chops and elegantly crafted sides, with a deep wine list (66 State Circle, 410-263-4332; dinner for two, about $100). After that first hard day on deck, revive your strength with sumptuous seafood and a pint or two of Guinness at Galway Bay (61-63 Maryland Avenue, 410-263-8333; dinner for two, about $60).

Do: You’ll begin each morning at 9 a.m. with an hour in the classroom, followed by two hours on the water in a specially designed 24-foot craft that for all practical purposes can’t sink. After lunch, there’s more classroom and sailing time.

And: Once you’ve completed any of its courses, the school offers lifetime discounts on future classes and boat rentals.

Travel time: Two and half hours south of Philadelphia. To avoid I-95, thread your way down the Delmarva peninsula on virtually empty Route 301, join Route 50 as it approaches the Chesapeake Bay Bridge, then sneak into Annapolis from the northeast on Route 450.