If you're not lucky enough to own your own sailboat or have a friend who does, you'll have to charter a boat to sail the bay. There are dozens of marinas and private individuals who charter sailboats for day sails, weekends, long weekends and even weeks at a time. And they are scattered up and down the bay, making the commute relatively easy.
Obviously, the longer you charter, the cheaper the cost is per day. Generally, for a 30-foot sloop (that's the traditional one-mast rig with a main and a headsail that sleeps two to four adults), you can expect to pay $150 to $300 for a weekend, depending on the boat's age, make and the equipment provided (for example, sophisticated electronics or an extra-well-equipped galley will cost more). A week costs $375 to $500.
You also have to pay a deposit, usually enough to cover whatever the deductible is for the chartered boat's insurance policy -- anywhere from $100 to $500 or more. The deposit is used to cover any damage you might cause. If there is no damage, the deposit usually will be sent back to you within two weeks.
Holiday weekends are reserved well in advance in most cases, and weekend charters for popular boat models can fill up quickly, too. So plan in advance.
Charters are easy to find. Check with any marina, a local publication on sailing called the Portbook or the classified ads of the Sunday Washington Post Sports section.
Most marinas serve as chartering agents for their slip holders. By far the largest number of marinas is in the Annapolis area. But outside Annapolis you can often find an equally good boat being chartered by a less-frequented marina for somewhat less money.
An excellent source of marina-managed chartering -- and other -- information dealing with sailing on the bay is the Portbook. You can obtain a copy from most marinas or other marine-related retailers or by mail for $2 (Portbook Publications Inc., P.O. Box 777, Easton, MD 21601).
Before anyone will charter a boat to you, they will want to know whether you know how to sail. So you will have to fill out an application that details your sailing experience. Generally, you must have captained a boat of similar size and rig before or had enough experience with different kinds of boats that the owner/charterer feels comfortable letting you take out a craft worth from $15,000 to $50,000.
But don't worry if you don't know how to sail or don't have the experience required to charter. There are a number of sailing schools on the bay that can teach you all you need to know.
Chances are, however, that you will need to have had at least a week's worth of instruction from a well-known school before anyone will let you charter a 30-footer. Check with the individual sailing school, because some of them guarantee that you'll qualify for a charter locally and elsewhere if you complete their course. Most schools offer weekend, extended (three- or four-day) weekend and week-long or longer courses.
Costs vary dramatically, not only from school to school but from course to course. You can pretty much count on it costing between $300 and $500 to learn at least enough to qualify as a charter candidate.
In deciding the kind of course you need, keep in mind what it is you want to do. Do you just want to putter around in a fun day sailer, or are you interested in full-blown chartering for extended periods of time? Your goals should determine what course and what school you choose.
Some of the schools on the bay include: Adventures Afloat, Annapolis, (301) 263-2625; Annapolis Sailing School, Annapolis, (301) 267-7205; Annapolis Yacht Sales (AYS), Annapolis, (301) 267-8181; C & C Charters, Queenstown, (301) 827-7888; Chesapeake Cruises, Annapolis, (301) 268-2144; Chesapeake Sailing School, Annapolis, (301) 269-1594; Coast Navigation, Annapolis, (301) 268-3122; Conklin Marine Centre, Annapolis, (301) 263-0706; Cruising Yacht Charters, Edgewater, (301) 956-5530; Jobson Sailing Associates, Annapolis, (301) 263-4630; North-East-Wind Yacht Charters, Annapolis, (301) 267-6333; Sailaway Charters, Crownsville, (301) 987-4618; Strandquist Yacht Charters, Annapolis, (301) 267-8022.
WHAT TO TAKE: Soft-soled shoes are important, and it's a good idea to take along a pair of waterproof binoculars. And charts of the areas you want to sail are a necessity; they are available at most marinas and ship chandleries, as well as at The Map Store, 1636 I St. NW.