Away. From our area, you can be at the dock of your chartered sailboat in about two hours. After stowing your gear and provisions, some paperwork, a briefing on the boat’s particulars, you cast off around 6. Heading for your first mark, motor rumbling, you’re headed for the Bay.

  And then it happens. You breathe in and note the stains of dusk on the evening sky. From the shallows, a great bird beats its wings and takes flight. Hors d'oeuvres emerge from the galley. Over your shoulder comes a breeze that has nothing to do with diesel and propeller, answering the question you have pondered all day. Wind!

  Yours is not an America’s Cup crew, but they get the job done. Sails are raised. The boat leans and adds momentum. The last remnant of land is the engine, now moot. You turn it off. And the boat keeps going.

  After several hours, you end the evening’s sail in a creek several miles down-Bay. The boat moved briskly on the open Bay, occasionally taking spray over the bow. But now you’re in calm, protected water again. In the darkness, you drop anchor. Dinner tonight will be store-bought delicatessen. Tomorrow will be more elaborate: maybe steaks on the grill. Or a visit to an onshore crab house.

  Post-dinner entertainment includes stargazing, story-telling, quacking ducks, maybe some poker and reminders about power and water use. If lifestyle seems spartan, keep in mind that morning will likely be never-forget beautiful.

  Cruising. Sailing from creek to creek, anchoring in whatever spot suits you, is a time-honored way to tour Chesapeake Bay. If you’re a decent cook, provision well, and choose your crew in part for amiability and conversation, you’ll find it easy to avoid the allures of harbor for three days, even a week.

   On the other hand, sailing the Chesapeake needn’t be the estuarine equivalent of wilderness camping. On shore, the Bay offers quaint villages (St. Michael’s, Oxford), substantial towns (Annapolis, Chestertown, Rock Hall), and last but not least, Baltimore. In such havens, you’ll find restaurant meals (especially if you like crab), unique shops (check out the antiques and duck decoys), not to mention flush toilets and satisfying levels of water pressure.

  Our recommendation, even if you occasionally visit the shore, is to spend evenings offshore at anchor. Docks can be noisy. And the boat is less comfortable when it’s all tied up. At anchor, it rocks you to sleep.

Choosing a Charter Company

  So, how to choose a charter company? Some say, it’s “all about the boats.” Others, “all about location.” Still others, “service.” Our advice: All the above. And more.

  On Location. Drive time from home to dock is important. You don’t want a cruise shortened by the burden of getting to it. BaySail in Havre de Grace — to your left and down as you pass south over the Susquehanna River on I-95 — is your closest option.

  But there’s more to location than home-to-dock. Think also about motoring time before you set sail. Generally, the farther south you drive, the less time your sailboat will have to run as a motorboat to reach open water.

  Also ask “can you get there from here?” If you’ve only got the weekend, and crabcakes in Crisfield are must-do, Oxford is a better place to start than, say, Worton Creek. If you want to swim, consider that the northern (aka “Upper”) Bay is usually nettle-free. (Nettles are jellyfish that can ruin your day.)

  The Middle Bay includes the most popular ports-of-call for cruisers — St. Michael’s, Annapolis, Rock Hall, Baltimore. Including the ship traffic, the Bay can feel pretty busy.   

  Farther south, the Bay widens and is less trafficked: good for sailing but port-to-port becomes a day-long affair.

  On Boats and Service. Beyond the obvious — size, number of berths, single-hull or catamaran — good condition is key. You do NOT want your cruise interrupted by breakdown. Think also about draft (depth of your boat’s bottom). It affects where you can go because much of the Bay is shallow.

  The newest boats tend to be found among larger charter companies (Beneteau Charters, LetsGoCruising, Annapolis Catamaran Charters, South River Boat Rentals).

  Be aware, though, that a well-maintained older boat can be as good as a young one. Owners who regularly use their own boats tend to take good care of them. Think about chartering directly from them and from small, well-established companies acting as agent-managers (Choptank Charters, Silver Star Catamaran, Chesapeake Sailing Charters). These smaller operations also tend to be less expensive and provide a more personal quality of service and relationship.

  But large or small, the charter groups do all the dirty work required of boat owners.

  With some preparation, it will be a happy day. Drive, cast off, and you’re away. On that day, you become a yachtsman: one who is that much wealthier because he’ll never have to buy a boat or clean a bilge. -CL-